CN111836545B - Method for producing steviol glycosides and use thereof - Google Patents

Abstract

Provided herein are methods for preparing steviol glycosides, including rebaudioside D, rebaudioside E, rebaudioside M, rebaudioside N, and rebaudioside O. Also provided herein are methods for preparing sweeteners and sweetened consumables comprising rebaudioside D, rebaudioside E, rebaudioside M, rebaudioside N, and rebaudioside O.

Description

Method for preparing steviol glycosides and use thereof

Field of the Invention

The present invention generally relates to methods for preparing one or more steviol glycosides, such as Rebaudioside D (Reb D), Reb E (Reb E), Reb M (Reb M), Reb N (Reb N), and Reb O (Reb O) from a mixture of steviol glycosides. The present invention also relates to sweetener compositions and sweetened consumables containing one or more steviol glycosides, including Reb D, Reb E, Reb M, Reb N, and Reb O, and methods for preparing the same. The present invention also relates to methods for providing a sugar-like flavor and temporal profile to sweetener compositions and sweetened consumables using Reb D, Reb E, Reb M, Reb N, and Reb O.

Background of the Invention

Natural caloric sugars, such as sucrose, fructose and glucose, are used to provide pleasant taste to beverages, foods, medicines and oral hygiene/cosmetic products. In particular, sucrose gives consumers preferred taste. Although sucrose provides a more excellent sweetness characteristic, it is a caloric type. Non-caloric or low-calorie sweeteners have been introduced to meet consumer demand. However, the sweeteners within this class are different from natural caloric sugars in the way of continuously frustrating consumers. Based on taste, non-caloric or low-calorie sweeteners show time characteristics, maximum response, flavor characteristics, mouthfeel and/or adaptation behavior that are different from sugar. In particular, non-caloric or low-calorie sweeteners show delayed sweetness start, linger sweet aftertaste, bitter taste, metallic taste, astringent taste, cool taste and/or liquorice-like taste. Based on source, many non-caloric or low-calorie sweeteners are synthetic chemicals. Still high is the expectation of natural non-caloric or low-calorie sweeteners that taste like sucrose. Stevia rebaudiana is a perennial shrub of the Asteraceae (Compositae) family native to certain areas of South America. Its leaves have been used traditionally for hundreds of years in Paraguay and Brazil to sweeten local teas and medicines. The plant is cultivated commercially in Japan, Singapore, China (including Taiwan), Malaysia, Korea, Israel, India, Brazil, Australia, and Paraguay.

The leaves of the plant contain a mixture of diterpene glycosides in an amount of about 10 to 20% of the total dry weight. The sweetness of these diterpene glycosides is about 150 to 450 times that of sugar. Structurally, diterpene glycosides are characterized by a single base, steviol, and differ in the presence of carbohydrate residues at positions C13 and C19. Generally, the four major steviol glycosides found in the leaves of Stevia are Dulcoside A (0.3%), Reb C (0.6-1.0%), Reb A (3.8%), and Stevioside (9.1%), based on dry weight. Other glycosides identified in Stevia extracts include Reb B, D, E, and F, Steviolbioside, and Rubusoside. Of these, only Stevioside and Reb A are available on an industrial scale. Both steviol glycosides and Reb A have undesirable taste characteristics such as bitterness, lingering, astringency and the inability to achieve a sweetness greater than 7-8% of sucrose equivalent.

On the other hand, Reb D, Reb E, Reb M, Reb N and Reb O have better taste properties and are able to deliver similar temporal and flavor profiles as sucrose.

Steviol glycosides can be extracted from the leaves using water or organic solvent extraction. Supercritical fluid extraction or steam distillation methods have also been described. Methods for recovering diterpene steviol glycosides from Stevia using supercritical _CO2 , membrane technology and water or organic solvents such as methanol and ethanol can also be used.

Therefore, there remains a need to develop methods for preparing natural reduced or non-caloric sweeteners that provide temporal and flavor profiles similar to sucrose.

There remains a further need to develop sweetened consumables, such as beverages and foods, containing natural reduced or non-caloric sweeteners that provide temporal and flavor profiles similar to sucrose.

Brief description of the invention

The present invention provides a method for preparing a steviol glycoside composition from a starting mixture of steviol glycosides, wherein the steviol glycoside composition comprises a higher content of Reb D, Reb E, Reb M, Reb N, Reb O and combinations thereof than the starting mixture of steviol glycosides (hereinafter, such a composition is referred to as "Reb DEMNO").

As used herein, the term “steviol glycoside” refers to glycosides of steviol, including but not limited to naturally occurring steviol glycosides, such as rebaudioside A (Reb A), rebaudioside B (Reb B), rebaudioside C (Reb C), rebaudioside D (Reb D), rebaudioside E (Reb E), rebaudioside F (Reb F), rebaudioside G (Reb G), rebaudioside H (Reb H), rebaudioside I (Reb I), rebaudioside J (Reb J), rebaudioside K (Reb K), rebaudioside L (Reb L), rebaudioside M (Reb M), rebaudioside N (Reb N), rebaudioside O (Reb O), rebaudioside Q (Reb Q), rebaudioside R (Reb R), rebaudioside S (Reb S), rebaudioside T (Reb T), rebaudioside U (Reb U), rebaudioside V (Reb V), rebaudioside W (Reb W), rebaudioside Y (Reb Y), steviol glycosides, steviol biosides, dulcoside A and rubusoside, etc., or synthetic or biosynthesized steviol glycosides, such as enzymatic glycosylated steviol glycosides, steviol glycoside products from biocatalyst bioconversion of steviol glycosides, steviol glycosides from fermentation of a recombinant microbial host capable of synthesizing steviol glycosides de novo, and combinations thereof.

The term "T13SG content" as used herein is calculated as the sum of the contents of the following 13 steviol glycosides on a dry (anhydrous) basis: rebaudioside A (Reb A), rebaudioside B (Reb B), rebaudioside C (Reb C), rebaudioside D (Reb D), rebaudioside E (Reb E), rebaudioside F (Reb F), rebaudioside M (Reb M), rebaudioside N (Reb N), rebaudioside O (Reb O) steviol glycosides, steviolbioside, dulcoside A and rubusoside.

As used herein, the term "Reb DEMNO content" refers to the collective sum of Reb D, Reb E, Reb M, Reb N, and Reb O on a dry (anhydrous) basis.

As used herein, the term "Reb DEMNO/T13SG ratio" is calculated as the ratio of "Reb DEMNO content" and "T13SG content" on a dry basis according to the following formula:

{Reb DEMNO content (% dry basis) / T13SG content (% dry basis)} × 100%

In one embodiment, the present invention is a method for preparing Reb DEMNO, comprising passing a feed solution of steviol glycosides through a column system packed with a polymer resin, and eluting a fraction having a higher Reb DEMNO content from the column to obtain an eluted solution having a higher Reb DEMNO content than the feed solution.

The source of the steviol glycoside feed solution comprising at least one or more of Reb D, Reb E, Reb M, Reb N and Reb O can vary. In one embodiment, the feed solution of steviol glycosides can be a commercially available stevia extract or a steviol glycoside mixture. In another embodiment, the feed solution of steviol glycosides can be prepared from plant material (e.g., leaves) of Stevia rebaudiana. Alternatively, the feed solution of steviol glycosides can be a byproduct of another process for separating and purifying steviol glycosides from stevia plant material. In other embodiments, the feed solution of steviol glycosides can be obtained by bioconversion of steviol glycosides by a biocatalyst. In still another embodiment, the feed solution of steviol glycosides can be obtained by fermentation of a recombinant microbial host capable of de novo synthesis of steviol glycosides.

According to the present invention, the polymer resin used to prepare Reb DEMNO is a homopolymer or copolymer prepared from at least one monomer selected from the following Group A, or at least one monomer selected from the following Group B, or at least one monomer selected from each of Group A and Group B. If more than one monomer is used, the mass percentage of each individual monomer relative to the sum of all monomers is from about 0.1% to about 99.9%, such as, for example, 0.1% to about 5%, about 5% to about 10%, about 10% to about 15%, about 15% to about 20%, about 20% to about 25%, about 25% to about 30%, about 30% to about 35%, about 35% to about 40%, about 40% to about 45%, about 45% to about 50%, about 50% to about 55%, about 55% to about 60%, about 60% to about 65%, about 65% to about 70%, about 70% to about 75%, about 75% to about 80%, about 80% to about 85%, about 85% to about 90%, about 90% to about 95%, about 95% to about 99.9%.

(a) Group A - Any monomer containing carbon, hydrogen, oxygen and/or nitrogen classified as N-vinylamide, acrylamide, methacrylamide, acrylates with attached amino substituents, methacrylates with attached amino substituents, acrylamides with attached amino substituents, methacrylamides with attached amino substituents, acrylic acid, methacrylic acid, styrene, including compounds in homologous series of said classes. Examples include, but are not limited to, N-vinylacetamide (CAS 5202-78-8), N-vinyl-2-pyrrolidone (CAS 88-12-0), N-vinyl-2-piperidone (CAS 4370-23-4), N-vinylcaprolactam (CAS 2235-00-9), N-methyl-N-vinylacetamide (CAS 3195-78-6), N-methyl-acrylamide (CAS 1187-59-3), N,N-dimethylacrylamide (CAS 2680-03-7), N-ethylacrylamide (CAS 5883-17-0), N,N-diethylacrylamide (CAS 2675-94-7), N-tert-butyl-acrylamide (CAS 107-58-4), N-benzylacrylamide (CAS 13304-62-6), N-methyl-methacrylamide (CAS 3887-02-3), N,N-dimethyl-methacrylamide (CAS 6976-91-6), N-ethyl-methacrylamide (CAS 7370-88-9), N,N-diethyl-methacrylamide (CAS 5441-99-6), N-tert-butyl-methacrylamide (CAS 6554-73-0), N-benzyl-methacrylamide (CAS 3219-55-4), 2-(dimethylamino)-ethyl methacrylate (CAS 2867-47-2), 2-(dimethylamino)-ethyl acrylate (CAS 2439-35-2), N-[2-(dimethylamino)ethyl]acrylamide (CAS 925-76-8), N-[2-(N,N-dimethylamino)ethyl]methacrylamide (CAS 13081-44-2), acrylic acid (CAS 79-10-7), methacrylic acid (CAS 79-41-4) and styrene (CAS 100-42-5).

(b) Group B - any crosslinker type monomers containing carbon, hydrogen and/or oxygen classified into the general classes of acrylates, methacrylates, divinylbenzene, including compounds in the homologous series of said classes. Examples include, but are not limited to, ethylene glycol diacrylate (CAS 2274-11-5), 1,2-propylene glycol diacrylate (CAS 25151-33-1), 1,3-propylene glycol diacrylate (CAS 24493-53-6), 1,4-butylene glycol diacrylate (CAS 1070-70-8), poly(ethylene glycol) diacrylate (CAS 26570-48-9), poly(propylene glycol) diacrylate (CAS 52496-08-9), ethylene glycol dimethacrylate (CAS 97-90-5), 1,2-propylene glycol dimethacrylate (CAS 7559-82-2), 1,3-propylene glycol dimethacrylate (CAS 1188-09-6), 1,4-butylene glycol dimethacrylate (CAS 2082-81-7), poly(ethylene glycol) dimethacrylate (CAS 25852-47-5), poly(propylene glycol) dimethacrylate (CAS 25852-49-7), trimethylolpropane trimethacrylate (CAS 3290-92-4), and divinylbenzene (CAS 105-06-6).

According to the present invention, the aforementioned polymer resin is prepared by stirring aqueous suspension polymerization, spray polymerization or emulsion polymerization.

Also provided herein are sweetener compositions comprising Reb DEMNO. In one embodiment, when present in a sweetened consumable, Reb DEMNO is present in an effective amount to provide a sucrose sweetness equivalent of about 0.5 to about 14 degrees Brix, such as, for example, about 0.5 degrees Brix to about 1.0 degrees Brix, about 1.0 degrees Brix to about 2.0 degrees Brix, about 2.0 degrees Brix to about 3.0 degrees Brix, about 3.0 degrees Brix to about 4.0 degrees Brix, about 4.0 degrees Brix to about 5.0 degrees Brix, about 5.0 degrees Brix to about 6.0 degrees Brix, about 6.0 degrees Brix to about 7.0 degrees Brix, about 7.0 degrees Brix to about 8.0 degrees Brix, about 8.0 degrees Brix to about 9.0 degrees Brix, about 9.0 degrees Brix to about 10.0 degrees Brix, about 10.0 degrees Brix to about 11.0 degrees Brix, about 11.0 degrees Brix to about 12.0 degrees Brix, about 12.0 degrees Brix to about 13.0 degrees Brix, about 13.0 degrees Brix to about 14.0 degrees Brix Brix to about 7.0 Brix, about 7.0 Brix to about 8.0 Brix, about 8.0 Brix to about 9.0 Brix, about 9.0 Brix to about 10.0 Brix, about 10.0 Brix to about 11.0 Brix, about 11.0 Brix to about 12.0 Brix, about 12.0 Brix to about 13.0 Brix, and about 13.0 Brix to about 14.0 Brix. In another embodiment, Reb DEMNO is present in an effective amount to provide greater than about 10% sucrose equivalence when present in a sweetened consumable, such as, for example, greater than about 20%, greater than about 30%, greater than about 40%, greater than about 50%, greater than about 60%, greater than about 70%, greater than about 80%, and greater than about 90%.

Reb DEMNO can be used in any form. In one embodiment, Reb DEMNO is the sole sweetener in a sweetener composition. In another embodiment, Reb DEMNO is provided as part of a composition or mixture. In one embodiment, Reb DEMNO is provided as a stevia extract, wherein the content of Reb DEMNO is from about 5% to about 99% of the stevia extract by weight on a dry basis, such as, for example, from about 5% to 10%, from about 10% to 20%, from about 20% to about 30%, from about 30% to 40%, from about 40% to 50%, from about 50% to about 60%, from about 60% to about 70%, from about 70% to 80%, from about 80% to about 90%, from about 90% to about 99%. In a further embodiment, Reb DEMNO is provided as a mixture of steviol glycosides, wherein Reb DEMNO comprises about 5% to about 99% by weight of the mixture of steviol glycosides on a dry basis, such as, for example, about 5% to 10%, about 10% to 20%, about 20% to about 30%, about 30% to 40%, about 40% to 50%, about 50% to about 60%, about 60% to about 70%, about 70% to 80%, about 80% to about 90%, about 90% to about 99% by weight.

The sweetener composition may also contain one or more additional sweeteners, including, for example, natural sweeteners, high-potency sweeteners, carbohydrate sweeteners, polyol sweeteners, synthetic sweeteners, and combinations thereof.

Particularly desirable sweetener compositions include Reb DEMNO and a compound selected from Reb A, Reb B, NSF-02, mogroside V, erythritol, or a combination thereof.

The sweetener composition may also contain one or more additives, including, for example, carbohydrates, polyols, amino acids and their corresponding salts, polyamino acids and their corresponding salts, sugar acids and their corresponding salts, nucleotides, organic acids, inorganic acids, organic salts (including organic acid salts and organic basic salts), inorganic salts, bitter compounds, flavoring agents and seasoning ingredients, astringent compounds, proteins or protein hydrolysates, surfactants, emulsifiers, flavonoids, alcohols, polymers and combinations thereof.

The sweetener composition may also contain one or more functional ingredients, such as, for example, saponins, antioxidants, dietary fiber sources, fatty acids, vitamins, glucosamine, minerals, preservatives, hydration agents, probiotics, prebiotics, weight management agents, osteoporosis management agents, phytoestrogens, long chain primary aliphatic saturated alcohols, plant sterols, and combinations thereof.

Also provided are methods of making a sweetener composition. In one embodiment, the method of making a sweetener composition comprises mixing Reb DEMNO and at least one sweetener and/or additive and/or functional ingredient. In another embodiment, the method of making a sweetener composition comprises mixing a composition comprising Reb DEMNO and at least one sweetener and/or additive and/or functional ingredient.

Also provided herein are sweetened consumables containing the sweetener compositions of the present invention. Sweetened consumables include, for example, pharmaceutical compositions, edible gel mixes and compositions, dental compositions, foods, beverages, and beverage products.

Also provided herein are methods for preparing sweetened consumer products. In one embodiment, the method for preparing sweetened consumer products comprises mixing a sweetenable composition and Reb DEMNO. The method may further comprise adding one or more sweeteners, additives, and/or functional ingredients. In another embodiment, the method for preparing sweetened consumer products comprises mixing a sweetenable composition and a sweetener composition comprising Reb DEMNO. The sweetener composition may optionally comprise one or more sweeteners, additives, and/or functional ingredients.

In particular embodiments, beverages containing Reb DEMNO or sweetener compositions of the present invention are also provided herein. The beverages contain a liquid base such as, for example, deionized water, distilled water, reverse osmosis water, carbon-treated water, purified water, demineralized water, phosphoric acid, phosphate buffer, citric acid, citrate buffer, and carbonated water.

Full-calorie, mid-calorie, low-calorie, and zero-calorie beverages containing Reb DEMNO or the sweetener compositions of the present invention are also provided.

Also provided herein are methods of preparing beverages. In one embodiment, the method for preparing a beverage comprises mixing Reb DEMNO and a liquid matrix. The method may further comprise adding one or more sweeteners, additives, and/or functional ingredients to the beverage. In another embodiment, the method for preparing a beverage comprises mixing a sweetener composition comprising Reb DEMNO and a liquid matrix.

Also provided herein is a tabletop sweetener composition containing the sweetener composition of the present invention. The tabletop composition may further include at least one filler, additive, anti-caking agent, functional ingredient and combination thereof. The tabletop sweetener composition may exist in the form of a solid or liquid. Liquid tabletop sweeteners may include water and optionally additives such as, for example, polyols (e.g., erythritol, sorbitol, propylene glycol or glycerol), acids (e.g., citric acid), antimicrobial agents (e.g., benzoic acid or its salt).

Also provided herein are delivery systems comprising Reb DEMNO or sweetener compositions of the present invention, such as, for example, sweetener compositions co-crystallized with sugars or polyols, agglomerated sweetener compositions, compacted sweetener compositions, dried sweetener compositions, particulate sweetener compositions, spheronized sweetener compositions, granulated sweetener compositions, and liquid sweetener compositions.

Finally, also provided herein are methods of imparting a more sugar-like temporal profile, flavor profile, or both to a sweetened consumable product, comprising mixing a sweetenable composition with Reb DEMNO or a sweetener composition of the present invention. The method may further comprise adding other sweeteners, additives, functional ingredients, and combinations thereof.

BRIEF DESCRIPTION OF THE DRAWINGS

The accompanying drawings are included to provide a further understanding of the present invention. The drawings illustrate embodiments of the present invention and together with the description serve to explain the principle of embodiments of the present invention.

FIG1 shows the HPLC chromatogram of steviol glycosides solution.

FIG. 2 shows the HPLC chromatogram of the fraction eluted with water, having a higher Reb DEMNO/T13SG ratio than the feed solution.

FIG3 shows the HPLC chromatogram of the fraction eluted with 15% aqueous ethanol, having a lower RebDEMNO/T13SG ratio than the feed solution.

DETAILED DESCRIPTION OF THE INVENTION

The advantages of the present invention will become apparent from the detailed description given below. However, it should be understood that although the detailed description and specific examples point out the preferred embodiments of the present invention, they are given by way of example only, because from this detailed description, various changes and modifications within the spirit and scope of the present invention will become apparent to those skilled in the art.

The present invention provides a method for preparing a steviol glycoside composition from a starting mixture of steviol glycosides, wherein the steviol glycoside composition comprises a higher content of Reb D, Reb E, Reb M, Reb N, Reb O and combinations thereof than the starting mixture of steviol glycosides (hereinafter, such a composition is referred to as "Reb DEMNO").

As used herein, the term “steviol glycoside” refers to glycosides of steviol, including but not limited to naturally occurring steviol glycosides, such as rebaudioside A (Reb A), rebaudioside B (Reb B), rebaudioside C (Reb C), rebaudioside D (Reb D), rebaudioside E (Reb E), rebaudioside F (Reb F), rebaudioside G (Reb G), rebaudioside H (Reb H), rebaudioside I (Reb I), rebaudioside J (Reb J), rebaudioside K (Reb K), rebaudioside L (Reb L), rebaudioside M (Reb M), rebaudioside N (Reb N), rebaudioside O (Reb O), rebaudioside Q (Reb Q), rebaudioside R (Reb R), rebaudioside S (Reb S), rebaudioside T (Reb T), rebaudioside U (Reb U), rebaudioside V (Reb V), rebaudioside W (Reb W), rebaudioside Y (Reb Y), steviol glycosides, steviolbiosides, dulcoside A and rubusoside, etc., or synthetic or biosynthesized steviol glycosides, such as enzymatically glycosylated steviol glycosides, steviol glycoside products from biocatalyst bioconversion of steviol glycosides, steviol glycosides from fermentation of a recombinant microbial host capable of synthesizing steviol glycosides de novo, and combinations thereof.

The term "T13SG content" as used herein is calculated as the sum of the contents of the following 13 steviol glycosides on a dry (water-free) basis: rebaudioside A (Reb A), rebaudioside B (Reb B), rebaudioside C (Reb C), rebaudioside D (Reb D), rebaudioside E (Reb E), rebaudioside F (Reb F), rebaudioside M (Reb M), rebaudioside N (Reb N), rebaudioside O (Reb O) steviol glycosides, steviolbioside, dulcoside A and rubusoside.

As used herein, the term "Reb DEMNO content" refers to the collective sum of Reb D, Reb E, Reb M, Reb N, and Reb O on a dry (anhydrous) basis.

As used herein, the term "Reb DEMNO/T13SG ratio" is calculated as the ratio of "Reb DEMNO content" and "T13SG content" on a dry basis according to the following formula:

{Reb DEMNO content (% dry basis) / T13SG content (% dry basis)} × 100%

In one aspect of the invention, a method for preparing Reb DEMNO comprises:

(a) passing a feed solution of steviol glycosides including at least one or more of Reb D, Reb E, Reb M, Reb N and Reb O through a column system packed with a polymer resin, and

(b) eluting the high Reb DEMNO content fraction from the column system using an initial solvent comprising pure water or water containing less than 40% by volume of alcohol to obtain an elution solution having a higher Reb DEMNO/T13SG ratio than the feed solution,

(c) eluting the low Reb DEMNO content fraction from the column system using one or more alcohol-water mixtures having 5-99% by volume of alcohol higher than the initial solvent to obtain one or more elution solutions having a lower Reb DEMNO/T13SG ratio than the feed solution.

In another embodiment, a method of preparing Reb DEMNO comprises:

(a) passing a feed solution of steviol glycosides including at least one or more of Reb D, Reb E, Reb M, Reb N and Reb O through a column system packed with a polymer resin, and

(b) eluting the high Reb DEMNO content fraction from the column system using an initial solvent comprising an acid solution or an acid solution containing less than 40% by volume of alcohol to obtain an eluted solution having a higher Reb DEMNO/T13SG ratio than the feed solution,

(c) eluting the low Reb DEMNO content fraction from the column system using one or more alcohol-aqueous acid mixtures having 5-99% by volume of alcohol higher than the initial solvent to obtain one or more elution solutions having a lower Reb DEMNO/T13SG ratio than the feed solution.

The source of the steviol glycoside feed solution comprising at least one or more of Reb D, Reb E, Reb M, Reb N, and Reb O can vary. In one embodiment, the feed solution of steviol glycosides can be a commercially available stevia extract or a steviol glycoside mixture. In another embodiment, the feed solution of steviol glycosides can be prepared from plant material (e.g., leaves) of the stevia plant. Alternatively, the feed solution of steviol glycosides can be a byproduct of another separation and purification process of steviol glycosides from stevia plant material. In other embodiments, the feed solution of steviol glycosides can be obtained by bioconversion of steviol glycosides by a biocatalyst. In still another embodiment, the feed solution of steviol glycosides can be obtained by fermentation of a recombinant microbial host capable of synthesizing steviol glycosides de novo.

In another aspect of the present invention, the polymer resin used in preparing Reb DEMNO is a homopolymer or copolymer prepared from at least one monomer selected from Group A described below, or at least one monomer selected from Group B described below, or at least one monomer selected from each of Groups A and B. If more than one monomer is used, the mass percentage of each individual monomer relative to the sum of all monomers is from about 0.1% to about 99.9%, such as, for example, 0.1% to about 5%, about 5% to about 10%, about 10% to about 15%, about 15% to about 20%, about 20% to about 25%, about 25% to about 30%, about 30% to about 35%, about 35% to about 40%, about 40% to about 45%, about 45% to about 50%, about 50% to about 55%, about 55% to about 60%, about 60% to about 65%, about 65% to about 70%, about 70% to about 75%, about 75% to about 80%, about 80% to about 85%, about 85% to about 90%, about 90% to about 95%, about 95% to about 99.9%.

(a) Group A - Any monomer containing carbon, hydrogen, oxygen and/or nitrogen classified as N-vinylamide, acrylamide, methacrylamide, acrylates with attached amino substituents, methacrylates with attached amino substituents, acrylamides with attached amino substituents, methacrylamides with attached amino substituents, acrylic acid, methacrylic acid, styrene, including compounds in homologous series of said classes. Examples include, but are not limited to, N-vinylacetamide (CAS 5202-78-8), N-vinyl-2-pyrrolidone (CAS 88-12-0), N-vinyl-2-piperidone (CAS 4370-23-4), N-vinylcaprolactam (CAS 2235-00-9), N-methyl-N-vinylacetamide (CAS 3195-78-6), N-methyl-acrylamide (CAS 1187-59-3), N,N-dimethylacrylamide (CAS 2680-03-7), N-ethylacrylamide (CAS 5883-17-0), N,N-diethylacrylamide (CAS 2675-94-7), N-tert-butyl-acrylamide (CAS 107-58-4), N-benzylacrylamide (CAS 13304-62-6), N-methyl-methacrylamide (CAS 3887-02-3), N,N-dimethyl-methacrylamide (CAS 6976-91-6), N-ethyl-methacrylamide (CAS 7370-88-9), N,N-diethyl-methacrylamide (CAS 5441-99-6), N-tert-butyl-methacrylamide (CAS 6554-73-0), N-benzyl-methacrylamide (CAS 3219-55-4), 2-(dimethylamino)-ethyl methacrylate (CAS 2867-47-2), 2-(dimethylamino)-ethyl acrylate (CAS 2439-35-2), N-[2-(dimethylamino)ethyl]acrylamide (CAS 925-76-8), N-[2-(N,N-dimethylamino)ethyl]methacrylamide (CAS 13081-44-2), acrylic acid (CAS 79-10-7), methacrylic acid (CAS 79-41-4) and styrene (CAS 100-42-5).

(b) Group B - any crosslinker type monomers containing carbon, hydrogen and/or oxygen classified into the general classes of acrylates, methacrylates, divinylbenzene, including compounds in the homologous series of said classes. Examples include, but are not limited to, ethylene glycol diacrylate (CAS 2274-11-5), 1,2-propylene glycol diacrylate (CAS 25151-33-1), 1,3-propylene glycol diacrylate (CAS 24493-53-6), 1,4-butylene glycol diacrylate (CAS 1070-70-8), poly(ethylene glycol) diacrylate (CAS 26570-48-9), poly(propylene glycol) diacrylate (CAS 52496-08-9), ethylene glycol dimethacrylate (CAS 97-90-5), 1,2-propylene glycol dimethacrylate (CAS 7559-82-2), 1,3-propylene glycol dimethacrylate (CAS 1188-09-6), 1,4-butylene glycol dimethacrylate (CAS 2082-81-7), poly(ethylene glycol) dimethacrylate (CAS 25852-47-5), poly(propylene glycol) dimethacrylate (CAS 25852-49-7), trimethylolpropane trimethacrylate (CAS 3290-92-4), and divinylbenzene (CAS 105-06-6).

In another aspect of the present invention, the aforementioned resin has the following characteristics:

(a) a particle size of from about 1 micron to about 1,200 microns, preferably having an average particle size (volume weighted average) of from about 5 microns to about 1,000 microns, such as, for example, an average particle size of from about 5 microns to about 15 microns, from about 15 microns to about 25 microns, from about 25 microns to about 35 microns, from about 35 microns to about 45 microns, from about 45 microns to about 55 microns, from about 55 microns to about 65 microns, from about 65 microns to about 75 microns, from about 75 microns to about 85 microns, from about 85 microns to about 95 microns, from about 95 microns to about 100 microns, from about 100 microns to about 200 microns, from about 200 microns to about 300 microns, from about 300 microns to about 400 microns, from about 400 microns to about 500 microns, from about 500 microns to about 600 microns, from about 600 microns to about 700 microns, from about 700 microns to about 800 microns, from about 800 microns to about 900 microns, from about 900 microns to about 1,000 microns;

(b) the nitrogen mass content is about 0% to about 99%, preferably about 0% to about 10.0%, such as, for example, about 0% to about 1.5%, about 1.5% to about 2.0%, about 2.0% to about 2.5%, about 2.5% to about 3.0%, about 3.0% to about 3.5%, about 3.5% to about 4.0%, about 4.0% to about 4.5%, about 4.5% to about 5.0%, about 5.0% to about 6.0%, about 6.0% to about 7.0%, about 7.0% to about 8.0%, about 8.0% to about 9.0% and about 9.0% to about 10.0%.

In another aspect of the present invention, the aforementioned resin is prepared in the presence of one or more of the following polymerization initiators:

(a) peroxide initiators, including but not limited to lauroyl peroxide (CAS no 105-74-8) and benzoyl peroxide (CAS no 94-36-0 );

(b) Azo initiators, including but not limited to 2,2′-azobis(2,4-dimethylvaleronitrile) ABDV (CAS no 2638-94-0).

In another aspect of the invention, the aforementioned resin is prepared in the presence of one or more or all of the following materials, including but not limited to, which are then removed by washing the resin prior to use:

Cyclohexanol (CAS no 108-93-0), 1-dodecanol (CAS no 112-53-8), toluene (CAS no 108-88-3), methyl isobutyl ketone (CAS no 108-10-1), calcium chloride dihydrate (CAS no 10035-04-8), sodium phosphate dodecahydrate (CAS no 10101-89-0), calcium lignin sulfonate (CAS no 8061-52-7), polyvinyl alcohol (CAS no 9002-89-5), hydrochloric acid (CAS no 7647-01-0), methanol (CAS no 67-56-1), ethyl acetate (CAS no 141-78-6), sodium chloride (CAS no 7647-14-5), water (CAS no 7732-18-5) and sodium dodecyl sulfate (CAS no 151-21-3).

In still another aspect of the present invention, the aforementioned polymer resin is prepared by stirred aqueous suspension polymerization, spray polymerization or emulsion polymerization.

Preparation of steviol glycoside solution

One skilled in the art will recognize that the techniques described hereinafter are also applicable to other starting materials containing Reb D, Reb E, Reb M, Reb N, and Reb O, including, but not limited to, commercially available stevia extracts, commercially available steviol glycoside mixtures, byproducts of other steviol glycoside isolation and purification processes thereof, synthetic or biosynthesized steviol glycosides, such as enzymatically glycosylated steviol glycosides, steviol glycoside products from biocatalyst bioconversion of steviol glycosides, steviol glycosides from fermentation of a recombinant microbial host capable of synthesizing steviol glycosides de novo, and combinations thereof.

Those skilled in the art will also appreciate that although the methods described below assume a certain order of steps described, this order may be changed or omitted in certain circumstances.

In some embodiments, the feed liquid of steviol glycosides is a resin-treated filtrate obtained from purified stevia leaves. In another embodiment, the feed liquid of steviol glycosides is a commercially available stevia extract dissolved in a solvent. In still another embodiment, the feed liquid of steviol glycosides is a commercially available extract from which insoluble materials and/or polymer compounds and/or salts have been removed. In still another embodiment, the feed liquid of steviol glycosides is an enzymatically glycosylated glycoside product. In other embodiments, the feed liquid of steviol glycosides can be obtained by bioconversion of steviol glycosides by biocatalysts. In still another embodiment, the feed liquid of steviol glycosides can be obtained by fermentation of a recombinant microbial host capable of synthesizing steviol glycosides from scratch.

The Reb DEMNO/T13SG ratio in the steviol glycoside stock solution will also vary depending on the source of the steviol glycosides. In one embodiment, the Reb DEMNO/T13SG in the steviol glycoside stock solution is about 0.5% to about 95%, such as, for example, about 0.5% to about 5%, about 5% to about 10%, about 10% to about 15%, about 15% to about 20%, about 20% to about 25%, about 25% to about 30%, about 30% to about 35%, about 35% to about 40%, about 40% to about 45%, about 45% to about 50%, about 50% to about 55%, about 55% to about 60%, about 60% to about 65%, about 65% to about 70%, about 70% to about 75%, about 75% to about 80%, about 80% to about 85%, about 85% to about 90%, about 90% to about 95%. In a specific embodiment, the Reb DEMNO/T13SG ratio in the steviol glycoside stock solution is about 55% to about 80%.

Steviol glycosides feed liquid can pass through the post (connected in series or in parallel) of the packed polymer resin connected one or more, to provide at least one post with the steviol glycosides of absorption.In certain embodiments, the quantity of post can be greater than 3, such as for example 5 posts, 6 posts, 7 posts, 8 posts, 9 posts, 10 posts, 11 posts, 12 posts, 13 posts, 14 posts or 15 posts. The temperature of the column can be maintained in the range of about 5-95°C, such as, for example, about 5°C to 10°C, about 10°C to 15°C, about 15°C to 20°C, about 20°C to 25°C, about 25°C to 30°C, about 30°C to 35°C, about 35°C to 40°C, about 40°C to 45°C, about 45°C to 50°C, about 50°C to 55°C, about 55°C to 60°C, about 60°C to 65°C, about 65°C to 70°C, about 70°C to 75°C, about 75°C to 80°C, about 80°C to 85°C, about 85°C to 90°C, about 90°C to 95°C.

The ratio of inner diameter to column height, or the so-called column "diameter:height ratio", should be between about 100:1 and about 1:100, such as, for example, about 2:1, about 6:1, about 10:1, about 13:1, about 16:1, about 20:1, about 1:2, about 1:6, about 1:10, about 1:13, about 1:16 or about 1:20.

In various embodiments where multiple column systems are connected in parallel, the inlet of each column can be connected to a different source, while the outlet of each column is connected to a different receiver. The ratio of the volume of the first column to the volume of the second column is preferably in the range of about 1:1 to 1:10. The ratio of the volume of the last column to the volume of the previous or penultimate column is preferably in the range of about 3:1 to 1:10.

The solvent that is loaded with the steviol glycoside solution through the column system can include alcohol, water, aqueous acid solution or its combination. In the embodiment where aqueous acid is used, the concentration of aqueous acid can be in the following range: about 0.01mM to 100.0mM, such as, for example, about 0.01mM to 0.1mM, about 0.1mM to 1.0mM, about 1.0mM to 10.0mM and about 10.0mM to 100.0mM. The ratio of water to alcohol (vol/vol) in the aqueous alcohol solvent can be in the range of 99.9:0.1 to about 0.1:99.9, such as, for example, from about 99:1 to about 90:10, from about 90:10 to about 80:20, from about 80:20 to about 70:30, from about 70:30 to about 60:40, from about 60:40 to about 50:50, from about 50:50 to about 40:60, from about 40:60 to about 30:70, from about 30:70 to about 20:80, from about 20:80 to about 10:90, and from about 10:90 to about 1:99. The ratio of aqueous acid to alcohol in the aqueous alcohol solvent (vol/vol) can be in the range of about 99.9:0.1 to about 0.1:99.9, such as, for example, about 99:1 to about 90:10, about 90:10 to about 80:20, about 80:20 to about 70:30, about 70:30 to about 60:40, about 60:40 to about 50:50, about 50:50 to about 40:60, about 40:60 to about 30:70, about 30:70 to about 20:80, about 20:80 to about 10:90, and about 10:90 to about 1:99. The specific velocity (SV) can be about 0.3 hr ^-1 to about 5.0 hr ^-1 , such as, for example, about 0.3 hr ^-1 to about 1.0 hr ^-1 , about 1.0 hr ^-1 to about 2.0 hr ^-1 , about 2.0 hr ^-1 to about 3.0 hr ^-1 , about 3.0 hr ^-1 to about 4.0 hr ^-1 , and about 4.0 hr ^-1 to about 5.0 hr ^-1 .

The alcohol may be selected from, for example, methanol, ethanol, n-propanol, 2-propanol, 1-butanol, 2-butanol, and mixtures thereof. The aqueous acid may be selected from aqueous hydrochloric acid, aqueous nitric acid, aqueous phosphoric acid, aqueous sulfuric acid, aqueous formic acid, aqueous acetic acid, and mixtures thereof.

Generally, Reb D, Reb E, Reb M, Reb N and Reb O are weakly retained and eluted with water or water containing less than 40% alcohol by volume at a concentration of about 0.1 mM aqueous acid. Thus, the initial mixture of steviol glycosides is separated into different fractions. The fractions differ from each other in their T13SG content and in their content of individual glycosides (particularly Reb DEMNO).

Desorption of Reb D, Reb E, Reb M, Reb N, and Reb O can be performed with pure water, water containing less than 40% alcohol by volume, aqueous acid, or aqueous acid containing less than 40% alcohol by volume to yield an elution solution having a high Reb DEMNO content. As used herein, "high Reb DEMNO content" refers to any material having a higher Reb DEMNO/T13SG ratio than the steviol glycoside feed solution before passing through the column system. The elution solution with high Reb DEMNO content has a Reb DEMNO/T13SG ratio of about 1% to about 99.5% higher than the feed solution, such as, for example, about 1%, about 5%, about 10%, about 15%, about 20%, about 25%, about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95%, and about 99.5% higher than the feed solution. In embodiments where an aqueous acid is used, the concentration of the aqueous acid can be in the range of about 0.01 mM to 100.0 mM, such as, for example, about 0.01 mM to 0.1 mM, about 0.1 mM to 1.0 mM, about 1.0 mM to 10.0 mM, and about 10.0 mM to 100.0 mM. Suitable alcohols include methanol, ethanol, n-propanol, 2-propanol, 1-butanol, 2-butanol and mixtures thereof. Suitable aqueous acids include aqueous hydrochloric acid, aqueous nitric acid, aqueous phosphoric acid, aqueous sulfuric acid, aqueous formic acid, aqueous acetic acid and mixtures thereof.

After desorption of Reb D, Reb E, Reb M, Reb N and Reb O from the column, the column can also be eluted with an aqueous alcohol solution or a mixture of aqueous acid and alcohol, and their eluates can be combined to obtain an elution solution of steviol glycosides with a low Reb DEMNO content. As used herein, "low Reb DEMNO content" refers to any material having a lower Reb DEMNO/T13SG ratio than the steviol glycoside feed solution before passing through the column system. "Low Reb DEMNO content" also refers to any material having zero Reb DEMNO content. In a particular embodiment, the aqueous alcohol solution or the mixture of aqueous acid and alcohol can contain an alcohol content between about 1% to about 100%, such as, for example, about 1% to 5%, about 5% to 10%, about 10% to about 20%, about 20% to about 30%, about 30% to about 40%, about 40% to about 50%, about 50% to about 60%, about 60% to about 70%, about 70% to about 80%, about 80% to about 90%, and about 90% to about 100%.

In another embodiment, after eluting the material with low Reb DEMNO content from the column, the column system is regenerated by washing with pure water, aqueous acid, water containing less than 5% by volume alcohol, or aqueous acid containing less than 5% by volume alcohol for subsequent loading of steviol glycoside feed solution.

The Reb DEMNO/T13SG ratio can be determined by HPLC experiments. For example, the chromatographic analysis can be performed on an HPLC system comprising an HPLC system, Agilent HP 1200, or an equivalent consisting of a pump, a column thermostat, an autosampler, a UV detector capable of background correction, and a data acquisition system. The column can be an "Agilent Poroshell 120 SB-C18, 4.6 mm×150 mm, 2.7 um" at 40°C. The mobile phase consists of two types of premixes, wherein premix 1 contains 75% 10 mmol/L phosphate buffer (pH 2.6) and 25% acetonitrile, and premix 2 contains 68% 10 mmol/L phosphate buffer (pH 2.6) and 32% acetonitrile, gradient elution—100% A from 0 to 12 minutes, a linear gradient from 100% A to 100% B from 12 to 13 minutes, and 100% B from 13 to 45 minutes. Steviol glycosides can be identified by their retention time and quantified using corresponding reference standards, such as those commercially available from ChromaDex Inc. (USA).

The eluted solution with a high Reb DEMNO content can be distilled or evaporated under vacuum to remove water or any alcohol solvent. Removal of water or any alcohol solvent can also be performed by other suitable methods such as, for example, nanofiltration.

Alternatively, the eluted solution having a high Reb DEMNO content can be dried by any suitable method, such as, for example, evaporation under reduced pressure, freeze drying, flash drying, spray drying, or a combination thereof, to provide a dry powder having a high Reb DEMNO content, wherein the Reb DEMNO/T13SG ratio is higher than the feed solution of steviol glycosides before passing through the column system.

Sweetener composition

As used herein, a sweetener composition refers to a composition containing at least one sweet component in combination with at least one other substance such as, for example, another sweetener or an additive.

As used herein, a sweetenable composition refers to a substance that comes into contact with the mouth of a human or animal, including substances that are ingested and subsequently expectorated from the mouth as well as substances that are drunk, eaten, swallowed or otherwise ingested, and is safe for human or animal consumption when used within generally acceptable ranges.

As used herein, a sweetened consumable refers to a substance containing a sweetenable composition and a sweetener or a sweetener combination.

For example, a beverage that does not contain a sweetener component is a class of compositions that can be sweetened. A sweetener composition comprising Reb DEMNO and erythritol can be added to an unsweetened beverage, thereby providing a sweetened beverage. Sweetened beverages are a class of sweetened consumables.

Reb DEMNO can be provided in a purified form or as a component of a mixture containing Reb DEMNO and one or more additional components (i.e., a sweetener composition comprising Reb DEMNO). In one embodiment, Reb DEMNO is provided as a component of a mixture. In a specific embodiment, the mixture is a stevia extract. The stevia extract can contain Reb DEMNO in an amount ranging from about 5% to about 99% by weight on a dry basis, such as, for example, from about 10% to about 99%, from about 20% to about 99%, from about 30% to about 99%, from about 40% to about 99%, from about 50% to about 99%, from about 60% to about 99%, from about 70% to about 99%, from about 80% to about 99%, and from about 90% to about 99%. In still further embodiments, the Stevia extract contains Reb DEMNO in an amount greater than about 90%, e.g., greater than about 91%, greater than about 92%, greater than about 93%, greater than about 94%, greater than about 95%, greater than about 96%, greater than about 97%, greater than about 98%, and greater than about 99% by weight on a dry basis.

In one embodiment, Reb DEMNO is provided in a sweetener composition as a component of a steviol glycoside mixture, i.e., a mixture of steviol glycosides wherein the remaining non-Reb DEMNO portion of the mixture consists entirely of steviol glycosides. The identity of steviol glycosides is known in the art and includes, but is not limited to, steviol monoside, rubusoside, steviolbioside, steviol glycoside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside F, and dulcoside A. The steviol glycoside mixture may contain from about 5% to about 99% by weight on a dry basis of Reb DEMNO. For example, the steviol glycoside mixture can contain about 10% to about 99%, about 20% to about 99%, about 30% to about 99%, about 40% to about 99%, about 50% to about 99%, about 60% to about 99%, about 70% to about 99%, about 80% to about 99%, and about 90% to about 99% Reb DEMNO by weight on a dry basis. In still further embodiments, the steviol glycoside mixture can contain Reb DEMNO in an amount greater than about 90%, e.g., greater than about 91%, greater than about 92%, greater than about 93%, greater than about 94%, greater than about 95%, greater than about 96%, greater than about 97%, greater than about 98%, and greater than about 99% by weight on a dry basis.

In one embodiment, Reb DEMNO is the only sweetener in the sweetener composition, i.e., Reb DEMNO is the only component present in the sweetener composition that provides sweetness. In another embodiment, Reb DEMNO is one of two or more sweetener components present in the sweetener composition.

The amount of sucrose in a reference solution can be described in degrees Brix (°Bx). One degree Brix is 1 g of sucrose in 100 g of solution, representing the strength of the solution in weight percent (% w/w) (strictly speaking, by mass). In one embodiment, when present in a sweetened consumable, the sweetener composition contains an effective amount of Reb DEMNO to provide a sugar sweetness equivalent of about 0.50 to 14 degrees Brix, such as, for example, about 0.5 degrees Brix to about 1.0 degrees Brix, about 1.0 degrees Brix to about 2.0 degrees Brix, about 2.0 degrees Brix to about 3.0 degrees Brix, about 3.0 degrees Brix to about 4.0 degrees Brix, about 4.0 degrees Brix to about 5.0 degrees Brix, about 5.0 degrees Brix to about 6.0 degrees Brix, about 6.0 degrees Brix to about 7.0 degrees Brix, about 7.0 degrees Brix to about 8.0 degrees Brix, about 8.0 degrees Brix to about 9.0 degrees Brix, about 9.0 degrees Brix to about 10.0 degrees Brix, about 10.0 degrees Brix to about 11.0 degrees Brix, about 12.0 degrees Brix to about 13.0 degrees Brix, about 14.0 degrees Brix to about 15.0 degrees Brix, about 16.0 degrees Brix to about 17.0 degrees Brix, about 18.0 degrees Brix to about 19.0 degrees Brix, about 19.0 degrees Brix to about 20.0 degrees Brix, about 18.0 degrees Brix to about 21.0 degrees Brix In another embodiment, Reb DEMNO is present in an amount effective to provide a sweetness equivalent of about 10 Brix when present in a sweetened consumable.

The sweetness of non-sucrose sweeteners can also be measured against a sucrose reference by determining the sucrose equivalent of the non-sucrose sweetener. Typically, taste panelists are trained to detect the sweetness of a reference sucrose solution containing sucrose (w/v) between 1-15%. Other non-sucrose sweeteners are then tasted in a series of dilutions to determine the concentration of the non-sucrose sweetener whose sweetness is a given percentage of sucrose reference. For example, if a 1% sweetener solution has the sweetness of a 10% sucrose solution, the sweetener is considered to have 10 times the potency of sucrose.

In one embodiment, Reb DEMNO is provided in an effective amount to provide greater than about 10% (w/v), such as, for example, greater than about 11%, greater than about 12%, greater than about 13%, or greater than about 14% sucrose equivalence when present in a sweetened consumable.

The content of Reb DEMNO in the sweetener composition can vary. In one embodiment, when the sweetener composition is present in a sweetened consumable, Reb DEMNO is present in the sweetener composition in any amount that imparts the desired sweetness. For example, when present in a sweetened consumable, Reb DEMNO is present in the sweetener composition in an effective amount that provides a Reb DEMNO concentration of about 1 ppm to about 10,000 ppm, such as, for example, about 1 ppm to about 4,000 ppm, about 1 ppm to about 3,000 ppm, about 1 ppm to about 2,000 ppm, about 1 ppm to about 1,000 ppm. In another embodiment, when present in a sweetened consumable, Reb DEMNO is present in the sweetener composition in an effective amount that provides a Reb DEMNO concentration of about 10 ppm to about 1,000 ppm, such as, for example, about 10 ppm to about 800 ppm, about 50 ppm to about 800 ppm, about 50 ppm to about 600 ppm, or about 200 ppm to about 250 ppm. In a particular embodiment, Reb DEMNO is present in the sweetener composition in an amount effective to provide a concentration of about 300 ppm to about 600 ppm Reb DEMNO.

In certain embodiments, the sweetener composition contains one or more additional sweeteners. Additional sweeteners can be any type of sweetener, such as natural, non-natural or synthetic sweeteners. In at least one embodiment, at least one additional sweetener is selected from natural sweeteners except stevia (Stevia) sweetener. In another embodiment, at least one additional sweetener is selected from synthetic high-efficiency sweeteners.

For example, the at least one additional sweetener may be a carbohydrate sweetener. Non-limiting examples of suitable carbohydrate sweeteners include sucrose, fructose, glucose, erythritol, maltitol, lactitol, sorbitol, mannitol, xylitol, tagatose, trehalose, galactose, rhamnose, cyclodextrins (e.g., α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin), ribulose, threose, arabinose, xylose, lyxose, allose, altrose, mannose, idose, lactose, maltose, invert sugar, isotrehalose, neotrehalose, palatinose or isomalt, erythrose, deoxyribose, gulose, talose, erythrulose, xylulose, psicose, turanose, cellobiose, glucosamine, mannosamine, fucose, fucose, glucuronic acid, gluconic acid, glucono-lactone, abequose, galactosamine, xylose- Oligosaccharides (xylotriose, xylobiose, etc.), gentio-oligosaccharides (gentiobiose, gentiotriose, gentiotetraose, etc.), galactose-oligosaccharides, sorbose, ketotriose (dihydroxyacetone), triose (glyceraldehyde), niger-oligosaccharides, fructo-oligosaccharides (kestose, mold erythralose, etc.), maltotetraose, maltotriol, tetrasaccharide, mannan-oligosaccharides, maltose-oligosaccharides (maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose, etc.), dextrin, lactulose, melibiose, raffinose, ribose, isomerized liquid sugars such as high fructose corn/starch syrup (HFCS/HFSS) (e.g., HFCS55, HFCS42 or HFCS90), coupling sugars, soybean oligosaccharides, glucose syrup and combinations thereof. When applicable, D- or L- configurations can be used.

In other embodiments, the additional sweetener is a carbohydrate sweetener selected from the group consisting of: glucose, fructose, sucrose, and combinations thereof.

In another embodiment, the additional sweetener is a carbohydrate sweetener selected from the group consisting of: D-allose, D-psicose, L-ribose, D-tagatose, L-glucose, L-fucose, L-arabinose, turanose, and combinations thereof.

Reb DEMNO and the carbohydrate sweetener may be present in any weight ratio, such as, for example, from about 0.001:14 to about 1:0.01, such as, for example, from about 0.001:14 to about 0.01:14, from about 0.01:14 to about 0.1:14, from about 0.1:14 to about 1.0:14, from about 1.0:14 to about 1.0:10, from about 1.0:10 to about 1.0:1.0, from about 1.0:1.0 to about 1.0:0.1, and from about 1.0:0.1 to about 1.0:0.01. When present in a sweetened consumable such as, for example, a beverage, the carbohydrate is present in the sweetener composition in an effective amount to provide a concentration of about 100 ppm to about 140,000 ppm, such as, for example, about 100 ppm to about 1,000 ppm, about 1,000 ppm to about 5,000 ppm, about 5,000 ppm to about 10,000 ppm, about 10,000 ppm to about 20,000 ppm, about 20,000 ppm to about 30,000 ppm, about 30,000 ppm to about 40,000 ppm, about 40,000 ppm to about 50,000 ppm. ppm, about 500,000 ppm to about 60,000 ppm, about 60,000 ppm to about 70,000 ppm, about 70,000 ppm to about 80,000 ppm, about 80,000 ppm to about 90,000 ppm, about 90,000 ppm to about 100,000 ppm, about 100,000 ppm to about 110,000 ppm, about 110,000 ppm to about 120,000 ppm, about 120,000 ppm to about 130,000 ppm, and about 130,000 ppm to about 140,000 ppm.

In still other embodiments, at least one additional sweetener is a synthetic sweetener. As used herein, the phrase "synthetic sweetener" refers to any composition that is not naturally found in nature and characteristically has a sweetness effect greater than sucrose, fructose or glucose, and still has less calories. Non-limiting examples of synthetic high-efficiency sweeteners suitable for embodiments of the present disclosure include sucralose, acesulfame potassium, acesulfame acid and its salts, aspartame, alitame, saccharin and its salts, neohesperidin dihydrochalcone, cyclamates, cyclohexanesulfamic acid and its salts, neotame, saccharin (advantame), glucosylated steviol glycosides (GSG) and combinations thereof. When present in a sweetened consumable, such as, for example, a beverage, the synthetic sweetener is present in the sweetener composition in an effective amount to provide a concentration of about 0.3 ppm to about 3,500 ppm, such as, for example, about 0.3 ppm to about 1.0 ppm, about 1.0 ppm to about 10 ppm, about 10 ppm to about 100 ppm, about 100 ppm to about 1,000 ppm, about 1,000 ppm to about 2,000 ppm, about 2,000 ppm to about 3,000 ppm, and about 3,000 ppm to about 3,500 ppm.

In still other embodiments, the additional sweetener can be a natural high-potency sweetener. Suitable natural high-potency sweeteners include, but are not limited to, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside F, rebaudioside I, rebaudioside H, rebaudioside L, rebaudioside K, rebaudioside J, dulcoside A, dulcoside B, sweet leaf rubusoside, stevia, steviol glycosides, stevioside, mogroside IV, mogroside V, monk fruit, simonoside, monatin and its salts (monatin SS, RR, RS, SR), curculin, glycyrrhizic acid and its salts, thaumatin (t Haumatin, monellin, mabinlin, sweet protein, hernandulcin, phyllodulcin, glycyphyllin, phloridzin, trilobtain, baiyunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I, periandrin I, abrusoside A, steviolbioside and cyclocarioside I. The natural high potency sweeteners may be provided as pure compounds or, alternatively, as part of an extract. For example, rebaudioside A can be provided as a separate compound or as part of a Stevia extract. When present in a sweetened consumable such as, for example, a beverage, the natural high potency sweetener is present in the sweetener composition in an effective amount to provide a concentration of about 0.1 ppm to about 3,000 ppm, such as, for example, about 0.1 ppm to about 1.0 ppm, about 1.0 ppm to 10 ppm, about 10 ppm to 100 ppm, about 100 ppm to about 1,000 ppm, about 1,000 ppm to about 2,000 ppm, and about 2,000 ppm to about 3,000 ppm.

In still other embodiments, additional sweeteners can be natural high-efficiency sweeteners modified by chemistry or enzymes. Modified natural high-efficiency sweeteners include glycosylated natural high-efficiency sweeteners, such as glucosyl-, galactosyl-, fructosyl-derivatives containing 1-50 glycoside residues. Glycosylated natural high-efficiency sweeteners can be prepared by various enzyme-catalyzed enzymatic transglycosylation reactions with transglycosylation activity.

In another specific embodiment, the sweetener composition comprises Reb DEMNO and at least one other sweetener that acts as the sweetener component (i.e., a substance that provides sweetness) of the sweetener composition. When mixed, the sweetener composition generally exhibits synergy and has improved flavor and temporal properties over each sweetener alone. In one embodiment, the sweetener composition contains Reb DEMNO and an additional sweetener. In other embodiments, the sweetener composition contains Reb DEMNO and more than one additional sweetener. At least one other sweetener can be selected from erythritol, Reb B, NSF-02, mogroside V, Reb A, and combinations thereof.

In one embodiment, the sweetener composition comprises Reb DEMNO and erythritol as a sweetener component. The relative weight percentages of Reb DEMNO and erythritol can vary. Typically, erythritol can account for about 0.1% to about 3.5% of the sweetener component, such as, for example, about 0.1% to about 0.5%, about 0.5% to about 1.0%, about 1.0% to about 1.5%, about 1.5% to about 2.0%, about 2.0% to about 2.5%, about 2.5% to about 3.0%, and about 3.0% to about 3.5% by weight.

In another embodiment, a sweetener composition comprises Reb DEMNO and Reb B as sweetener components. The relative weight percentages of Reb DEMNO and Reb B can each vary from about 1% to about 99%, such as, for example, about 95% Reb DEMNO/5% Reb B, about 90% Reb DEMNO/10% Reb B, about 85% Reb DEMNO/15% Reb B, about 80% Reb DEMNO/20% Reb B, about 75% Reb DEMNO/25% Reb B, about 70% Reb DEMNO/30% Reb B, about 65% Reb DEMNO/35% Reb B, about 60% Reb DEMNO/40% Reb B, about 55% Reb DEMNO/45% Reb B, about 50% Reb DEMNO/50% Reb B, about 45% Reb DEMNO/55% Reb B, about 40% Reb DEMNO/60% Reb B, about 35% Reb DEMNO/65% Reb B. In some embodiments, Reb DEMNO comprises about 30% Reb DEMNO/70% Reb B, about 25% Reb DEMNO/75% Reb B, about 20% Reb DEMNO/80% Reb B, about 15% Reb DEMNO/85% Reb B, about 10% Reb DEMNO/90% Reb B or about 5% Reb DEMNO/95% Reb B. In a particular embodiment, Reb B comprises about 5% to about 40% of the sweetener component, such as, for example, about 10% to about 30%, or about 15% to about 25%.

In yet another embodiment, a sweetener composition comprises Reb DEMNO and NSF-02 (a GSG-type sweetener available from PureCircle) as sweetener components. The relative weight percentages of Reb DEMNO and NSF-02 can each vary from about 1% to about 99%, such as, for example, about 95% Reb DEMNO/5% NSF-02, about 90% Reb DEMNO/10% NSF-02, about 85% Reb DEMNO/15% NSF-02, about 80% Reb DEMNO/20% NSF-02, about 75% Reb DEMNO/25% NSF-02, about 70% Reb DEMNO/30% NSF-02, about 65% Reb DEMNO/35% NSF-02, about 60% Reb DEMNO/40% NSF-02, about 55% Reb DEMNO/45% NSF-02, about 50% Reb DEMNO/50% NSF-02, about 45% Reb DEMNO/55% NSF-02, about 40% Reb DEMNO/50% NSF-02. In one embodiment, NSF-02 comprises about 5% to about 50% of the sweetener component, such as, for example, about 10% to about 40%, or 20% to about 30%.

In yet another embodiment, a sweetener composition comprises Reb DEMNO and mogroside V as sweetener components. The relative weight percentages of Reb DEMNO and mogroside V can each vary from about 1% to about 99%, such as, for example, about 95% Reb DEMNO/5% mogroside V, about 90% Reb DEMNO/10% mogroside V, about 85% Reb DEMNO/15% mogroside V, about 80% Reb DEMNO/20% mogroside V, about 75% Reb DEMNO/25% mogroside V, about 70% Reb DEMNO/30% mogroside V, about 65% Reb DEMNO/35% mogroside V, about 60% Reb DEMNO/40% mogroside V, about 55% Reb DEMNO/45% mogroside V, about 50% Reb DEMNO/50% mogroside V, about 45% Reb DEMNO/55% mogroside V, about 40% Reb DEMNO/55% mogroside V, about 45% Reb DEMNO/50% mogroside V, about 45% Reb DEMNO/55% mogroside V, about 40% Reb DEMNO/60% Mogroside V, about 35% Reb DEMNO/65% Mogroside V, about 30% Reb DEMNO/70% Mogroside V, about 25% Reb DEMNO/75% Mogroside V, about 20% Reb DEMNO/80% Mogroside V, about 15% Reb DEMNO/85% Mogroside V, about 10% Reb DEMNO/90% Mogroside V, or about 5% Reb DEMNO/95% Mogroside V. In a particular embodiment, mogroside V comprises about 5% to about 50% of the sweetener component, such as, for example, about 10% to about 40%, or about 20% to about 30%.

In another embodiment, a sweetener composition comprises Reb DEMNO and Reb A as sweetener components. The relative weight percentages of Reb DEMNO and Reb A can each vary from about 1% to about 99%, such as, for example, about 95% Reb DEMNO/5% Reb A, about 90% Reb DEMNO/10% Reb A, about 85% Reb DEMNO/15% Reb A, about 80% Reb DEMNO/20% Reb A, about 75% Reb DEMNO/25% Reb A, about 70% Reb DEMNO/30% Reb A, about 65% Reb DEMNO/35% Reb A, about 60% Reb DEMNO/40% Reb A, about 55% Reb DEMNO/45% Reb A, about 50% Reb DEMNO/50% Reb A, about 45% Reb DEMNO/55% Reb A, about 40% Reb DEMNO/60% Reb A, about 35% Reb DEMNO/65% Reb A. In some embodiments, Reb A comprises about 30% Reb DEMNO/70% Reb A, about 25% Reb DEMNO/75% Reb A, about 20% Reb DEMNO/80% Reb A, about 15% Reb DEMNO/85% Reb A, about 10% Reb DEMNO/90% Reb A or about 5% Reb DEMNO/95% Reb A. In a particular embodiment, Reb A comprises about 5% to about 40% of the sweetener component, such as, for example, about 10% to about 30% or about 15% to about 25%.

Sweetener compositions can be customized to provide the caloric content of expectation.For example, sweetener compositions can be "rich in calories", so that when added to the composition that can be sweetened (such as, for example, beverage), they give the desired sweetness, and have about 120 calories/8 ounces.Alternatively, sweetener compositions can be "median value calories", so that when added to the composition that can be sweetened (such as, for example, beverage), they give the desired sweetness, and have less than about 60 calories/8 ounces.In other embodiments, sweetener compositions can be "low calories", so that when added to the composition that can be sweetened (such as, for example, beverage), they give the desired sweetness, and have less than about 40 calories/8 ounces.In still other embodiments, sweetener compositions can be "zero calories", so that when added to the composition that can be sweetened (such as, for example, beverage), they give the desired sweetness, and have less than about 5 calories/8 ounces.

additive

In addition to Reb DEMNO and optional other sweeteners, the sweetener composition can optionally include other additives described in detail below herein. In certain embodiments, the sweetener composition contains additives, including but not limited to carbohydrates, polyols, amino acids and their corresponding salts, poly-amino acids and their corresponding salts, sugar acids and their corresponding salts, nucleotides, organic acids, inorganic acids, organic salts (including organic acid salts and organic base salts), inorganic salts, bitter compounds, flavors and flavoring ingredients, astringent compounds, proteins or protein hydrolysates, surfactants, emulsifiers, weighting agents (weighing agents), gums, antioxidants, coloring agents, flavonoids, alcohol, polymers and combinations thereof. In certain embodiments, additives improve the time and flavor characteristics of sweeteners to provide a sweetener composition with a taste similar to sucrose.

In one embodiment, the sweetener composition contains one or more polyols. As used herein, the term "polyol" refers to a molecule containing more than one hydroxyl group. Polyols can be diols, triols or tetraols containing 2, 3 and 4 hydroxyls, respectively. Polyols may also contain more than 4 hydroxyls, such as pentahydric alcohols, hexahydric alcohols, heptahydric alcohols, etc. containing 5, 6 or 7 hydroxyls, respectively. In addition, polyols may also be sugar alcohols, polyhydroxy alcohols or polyols in a reduced form of carbohydrates, wherein the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.

In certain embodiments, non-limiting examples of polyols include erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, isomalt, propylene glycol, glycerol (glycerine), threitol, dulcitol, palatinose, reduced isomalt-oligosaccharides, reduced xylo-oligosaccharides, reduced gentio-oligosaccharides, reduced maltose syrup, reduced glucose syrup, and sugar alcohols or any other carbohydrate that can be reduced that adversely affects the taste of the sweetener composition.

In some embodiments, the polyol is present in the sweetener composition in an effective amount to provide a concentration of about 100 ppm to about 250,000 ppm, such as, for example, about 100 ppm to about 1,000 ppm, about 1,000 ppm to about 10,000 ppm, about 10,000 ppm to about 50,000 ppm, about 50,000 ppm to about 100,000 ppm, about 100,000 ppm to about 150,000 ppm, about 150,000 ppm to about 200,000 ppm, and about 200,000 ppm to about 250,000 ppm when present in a sweetened consumable such as, for example, a beverage. In other embodiments, the polyol is present in the sweetener composition in an effective amount to provide a concentration of about 400 ppm to about 80,000, such as, for example, about 400 ppm to about 1,000 ppm, about 1,000 ppm to about 5,000 ppm, about 5,000 ppm to about 10,000 ppm, about 10,000 ppm to about 50,000 ppm, and about 50,000 ppm to about 80,000 ppm when present in a sweetened consumable.

In other embodiments, Reb DEMNO and the polyol are present in the sweetened composition in a weight ratio of about 1:1 to about 1:800, such as, for example, about 1:4 to about 1:800, about 1:20 to about 1:600, about 1:50 to about 1:300, or about 1:75 to about 1:150.

Suitable amino acid additives include, but are not limited to, aspartic acid, arginine, glycine, glutamic acid, proline, threonine, theanine, cysteine, cystine, alanine, valine, tyrosine, leucine, trans-4-hydroxyproline, isoleucine, asparagine, serine, lysine, histidine, ornithine, methionine, carnitine, aminobutyric acid, (α-, β-, γ- and/or δ-isomers), glutamine, phenylalanine, tryptophan, hydroxyproline, taurine, norvaline, sarcosine, and salt forms thereof such as sodium or potassium salts or acid salts. Amino acid additives may also be in the D- or L- configuration, and mono-, di- or tri- forms of the same or different amino acids. In addition, amino acids may be α-, β-, γ- and/or δ-isomers (if appropriate). In some embodiments, combinations of the aforementioned amino acids and their corresponding salts (e.g., sodium, potassium, calcium, magnesium salts or other alkali metal or alkaline earth metal salts, or acid salts) are also suitable additives. Amino acids may be natural or synthetic. Amino acids can also be modified. Modified amino acids refer to any amino acid (e.g., N-alkyl amino acids, N-acyl amino acids, or N-methyl amino acids) in which at least one atom is added, removed, substituted, or a combination thereof. Non-limiting examples of modified amino acids include amino acid derivatives such as trimethylglycine, N-methyl-glycine, and N-methyl-alanine. Modified amino acids as used herein encompass modified and unmodified amino acids. Amino acids as used herein also encompass peptides and polypeptides (e.g., dipeptides, tripeptides, tetrapeptides, and pentapeptides) such as glutathione and L-alanyl-L-glutamine. Suitable polyamino acid additives include poly-L-aspartic acid, poly-L-lysine (e.g., poly-L-α-lysine or poly-L-ε-lysine), poly-L-ornithine (e.g., poly-L-α-ornithine or poly-L-ε-ornithine), poly-L-arginine, other amino acid polymeric forms, and salt forms thereof (e.g., calcium salts, potassium salts, sodium salts, or magnesium salts such as L-glutamic acid monosodium salt). The polyamino acid additive can also be D- or L- configuration. In addition, the polyamino acid can be α-, β-, γ-, δ- and ε--isomers (if appropriate). The combination of the aforementioned amino acids and their corresponding salts (e.g., sodium, potassium, calcium, magnesium salts or other alkali metal or alkaline earth metal salts, or acid salts) is also a suitable additive. In certain embodiments, the polyamino acids described herein can also include copolymers of different amino acids. The polyamino acid can be natural or synthetic. The polyamino acid can also be modified so that at least one atom is added, removed, substituted or a combination thereof (e.g., N- alkyl polyamino acids or N- acyl polyamino acids). The polyamino acids used herein include modified and unmodified polyamino acids. For example, modified polyamino acids include but are not limited to polyamino acids (MW) of various molecular weights, such as poly-L-α-lysine with MW about 1,500, MW about 6,000, MW about 25,200, MW about 63,000, MW about 83,000 or MW about 300,000.

In a specific embodiment, when present in a sweetened consumable such as, for example, a beverage, the amino acid is present in the sweetener composition in an effective amount to provide a concentration of about 10 ppm to about 50,000 ppm, such as, for example, about 10 ppm to about 100 ppm, about 100 ppm to about 1,000 ppm, about 1,000 ppm to about 10,000 ppm, and about 10,000 ppm to about 50,000 ppm. In another embodiment, when present in a sweetened consumable, the amino acid is present in the sweetener composition in an effective amount to provide a concentration of about 100 ppm to about 10,000 ppm, such as, for example, about 2,500 ppm to about 5,000 ppm or about 250 ppm to about 7,500 ppm.

Suitable sugar acid additives include, but are not limited to, aldonic acid, uronic acid, aldaric acid, alginic acid, gluconic acid, glucuronic acid, glucaric acid, galactaric acid, galacturonic acid and salts thereof (e.g., sodium, potassium, calcium, magnesium salts or physiologically acceptable salts thereof), and combinations thereof.

When present in a sweetened consumable such as, for example, a beverage, the sugar acid additive is present in the sweetener composition in an effective amount to provide a concentration of about 5 ppm to about 1,000 ppm, such as, for example, about 5 ppm to about 10 ppm, about 10 ppm to about 100 ppm, about 100 ppm to about 500 ppm, and about 500 ppm to about 1,000 ppm.

Suitable nucleotide additives include, but are not limited to, inosine monophosphate ("IMP"), guanosine monophosphate ("GMP"), adenosine monophosphate ("AMP"), cytosine monophosphate (CMP), uracil monophosphate (UMP), inosine diphosphate, guanosine diphosphate, adenosine diphosphate, cytosine diphosphate, uracil diphosphate, inosine triphosphate, guanosine triphosphate, adenosine triphosphate, cytosine triphosphate, uracil triphosphate, alkali or alkaline earth metal salts thereof, and combinations thereof. The nucleotides described herein may also include nucleotide-related additives, such as, for example, nucleosides or nucleic acid bases (e.g., guanine, cytosine, adenine, thymine, uracil).

When present in a sweetened consumable such as, for example, a beverage, the nucleotides are present in the sweetener composition in an effective amount to provide a concentration of about 5 ppm to about 1,000 ppm, such as, for example, about 5 ppm to about 10 ppm, about 10 ppm to about 100 ppm, and about 100 ppm to about 1,000 ppm.

Suitable organic acid additives include any compound containing a -COOH moiety, such as, for example, C2-C30 carboxylic acids, substituted hydroxy C2-C30 carboxylic acids, butyric acid (ethyl ester), substituted butyric acid (ethyl ester), benzoic acid, substituted benzoic acid (e.g., 2,4-dihydroxybenzoic acid), substituted cinnamic acid, alcoholic acid, substituted hydroxybenzoic acid, anisic acid substituted cyclohexyl carboxylic acid, tannic acid, aconitic acid, lactic acid, tartaric acid, citric acid, isocitric acid, gluconic acid, glucoheptonic acid, adipic acid, hydroxycitric acid, malic acid, fruitaric acid (a mixture of malic acid, fumaric acid and tartaric acid), fumaric acid, maleic acid, succinic acid, chlorogenic acid, salicylic acid, creatine, caffeic acid, bile acid, acetic acid, ascorbic acid, alginic acid, isoascorbic acid, polyglutamic acid, glucono delta lactone, and alkali or alkaline earth metal salt derivatives thereof. In addition, the organic acid additive may also be in D- or L- configuration.

Suitable organic acid addition salts include, but are not limited to, sodium, calcium, potassium, and magnesium salts of all organic acids, such as salts of citric acid, malic acid, tartaric acid, fumaric acid, lactic acid (e.g., sodium lactate), alginic acid (e.g., sodium alginate), ascorbic acid (e.g., sodium ascorbate), benzoic acid (e.g., sodium benzoate or potassium benzoate), sorbic acid, and adipic acid. The examples of organic acid additives described may be substituted with at least one group selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, halogen, haloalkyl, carboxyl, acyl, acyloxy, amino, amido, carboxyl derivatives, alkylamino, dialkylamino, arylamino, alkoxy, aryloxy, nitro, cyano, sulfo, thiol, imine, sulfonyl, sulfinyl, sulfinyl, sulfamoyl, carboxyalkoxy, carboxamido, phosphonyl, phosphinyl, phosphoryl, phosphino, thioester, thioether, anhydride, oxime, hydrazine, carbamoyl, phosphor or phosphonato. In specific embodiments, when present in a sweetened consumable such as, for example, a beverage, the organic acid additive is present in the sweetener composition in an amount from about 10 ppm to about 5,000 ppm, such as, for example, from about 10 ppm to about 100 ppm, from about 100 ppm to about 500 ppm, from about 500 ppm to about 1,000 ppm, and from about 1,000 ppm to about 5,000 ppm.

Suitable inorganic acid additives include, but are not limited to, phosphoric acid, phosphorous acid, polyphosphoric acid, hydrochloric acid, sulfuric acid, carbonic acid, sodium dihydrogen phosphate, and alkali or alkaline earth metal salts thereof (eg, phytic acid Mg/Ca).

When present in a sweetened consumable such as, for example, a beverage, the inorganic acid additive is present in the sweetener composition in an effective amount to provide a concentration of about 25 ppm to about 25,000 ppm, such as, for example, about 25 ppm to about 250 ppm, about 250 ppm to about 2500 ppm, and about 2500 ppm to about 25000 ppm.

Suitable bitter compound additives include, but are not limited to, caffeine, quinine, urea, bitter orange oil, naringin, quassia and their salts.

When present in a sweetened consumable such as, for example, a beverage, the bitter compound is present in the sweetener composition in an effective amount to provide a concentration of about 25 ppm to about 25,000 ppm, such as, for example, about 25 ppm to about 250 ppm, about 250 ppm to about 2,500 ppm, and about 2,500 ppm to about 25,000 ppm.

Suitable flavoring and flavoring ingredient additives include, but are not limited to, vanillin, pandan extract, mango extract, cinnamon, citrus, coconut, ginger, viridiflorol, almond, menthol (including menthol, mint-free), grape skin extract, and grape seed extract. "Flavoring" and "flavoring ingredient" are synonymous and may include natural or synthetic substances or combinations thereof. Flavoring also includes any other substance that imparts flavor and may include natural or non-natural (synthetic) substances that are safe for humans or animals when used in a generally accepted range. Non-limiting examples of proprietary flavorings include: Natural flavoring sweetness enhancer K14323( Darmstadt, Germany), Symrise ^™ natural taste masking for sweeteners 161453 and 164126 (Symrise ^™ , Holzminden, Germany), Natural Advantage ^™ bitter blockers 1, 2, 9 and 10 (Natural Advantage ^™ , Freehold, NJ, USA), and Sucramask ^™ (Creative Research Management, Stockton, Calif., USA).

When present in a sweetened consumable, such as, for example, a beverage, the flavoring agent is present in the sweetener composition in an effective amount to provide a concentration of about 0.1 ppm to about 4,000 ppm, such as, for example, about 0.1 ppm to about 1 ppm, about 1 ppm to about 10 ppm, about 10 ppm to about 100 ppm, about 100 ppm to about 1,000 ppm, about 1,000 ppm to about 2,000 ppm, about 2,000 ppm to about 3,000 ppm, and about 3,000 ppm to about 4,000 ppm.

Suitable polymer additives include, but are not limited to, chitosan, pectin, pectic, pectinic acid, polyuronic acid, polygalacturonic acid, starch, food hydrocolloids or crude extracts thereof (e.g., gum arabic senegal (Fibergum ^™ ), gum arabic red acacia, carrageenan), poly-L-lysine (e.g., poly-L-α-lysine or poly-L-ε-lysine), poly-L-ornithine (e.g., poly-L-α-ornithine or poly-L-ε-ornithine), polypropylene glycol, polyethylene glycol, poly(ethylene glycol methyl ether), polyarginine, polyaspartic acid, polyglutamic acid, polyethyleneimine, alginic acid, sodium alginate, propylene glycol alginate and polyethylene glycol sodium alginate, sodium hexametaphosphate and its salts, and other cationic and anionic polymers.

When present in a sweetened consumable, such as, for example, a beverage, the polymer is present in the sweetener composition in an effective amount to provide a concentration of about 30 ppm to about 2,000 ppm, such as, for example, about 30 ppm to about 50 ppm, about 50 ppm to about 100 ppm, about 100 ppm to about 500 ppm, about 500 ppm to about 1,000 ppm, about 1,000 ppm to about 1,500 ppm, and about 1,500 ppm to about 2,000 ppm.

Suitable protein or protein hydrolysate additives include, but are not limited to, bovine serum albumin (BSA), whey protein (including fractions or concentrates thereof, such as 90% immediate whey protein isolate, 34% whey protein, 50% hydrolyzed whey protein and 80% whey protein concentrate), soluble rice protein, soy protein, protein isolate, protein hydrolysate, reaction products of protein hydrolysate, glycoproteins and/or proteoglycans containing amino acids (e.g., glycine, alanine, serine, threonine, asparagine, glutamine, arginine, valine, isoleucine, leucine, norvaline, methionine, proline, tyrosine, hydroxyproline, etc.), collagen (e.g., gelatin), partially hydrolyzed collagen (e.g., hydrolyzed fish collagen), and collagen hydrolysate (e.g., porcine collagen hydrolysate).

When present in a sweetened consumable, such as, for example, a beverage, the protein hydrolysate is present in the sweetener composition in an effective amount to provide a concentration of about 200 ppm to about 50,000 ppm, such as, for example, about 200 ppm to about 500 ppm, about 500 ppm to about 1,000 ppm, about 1,000 ppm to about 5,000 ppm, about 5,000 ppm to about 10,000 ppm, about 10,000 ppm to about 25,000 ppm, and about 25,000 ppm to about 50,000 ppm.

Suitable surfactant additives include, but are not limited to, polysorbates (e.g., polyoxyethylene sorbitan monooleate (polysorbate 80), polysorbate 20, polysorbate 60), sodium dodecylbenzenesulfonate, dioctyl sulfosuccinate or sodium dioctyl sulfosuccinate, sodium lauryl sulfate, cetylpyridinium chloride (cetylpyridinium chloride), cetyltrimethylammonium bromide, sodium cholate, carbamoyl, choline chloride, sodium glycocholate, sodium taurodeoxycholate, arginine laurate, sodium stearoyl lactylate, sodium taurocholate, lecithin, sucrose oleate, sucrose stearate, sucrose palmitate, sucrose laurate, and other emulsifiers.

When present in a sweetened consumable, such as, for example, a beverage, the surfactant additive is present in the sweetener composition in an effective amount to provide a concentration of about 30 ppm to about 2,000 ppm, such as, for example, about 30 ppm to about 50 ppm, about 50 ppm to about 100 ppm, about 100 ppm to about 500 ppm, about 500 ppm to about 1,000 ppm, about 1,000 ppm to about 1,500 ppm, and about 1,500 ppm to about 2,000 ppm.

Suitable flavonoid additives are classified as flavonols, flavones, flavanones, flavan-3-ols, isoflavones or anthocyanidins. Non-limiting examples of flavonoid additives include, but are not limited to catechins (e.g., green tea extracts such as Polyphenon ^™ 60, Polyphenon ^™ 30 and Polyphenon ^™ 25 (Mitsui Norin Co., Ltd., Japan), polyphenols, rutin (e.g., enzyme-modified rutin Sanmelin ^™ AO (San-fi Gen FFI, Inc., Osaka, Japan)), neohesperidin, naringin, neohesperidin dihydrochalcone, etc.

When present in a sweetened consumable, such as, for example, a beverage, the flavonoid additive is present in the sweetener composition in an effective amount to provide a concentration of about 0.1 ppm to about 1,000 ppm, such as, for example, about 0.1 ppm to about 1 ppm, about 1 ppm to about 10 ppm, about 10 ppm to about 100 ppm, about 100 ppm to about 250 ppm, about 250 ppm to about 500 ppm, and about 500 ppm to about 1,000 ppm.

Suitable alcohol additives include, but are not limited to ethanol. In a particular embodiment, when present in a sweetened consumable such as, for example, an added beverage, the alcohol additive is present in the sweetener composition in an effective amount to provide a concentration of about 625 ppm to about 10,000 ppm, such as, for example, about 625 ppm to about 1,000 ppm, about 1,000 ppm to about 2,500 ppm, about 2,500 ppm to about 5,000 ppm, and about 5,000 ppm to about 10,000 ppm.

Suitable astringent compound additives include, but are not limited to, tannic acid, europium chloride (EuCl ₃ ), gadolinium chloride (GdCl ₃ ), terbium chloride (TbCl ₃ ), alum, tannic acid, and polyphenols (e.g., tea polyphenols). When present in a sweetened consumable such as, for example, a beverage, the astringent additive is present in the sweetener composition in an effective amount to provide a concentration of about 10 ppm to about 5,000 ppm, such as, for example, about 10 ppm to about 50 ppm, about 50 ppm to about 100 ppm, about 100 ppm to about 500 ppm, about 500 ppm to about 1,000 ppm, about 1,000 ppm to about 2,500 ppm, and about 2,500 ppm to about 5,000 ppm.

In a specific embodiment, the sweetener composition comprises Reb DEMNO; a polyol selected from erythritol, maltitol, mannitol, xylitol, sorbitol, and combinations thereof; and optionally at least one additional sweetener and/or functional ingredient. Reb DEMNO can be provided as a pure component or as part of a stevia extract or a steviol glycoside mixture, as described above. Reb DEMNO can be present in the steviol glycoside mixture or stevia extract in an amount of about 5% to about 99% by weight on a dry basis. In one embodiment, Reb DEMNO and the polyol are present in the sweetener composition in a weight ratio of about 1:1 to about 1:800, such as, for example, about 1:4 to about 1:800, about 1:20 to about 1:600, about 1:50 to about 1:300, or about 1:75 to about 1:150. In another embodiment, Reb DEMNO is present in the sweetener composition in an effective amount to provide a concentration from about 1 ppm to about 10,000 ppm, such as, for example, from about 1 ppm to about 5 ppm, from about 5 ppm to about 10 ppm, from about 10 ppm to about 50 ppm, from about 50 ppm to about 100 ppm, from about 100 ppm to about 500 ppm, from about 500 ppm to about 1,000 ppm, from about 1,000 ppm to about 5,000 ppm, and from about 5,000 ppm to about 10,000 ppm when present in a sweetened consumable. When present in a sweetened consumable, a polyol such as, for example, erythritol may be present in the sweetener composition in an effective amount to provide a concentration of about 100 ppm to about 250,000 ppm, such as, for example, about 100 ppm to about 1,000 ppm, about 1,000 ppm to about 10,000 ppm, about 10,000 ppm to 100,000 ppm, and about 100,000 ppm to about 250,000 ppm.

In a specific embodiment, the sweetener composition comprises Reb DEMNO; a carbohydrate sweetener selected from sucrose, fructose, glucose, maltose, and combinations thereof; and optionally at least one additional sweetener and/or functional ingredient. Reb DEMNO can be provided as a pure component or as part of a stevia extract or steviol glycoside mixture, as described above. Reb DEMNO can be present in a steviol glycoside mixture or a stevia extract in an amount of about 5% to about 99% by weight on a dry basis. In one embodiment, Reb DEMNO and the carbohydrate are present in the sweetener composition in a weight ratio of about 0.001:14 to about 1:0.01, such as, for example, about 0.001:14 to about 0.01:14, about 0.01:14 to about 0.1:14, about 0.1:14 to about 1:14, about 1:14 to about 1:10, about 1:10 to about 1:1, about 1:1 to about 1:0.1, and about 1:0.1 to about 1:0.01. In one embodiment, when present in a sweetened consumable, Reb DEMNO is present in the sweetener composition in an effective amount to provide a concentration of about 1 ppm to about 10,000 ppm, such as, for example, about 1 ppm to about 10 ppm, about 100 ppm to about 1000 ppm, about 100 ppm to about 1,000 ppm, and about 1,000 ppm to about 10,000 ppm. When present in a sweetened consumable, carbohydrates such as, for example, sucrose may be present in the sweetener composition in an effective amount to provide a concentration of about 100 ppm to about 140,000 ppm, such as, for example, about 100 ppm to about 1,000 ppm, about 1,000 ppm to about 10,000 ppm, about 10,000 ppm to about 100,000 ppm, and about 100,000 ppm to about 140,000 ppm.

In a specific embodiment, the sweetener composition comprises Reb DEMNO; an amino acid selected from glycine, alanine, proline, and combinations thereof; and optionally at least one additional sweetener and/or functional ingredient. Reb DEMNO can be provided as a pure component or as part of a stevia extract or a steviol glycoside mixture, as described above. Reb DEMNO can be present in a steviol glycoside mixture or a stevia extract in an amount of about 5% to about 99% by weight on a dry basis, such as, for example, about 5% to about 10%, about 10% to about 25%, about 25% to about 50%, about 50% to about 75%, and about 75% to about 99%. In another embodiment, when present in a sweetened consumable, Reb DEMNO is present in the sweetener composition in an effective amount to provide a concentration of about 1 ppm to about 10,000 ppm, such as, for example, about 1 ppm to about 10 ppm, about 10 ppm to about 100 ppm, about 100 ppm to about 1,000 ppm, and about 1,000 ppm to about 10,000 ppm. When present in a sweetened consumable, an amino acid such as, for example, glycine can be present in the sweetener composition in an effective amount to provide a concentration of about 10 ppm to about 50,000 ppm, such as, for example, about 10 ppm to about 100 ppm, about 100 ppm to about 1,000 ppm, about 1,000 ppm to about 10,000 ppm, and about 10,000 ppm to about 50,000 ppm.

In a specific embodiment, the sweetener composition comprises Reb DEMNO; a salt selected from sodium chloride, magnesium chloride, potassium chloride, calcium chloride, and combinations thereof; and optionally at least one additional sweetener and/or functional ingredient. Reb DEMNO can be provided as a pure component or as part of a stevia extract or steviol glycoside mixture as described above. Reb DEMNO can be present in the steviol glycoside mixture or stevia extract in an amount of about 5% to about 99% by weight on a dry basis. In one embodiment, Reb DEMNO is present in the sweetener composition in an effective amount to provide a concentration of about 1 ppm to about 10,000 ppm, such as, for example, about 1 ppm to about 10 ppm, about 10 ppm to about 100 ppm, about 100 ppm to about 1,000 ppm, and about 1,000 ppm to about 10,000 ppm. When present in a sweetened consumable, an inorganic salt such as, for example, magnesium chloride may be present in the sweetener composition in an effective amount to provide a concentration of about 25 ppm to about 25,000 ppm, such as, for example, about 25 ppm to 250 ppm, about 250 ppm to about 2,500 ppm, and about 2,500 ppm to about 25,000 ppm.

Functional Ingredients

The sweetener composition may also contain one or more functional ingredients that provide real or perceived health benefits to the composition. Functional ingredients include, but are not limited to, saponins, antioxidants, dietary fiber sources, fatty acids, vitamins, glucosamine, minerals, preservatives, hydration agents, probiotics, prebiotics, weight management agents, osteoporosis control agents, phytoestrogens, long chain primary aliphatic saturated alcohols, phytosterols, and combinations thereof.

Saponin

In some embodiments, the functional ingredient is at least one saponin. In one embodiment, the sweetener composition comprises at least one saponin, Reb DEMNO, and optionally at least one additive. In another embodiment, the sweetened consumable comprises a sweetenable composition, at least one saponin, Reb DEMNO, and optionally at least one additive. In still another embodiment, the sweetened consumable comprises a sweetenable composition and a sweetener composition, wherein the sweetener composition comprises at least one saponin, Reb DEMNO, and optionally at least one additive.

At least one saponin as used herein can comprise a single saponin or a plurality of saponins as the functional ingredient of the sweetener composition or the sweetened consumable provided herein. Typically, according to a specific embodiment of the present invention, at least one saponin is present in the sweetener composition or the sweetened consumable in an amount sufficient to promote health and wellness.

Saponins are glycoside natural plant products comprising an aglycone ring structure and one or more sugar moieties. The combination of the non-polar aglycone and the water-soluble sugar moieties gives saponins surface-active properties, which causes them to form foams when shaken in aqueous solutions.

Saponin is based on several common properties combined together. Especially, saponin is a surfactant that shows hemolytic activity and forms a complex with cholesterol. Although saponins share these properties, they are structurally diverse. The type of aglycon ring structure that forms a ring structure in saponin can be greatly changed. Non-limiting examples of the type of aglycon ring structure in the saponin used in a specific embodiment of the present invention include steroids, triterpenes and steroidal alkaloids. Non-limiting examples of the specific aglycon ring structure used in a specific embodiment of the present invention include soyasapogenin (soyasapogenol) A, soyasapogenin B and soyasapogenin E. The quantity and type of the sugar moiety connecting the aglycon ring structure can also be greatly changed. Non-limiting examples of the sugar moiety used in a specific embodiment of the present invention include glucose, galactose, glucuronic acid, xylose, rhamnose and methylpentose moieties. Non-limiting examples of the specific saponin used in a specific embodiment of the present invention include A group acetyl saponin, B group acetyl saponin and E group acetyl saponin.

Saponins are found in a wide variety of plants and plant products, and are particularly prevalent in plant skins and barks, where they form a waxy protective coating. Several common sources of saponins include soybeans, which have a saponin content of about 5% by dry weight; the soapwort plant (Saponaria), whose roots have been used historically as soap; and alfalfa, aloe, asparagus, grapes, chickpeas, yucca, and various other beans and weeds. Saponins can be obtained from these sources using extraction techniques well known to those of ordinary skill in the art. A description of conventional extraction techniques can be found in U.S. Patent Application No. 2005/0123662, the disclosure of which is expressly incorporated by reference.

Antioxidants

In some embodiments, the functional ingredient is at least one antioxidant. In one embodiment, the sweetener composition comprises at least one antioxidant, Reb DEMNO, and optionally at least one additive. In another embodiment, the sweetened consumable comprises a sweetenable composition, at least one antioxidant, Reb DEMNO, and optionally at least one additive. In still another embodiment, the sweetened consumable comprises a sweetenable composition and a sweetener composition, wherein the sweetener composition comprises at least one antioxidant, Reb DEMNO, and optionally at least one additive.

At least one antioxidant as used herein can include a single antioxidant or multiple antioxidants as the functional ingredients of the sweetener compositions or sweetened consumables provided herein. Typically, according to a specific embodiment of the present invention, at least one antioxidant is present in the sweetener compositions or sweetened consumables in an amount sufficient to promote health and wellness.

As used herein, "antioxidant" refers to any substance that inhibits, curbs, or reduces oxidative damage to cells and biomolecules. Without being bound by theory, it is believed that antioxidants inhibit, curb, or reduce oxidative damage to cells or biomolecules by stabilizing free radicals before they can cause harmful reactions. Thus, antioxidants can prevent or delay the onset of some degenerative diseases.

For embodiments of the present invention, examples of suitable antioxidants include, but are not limited to, vitamins, vitamin cofactors, minerals, hormones, carotenoids, carotenoid terpenoids, non-carotenoid terpenoids, flavonoids, flavonoid polyphenols (e.g., bioflavonoids), flavonols, flavones, phenols, polyphenols, esters of phenols, esters of polyphenols, non-flavonoid phenols, isothiocyanates, and combinations thereof. In certain embodiments, the antioxidant is vitamin A, vitamin C, vitamin E, ubiquinone, the mineral selenium, manganese, melatonin, alpha-carotene, beta-carotene, lycopene, lutein, zeanthin, crypoxanthin, resveratrol, eugenol, quercetin, catechins, gossypol, hesperidin, curcumin, ferulic acid, thymol, hydroxytyrosol, turmeric, thyme, olive oil, lipoic acid, glutathione, glutamine, oxalic acid, compounds derived from tocopherol, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), ethylenediaminetetraacetic acid (EDTA), tert-butylhydroquinone, ethyl acid, pectin, tocotrienols, tocopherol, coenzyme Q10, zeaxanthin, astaxanthin, canthaxanthin, saponins, limonoids, kaempfedrol, myricetin, isorhamnetin, proanthocyanidins, quercetin, rutin, luteolin, apigenin, citrus flavonoids, hesperidin, naringenin, eriodictyol, flavan-3-ols (e.g., anthocyanidins), catechin, epicatechin and its gallate forms, epigallocatechin and its gallate forms (ECGC) theaflavins and its gallate forms, thearubigins, isoflavone phytoestrogens, genistein, daidzein, glycitein, anthocyanidins, cyanidins, delphinidin, malvaceae , pelargonium pigment, peonidin, petunidin, ellagic acid, gallic acid, salicylic acid, rosmarinic acid, cinnamic acid and its derivatives (e.g., ferulic acid), chlorogenic acid, chicoric acid, gallotannin, ellagitannins, anthocyanins, beta-anthocyanidins and other plant pigments, silymarin, citric acid, lignans, antinutrients, bilirubin, uric acid, R-α-lipoic acid, N-acetylcysteine, emblicanin, apple extract, apple peel extract (apple polyphenols), rooibos extract red, rooibos extract green, hawthorn berry extract, red raspberry extract, green coffee antioxidant (GCA), aronia extract 20%, grape seed extract (VinOseed), cocoa extract, hops extract, mangosteen extract, mangosteen shell extract, cranberry extract, pomegranate extract, pomegranate shell extract, pomegranate seed extract, hawthorn berry extract, pomella pomegranate extract, cinnamon bark extract, grape skin extract, bilberry extract, pine bark extract, pycnogenol, elderberry extract, mulberry root extract, gogi extract, blackberry extract, blueberry extract, blueberry leaf extract, raspberry extract, turmeric extract, citrus bioflavonoids, black currant, ginger, acai powder, green coffee bean extract, green tea extract, and phytic acid, or a combination thereof. In an alternative embodiment, the antioxidant is a synthetic antioxidant, such as, for example, butylated hydroxytoluene or butylated hydroxyanisole. Other sources of antioxidants suitable for embodiments of the present invention include, but are not limited to, fruits, plants, tea, cocoa, chocolate, spices, grasses, rice, organ meats from livestock, yeast, whole grains or cereal grains.

Specific antioxidants belonging to the class of phytonutrients are known as polyphenols (also known as "polyphenols"), which are a group of chemicals found in plants characterized by the presence of more than one phenol group per molecule. Various health benefits can be derived from polyphenols, including, for example, prevention of cancer, heart disease, and chronic inflammatory diseases, and improved mental and physical strength. Suitable polyphenols for embodiments of the present invention include catechins, proanthocyanidins, proanthocyanidins, anthocyanidins, quercetin, rutin, resveratrol, isoflavones, curcumin, punicalagins, ellagitannins, hesperidin, naringin, citrus flavonoids, chlorogenic acid, other similar substances, and combinations thereof.

In a specific embodiment, the antioxidant is epigallocatechin gallate (EGCG). Suitable sources of catechins for embodiments of the present invention include, but are not limited to, green tea, white tea, black tea, oolong tea, chocolate, cocoa, red wine, grape seeds, red grape skins, purple grape skins, red grape juice, purple grape juice, berries, pycnogenol, and red apple peels.

In certain embodiments, the antioxidant is selected from proanthocyanidins, proanthocyanidins, or a combination thereof. Suitable sources of proanthocyanidins and proanthocyanidins for embodiments of the present invention include, but are not limited to, red grapes, purple grapes, cocoa, chocolate, grape seeds, red wine, cocoa beans, cranberries, apple peels, plums, blueberries, black currants, ash berries, green tea, sorghum, cinnamon, barley, red kidney beans, pinto beans, hops, almonds, hazelnuts, pecans, pistachios, pycnogenol, and colorful berries.

In a specific embodiment, the antioxidant is an anthocyanin. Suitable sources of anthocyanins for embodiments of the present invention include, but are not limited to, red berries, blueberries, bilberries, cranberries, raspberries, cherries, pomegranates, strawberries, elderberries, aronia berries, red grape skins, purple grape skins, grape seeds, red wine, black currants, red currants, cocoa, plums, apple skins, peaches, red pears, red cabbage, red onions, red oranges, and blackberries.

In certain embodiments, the antioxidant is selected from quercetin, rutin, or a combination thereof. Suitable sources of quercetin and rutin for embodiments of the present invention include, but are not limited to, red apples, onions, kale, bogwhortleberry, lingonberry, aronia, cranberry, blackberry, blueberry, strawberry, raspberry, blackcurrant, green tea, black tea, plums, apricots, parsley, leeks, broccoli, red peppers, berry wine, and ginkgo.

In certain embodiments, the antioxidant is resveratrol. Suitable sources of resveratrol for use in embodiments of the present invention include, but are not limited to, red grapes, peanuts, cranberries, blueberries, bilberries, mulberries, Japanese knotweed tea, and red wine.

In a specific embodiment, the antioxidant is an isoflavone. Suitable sources of isoflavones for use in embodiments of the present invention include, but are not limited to, soybeans, soy products, beans, alfalfa spouts, chickpeas, peanuts, and red clover.

In certain embodiments, the antioxidant is curcumin. Suitable sources of curcumin for use in embodiments of the present invention include, but are not limited to, turmeric and mustard.

In a specific embodiment, the antioxidant is selected from punicalagins, ellagitannins, or a combination thereof. Suitable sources of punicalagins and ellagitannins for use in embodiments of the present invention include, but are not limited to, pomegranates, raspberries, strawberries, walnuts, and oak-aged red wine.

In certain embodiments, the antioxidant is a citrus flavonoid, such as hesperidin or naringin. Suitable sources of citrus flavonoids (such as hesperidin or naringin) for use in embodiments of the present invention include, but are not limited to, oranges, grapefruits, and citrus juice.

In a specific embodiment, the antioxidant is chlorogenic acid. Suitable sources of chlorogenic acid for use in embodiments of the present invention include, but are not limited to, green coffee, yerba mate, red wine, grape seeds, red grape skins, purple grape skins, red grape juice, purple grape juice, apple juice, cranberries, pomegranates, blueberries, strawberries, sunflowers, echinacea, pycnogenol, and apple peels.

Dietary fiber

In some embodiments, the functional ingredient is at least one dietary fiber source. In one embodiment, the sweetener composition comprises at least one dietary fiber source, Reb DEMNO, and optionally at least one additive. In another embodiment, the sweetened consumable comprises a sweetenable composition, at least one dietary fiber source, Reb DEMNO, and optionally at least one additive. In still another embodiment, the sweetened consumable comprises a sweetenable composition and a sweetener composition, wherein the sweetener composition comprises at least one dietary fiber source, Reb DEMNO, and optionally at least one additive.

At least one dietary fiber source as used herein can comprise a single dietary fiber source or multiple dietary fiber sources as a functional ingredient for the sweetener compositions or sweetened consumables provided herein. Typically, according to a specific embodiment of the present invention, at least one dietary fiber source is present in the composition in an amount sufficient to promote health and wellness.

Polymeric carbohydrates having significantly different structures in many compositions and connections fall within the definition of dietary fiber. Such compounds are well known to those skilled in the art, and non-limiting examples thereof include non-starch polysaccharides, lignin, cellulose, methylcellulose, hemicellulose, beta-glucan, pectin, gums, mucus, waxes, inulin, oligosaccharides, fructooligosaccharides, cyclodextrins, chitin, and combinations thereof.

Polysaccharides are complex carbohydrates composed of monosaccharides linked by glycosidic bonds. Non-starch polysaccharides are bonded by β-bonds and cannot be digested by humans due to the lack of enzymes that break β-bonds. In contrast, digestible starch polysaccharides usually contain α(1-4) bonds.

Lignin is a large, highly branched and cross-linked polymer based on oxidized phenylpropane units. Cellulose is a linear polymer of glucose molecules bound by β (1-4) bonds, which cannot be hydrolyzed by mammalian amylases. Methylcellulose is a methyl ester of cellulose, which is commonly used in foods as a thickener and emulsifier. It is commercially available (e.g., Citrucel from GlaxoSmithKline, Celevac from Shire Pharmaceuticals). Hemicellulose is a highly branched polymer composed mainly of glucuronic acid- and 4-O-methylglucuronic acid xylans. β-Glucans are mixed-bond (1-3), (1-4) β-D-glucose polymers found primarily in cereals such as oats and barley. Pectins, such as β-pectin, are a group of polysaccharides composed primarily of D-galacturonic acid (which is methoxylated to varying degrees).

Gums and mucilages represent a wide range of different branched structures. Guar gum, derived from the endosperm of ground guar seeds, is a galactomannan. Guar gum is commercially available (e.g., Benefiber by Novartis AG). Other gums, such as gum arabic and pectin, have more different structures. Still other gums include xanthan gum, gellan gum, tara gum, psyllium seed husk gum, and locust bean gum.

Waxes are esters of ethylene glycol and two fatty acids and usually occur as hydrophobic liquids that are insoluble in water.

Inulin contains naturally occurring oligosaccharides belonging to a class of carbohydrates called fructans. They are usually composed of fructose monomers linked by β(2-1) glycosidic bonds with a terminal glucose monomer. Oligosaccharides are sugar polymers that usually contain three to six component sugars. They are usually found O- or N-linked to compatible amino acid side chains in proteins or lipid molecules. Fructo-oligosaccharides are oligosaccharides composed of short chains of fructose molecules.

Food sources of dietary fiber include, but are not limited to, grains, legumes, fruits, and vegetables. Grains that provide dietary fiber include, but are not limited to oats, rye, barley, and wheat. Legumes that provide fiber include, but are not limited to, peas and beans, such as soybeans. Fruits and vegetables that provide fiber sources include, but are not limited to apples, oranges, pears, bananas, berries, tomatoes, mung beans, broccoli, cauliflower, carrots, potatoes, and celery. Plant foods such as bran, nuts, and seeds (such as flax seeds) are also sources of dietary fiber. Parts of plants that provide dietary fiber include, but are not limited to stems, roots, leaves, seeds, pulp, and skin.

Although dietary fiber is usually derived from plant sources, indigestible animal products such as chitin can also be classified as dietary fiber. Chitin is a polysaccharide composed of acetylglucosamine monomers linked by β(1-4) bonds, similar to the bonds of cellulose.

Sources of dietary fiber are generally divided into soluble and insoluble fiber categories based on their solubility in water. Both soluble and insoluble fiber can be found in plant foods to varying degrees, depending on the characteristics of the plant. Although insoluble in water, insoluble fiber has passive hydrophilic properties, which helps to increase bulk, soften stool, and shorten the transit time of fecal solids through the intestines.

Unlike insoluble fiber, soluble fiber is easily soluble in water. Soluble fiber undergoes active metabolic processing by fermentation in the colon, increasing colonic flora and thus increasing the quality of excrement solids. End products with significant health benefits are also produced by colonic bacterial fermentation of fiber. For example, the fermentation of food substances produces gas and short-chain fatty acids. The acid produced during the fermentation process includes butyric acid, acetic acid, propionic acid and valeric acid, which have various beneficial properties, such as stabilizing blood sugar levels by acting on pancreatic insulin release, and providing liver control by glycogenolysis. In addition, fiber fermentation can reduce atherosclerosis by reducing cholesterol synthesis in the liver and reducing blood levels of LDL and triglycerides. The acid produced during the fermentation process reduces colon pH, thereby protecting the colon mucosa from cancer polyp formation. Lower colon pH also improves mineral absorption, improves the barrier properties of the colon mucosal layer, and inhibits inflammation and adhesion stimulation. The fermentation of fiber is also beneficial to the immune system by stimulating the formation of T-helper cells, antibodies, leukocytes, splenocytes, cytokines and lymphocytes.

fatty acid

In some embodiments, the functional ingredient is at least one fatty acid. In one embodiment, the sweetener composition comprises at least one fatty acid, Reb DEMNO, and optionally at least one additive. In another embodiment, the sweetened consumable comprises a sweetenable composition, at least one fatty acid, Reb DEMNO, and optionally at least one additive. In still another embodiment, the sweetened consumable comprises a sweetenable composition and a sweetener composition, wherein the sweetener composition comprises at least one fatty acid, Reb DEMNO, and optionally at least one additive.

At least one fatty acid as used herein can be a single fatty acid or multiple fatty acids, as a functional ingredient for the sweetener compositions or sweetened consumables provided herein. Typically, according to a specific embodiment of the present invention, at least one fatty acid is present in the sweetener compositions or sweetened consumables in an amount sufficient to promote health and wellness.

As used herein, " fatty acid " refers to any straight-chain monocarboxylic acid, and includes saturated fatty acids, unsaturated fatty acids, long-chain fatty acids, medium-chain fatty acids, short-chain fatty acids, fatty acid precursors (including ω-9 fatty acid precursors) and esterified fatty acids. As used herein, " long-chain polyunsaturated fatty acids " refers to any polyunsaturated carboxylic acid or organic acid with a long aliphatic tail. As used herein, " ω-3 fatty acids " refers to any polyunsaturated fatty acids with the first double bond as the third carbon-carbon bond from its carbon chain terminal methyl end. In a specific embodiment, ω-3 fatty acids can include long-chain ω-3 fatty acids. As used herein, " ω-6 fatty acids " refers to any polyunsaturated fatty acids with the first double bond as the sixth carbon-carbon bond from its carbon chain terminal methyl end.

Suitable ω-3 fatty acids for embodiments of the present invention can be derived from, for example, seaweed, fish, animals, plants, or a combination thereof. Examples of suitable ω-3 fatty acids include, but are not limited to, linolenic acid, α-linolenic acid, eicosapentaenoic acid, docosahexaenoic acid, octadecatetraenoic acid, eicosatetraenoic acid, and a combination thereof. In some embodiments, suitable ω-3 fatty acids can be provided in fish oil (for example, herring oil, tuna oil, salmon oil, bonito oil, and cod oil), microalgae ω-3 oil, or a combination thereof. In specific embodiments, suitable ω-3 fatty acids can be derived from commercially available ω-3 fatty acid oils, such as microalgae DHA oil (from Martek, Columbia, Md.), OmegaPure (from Omega Protein, Houston, Tex.), Marinol C-38 (from Lipid Nutrition, Channahon, Ill.), bonito oil and MEG-3 (from Ocean Nutrition, Dartmouth, NS), Evogel (from Symrise, Holzminden, Germany), marine oil from tuna or salmon (from Arista Wilton, CT), OmegaSource 2000, marine oil from herring, and marine oil from cod (from OmegaSource, RTP, NC).

Suitable omega-6 fatty acids include, but are not limited to, linoleic acid, gamma-linoleic acid, dihomo-gamma-linoleic acid, arachidonic acid, eicosadienoic acid, docosadienoic acid, adrenic acid, docosapentaenoic acid, and combinations thereof.

Suitable esterified fatty acids for use in embodiments of the present invention may include, but are not limited to, monoacylglycerols containing ω-3 and/or ω-6 fatty acids, diacylglycerols containing ω-3 and/or ω-6 fatty acids, or triacylglycerols containing ω-3 and/or ω-6 fatty acids, and combinations thereof.

Vitamins

In some embodiments, the functional ingredient is at least one vitamin. In one embodiment, the sweetener composition comprises at least one vitamin, Reb DEMNO, and optionally at least one additive. In another embodiment, the sweetened consumable comprises a sweetenable composition, at least one vitamin, Reb DEMNO, and optionally at least one additive. In still another embodiment, the sweetened consumable comprises a sweetenable composition and a sweetener composition, wherein the sweetener composition comprises at least one vitamin, Reb DEMNO, and optionally at least one additive.

As used herein, at least one vitamin can be a single vitamin or multiple vitamins as a functional ingredient for the compositions provided herein. Typically, according to a specific embodiment of the present invention, at least one vitamin is present in the sweetener composition or sweetened consumable in an amount sufficient to promote health and wellness.

Vitamin is an organic compound that human body needs for normal function in small amounts. The body utilizes vitamins without breaking them down, unlike other nutrients such as carbohydrates and proteins. So far, 13 kinds of vitamins have been identified, and one or more can be used in the functional sweeteners and sweetened consumer's products of this paper. Suitable vitamins include vitamin A, vitamin D, vitamin E, vitamin K, vitamin B1, vitamin B2, vitamin B3, vitamin B5, vitamin B6, vitamin B7, vitamin B9, vitamin B12 and vitamin C. Many vitamins also have alternative chemical names, and non-limiting examples thereof are provided below.

Various other compounds have been classified as vitamins by some agencies. These compounds may be referred to as pseudovitamins, and include, but are not limited to compounds such as ubiquinone (coenzyme Q10), pangamic acid, dimethylglycine, taestrile, amygdalin, flavonoids, p-aminobenzoic acid, adenine, adenylic acid, and s-methylmethionine. The term vitamin as used herein includes pseudovitamins.

In certain embodiments, the vitamin is a fat-soluble vitamin selected from vitamin A, D, E, K, and combinations thereof.

In other embodiments, the vitamin is a water-soluble vitamin selected from vitamin B1, vitamin B2, vitamin B3, vitamin B6, vitamin B12, folic acid, biotin, pantothenic acid, vitamin C, and combinations thereof.

Glucosamine

In some embodiments, the functional ingredient is glucosamine. In one embodiment, the sweetener composition comprises glucosamine, Reb DEMNO, and optionally at least one additive. In another embodiment, the sweetened consumable comprises a sweetenable composition, glucosamine, Reb DEMNO, and optionally at least one additive. In still another embodiment, the sweetened consumable comprises a sweetenable composition and a sweetener composition, wherein the sweetener composition comprises glucosamine, Reb DEMNO, and optionally at least one additive.

Generally, according to particular embodiments of this invention, glucosamine is present in the functional sweetener composition or sweetened consumable product in an amount sufficient to promote health and wellness.

Glucosamine, also known as chitosan, is an amino sugar that is considered an important precursor in the biochemical synthesis of glycosylated proteins and lipids. D-glucosamine occurs naturally in cartilage in the form of glucosamine-6-phosphate, which is synthesized from fructose-6-phosphate and glutamine. However, glucosamine may also be available in other forms, non-limiting examples of which include glucosamine hydrochloride, glucosamine sulfate, N-acetyl-glucosamine, or any other salt form or combination thereof. Glucosamine may be obtained by acid hydrolysis of the shells of lobsters, crabs, shrimps, or prawns using methods well known to those of ordinary skill in the art. In a specific embodiment, glucosamine may be derived from fungal biomass containing chitin, as described in U.S. Patent Application No. 2006/0172392.

The sweetener composition or sweetened consumable may further comprise chondroitin sulfate.

Minerals

In some embodiments, the functional ingredient is at least one mineral. In one embodiment, the sweetener composition comprises at least one mineral, Reb DEMNO, and optionally at least one additive. In another embodiment, the sweetened consumable comprises a sweetenable composition, at least one mineral, Reb DEMNO, and optionally at least one additive. In still another embodiment, the sweetened consumable comprises a sweetenable composition and a sweetener composition, wherein the sweetener composition comprises at least one mineral, Reb DEMNO, and optionally at least one additive.

As used herein, at least one mineral can be a single mineral or multiple minerals, as a functional ingredient for the sweetener compositions or sweetened consumables provided herein. Typically, according to a specific embodiment of the present invention, at least one mineral is present in the sweetener compositions or sweetened consumables in an amount sufficient to promote health and wellness.

According to the teaching of the present invention, mineral substances include inorganic chemical elements that living organisms need. Mineral substances are composed of a large amount of compositions (e.g., elements, simple salts and composite silicates), and the crystal structures are also widely different. They can be naturally present in food and beverages, can be added as supplements, or can be consumed or given separately from food or beverages.

Minerals can be classified as macrominerals (which are required in relatively large amounts) or trace minerals (which are required in relatively small amounts). Macrominerals are generally required in amounts greater than or equal to about 100 mg/day, while trace minerals are those required in amounts less than about 100 mg/day.

In a specific embodiment of the present invention, minerals are selected from macrominerals, trace minerals or combinations thereof. Non-limiting examples of macrominerals include calcium, chlorine, magnesium, phosphorus, potassium, sodium and sulfur. Non-limiting examples of trace minerals include chromium, cobalt, copper, fluorine, iron, manganese, molybdenum, selenium, zinc and iodine. Although iodine is usually classified as a trace mineral, its requirement is greater than other trace minerals and is often classified as a macromineral.

In other specific embodiments of the invention, the mineral is a trace mineral considered essential for human nutrition, non-limiting examples of which include bismuth, boron, lithium, nickel, rubidium, silicon, strontium, tellurium, tin, titanium, tungsten, and vanadium.

The minerals exemplified herein can be in any form known to those of ordinary skill in the art. For example, in a specific embodiment, the mineral can be in its ionic form, with a positive or negative charge. In another specific embodiment, the mineral can be in its molecular form. For example, sulfur and phosphorus often exist naturally as sulfates, sulfides, and phosphates.

preservative

In some embodiments, the functional ingredient is at least one preservative. In one embodiment, the sweetener composition comprises at least one preservative, Reb DEMNO, and optionally at least one additive. In another embodiment, the sweetened consumable comprises a sweetenable composition, at least one preservative, Reb DEMNO, and optionally at least one additive. In still another embodiment, the sweetened consumable comprises a sweetenable composition and a sweetener composition, wherein the sweetener composition comprises at least one preservative, Reb DEMNO, and optionally at least one additive.

As used herein, at least one preservative can be a single preservative or multiple preservatives, as a functional ingredient for the sweetener compositions or sweetened consumables provided herein. Typically, according to a specific embodiment of the invention, at least one preservative is present in the sweetener compositions or sweetened consumables in an amount sufficient to promote health and wellness.

In a specific embodiment of the present invention, the preservative is selected from an antimicrobial, an antioxidant, an antienzyme or a combination thereof. Non-limiting examples of antimicrobials include sulfites, propionates, benzoates, sorbates, nitrates, nitrites, bacteriocins, salts, sugars, acetic acid, dimethyl dicarbonate (DMDC), ethanol and ozone.

According to a specific embodiment, the preservative is a sulfite. Sulfites include, but are not limited to, sulfur dioxide, sodium bisulfate, and potassium bisulfite.

According to another specific embodiment, the preservative is a propionate. Propionates include, but are not limited to, propionic acid, calcium propionate, and sodium propionate.

According to yet another specific embodiment, the preservative is a benzoate. Benzoates include, but are not limited to, sodium benzoate and benzoic acid.

In another specific embodiment, the preservative is a sorbate. Sorbic acid esters include, but are not limited to, potassium sorbate, sodium sorbate, calcium sorbate and sorbic acid.

In yet another specific embodiment, the preservative is a nitrate and/or a nitrite. Nitrates and nitrites include, but are not limited to, sodium nitrate and sodium nitrite.

In yet another specific embodiment, at least one preservative is a bacteriocin, such as, for example, nisin.

In another specific embodiment, the preservative is ethanol.

In yet another specific embodiment, the preservative is ozone.

Non-limiting examples of anti-enzyme agents suitable for use as preservatives in particular embodiments of the present invention include ascorbic acid, citric acid, and metal chelators, such as ethylenediaminetetraacetic acid (EDTA).

Hydration reagents

In some embodiments, the functional ingredient is at least one hydrating agent. In one embodiment, the sweetener composition comprises at least one hydrating agent, Reb DEMNO, and optionally at least one additive. In another embodiment, the sweetened consumable comprises a sweetenable composition, at least one hydrating agent, Reb DEMNO, and optionally at least one additive. In still another embodiment, the sweetened consumable comprises a sweetenable composition and a sweetener composition, wherein the sweetener composition comprises at least one hydrating agent, Reb DEMNO, and optionally at least one additive.

As used herein, at least one hydrating agent can be a single hydrating agent or multiple hydrating agents, as a functional ingredient for the sweetener composition or the sweetened consumer's products provided herein. Typically, according to a specific embodiment of the present invention, at least one hydrating agent is present in the sweetener composition or the sweetened consumer's products in an amount sufficient to promote health and wellness.

Hydration products help the body replace fluids lost through excretion. For example, to regulate body temperature, fluids are lost as sweat, to excrete waste, as urine, and to exchange gases in the lungs, as water vapor. Fluid loss can also occur due to a large number of external causes, non-limiting examples include physical activity, exposure to dry air, diarrhea, vomiting, high temperature, shock, blood loss and hypotension. Diseases that cause fluid loss include diabetes, cholera, gastroenteritis, shigellosis and yellow fever. Forms of malnutrition that cause fluid loss include excessive drinking, electrolyte imbalance, fasting and rapid weight loss.

In a specific embodiment, the hydration product is a composition that helps the body replace the fluid lost during exercise. Therefore, in a specific embodiment, the hydration product is an electrolyte, and non-limiting examples include sodium, potassium, calcium, magnesium, chloride, phosphate, bicarbonate, and combinations thereof. Suitable electrolytes for use in specific embodiments of the present invention are also described in U.S. Patent No. 5,681,569, and its disclosure is explicitly incorporated herein by reference. In a specific embodiment, the electrolyte is obtained by its corresponding water-soluble salt. Non-limiting examples of salts used in specific embodiments include chlorides, carbonates, sulfates, acetates, bicarbonates, citrates, phosphates, hydrogen phosphates, tartrates, sorbates, citrates, benzoates, or combinations thereof. In other embodiments, electrolytes are provided by juice, fruit extracts, vegetable extracts, teas or tea extracts.

In a specific embodiment of the present invention, the hydration product is a carbohydrate for replenishing the energy storage of muscle burning. Suitable carbohydrates for use in a specific embodiment of the present invention are described in U.S. Patent numbers 4,312,856, 4,853,237, 5,681,569 and 6,989,171, and their disclosure is explicitly incorporated herein by reference. The limiting examples of suitable carbohydrates include monosaccharides, disaccharides, oligosaccharides, complex polysaccharides or their combinations. The limiting examples of monosaccharides for use in a specific embodiment include trisaccharides, tetrasaccharides, pentoses, hexoses, heptoses, octose and nonoses. The limiting examples of suitable monosaccharides of specific types include glyceraldehyde, dihydroxyacetone, erythrose, threose, erythrulose, arabinose, lyxose, ribose, xylose, ribulose, xylulose, allose, altrose, galactose, glucose, gulose, idose, mannose, talose, fructose, psicose, sorbose, tagatose, mannoheptulose, sedoheptose, octolose and sialic sugar. The limiting examples of suitable disaccharides include sucrose, lactose and maltose. The limiting examples of suitable oligosaccharides include sucrose, maltotriose and maltodextrin. In other specific embodiments, carbohydrates are provided by corn syrup, beet sugar, cane sugar, juice or tea.

In another specific embodiment, the hydration product is a flavanol that provides cell rehydration. Flavanols are a class of natural substances present in plants, and generally comprise a 2-phenylbenzopyrone molecular skeleton connected to one or more chemical moieties. Non-limiting examples of suitable flavanols for use in specific embodiments of the present invention include catechins, epicatechin, catechin gallate, epigallocatechin, epicatechin gallate, epigallocatechin 3-gallate, theaflavins, theaflavins-3-gallate, theaflavins 3'-gallate, theaflavins 3,3'-gallate, thearubigins or a combination thereof. Several common sources of flavanols include tea plants, fruits, vegetables and flowers. In a preferred embodiment, flavanols are extracted from green tea.

In a specific embodiment, the hydration product is a glycerol solution to enhance exercise endurance. Ingestion of glycerol-containing solutions has been shown to provide beneficial physiological effects, such as expanded blood volume, lower heart rate, and lower rectal temperature.

Probiotics/Prebiotics

In some embodiments, the functional ingredient is selected from at least one probiotic, prebiotic, and combinations thereof. In one embodiment, the sweetener composition comprises at least one probiotic, prebiotic, and combinations thereof; Reb DEMNO; and optionally at least one additive. In another embodiment; the sweetened consumable comprises a sweetenable composition, at least one probiotic, prebiotic, and combinations thereof; Reb DEMNO; and optionally at least one additive. In yet another embodiment, the sweetened consumable comprises a sweetenable composition and a sweetener composition, wherein the sweetener composition comprises at least one probiotic, prebiotic, and combinations thereof; Reb DEMNO; and optionally at least one additive.

At least one probiotic or prebiotic as used herein can be a single probiotic or prebiotic or a plurality of probiotics or prebiotics as a functional ingredient for the sweetener composition or sweetened consumable provided herein. Typically, according to a particular embodiment of the invention, at least one probiotic, prebiotic or combination thereof is present in the composition in an amount sufficient to promote health and wellness.

According to the teachings of the present invention, probiotics include microorganisms that are beneficial to health when consumed in effective amounts. Ideally, probiotics beneficially affect the gastrointestinal microflora naturally occurring in the human body and give other health benefits in addition to nutrients. Probiotics can include, but are not limited to, bacteria, yeasts, and fungi.

According to the teachings of the present invention, probiotics are beneficial microorganisms that favorably affect the gastrointestinal microflora naturally present in the human body and impart other health benefits in addition to nutrition. Examples of probiotics may include, but are not limited to, Lactobacilli, Bifidobacteria, Streptococci bacteria or combinations thereof, which impart beneficial effects to humans.

In a particular embodiment of the present invention, at least one probiotic is selected from the genus Lactobacillus. Lactobacillus (i.e., bacteria of the genus Lactobacillus, hereinafter referred to as "L.") has been used as a food preservative and for promoting human health for hundreds of years. Non-limiting examples of Lactobacillus species found in the human intestinal tract include Lactobacillus acidophilus, Lactobacillus casei, Lactobacillus fermentum, Lactobacillus saliva roes, Lactobacillus brevis, Lactobacillus leichmannii, Lactobacillus plantarum, Lactobacillus cellobiosus, Lactobacillus reuteri, Lactobacillus rhamnosus, L.GG, Lactobacillus bulgaricus and Lactobacillus thermophilus.

According to other specific embodiments of the present invention, the probiotic is selected from the genus Bifidobacteria. Bifidobacteria are also known to exert beneficial effects on human health by producing short-chain fatty acids (e.g., acetic acid, propionic acid and butyric acid), lactic acid and formic acid as a result of carbohydrate metabolism. Non-limiting species of Bifidobacterium found in the gastrointestinal tract include B. angulata, B. animalis, B. asteroides, B. bifidum, B. bourn, B. breve, B. catenulatum, B. choerinum, B. coryneforme, B. cuniculi, B. dentium, B. gallicum, B. gallinarum, B. indicum, B. longum, B. magnum, B. rumen, B. stoloniferum ... Bifidobacterium (B. merycicum), Bifidobacterium minimum (B. minimum), Bifidobacterium pseudocatenulatum (B. pseudolongum), Bifidobacterium psychraerophilum (B. psychraerophilum), Bifidobacterium pullorum (B. pullorum), Bifidobacterium ruminantium (B. ruminantium), Bifidobacterium saeculare (B. scardovii), Bifidobacterium simiae (B. simiae), Bifidobacterium subtile (B. subtile), Bifidobacterium thermoacidophilum (B. thermophilum), Bifidobacterium urinalis (B. urinalis) and Bifidobacterium sp.

According to other specific embodiments of the present invention, probiotics are selected from Streptococcus. Streptococcus thermophilus is a Gram-positive facultative anaerobic organism. It is classified as lactic acid bacteria, and is generally found in milk and dairy products, and is used for the production of yogurt. Other non-restrictive probiotic species of this bacterium include Streptococcus salivarus and Streptococcus cremoris.

Probiotics used in accordance with the present invention are well known to those skilled in the art. Non-limiting examples of foods containing probiotics include yogurt, sauerkraut, kefir, kimchi, fermented vegetables, and other foods containing microbial elements that beneficially affect the host animal by improving intestinal microbiota balance.

According to the teaching of the present invention, prebiotics include compositions for promoting the growth of beneficial bacteria in the intestine. Prebiotic substances can be consumed by relevant probiotics, or otherwise assist in keeping relevant probiotics alive or stimulating their growth. When consumed in effective amounts, prebiotics also beneficially affect the naturally occurring gastrointestinal microflora of human body, and thus give only the health benefits except nutrition. Prebiotic foods enter the colon and as substrates for endogenous bacteria, thus indirectly providing host energy, metabolic substrates and essential micronutrients. The digestion and absorption of the body of prebiotic foods depend on bacterial metabolic activity, which saves the energy of the nutrition that escapes digestion and absorption in the small intestine for the host.

According to an embodiment of the present invention, prebiotics include, but are not limited to, mucopolysaccharides, oligosaccharides, polysaccharides, amino acids, vitamins, nutrient precursors, proteins, and combinations thereof.

According to a specific embodiment of the present invention, prebiotics are selected from dietary fibers, including, but not limited to polysaccharides and oligosaccharides. These compounds have the ability to increase the number of probiotics, which results in the benefits conferred by probiotics. Non-limiting examples of oligosaccharides classified as prebiotics according to a specific embodiment of the present invention include fructooligosaccharides, inulin, isomaltooligosaccharides, lactitol, lactosucrose (lactosucrose), lactulose, pyrodextrin, soybean oligosaccharides, transgalacto-oligosaccharides and xylo-oligosaccharides.

According to other specific embodiments of the present invention, the prebiotic is an amino acid. Although various known prebiotics break down to provide carbohydrates for probiotics, some probiotics also require amino acids for nutrition.

Prebiotics occur naturally in a variety of foods including, but not limited to, bananas, berries, asparagus, garlic, wheat, oats, barley (and other whole grains), flaxseed, tomatoes, Jerusalem artichokes, onions and chicory, leafy greens (e.g., dandelion greens, spinach, collard greens, beets, kale, mustard greens, turnip greens), and legumes (e.g., lentils, kidney beans, chickpeas, navy beans, white beans, black beans).

Weight control agent

In some embodiments, the functional ingredient is at least one weight control. In one embodiment, the sweetener composition comprises at least one weight control agent, Reb DEMNO, and optionally at least one additive. In another embodiment, the sweetened consumer product comprises a sweetenable composition, at least one weight control agent, Reb DEMNO, and optionally at least one additive. In still another embodiment, the sweetened consumer product comprises a sweetenable composition and a sweetener composition, wherein the sweetener composition comprises at least one weight control agent, Reb DEMNO, and optionally at least one additive.

At least one weight control agent as used herein can be a single weight control agent or a plurality of weight control agents, as a functional ingredient for the sweetener composition or sweetened consumables provided herein. Typically, according to a specific embodiment of the present invention, at least one weight control agent is present in the sweetener composition or sweetened consumables in an amount sufficient to promote health and wellness.

As used herein, "weight control agents" include appetite suppressants and/or thermogenic agents. As used herein, the phrases "appetite suppressants," "appetite satiety compositions," "satiants," and "satiating ingredients" are synonymous. The phrase "appetite suppressants" describes macronutrients, herbal extracts, exogenous hormones, anorexiants, anorectics, drugs, and combinations thereof that curb, inhibit, reduce, or otherwise curtail a person's appetite when delivered in effective amounts. The phrase "pyrogenic agents" describes macronutrients, herbal extracts, exogenous hormones, anorexiants, anorectics, drugs, and combinations thereof that activate or otherwise enhance a person's thermogenesis or metabolism when delivered in effective amounts.

Suitable weight management agents include macronutrients selected from protein, carbohydrates, dietary fats, and combinations thereof. The consumption of protein, carbohydrates, and dietary fats stimulates the release of peptides that have an appetite-suppressing effect. For example, the consumption of protein and dietary fats stimulates the release of the intestinal hormone cholecystokinin (CCK), while the consumption of carbohydrates and dietary fats stimulates the release of glucagon-like peptide 1 (GLP-1).

Suitable macronutrient weight control agents also include carbohydrates. Carbohydrates generally include sugars, starches, cellulose and gums, which the body converts into glucose for energy. Carbohydrates are often classified into two categories, digestible carbohydrates (e.g., monosaccharides, disaccharides and starch) and indigestible carbohydrates (e.g., dietary fiber). Studies have shown that indigestible carbohydrates and complex polymeric carbohydrates with reduced absorption and digestibility in the small intestine stimulate physiological responses that inhibit food intake. Therefore, the carbohydrates exemplified herein ideally include indigestible carbohydrates or carbohydrates with reduced digestibility. Non-limiting examples of such carbohydrates include polydextrose; inulin; monosaccharide-derived polyols, such as erythritol, mannitol, xylitol and sorbitol; disaccharide-derived alcohols, such as isomalt, lactitol and maltitol; and hydrogenated starch hydrolysates. Carbohydrates will be described in more detail below.

In another specific embodiment, the weight control agent is dietary fat.Dietary fat is the lipid of the composition including saturated and unsaturated fatty acids.Polyunsaturated fatty acids have shown greater satiety (satiating) ability than monounsaturated fatty acids.Therefore, the dietary fatty acids exemplified herein ideally include polyunsaturated fatty acids, and its non-limiting examples include triglycerides.

In a specific embodiment, the weight control agent is an herbal extract. Extracts from various types of plants have been identified as having appetite suppressant properties. Non-limiting examples of plants whose extracts have appetite suppressant properties include Hoodia, Trichocaulon, Caralluma, Stapelia, Orbea, Asclepias, and Camellia. Other embodiments include extracts derived from Gymnema Sylvestre, Kola Nut, Citrus Aurantium, Yerba Mate, Griffonia Simplicifolia, Guarana, Myrrh, Guggul Lipid, and Blackcurrant Seed Oil.

The herbal extracts can be prepared from any type of plant material or plant biomass. Non-limiting examples of plant materials and biomass include stems, roots, leaves, dry powders obtained from plant materials, and sap or dried sap. The herbal extracts are typically prepared by extracting juice from the plant and then drying the juice. Alternatively, solvent extraction methods can be used. After the initial extraction, it is desirable to further fractionate the initial extract (e.g., by column chromatography) to obtain an herbal extract with enhanced activity. Such techniques are well known to those of ordinary skill in the art.

In a specific embodiment, the herbal extract is derived from the genus Hoodia, whose species include H.alstonii, H.currorii, H.dregei, H.flava, H.gordonii, H.jutatae, H.mossamedensis, H.officinalis, H.parviflorai, H.pedicellata, H.pilifera, H.ruschii, and H.triebneri. Hoodia plants are stem succulent plants that grow naturally in southern Africa. A sterol glycoside of Hoodia, known as P57, is believed to be responsible for the appetite-suppressing effects of Hoodia species.

In another embodiment, the herbal extract is derived from plants of the genus Buffalo, species of which include C. indica, C. fimbriata, C. attenuate, C. tuberculata, C. edulis, C. adscendens, C. stalagmifera, C. umbellate, C. penicillata, C. russeliana, C. retrospicens, C. Arabica, and C. lasiantha. Plants of the genus Buffalo belong to the same subfamily as the genus Hoodia, Asclepiadaceae. Caratuberside A is a small, erect and fleshy plant native to India, which has medicinal properties such as appetite suppressant, generally attributed to glycosides belonging to the pregnane group of the glycoside, non-limiting examples of which include caratuberside A, caratuberside B, bouceroside I, bouceroside II, bouceroside III, bouceroside IV, bouceroside V, bouceroside VI, bouceroside VII, bouceroside VIII, bouceroside IX and bouceroside X.

In another specific embodiment, at least one of the herbal extracts is derived from a plant of the genus T. Thunbergia. T. Thunbergia is a succulent plant native to southern Africa, similar to the genus T. Piliferum and T. Officinale.

In another specific embodiment, the herbal extract is derived from plants of the genus Stapelia or Obea, species of which include S. gigantean and O. variegate, respectively. Stapelia and Hoodia plants belong to the same subfamily, Asclepiadaceae, as Hoodia. Without wishing to be bound by any theory, it is believed that the compound that exhibits appetite suppressant activity is a saponin, such as pregnane glycosides, including S. variegate A, B, C, D, E, F, G, H, I, J, and K.

In another specific embodiment, the herbal extract is derived from a plant of the genus Asclepiadaceae. The genus Asclepiadaceae also belongs to the Asclepiadaceae family of plants. Non-limiting examples of the genus Asclepiadaceae include A. incarnate, A. curassayica, A. syriaca, and A. tuberose. Without wishing to be bound by any theory, it is believed that the extract contains steroidal compounds such as pregnane glycosides and pregnane aglycones that have an appetite suppressant effect.

In a specific embodiment, the weight control agent is an exogenous hormone with a weight control effect. Non-limiting examples of such hormones include CCK, peptide YY, ghrelin, bombesin and gastrin-releasing peptide (GRP), enterostatin, apolipoprotein A-IV, GLP-1, amylin, somastatin and leptin.

In another embodiment, the weight management agent is a drug. Non-limiting examples include phentenime, diethylpropion, phendimetrazine, sibutramine, rimonabant, oxyntomodulin, fluoxetine hydrochloride, ephedrine, phenylethylamine and other stimulants.

At least one weight control agent can be used alone or in combination as a functional ingredient of the sweetener composition provided by the present invention.

Osteoporosis control agents

In some embodiments, the functional ingredient is at least one osteoporosis controller. In one embodiment, the sweetener composition comprises at least one osteoporosis controller, Reb DEMNO, and optionally at least one additive. In another embodiment, the sweetened consumable comprises a sweetenable composition, at least one osteoporosis controller, Reb DEMNO, and optionally at least one additive. In still another embodiment, the sweetened consumable comprises a sweetenable composition and a sweetener composition, wherein the sweetener composition comprises at least one osteoporosis controller, Reb DEMNO, and optionally at least one additive.

At least one osteoporosis control agent as used herein can be a single osteoporosis control agent or a plurality of osteoporosis control agents as a functional ingredient for a sweetener composition or a sweetened consumable provided herein. Typically, according to a specific embodiment of the present invention, at least one osteoporosis control agent is present in a sweetener composition or a sweetened consumable in an amount sufficient to promote health and wellness.

Osteoporosis is a skeletal disease in which bone strength is impaired, leading to an increased risk of fractures. In general, osteoporosis is characterized by decreased bone mineral density (BMD), disruption of bone microarchitecture, and changes in the amount and type of non-collagenous proteins in bone.

In some embodiments, the osteoporosis control agent is at least one calcium source. According to a specific embodiment, the calcium source is any calcium-containing compound, including salt complexes, dissolved substances and other forms of calcium. Non-limiting examples of calcium sources include amino acid chelated calcium, calcium carbonate, calcium oxide, calcium hydroxide, calcium sulfate, calcium chloride, calcium phosphate, calcium hydrogen phosphate, calcium dihydrogen phosphate, calcium citrate, calcium malate, calcium citrate malate, calcium gluconate, calcium tartrate, calcium lactate, dissolved substances thereof, and combinations thereof.

According to a specific embodiment, the osteoporosis control agent is a magnesium source. The magnesium source can be any magnesium-containing compound, including salt complexes, dissolved substances and other forms of magnesium. Non-limiting examples of magnesium sources include magnesium chloride, magnesium citrate, magnesium glucoheptonic acid, magnesium gluconate, magnesium lactate, magnesium hydroxide, magnesium picolinate, magnesium sulfate, dissolved substances thereof, and mixtures thereof. In another specific embodiment, the magnesium source includes amino acid chelated or creatine chelated magnesium.

In other embodiments, the osteoporosis agent is selected from vitamin D, C, K, precursors thereof and/or beta-carotene, and combinations thereof.

Various plants and plant extracts are also identified as being effective in the prevention or treatment of osteoporosis. Without wishing to be bound by any theory, it is believed that plants and plant extracts stimulate bone morphogenetic protein and/or inhibit bone resorption, thereby stimulating bone regeneration and strength. Non-limiting examples of suitable plants and plant extracts as osteoporosis control agents include species of Taraxacum and Amelanchier, as disclosed in U.S. Patent Publication No. 2005/0106215, and Lindera, Artemisia, Acorus, Carthamus, Carum, Cnidium, Curcuma, Cyperus, Juniperus, Prunus, Iris, Chicory, Cichorium, Dodonaea, Epimedium, Erigonoum, Soya, Mentha, Ocimum, Thymus, Tanacetum, Plantago, Spearmint, Bixa, Vitis, Rosemarinus, Rhus, and Anethum, as disclosed in U.S. Patent Publication No. 2005/0079232.

Phytoestrogens

In some embodiments, the functional ingredient is at least one phytoestrogen. In one embodiment, the sweetener composition comprises at least one phytoestrogen, Reb DEMNO, and optionally at least one additive. In another embodiment, the sweetened consumable comprises a sweetenable composition, at least one phytoestrogen, Reb DEMNO, and optionally at least one additive. In still another embodiment, the sweetened consumable comprises a sweetenable composition and a sweetener composition, wherein the sweetener composition comprises at least one phytoestrogen, Reb DEMNO, and optionally at least one additive.

At least one phytoestrogen as used herein can be a single phytoestrogen or a plurality of phytoestrogens, as a functional ingredient for the sweetener compositions or sweetened consumables provided herein. Typically, according to a specific embodiment of the present invention, at least one phytoestrogen is present in the sweetener compositions or sweetened consumables in an amount sufficient to promote health and wellness.

Phytoestrogens are found in plants and can be delivered to the human body by ingesting plants or plant parts that have phytoestrogens. As used herein, "phytoestrogens" refer to any substance that causes any degree of estrogen-like effects when introduced into the body. For example, phytoestrogens can bind to estrogen receptors in the body and have little estrogen-like effects.

Examples of suitable phytoestrogens for embodiments of the present invention include, but are not limited to, isoflavones, stilbenes, lignans, dihydroxybenzoic acid lactones, coumestans, pseudoestrol, equol, and combinations thereof. Suitable sources of phytoestrogens include, but are not limited to, whole grains, cereals, fibers, fruits, vegetables, black cohosh, agave root, black currant, black hawthorn, chasteberry, cramp bark, angelica root, Aralia thorny root, Lilium root, Ginseng root, Senecio, licorice, living root, motherwort, peony root, raspberry leaf, rose family plant, sage leaf, Sarsaparilla root, saw palmetto berry, wild yam root, yarrow flower, beans, soy, soy products (e.g., miso, soy flour, soy milk, soy kernels, soy protein isolate, malay soy ferment) and soy milk. tempen or tofu), chickpeas, nuts, lentils, seeds, clover, red clover, dandelion leaves, dandelion roots, fenugreek seeds, green tea, hops, red wine, flaxseed, garlic, onions, linseed, borage, butterfly weed, coriander, wattle, vitex, dates, fennel, fennel seeds, gotu kola, milk thistle, pennyroyal, pomegranate, wormwood, soy flour, tansy and kudzu (pueraria) root, etc., and combinations thereof.

Isoflavones belong to a group of phytonutrients called polyphenols. In general, polyphenols (also called "polyphenolics"), are a group of chemicals found in plants characterized by the presence of more than one phenolic group per molecule.

Suitable phytoestrogen isoflavones according to embodiments of the present invention include genistein, daidzein, glycitein, biochanin A, formononetin, their respective naturally occurring glycosides and glycoside conjugates, matairesinol, secoisolariciresinol, enterolactone, enterodiol, texturized vegetable protein, and combinations thereof.

Suitable sources of isoflavones for use in embodiments of the present invention include, but are not limited to, soybeans, soy products, beans, alfalfa sprouts, chickpeas, peanuts, and red clover.

Long chain primary aliphatic saturated alcohol

In some embodiments, the functional ingredient is at least one long-chain primary aliphatic saturated alcohol. In one embodiment, the sweetener composition comprises at least one long-chain primary aliphatic saturated alcohol, Reb DEMNO, and optionally at least one additive. In another embodiment, the sweetened consumable comprises a sweetenable composition, at least one long-chain primary aliphatic saturated alcohol, Reb DEMNO, and optionally at least one additive. In still another embodiment, the sweetened consumable comprises a sweetenable composition and a sweetener composition, wherein the sweetener composition comprises at least one long-chain primary aliphatic saturated alcohol, Reb DEMNO, and optionally at least one additive.

As used herein, at least one long-chain primary aliphatic saturated alcohol can be a single long-chain primary aliphatic saturated alcohol or a plurality of long-chain primary aliphatic saturated alcohols as a functional ingredient for the sweetener composition or sweetened consumables provided herein. Typically, according to a specific embodiment of the present invention, at least one long-chain primary aliphatic saturated alcohol is present in the sweetener composition or sweetened consumables in an amount sufficient to promote health and wellness.

Long chain primary aliphatic saturated alcohols are a diverse group of organic compounds. The term alcohol refers to compounds characterized by a hydroxyl group (-OH) bonded to a carbon atom. The term primary refers to compounds characterized by the carbon atom to which the hydroxyl group is bonded to only one other carbon atom. The term saturated refers to compounds characterized by the absence of carbon-carbon pi bonds. The term aliphatic refers to compounds characterized by the carbon atoms being linked together in straight or branched chains rather than in rings. The term long chain refers to compounds characterized by at least 8 carbons.

Non-limiting examples of specific long chain primary aliphatic saturated alcohols for use in particular embodiments of the present invention include 8 carbon atom 1-octanol, 9 carbon 1-nonanol, 10 carbon atom 1-decanol, 12 carbon atom 1-dodecanol, 14 carbon atom 1-tetradecanol, 16 carbon atom 1-hexadecanol, 18 carbon atom 1-octadecanol, 20 carbon atom 1-eicosanol, 22 carbon 1-docosanol, 24 carbon 1-tetracosanol, 26 carbon 1-hexacosanol, 27 carbon 1-heptacosanol, 28 carbon 1-octacosanol, 29 carbon 1-nonacosanol, 30 carbon 1-triacontanol, 32 carbon 1-dotriacontanol, and 34 carbon 1-tetracosanol.

In one particularly desirable embodiment of the present invention, the long chain primary aliphatic saturated alcohol is policosanol. Policosanol is a term used for a mixture of long chain primary aliphatic saturated alcohols consisting primarily of 28 carbon 1-octacosanol and 30 carbon 1-triacontanol, as well as other alcohols in lower concentrations, such as 22 carbon 1-docosahexadecanoic acid, 24 carbon 1-tetradecanoic acid, 26 carbon 1-hexadecanoic acid, 27 carbon 1-heptadecanoic acid, 29 carbon 1-nonaconic acid, 32 carbon 1-dodecanoic acid, and 34 carbon 1-tetradecanoic acid.

Long chain primary aliphatic saturated alcohols are derived from natural fats and oils. They can be obtained from these sources by using extraction techniques well known to those of ordinary skill in the art. Policosanol can be isolated from various plants and materials, including sugar cane (Saccharum officinarium), yams (e.g., Dioscorea opposite), bran from rice (e.g., Oryza sativa), and beeswax. Policosanol can be obtained from these sources by using extraction techniques well known to those of ordinary skill in the art. A description of such extraction techniques can be found in U.S. Patent Application No. 2005/0220868, the disclosure of which is expressly incorporated by reference.

Phytosterols

In some embodiments, the functional ingredient is at least one phytosterol, phytostanol, or a combination thereof. In one embodiment, the sweetener composition comprises at least one phytosterol, phytostanol, or a combination thereof; Reb DEMNO; and optionally at least one additive. In another embodiment, the sweetened consumable comprises a sweetenable composition, at least one phytosterol, phytostanol, or a combination thereof; Reb DEMNO; and optionally at least one additive. In still another embodiment, the sweetened consumable comprises a sweetenable composition and a sweetener composition, wherein the sweetener composition comprises at least one phytosterol, phytostanol, or a combination thereof; Reb DEMNO; and optionally at least one additive.

Generally, according to particular embodiments of this invention, at least one phytosterol, phytostanol, or combination thereof is present in the sweetener composition or sweetened consumable in an amount sufficient to promote health and wellness.

As used herein, the phrases "stanol," "plant stanol," and "phytostanol" are synonymous.

Plant sterols and stanols are naturally present in small amounts in many fruits, vegetables, nuts, seeds, cereals, beans, vegetable oils, bark and other plant sources. Although people normally consume plant sterols and stanols every day, the amount consumed is not enough to have a significant cholesterol-lowering effect or other health benefits. Therefore, it is desirable to supplement health foods and beverages with plant sterols and stanols.

Stanols are a subgroup of steroids with a hydroxyl group at C-3. Typically, phytosterols have a double bond within the steroid nucleus, such as cholesterol; however, phytosterols may also contain substituted side chains (R) at C-24, such as ethyl or methyl, or additional double bonds. The structure of phytosterols is well known to those skilled in the art.

At least 44 naturally occurring phytosterols have been found, and are generally derived from plants such as corn, soybeans, wheat and wood oils; however, they can also be produced synthetically to form compositions identical to those in nature or having properties similar to those of naturally occurring phytosterols. According to a specific embodiment of the present invention, non-limiting examples of phytosterols well known to those of ordinary skill in the art include 4-demethyl sterols (e.g., β-sitosterol, campesterol, stigmasterol, rapeseed sterol, 22-dehydrorapeseed sterol and Δ5-avenasterol), 4-monomethyl sterols and 4,4-dimethyl sterols (triterpenoid alcohols) (e.g., cycloartenol, 24-methylenecycloartenol and cyclobranol).

As used herein, the phrases "stanol," "plant stanol," and "phytostanol" are synonymous. Phytostanols are saturated sterol alcohols found in nature in only trace amounts and may also be produced synthetically, such as by hydrogenation of phytosterols. According to specific embodiments of the invention, non-limiting examples of phytostanols include β-sitosterol, campesterol, cycloartanol, and saturated forms of other triterpene alcohols.

As used herein, both phytosterols and phytostanols include various isomers, such as α and β isomers (eg, α-sitosterol and β-sitosterol, which comprise one of the most effective phytosterols and phytostanols, respectively, for lowering serum cholesterol in mammals).

Phytosterol and phytostanol of the present invention can also be in the form of its ester. Suitable methods for deriving the ester of phytosterol and phytostanol are well known to those of ordinary skill in the art, and are disclosed in U.S. Patent No. 6,589,588, 6,635,774, 6,800,317 and U.S. Patent Publication No. 2003/0045473, all of which are incorporated herein by reference. Non-limiting examples of suitable phytosterol and phytostanol include sitosterol acetate, sitosterol oleate, stigmasterol oleate, and corresponding phytostanol esters thereof. Phytosterol and phytostanol of the present invention can also include derivatives thereof.

Typically, the amount of the functional ingredient in a sweetener composition or a sweetened consumable widely changes according to a specific sweetener composition or a sweetened consumable and desired functional ingredient. One of ordinary skill in the art will readily determine the suitable amount of the functional ingredient for each sweetener composition or sweetened consumable.

In one embodiment, a method for preparing a sweetener composition comprises mixing Reb DEMNO and at least one sweetener and/or additive and/or functional ingredient. In another embodiment, a method for preparing a sweetener composition comprises mixing a composition comprising Reb DEMNO and at least one sweetener and/or additive and/or functional ingredient. Reb DEMNO can be provided in its pure form as a separate sweetener in a sweetener composition, or it can be provided as part of a steviol glycoside mixture of a stevia extract. Any of the sweeteners, additives, and functional ingredients described herein can be used in the sweetener compositions of the present invention.

Sweetened consumer products

Reb DEMNO or a sweetener composition comprising Reb DEMNO can be incorporated into any known edible substance (referred to herein as a "sweetenable composition"), such as, for example, pharmaceutical compositions, edible gel mixes and compositions, dental compositions, foods (sweets, condiments, chewing gum, cereal compositions, baked goods, dairy products, and tabletop sweetener compositions), beverages, and beverage products.

In one embodiment, a sweetened consumable comprises a sweetenable composition and Reb DEMNO. In another embodiment, a sweetened consumable comprises a sweetenable composition and a sweetener composition comprising Reb DEMNO. The sweetened consumable may optionally include additives, sweeteners, functional ingredients, and combinations thereof.

In one embodiment, a method for preparing a sweetened consumer product comprises mixing a sweetenable composition and Reb DEMNO. The method may further comprise adding at least one sweetener and/or additive and/or functional ingredient. In another embodiment, a method for preparing a sweetened consumer product comprises mixing a sweetenable composition comprising Reb DEMNO and a sweetener composition. Reb DEMNO may be provided in its pure form as a separate sweetener in a sweetener composition, or it may be provided as part of a steviol glycoside mixture of a stevia extract. Any sweetener, additive, and functional ingredient described herein may be used in the added consumer product of the present invention. In a specific embodiment, the sweetenable composition is a beverage.

Pharmaceutical composition

In one embodiment, the pharmaceutical composition contains a pharmaceutically active substance and Reb DEMNO. In another embodiment, the pharmaceutical composition contains a pharmaceutically active substance and a sweetener composition comprising Reb DEMNO. Reb DEMNO or the Reb DEMNO sweetener composition can be present in the pharmaceutical composition as an excipient substance, which can mask the bitter or otherwise undesirable taste of the pharmaceutically active substance or another excipient substance. The pharmaceutical composition can be in the form of a tablet, capsule, liquid, aerosol, powder, effervescent tablet or powder, syrup, emulsion, suspension, solution, or any other form of providing the pharmaceutical composition to a patient. In a specific embodiment, the pharmaceutical composition can be in the form of oral administration, buccal administration, sublingual administration, or any other route of administration as known in the art.

As used herein, "pharmaceutically active substance" refers to any drug, pharmaceutical preparation, medicament, prophylactic agent, therapeutic agent, or any other substance with biological activity. As used herein, "excipient substance" refers to any inactive substance used as a carrier for an active ingredient, such as any substance that aids in handling, stability, dispersibility, wettability, and/or release kinetics of a pharmaceutically active substance.

Suitable pharmaceutically active substances include, but are not limited to, drugs for the gastrointestinal tract or digestive system, for the cardiovascular system, for the central nervous system, for pain or consciousness, for musculo-skeletal diseases, for the eyes, for the ears, nose and oropharynx, for the respiratory system, for endocrine problems, for the reproductive system or urinary system, for contraception, for obstetrics and gynecology, for the skin, for infections and contagions, for immunity, for allergic diseases, for nutrition, for neoplastic diseases, for diagnosis or other biological functions or diseases. Examples of suitable pharmaceutically active substances for use in embodiments of the present invention include, but are not limited to, antacids, reflux inhibitors, antiflatulents, antidopaminers, proton pump inhibitors, cytoprotectants, prostaglandin analogs, laxatives, antispasmodics, antidiarrheals, bile acid sequestrants, opioids, beta-blockers, calcium channel blockers, diuretics, cardiac glycosides, antiarrhythmics, nitrates, antianginals, vasoconstrictors, vasodilators, peripheral activators, ACE inhibitors, angiotensin receptor blockers, alpha-blockers, anticoagulants, heparins, antiplatelet agents, fibrinolytics, antihemophilic factor, hemostatics, hypolipidemics, statins, hynoptics, anesthetics, antipsychotics, antidepressants, antiemetics, anticonvulsants, antiepileptics, anti Anxiety medications, barbiturates, movement disorder medications, stimulants, benzodiazepines, ciclopirox, dopamine antagonists, antihistamines, cholinergics, anticholinergics, emetics, cannabinoids, analgesics, muscle relaxants, antibiotics, aminoglycosides, antivirals, antifungals, anti-inflammatory drugs, antiglaucoma drugs, sympathomimetics, steroids, cerumen-lytics, bronchodilators, NSAIDS, cough suppressants, mucolytics, decongestants, corticosteroids, androgens, antiandrogens, gonadotropins, growth hormones, insulin, antidiabetic drugs, thyroid hormones, calcitonin, bisphosphonates, vasopressin analogs, alkalinizing agents, quinolones, anticholinesterases, sildenafil, oral contraceptives, hormone replacement therapy, bone regulators, follicle-stimulating hormone, luteinizing hormone, gammonolone ( gamolenic acid), progestogen, dopamine agonist, estrogen, prostaglandin, gonadotropin-releasing hormone, clomiphene, tamoxifen, diethylstilbestrol, anti-leprosy drugs, anti-tuberculosis drugs, antimalarial drugs, anthelmintics, antiprotozoal drugs, antiserum, vaccines, interferons, toxins, vitamins, cytotoxic drugs, sex hormones, aromatase inhibitors, somatostatin inhibitors, or similar types of substances, or combinations thereof. Such components are generally recognized as safe (GRAS) and/or are approved by the U.S. Food and Drug Administration (FDA).

The pharmaceutically active substance is present in the pharmaceutical composition in a wide range of contents depending on the specific pharmaceutically active agent to be used and its intended application. Any effective dose of the pharmaceutically active substance described herein can be easily determined by using conventional techniques and by observing the results obtained under similar circumstances. In determining the effective dose, a large number of factors are considered, including but not limited to: the species of the patient; its size, age and overall health; the specific disease involved; the degree of involvement or severity of the disease; the response of the individual patient; the specific pharmaceutically active agent administered; the mode of administration; the bioavailability characteristics of the administration formulation; the selected dosage regimen; and the drugs used simultaneously. In the absence of severe toxic effects when used in a generally acceptable amount, the pharmaceutically active substance is included in a pharmaceutically acceptable carrier, diluent or excipient in an amount sufficient to deliver a therapeutic amount of the pharmaceutically active substance to the patient. Therefore, a person skilled in the art can easily determine the appropriate amount.

According to a specific embodiment of the present invention, the concentration of the pharmaceutically active substance in the pharmaceutical composition will depend on the absorption, inactivation and excretion rate of the drug and other factors known to those skilled in the art. It should be noted that the dosage value should also change with the severity of the disease to be alleviated. It should be further understood that for any specific subject, the specific dosage regimen should be adjusted over time according to the professional judgment of the personnel who need to administer and supervise the administration of the pharmaceutical composition according to the individual needs, and the dosage range listed herein is only exemplary, and does not mean the scope or implementation of the composition of the claim. The pharmaceutically active substance can be administered once, or it can be divided into multiple smaller doses to be administered at different time intervals.

In addition to Reb DEMNO or a sweetener composition comprising Reb DEMNO, the pharmaceutical composition may also include other pharmaceutically acceptable excipient materials. Examples of suitable excipients for embodiments of the present invention include, but are not limited to, anti-adherents, binders (e.g., macrocrystalline cellulose, gum tragacanth, or gelatin), coatings, disintegrants, fillers, diluents, softeners, emulsifiers, flavoring agents, colorants, adjuvants, lubricants, functional agents (e.g., nutraceuticals), viscosity modifiers, bulking agents, glidants (e.g., colloidal silicon dioxide), surfactants, osmotic agents, diluents, or any other inactive ingredients, or combinations thereof. For example, the pharmaceutical composition of the present invention may include an excipient material selected from the group consisting of calcium carbonate, colorants, whitening agents, preservatives and flavoring agents, triacetin, magnesium stearate, sterotes, natural or artificial flavoring agents, essential oils, plant extracts, fruit essences, gelatin, or combinations thereof.

The excipient material of pharmaceutical composition can optionally include other artificial or natural sweeteners, incremental sweeteners, or its combination.Incremental sweeteners include heat and non-caloric compounds.In a specific embodiment, additives play the effect of incremental sweeteners.The limiting examples of incremental sweeteners include sucrose, glucose, maltose, dextrin, dry invert sugar, fructose, high fructose corn syrup, levulose, galactose, starch syrup powder, tagatose, polyols (for example, sorbitol, mannitol, xylitol, lactitol, erythritol and maltitol), hydrogenated starch hydrolysate, isomalt, trehalose and composition thereof.In a specific embodiment, incremental sweeteners are present in pharmaceutical composition according to the content of the desired sweetness level with a wide range.The appropriate amount of two kinds of sweeteners will be easily determined by those skilled in the art.

Edible gel mixture and edible gel composition

In one embodiment, the edible gel or edible gel mix comprises Reb DEMNO. In another embodiment, the edible gel or edible gel mix comprises a sweetener composition comprising Reb DEMNO. The edible gel or edible gel mix may optionally include additives, functional ingredients, or combinations thereof.

Edible gels are edible gels. Gels are colloidal systems in which a network of particles spans the volume of a liquid medium. Although gels are primarily composed of liquids, and therefore present a density similar to that of liquids, gels have a solid structural consistency due to the network of particles spanning the liquid medium. For this reason, gels are typically presented as solid, jelly-like materials. Gels can be used in a large number of applications. For example, gels can be used in foods, pigments, and adhesives.

The non-limiting examples of edible gel compositions in the specific embodiments include gel desserts, puddings, jellies, pastes, cakes, aspic, marshmallows, gummy candies, etc. Edible gel mixtures are typically powdered or granular solids, to which fluids can be added to form edible gel compositions. The non-limiting examples of fluids in the specific embodiments include water, dairy fluids, dairy-like fluids, juices, alcohol, alcoholic beverages, and combinations thereof. The non-limiting examples of dairy fluids that can be used in the specific embodiments include milk, fermented milk, cream, fluid whey, and mixtures thereof. The non-limiting examples of dairy-like fluids that can be used in the specific embodiments include, for example, soy milk and non-dairy coffee companions. Because the edible gel products found on the market are typically sweetened with sucrose, it is desirable to sweeten edible gels with alternative sweeteners to provide low-calorie or no-calorie substitutes.

As used herein, the term "gelling ingredient" refers to any material that can form a colloidal system within a liquid medium. Non-limiting examples of gelling ingredients for specific embodiments include gelatin, alginate, carageenan, gum, pectin, konjac, agar, food acid, rennet, starch, starch derivatives, and combinations thereof. It is well known to those of ordinary skill in the art that the amount of the gelling ingredient used in an edible gel mixture or edible gel composition will vary considerably depending on various factors, such as the specific gelling ingredient used, the specific fluid base used, and the desired gel properties.

It is well known to those of ordinary skill in the art that other ingredients and gelling agents in addition to Reb DEMNO or a sweetener composition comprising Reb DEMNO can be used to prepare edible gel mixtures and edible gels. Non-limiting examples of other ingredients used in specific embodiments include edible acids, salts of edible acids, buffer systems, bulking agents, sequestrants, cross-linking agents, one or more flavoring agents, one or more pigments, and combinations thereof. Non-limiting examples of edible acids used in specific embodiments include citric acid, adipic acid, fumaric acid, lactic acid, malic acid, and combinations thereof. Non-limiting examples of salts of edible acids used in specific embodiments include sodium salts of edible acids, potassium salts of edible acids, and combinations thereof. Non-limiting examples of bulking agents used in specific embodiments include raftilose, isomalt, sorbitol, polydextrose, maltodextrin, and combinations thereof. Non-limiting examples of chelating agents used in specific embodiments include calcium disodium ethylenetetraacetate, glucose delta-lactone, sodium gluconate, potassium gluconate, ethylenediaminetetraacetic acid (EDTA), and combinations thereof. Non-limiting examples of cross-linking agents for use in particular embodiments include calcium ions, magnesium ions, sodium ions, and combinations thereof.

Dental composition

In one embodiment, the dental composition comprises Reb DEMNO. In another embodiment, the dental composition comprises a sweetener composition comprising Reb DEMNO. Dental compositions generally comprise an active dental substance and a matrix material. Reb DEMNO or a sweetener composition comprising Reb DEMNO can be used as a matrix material to sweeten the dental composition. The dental composition can be in the form of any oral composition for use in the oral cavity, such as, for example, a mouth freshener, a gargle, a mouthwash, a toothpaste, a tooth polish, a tooth powder, a mouth spray, a tooth whitener, a dental floss, and the like.

As used herein, an "active dental substance" is any composition that can be used to improve the aesthetic appearance and/or health of teeth or gums or to prevent dental caries. As used herein, a "matrix material" refers to any inactive substance used as a carrier for an active dental substance, such as any material that promotes the handling, stability, dispersibility, wettability, foaming and/or release kinetics of an active dental substance.

Suitable active dental substances for use in embodiments of the present invention include, but are not limited to, substances that remove plaque, remove food from teeth, help eliminate and/or mask bad breath, prevent tooth decay, and prevent gum disease (i.e., gums). Examples of suitable active dental substances for use in embodiments of the present invention include, but are not limited to, anti-caries drugs, fluoride, sodium fluoride, sodium monofluorophosphate, stannous fluoride, hydrogen peroxide, carbamide peroxide (i.e., urea peroxide), antibacterial agents, plaque removers, stain removers, anti-tartar agents, abrasives, sodium bicarbonate, alkali and alkaline earth metal potassium percarbonates, perborates, or similar types of substances, or combinations thereof. Such components are generally recognized as safe (GRAS) and/or are approved by the U.S. Food and Drug Administration (FDA).

According to a specific embodiment of the present invention, the active dental substance is present in the dental composition in an amount of about 50 ppm to about 3,000 ppm of the dental composition, such as about 50 ppm to about 100 ppm, about 100 ppm to about 1,000 ppm, and about 1,000 ppm to about 3,000 ppm. Typically, the active dental substance is present in the dental composition in an effective amount to at least improve the aesthetic appearance and/or health of the teeth or gum margin or prevent caries. For example, a dental composition comprising a toothpaste can include an active dental substance comprising fluoride in an amount of about 850 to about 1,150 ppm.

In addition to Reb DEMNO or a sweetener composition comprising Reb DEMNO, the dental composition may also include other matrix materials. Examples of suitable matrix materials for embodiments of the present invention include, but are not limited to, water, sodium lauryl sulfate or other sulfates, humectants, enzymes, vitamins, herbs, calcium, flavorings (e.g., mint, bubble gum, cinnamon, lemon, or orange), surfactants, binders, preservatives, gelling agents, pH adjusters, peroxide activators, stabilizers, colorants, or similar types of materials, and combinations thereof.

The host material of dental composition can optionally include other artificial or natural sweeteners, incremental sweeteners, or its combination.Incremental sweeteners include heat and non-caloric compounds.The limiting examples of incremental sweeteners include sucrose, dextrose, maltose, dextrin, dry invert sugar, fructose, high fructose corn syrup, levulose, galactose, corn syrup solids, tagatose, polyols (for example, sorbitol, mannitol, xylitol, lactitol, erythritol and maltitol), hydrogenated starch hydrolysate, isomalt, trehalose, and composition thereof.Usually, the content range of the incremental sweetener present in dental composition widely depends on the specific embodiment of dental composition and the sweetness degree of expectation.Those of ordinary skill in the art will easily determine the appropriate amount of incremental sweeteners. In specific embodiments, the bulk sweetener is present in the dental composition in an amount in the range of about 0.1 to about 5 wt %, such as, for example, in the range of about 0.1 wt % to about 1 wt %, about 1 wt % to about 2 wt %, about 2 wt % to about 3 wt %, about 3 wt % to about 4 wt %, and about 4 wt % to about 5 wt % of the dental composition.

According to a specific embodiment of the invention, the matrix material is present in the dental composition in an amount ranging from about 20% to about 99% by weight of the dental composition, such as, for example, from about 20% to about 50% by weight, from about 50% to about 75% by weight, and from about 75% to about 99% by weight. Typically, the matrix material is present in an effective amount to provide a carrier for the active dental substance.

In one embodiment, a dental composition comprises Reb DEMNO and an active dental substance. In another embodiment, a dental composition comprises a sweetener composition comprising Reb DEMNO and an active dental substance. Generally, the amount of sweetener varies widely depending on the nature of the specific dental composition and the desired degree of sweetness. One skilled in the art will be able to identify the appropriate amount of sweetener for such a dental composition. In a specific embodiment, Reb DEMNO is present in the dental composition in an amount ranging from about 1 ppm to about 5,000 ppm of the dental composition, such as, for example, from about 1 ppm to about 10 ppm, from about 10 ppm to about 100 ppm, from about 100 ppm to about 1,000 ppm, from about 1,000 ppm to about 5,000 ppm, and at least one additive is present in the dental composition in an amount ranging from about 0.1 ppm to about 100,000 ppm of the dental composition, such as, for example, from about 0.1 ppm to about 1 ppm, from about 1 ppm to about 10 ppm, from about 10 ppm to about 100 ppm, from about 100 ppm to about 1,000 ppm, from about 1,000 ppm to about 10,000 ppm, and from about 10,000 ppm to about 100,000 ppm.

Food products include, but are not limited to, confectionery, condiments, chewing gum, cereals, baked goods, and dairy products.

Sweets

In one embodiment, a dessert comprises Reb DEMNO. In another embodiment, a dessert comprises a sweetener composition comprising Reb DEMNO.

As used herein, "sweets" may refer to sweets, lollies, candies, or similar terms. Sweets typically contain a base composition component and a sweetener component. Reb DEMNO or a sweetener composition comprising Reb DEMNO may serve as the sweetener component. Sweets may be any food form that is generally perceived to be rich in sugar or generally sweet. According to a specific embodiment of the present invention, sweets can be baked products, such as cakes; desserts, such as yogurt, jelly, drinkable jelly, pudding, Bavarian cream, milk jelly, cake, brownie, mousse, etc., sweetened foods used during tea time or after meals; frozen foods; cold desserts, for example, ice cream types, such as ice cream, frozen milk, yogurt ice, etc. (foods in which sweeteners and various other types of raw materials are added to dairy products and the resulting mixture is stirred and frozen), and ice desserts, such as juice jelly, dessert ice, etc. (foods in which various other types of raw materials are added to sugary liquids and the resulting mixture is stirred and frozen); general sweets, for example, baked sweets or steamed sweets, such as crackers, biscuits, round buns with bean paste fillings, ha fa gao, sweet milk sandwich biscuits, etc.; rice cakes and snacks; tabletop products products; general sugar sweets, such as chewing gum (for example, including compositions containing a substantially water-insoluble, chewable gum base, such as chicle or its substitutes, including jetulong, guttakay rubber or certain edible natural synthetic resins or waxes), hard candy, soft candy, mint, nougat, jelly beans, fudge, toffee, taffy, condensed milk slices, liquorice candy, chocolate, gelatin candy, marshmallow, almond meringue, cream meringue (divinity), cotton candy, etc.; sauces, including fruit flavored sauces, chocolate sauces, etc.; edible gels; cheeses, including butter cheese, flour paste, whipped cream, etc.; sauces, including strawberry jam, orange jam, etc.; and breads, including sweet bread, etc., or other starch products, and combinations thereof.

As used herein, a "matrix composition" refers to any composition, which may be a food item, and which provides a matrix for carrying a sweetener component.

Suitable matrix compositions for embodiments of the present invention may include flour, yeast, water, salt, butter, egg, milk, milk powder, wine, gelatin, nuts, chocolate, citric acid, tartaric acid, fumaric acid, natural flavors, artificial flavors, coloring agents, polyols, sorbitol, maltitol, lactitol, malic acid, magnesium stearate, lecithin, hydrogenated glucose syrup, glycerine, natural or synthetic gums, starch, etc., and combinations thereof. Such components are generally considered to be safe (GRA) and/or are approved by the U.S. Food and Drug Administration (FDA). According to a specific embodiment of the present invention, matrix compositions are present in the sweet in the range of about 0.1 % by weight to about 99 % by weight, such as, for example, about 0.1 % by weight to about 1 % by weight, about 1 % by weight to about 10 % by weight, about 10 % by weight to about 25 % by weight, about 25 % by weight to about 50 % by weight, about 50 % by weight to about 75 % by weight, and about 75 % by weight to about 99 % by weight. Typically, the base composition is present in a sweet food in an amount that is combined with Reb DEMNO or a sweetener composition comprising Reb DEMNO to provide a food product.

The matrix composition of sweet food can optionally include other artificial or natural sweeteners, incremental sweetener or its combination.Incremental sweetener includes heat and non-caloric compound, and the limiting examples of incremental sweetener includes sucrose, dextrose, maltose, dextrin, dry invert sugar, fructose, high fructose corn syrup, levulose, galactose, corn syrup solids, tagatose, polyol (for example, sorbitol, mannitol, xylitol, lactitol, erythritol and maltitol), hydrogenated starch hydrolyzate, isomalt, trehalose, and composition thereof.Usually, the content range of the incremental sweetener that sweet food exists depends widely on the specific embodiment of sweet food and the sweetness degree of expectation.Those of ordinary skill in the art will easily determine the appropriate amount of incremental sweetener.

In a specific embodiment, the sweet comprises Reb DEMNO or a sweetener composition and a matrix composition comprising Reb DEMNO. Generally, the sweet is present in an amount of Reb DEMNO ranging widely depending on the specific embodiment of the sweet and the desired degree of sweetness. One of ordinary skill in the art will readily determine the appropriate amount of sweetener. In a specific embodiment, Reb DEMNO is present in the sweet in an amount ranging from about 30 ppm to about 6,000 ppm of the sweet, such as, for example, from about 30 ppm to about 100 ppm, from about 100 ppm to about 500 ppm, from about 500 ppm to about 1,000 ppm, from about 1,000 ppm to about 3,000 ppm, and from about 3,000 ppm to about 6,000 ppm. In another embodiment, Reb DEMNO is present in the confection in an amount ranging from about 1 ppm to about 10,000 ppm of the confection, such as, for example, from about 1 ppm to about 10 ppm, from about 10 ppm to about 100 ppm, from about 100 ppm to about 1,000 ppm, and from about 1,000 ppm to about 10,000 ppm. In embodiments where the confection comprises hard candy, Reb DEMNO is present in an amount ranging from about 150 ppm to about 2,250 ppm of the hard candy, such as, for example, from about 150 ppm to about 500 ppm, from about 500 ppm to about 1,000 ppm, from about 1,000 ppm to about 1,500 ppm, from about 1,500 ppm to about 2,000 ppm, and from about 2,000 ppm to about 2,250 ppm.

Seasoning composition

In one embodiment, the condiment comprises Reb DEMNO. In another embodiment, the condiment comprises a sweetener composition comprising Reb DEMNO. As used herein, a condiment is a composition for enhancing or improving the flavor of a food or beverage. Non-limiting examples of condiments include ketchup (ketchup); mustard; barbecue sauce; butter; hot sauce; chutney; cocktail sauce; curry; dips; fish sauce; horseradish; hot sauce; jelly, jam, marmalade or preserves; mayonnaise; peanut butter; relish; remoulade; salad dressings (e.g., oil and vinegar, Caesar dressing, French dressing, ranch dressing, blue cheese, Russian dressing, Thousand Island dressing, Italian dressing and sweet vinegar), salsa; sauerkraut; soy sauce; steak sauce; syrup; tartar sauce; and Worcestershire sauce.

The seasoning base generally comprises a mixture of different ingredients, non-limiting examples of which include carriers (e.g., water and vinegar); spices or seasonings (e.g., salt, pepper, garlic, mustard seeds, onions, paprika, turmeric, and combinations thereof); fruits, vegetables, or products thereof (e.g., tomatoes or tomato-based products (sauces, purees), juices, juice peels, and combinations thereof); oils or oil emulsions, particularly vegetable oils; thickeners (e.g., xanthan gum, food starch, other hydrocolloids, and combinations thereof); and emulsifiers (e.g., egg yolk solids, proteins, gum arabic, carob bean gum, guar gum, karaya gum, tragacanth gum, carrageenan, pectin, propylene glycol esters of alginic acid, sodium carboxymethylcellulose, polysorbates, and combinations thereof). The formulations for the seasoning base and methods of preparing the seasoning base are well known to those of ordinary skill in the art.

Typically, the condiments also include a caloric sweetener, such as sucrose, high fructose corn syrup, molasses, honey, or brown sugar. In the exemplary embodiments of the condiments provided herein, Reb DEMNO or a sweetener composition comprising Reb DEMNO is used in place of a traditional caloric sweetener. Thus, the condiment composition desirably includes Reb DEMNO or a composition comprising Reb DEMNO and a condiment base.

The seasoning composition optionally may include natural and/or other synthetic high-potency sweeteners, bulk sweeteners, pH adjusters (e.g., lactic acid, citric acid, phosphoric acid, hydrochloric acid, acetic acid, and combinations thereof), fillers, functional agents (e.g., pharmaceutical agents, nutrients, or components of foods or plants), flavors, colorants, or combinations thereof.

Chewing gum composition

In one embodiment, the chewing gum composition comprises Reb DEMNO. In another embodiment, the chewing gum composition comprises a sweetener composition comprising Reb DEMNO. The chewing gum composition generally comprises a water soluble portion and a water insoluble chewable gum base portion. The water soluble portion, which generally comprises a sweetener or sweetener composition, dissipates over a period of time during chewing along with a portion of the flavoring, while the insoluble gum base portion remains in the mouth. The insoluble gum base generally determines whether the colloid is considered a chewing gum, bubble gum, or functional gum.

Insoluble gum base, which is generally present in the chewing gum composition in an amount ranging from about 15 to about 35% by weight of the chewing gum composition, such as, for example, from about 15% to about 20% by weight, from about 20% to about 25% by weight, from about 25% to about 30% by weight, and from about 30% to about 35% by weight of the chewing gum composition, generally comprises a combination of elastomers, softeners (plasticizers), emulsifiers, resins, and fillers. Such components are generally considered food grade, recognized as safe (GRAS), and/or approved by the U.S. Food and Drug Administration (FDA).

Elastomers, the main component of the gum matrix, provide the elastic, adhesive properties of the gum and may include one or more natural rubbers (e.g., smoked latex, liquid latex, or guayule); natural gums (e.g., jelutong, perillo, sorva, massaranduba balata, massaranduba chocolate, nispero, rosindinha, chicle, and guttahangkang); or synthetic elastomers (e.g., butadiene-styrene copolymers, isobutylene-isoprene copolymers, polybutadiene, polyisobutylene, and vinyl polymerized elastomers). In a particular embodiment, the elastomer is present in the gum matrix in an amount ranging from about 3 wt % to about 50 wt % of the gum matrix, such as, for example, ranging from about 3 wt % to about 5 wt %, from about 5 wt % to about 10 wt %, from about 10 wt % to about 20 wt %, from about 20 wt % to about 30 wt %, from about 30 wt % to about 40 wt %, and from about 40 wt % to about 50 wt % of the gum matrix.

Resin is used to change the hardness of the glue matrix, and helps to soften the elastomer component of the glue matrix. The limiting examples of suitable resins include rosin esters, terpene resins (for example, from α-pinene, β-pinene and/or d-limonene), polyvinyl acetate, polyvinyl alcohol, ethylene-vinyl acetate copolymers and vinyl acetate-vinyl laurate copolymers. The limiting examples of rosin esters include glycerol esters of partially hydrogenated rosin, glycerol esters of polymerized rosin, glycerol esters of partly dimerized rosin, glycerol esters of rosin, pentaerythritol esters of partially hydrogenated rosin, methyl esters of rosin or methyl esters of partially hydrogenated rosin. In a particular embodiment, the resin is present in the gum matrix in an amount ranging from about 5 wt % to about 75 wt % of the gum matrix, such as, for example, from about 5 wt % to about 15 wt %, from about 15 wt % to about 25 wt %, from about 25 wt % to about 35 wt %, from about 35 wt % to about 45 wt %, from about 45 wt % to about 55 wt %, from about 55 wt % to about 65 wt %, and from about 65 wt % to about 75 wt % of the gum matrix.

Softener, also referred to as plasticizer, is used to change the ease of chewing and/or the mouthfeel of chewing gum composition.Usually, softener includes oil, fat, wax and emulsifier.The non-limiting examples of oil and fat include tallow, hydrogenated tallow, large hydrogenated or partially hydrogenated vegetable oil (for example, soybean oil, canola oil (canola), cottonseed oil, sunflower oil, palm oil, coconut oil, corn oil, safflower oil or palm kernel oil), cocoa butter, glyceryl monostearate, triacetin, rosin acid glyceride, lecithin, monoglyceride, diglyceride, triglyceride, acetylated monoglyceride and free fatty acid.The non-limiting examples of wax include polypropylene/polyethylene/Fisher-Tropsch wax, paraffin and microcrystalline and natural wax (for example, candelilla wax, beeswax and carnauba wax).Microcrystalline wax, especially those with high crystallinity and high melting point, can also be considered as thickener or texture regulator. In specific embodiments, the softener is present in the gum matrix in an amount ranging from about 0.5% to about 25% by weight of the gum matrix, such as, for example, in the range of about 0.5% to about 1%, about 1% to about 5%, about 5% to about 10%, about 10% to about 15%, about 15% to about 20%, and about 20% to about 25% by weight of the gum matrix.

Emulsifier is used to form the dispersant of the uniformity of the insoluble and soluble phase of chewing gum composition, and has plasticizing property.Suitable emulsifier comprises glyceryl monostearate (GMS), lecithin (phosphatidylcholine), polyglycerol polyricinoleic acid (PPGR), monoglyceride and diglyceride of fatty acid, distearin, triacetin, acetylated monoglyceride, triacetin and magnesium stearate.In a particular embodiment, emulsifier is with in the range of about 2 % by weight to about 30 % by weight of gum base, as for example in the range of about 2 % by weight to about 5 % by weight of gum base, about 5 % by weight to about 10 % by weight, about 10 % by weight to about 15 % by weight, about 15 % by weight to about 20 % by weight, about 20 % by weight to about 25 % by weight and about 25 % by weight to about 30 % by weight, be present in gum base.

The chewing gum composition can also include auxiliary agents or fillers in the gum matrix and/or soluble part of the chewing gum composition. Suitable auxiliary agents and fillers include lecithin, inulin, polydextrin, calcium carbonate, magnesium carbonate, magnesium silicate, ground limestone, aluminum hydroxide, aluminum silicate, talc, clay, aluminum oxide, titanium dioxide and calcium phosphate. In a specific embodiment, lecithin can be used as an inert filler to reduce the viscosity of the chewing gum composition. In other specific embodiments, lactic acid copolymers, proteins (for example, gluten and/or zein) and/or guar gum can be used to produce more biodegradable colloids. Auxiliary agents or fillers are usually present in the gum matrix in an amount of about 20% weight at most of the gum matrix. Other optional ingredients include coloring agents, whitening agents, preservatives and flavoring agents.

In a specific embodiment of the chewing gum composition, the gum base comprises from about 5 to about 95 weight % of the chewing gum composition, such as, for example, from about 5 weight % to about 10 weight %, from about 10 weight % to about 15 weight %, from about 15 weight % to about 20 weight %, from about 20 weight % to about 25 weight %, from about 25 weight % to about 30 weight %, from about 30 weight % to about 50 weight %, and from about 50 weight % to about 95 weight %, more desirably from about 15 to about 50 weight %, and even from about 20 to about 30 weight % of the chewing gum composition.

The soluble part of chewing gum composition can optionally include other artificial or natural sweeteners, bulk sweeteners, softeners, emulsifiers, flavoring agents, coloring agents, adjuvants, fillers, functional agents (e.g., pharmaceutical agents or nutrients), or combinations thereof. Suitable examples of softeners and emulsifiers are those mentioned above.

Incremental sweeteners include caloric and non-caloric compounds, and the non-limiting examples of incremental sweeteners include sucrose, dextrose, maltose, dextrin, dried invert sugar, fructose, high fructose corn syrup, levulose, galactose, corn syrup solids, tagatose, polyols (e.g., sorbitol, mannitol, xylitol, lactitol, erythritol and maltitol), hydrogenated starch hydrolysates, isomalt, trehalose, and mixtures thereof. In a particular embodiment, the incremental sweetener is present in the chewing gum composition in an amount ranging from about 1% by weight to about 75% by weight of the chewing gum composition, such as, for example, from about 1% by weight to about 15% by weight, from about 15% by weight to about 30% by weight, from about 30% by weight to about 45% by weight, from about 45% by weight to about 60% by weight, and from about 60% by weight to about 75% by weight.

Flavoring agent can be used in the insoluble gum matrix or the soluble part of chewing gum composition.Such flavoring agent can be natural or artificial flavoring agent.In a specific embodiment, flavoring agent comprises essential oil, such as oil, peppermint oil, spearmint oil, other peppermint oils, clove oil, cinnamon oil, wintergreen oil, laurel, thyme, cypress leaf, nutmeg, allspice, sage, mace and almond derived from plant or fruit.In another specific embodiment, flavoring agent comprises plant extract or fruit essence, such as apple, banana, watermelon, pear, peach, grape, strawberry, raspberry, cherry, plum, pineapple, apricot and composition thereof.In still another specific embodiment, flavoring agent comprises citrus flavoring agent, such as extract, essence or oil of lemon, sour orange, orange, tangerine, grapefruit, citron or kumquat.

In a specific embodiment, a chewing gum composition comprises Reb DEMNO and a gum base or a sweetener composition comprising Reb DEMNO and a gum base. In a specific embodiment, Reb DEMNO is present in the chewing gum composition in an amount ranging from about 1 ppm to about 10,000 ppm of the chewing gum composition, such as, for example, ranging from about 1 ppm to about 10 ppm, from about 10 ppm to about 100 ppm, from about 100 ppm to about 1,000 ppm, and from about 1,000 ppm to about 10,000 ppm.

Cereal composition

In one embodiment, the cereal composition comprises Reb DEMNO. In another embodiment, the cereal composition comprises a sweetener composition comprising Reb DEMNO. The cereal composition is typically consumed as a staple food or as a snack. Non-limiting examples of cereal compositions used in specific embodiments include ready-to-eat cereals and hot cereals. Ready-to-eat cereals are cereals that can be eaten without further processing (i.e., cooking) by the consumer. Examples of ready-to-eat cereals include breakfast cereals and snack bars. Breakfast cereals are typically processed to produce chopped, flaked, puffed or extruded forms. Breakfast cereals are typically eaten cold and are often mixed with milk and/or fruit. Snack bars include, for example, energy bars, rice cakes, granola bars, and nutrition bars. Hot cereals are typically cooked before consumption, typically in milk or water. Non-limiting examples of hot cereals include grits, porridge, polenta, rice, and oatmeal.

Cereal compositions typically include at least one cereal ingredient. The term "cereal ingredient" as used herein refers to materials such as whole or partial grains, whole or partial seeds, and whole or partial grasses. Non-limiting examples of cereal ingredients for specific embodiments include corn, wheat, rice, barley, bran, bran endosperm, bulgur, soghum, millet, oats, rye, triticale, buckwheat, fonio, quinoa, beans, soybeans, amaranth, teff, spelt, and kaniwa.

In a specific embodiment, a cereal composition comprises Reb DEMNO and a sweetener composition comprising Reb DEMNO and at least one cereal ingredient. Reb DEMNO or a sweetener composition comprising Reb DEMNO can be added to the cereal composition in a variety of ways, such as, for example, as a coating, as a frosting, as a glaze, or as a base mix (i.e., added as an ingredient to a cereal recipe prior to making the final cereal product).

Thus, in one specific embodiment, Reb DEMNO or a sweetener composition comprising Reb DEMNO is added to a cereal composition as a base blend. In one embodiment, Reb DEMNO or a sweetener composition comprising Reb DEMNO is mixed with hot cereal prior to cooking to provide a sweetened hot cereal product. In another embodiment, Reb DEMNO or a sweetener comprising Reb DEMNO is mixed with a cereal base prior to extrusion of the cereal.

In another specific embodiment, Reb DEMNO or a sweetener composition comprising Reb DEMNO is added to a cereal composition as a coating, such as by mixing Reb DEMNO or a sweetener comprising Reb DEMNO with a food grade oil and applying the mixture to the cereal. In various embodiments, Reb DEMNO or a sweetener composition comprising Reb DEMNO and a food grade oil can be applied to the cereal separately by first applying the oil or sweetener. Non-limiting examples of food grade oils used in specific embodiments include vegetable oils, such as corn oil, soybean oil, cottonseed oil, peanut oil, coconut oil, canola oil, olive oil, sesame seed oil, palm oil, palm kernel oil, and mixtures thereof. In still another embodiment, food grade fats can be used to replace the oils, provided that the fats are melted before being applied to the cereals.

In another embodiment, Reb DEMNO or a sweetener composition comprising Reb DEMNO is added to a cereal composition as a glaze. The limiting examples of the glazing agent used in a specific embodiment include corn syrup, honey syrup and honey syrup solids, maple syrup and maple syrup solids, sucrose, isomalt, polydextrose, polyols, hydrogenated starch hydrolysate, its aqueous solution, and mixtures thereof. In another such embodiment, Reb DEMNO or a sweetener composition comprising Reb DEMNO is added as a glaze by combining with a glazing agent and edible grade oil or fat and applying the mixture to cereals. In still another embodiment, a gum system such as acacia gum, carboxymethyl cellulose or seaweed can be added to the glaze to provide structural support. In addition, the glaze also can include a coloring agent, and can include flavoring agents.

In another embodiment, Reb DEMNO or a sweetener composition comprising Reb DEMNO is added to a cereal composition as a frosting. In one such embodiment, Reb DEMNO or a sweetener composition comprising Reb DEMNO is mixed with water and an frosting agent and then applied to the cereal. Non-limiting examples of frosting agents for specific embodiments include maltodextrin, sucrose, starch, polyols, and mixtures thereof. The frosting may also include food grade oils, food grade fats, coloring agents, and/or flavoring agents.

In general, the amount of Reb DEMNO in a cereal composition varies widely depending on the particular type of cereal composition and its desired sweetness. One of ordinary skill in the art can readily determine the appropriate amount of sweetener to add to a cereal composition. In a specific embodiment, Reb DEMNO is present in the cereal composition in an amount within the range of about 0.02% to about 1.5% by weight of the cereal composition, such as, for example, within the range of about 0.02% to about 0.2%, about 0.2% to about 1%, and about 1% to about 1.5% by weight, and at least one additive is present in the cereal composition in an amount within the range of about 1% to about 5% by weight of the cereal composition, such as, for example, within the range of about 1% to about 2%, about 2% to about 3%, about 3% to about 4%, and about 4% to about 5%.

Bakery products

In one embodiment, the baked good comprises Reb DEMNO. In another embodiment, the baked good comprises a sweetener composition comprising Reb DEMNO. As used herein, baked goods include ready-to-eat and all prepared baked goods, flours, and mixes that need to be prepared before serving. Non-limiting examples of baked goods include cakes, crackers, sweet cookies, brownies, muffins, rolls, bagels, donuts, strudels, pastries, croissants, small pastries, bread, bread products, and buns.

Preferred baked products according to embodiments of the present invention can be categorized into three groups: bread-type doughs (e.g., white bread, various breads, soft bread, hard bread, bagels, pizza dough, and flour wafers), sweet doughs (e.g., Danish bread, croissants, crackers, pastries, pie crusts, cookies, and sweet cookies), and batters (e.g., cakes, such as sponge cakes, pound cakes, devil's food, cheesecakes and layer cakes, donuts or other yeast-raised cakes, brownies, and muffins). Doughs are generally characterized as being flour-based, while batters are more water-based.

The baked goods according to a specific embodiment of the present invention generally comprise a mixture of sweetener, water and fat. The baked goods made according to many embodiments of the present invention also contain flour, to prepare dough or batter. The term "dough" as used herein is a mixture of flour and other ingredients, and its hardness is enough to knead or roll. The term "batter" as used herein is composed of flour, liquid (such as milk or water) and other ingredients, and is sufficiently thin, to pour out or drip from a spoon. Ideally, according to a specific embodiment of the present invention, flour is present in the baked goods with an amount based on about 15 to about 60% scope of dry weight, more ideally based on about 15% to about 23%, about 23% to about 35%, about 35% to about 48% and about 48% to about 60% of dry weight.

The type of flour can be selected based on the desired product. Typically, flour comprises edible non-toxic flour conventionally used in baked goods. According to a specific embodiment, flour can be bleached baking flour, all-purpose flour or unbleached flour. In other specific embodiments, flour that has been treated in other ways can also be used. For example, in a specific embodiment, flour can be enriched with other vitamins, minerals or proteins. Non-limiting examples of flour suitable for specific embodiments of the present invention include wheat, corn flour, whole grains, a part of whole grains (wheat, bran and oat flour), and combinations thereof. In a specific embodiment, starch or starch-containing materials can also be used as flour. Common food starch is usually derived from potatoes, corn, wheat, barley, oats, cassava, bamboo shoots and sago. Modified starch and pregelatinized starch can also be used in specific embodiments of the present invention.

The type of fat or oil used in a specific embodiment of the present invention can include any edible fat, oil, or combination thereof that is applicable to baking. Non-limiting examples of fats applicable to a specific embodiment of the present invention include vegetable oils, tallow, lard, marine oils, and combinations thereof. According to a specific embodiment, fat can be graded, partially hydrogenated and/or strengthened. In another specific embodiment, fat desirably comprises reduced, low-calorie or indigestible fats, fat substitutes, or synthetic fats. In still another specific embodiment, a mixture of shortening, fat, or hard fat or soft fat can also be used. In a specific embodiment, shortening is mainly derived from triglycerides (for example, cottonseed oil, soybean oil, peanut oil, linseed oil, sesame oil, palm oil, palm kernel oil, rapeseed oil, safflower oil, coconut oil, corn oil, sunflower oil, and mixtures thereof) obtained from plant sources. Synthesis or natural triglycerides with fatty acids having a chain length of 8 to 24 carbon atoms can also be used in a specific embodiment. Desirably, according to particular embodiments of the invention, fat is present in the baked good in an amount ranging from about 2 to about 35 weight percent on a dry weight basis, more desirably from about 2% to about 12%, from about 12% to about 22%, from about 22% to about 29%, and from about 29% to about 35 weight percent on a dry weight basis.

The baked goods according to a specific embodiment of the present invention also include water that is enough to provide required consistency, can make the baked goods before or after cooking, the amount of suitable shaping, machining and cutting. The total moisture content of the baked goods includes any water directly added to the baked goods and the water present in the ingredients (e.g., flour, which generally includes about 12 to about 14% by weight of moisture) added respectively. Ideally, according to a specific embodiment of the present invention, water is present in the baked goods in an amount of at most about 25%, such as at most about 5%, at most about 10%, at most about 15%, at most about 20% and at most about 25%, by weight of the baked goods.

Baked goods according to a specific embodiment of the present invention may also include a large number of additional conventional ingredients, such as leavening agents, flavoring agents, pigments, milk, milk byproducts, eggs, egg byproducts, cocoa, vanilla or other flavoring agents, and inclusions such as nuts, raisins, cherries, apples, apricots, peaches, other fruits, citrus peels, candied fruits (preservative), coconut, flavored chips (such as chocolate chips, butterscotch chips and caramel chips), and combinations thereof. In a specific embodiment, baked goods may also include emulsifiers, such as lecithin and monoglycerides.

According to a specific embodiment of the present invention, the leavening agent can include a chemical leavening agent or a yeast leavening agent. Non-limiting examples of chemical leavening agents suitable for use in a specific embodiment of the present invention include sodium bicarbonate (e.g., sodium bicarbonate, potassium bicarbonate or aluminum bicarbonate), fermentation acid (e.g., sodium aluminum phosphate, monocalcium phosphate or dicalcium phosphate), and combinations thereof.

According to another embodiment of the present invention, cocoa may comprise natural or "Dutched" chocolate from which a substantial portion of the fat or cocoa butter has been squeezed out or removed by solvent extraction, pressing or other means. In a particular embodiment, it may be desirable to reduce the fat content of a baked product comprising chocolate due to the additional fat present in cocoa butter. In a particular embodiment, it may be desirable to add a larger amount of chocolate than cocoa to provide an equivalent amount of flavor and color.

Baked goods also comprise caloric sweeteners usually, such as sucrose, high fructose corn syrup, erythritol, molasses, honey or brown sugar. In the exemplary embodiment of baked goods provided herein, caloric sweeteners are partially or entirely substituted with Reb DEMNO or a sweetener composition comprising Reb DEMNO. Therefore, in one embodiment, baked goods comprise Reb DEMNO or a composition containing a combination of Reb DEMNO and fat, water and optional flour. In a specific embodiment, baked goods optionally can include other natural and/or synthetic high-potency sweeteners and/or bulk sweeteners.

Dairy

In one embodiment, the dairy product comprises Reb DEMNO. In another embodiment, the dairy product comprises a sweetener composition comprising Reb DEMNO. Dairy products suitable for use in the present invention and methods for preparing dairy products are well known to those of ordinary skill in the art. As used herein, a dairy product comprises milk or a food product produced from milk. Non-limiting examples of dairy products suitable for use in embodiments of the present invention include milk, cream, sour cream, crème fraiche, buttermilk, fermented buttermilk, milk powder, condensed milk, evaporated milk, butter, cheese, cottage cheese, cream cheese, yogurt, ice cream, frozen custard, frozen yogurt, gelato, vla, piima, yogurt, Yogurt kajmak, kephir, viili, kumiss, airag, ice milk, casein, ayran, lassi, khoa, or a combination thereof.

Milk is the fluid secreted by the mammary glands of female mammals for the nutrition of their young children. The ability of females to produce milk is one of the defining characteristics of mammals and provides the primary source of nutrition for newborns before they are able to digest more diverse foods. In a particular embodiment of the invention, the dairy product is derived from the fresh milk of cattle, goats, sheep, horses, donkeys, camels, buffaloes, yaks, reindeers, moose or humans.

In a specific embodiment of the present invention, processing dairy products from fresh milk generally includes the steps of pasteurization, creaming and homogenization. Although fresh milk can be consumed without pasteurization, it is generally pasteurized to destroy harmful microorganisms such as bacteria, viruses, protozoa, molds and yeasts. Pasteurization generally involves heating milk to a high temperature for a short period of time to substantially reduce the number of microorganisms, thereby reducing the risk of disease.

Creaming traditionally follows the pasteurization step and involves separating the milk into a higher fat cream layer and a lower fat milk layer. The milk will separate into milk and cream layers when left to stand for twelve to twenty-four hours. The cream rises to the top of the milk layer and can be skimmed and used as a separate dairy product. Alternatively, centrifugation can be used to separate the cream from the milk. The remaining milk is classified according to its fat content, non-limiting examples of which include whole, 2%, 1%, and skim milk.

After removing the desired amount of fat from the milk by creaming, the milk is often homogenized. Homogenization prevents the cream from separating from the milk and generally involves pumping the milk through a narrow tube at high pressure to destroy the fat globules in the milk. Pasteurization, creaming and homogenization of milk are common, but are not necessary for producing consumable dairy products. Therefore, suitable dairy products for use in embodiments of the present invention may not undergo processing steps as described herein, undergo a single processing step or a combination of processing steps. Suitable dairy products for use in embodiments of the present invention may also undergo processing steps in addition to the processing steps described herein.

Specific embodiments of the present invention include dairy products produced from milk by other processing steps. As mentioned above, cream can be skimmed from the top of the milk, or separated from the milk using a mechanical centrifuge. In a specific embodiment, the dairy product comprises sour cream, a fat-rich dairy product obtained by fermenting cream using a bacterial culture. The bacteria produce lactic acid during the fermentation process, which makes the cream sour and thicken. In another specific embodiment, the dairy product includes French yogurt, a thick cream slightly acidified with a bacterial culture in a method similar to sour cream. French yogurt is generally not as thick as sour cream, nor is it so sour. In still another specific embodiment, the dairy product includes fermented buttermilk. Fermented buttermilk is obtained by adding bacteria to milk. The fermentation obtained by the bacterial culture converting lactose into lactic acid gives the fermented buttermilk a sour taste. Although produced in different ways, fermented buttermilk is generally similar to traditional buttermilk, which is a byproduct of butter manufacturing.

According to other specific embodiments of the present invention, the dairy product comprises milk powder, condensed milk, evaporated milk, or a combination thereof. Milk powder, condensed milk and evaporated milk are generally produced by removing water from milk. In a specific embodiment, the dairy product comprises milk powder comprising dry milk solids with a low water content. In another specific embodiment, the dairy product comprises condensed milk. Condensed milk generally comprises milk with a reduced water content and an added sweetener, producing a thick sweet product with a long shelf life. In still another specific embodiment, the dairy product comprises evaporated milk. Evaporated milk generally comprises fresh, about 60% water has been removed therefrom, refrigerated, fortified with additives (such as vitamins and stabilizers), packaged and finally sterilized homogenized milk. According to another specific embodiment of the present invention, the dairy product comprises dry creamer and Reb DEMNO or Reb DEMNO sweetener composition.

In another specific embodiment, the dairy product provided herein comprises butter. Butter is usually prepared by stirring fresh or fermented cream or milk. Butter usually comprises milk fat around small droplets, which mainly comprise water and milk proteins. The stirring process destroys the membrane around the milk fat microglobules, allowing the milk fat to combine and separate from the rest of the cream. In still another specific embodiment, the dairy product comprises buttermilk, which is the sour liquid remaining after butter is produced from whole milk by a stirring process.

In still another specific embodiment, the dairy product comprises cheese, which is a solid food produced by coagulating milk using a combination of rennet or a rennet substitute and acidification. Rennet is a natural enzyme complex produced in the stomach of mammals for digesting milk, which is used in cheese preparation to coagulate milk and separate it into a solid called curd and a liquid called whey. Typically, rennet is obtained from the stomach of young ruminants (e.g., calves); however, alternative sources of rennet include some plants, microbial organisms, and genetically modified bacteria, fungi, or yeast. In addition, milk can be coagulated by adding acid (e.g., citric acid). Typically, a combination of rennet and/or acidification is used to coagulate milk. After milk is separated into curd and whey, some cheeses are prepared by simply draining, salting, and packaging the curd. However, for most cheeses, more processing is required. Many different methods can be used to prepare hundreds of available cheese varieties. Processing methods include heating, dicing, draining, salting, stretching, cheddaring, washing, molding, aging, and ripening the cheese. Some cheeses, such as blue cheese, introduce other bacteria or molds before or during aging to give the final product flavor and fragrance. Cottage cheese is a cheese curd product with a mild flavor, which is drained but not compressed so that some whey is retained. The curd is usually washed to remove acidity. Cream cheese is a white cheese with a soft, mild taste, which is formed by adding cream to milk and then coagulating to form a rich curd, with a high fat content. Alternatively, cream is added to the curd to make cream cheese from skim milk. It should be understood that cheese as used herein comprises all solid foods produced by milk coagulation.

In another specific embodiment of the present invention, the dairy product comprises yogurt. Yogurt is usually produced by bacterial fermentation of milk. The fermentation of lactose produces lactic acid, which acts on the protein in the milk to obtain a gel-like texture and sour yogurt. In a particularly desirable embodiment, yogurt can be sweetened and/or flavored with a sweetener. Non-limiting examples of flavoring agents include, but are not limited to, fruit (e.g., peach, strawberry, banana), vanilla and chocolate. Yogurt as used herein also includes yogurt varieties with different consistencies and viscosities, such as dahi, dadih or dadih, labneh or labaneh, bulgarian, kefir and matsoni. In another specific embodiment, the dairy product comprises a beverage based on yogurt, also referred to as drinkable yogurt or yogurt smoothie. In a particularly desirable embodiment, a beverage based on yogurt can include a sweetener, flavoring, other ingredients, or a combination thereof.

Other dairy products besides those described herein may be used in specific embodiments of the present invention. Such dairy products are well known to those of ordinary skill in the art, and non-limiting examples thereof include milk, milk and juice, coffee, tea, vla, healthy yogurt, filmjolk, kajmak, kephir, viili, kumiss, airag, ice milk, casein, ayran, lassi, and khoa.

According to a specific embodiment of the present invention, dairy composition can also include other additives. Non-limiting examples of suitable additives include sweeteners and flavorings, such as chocolate, strawberry and banana. Specific embodiments of dairy composition provided herein can also include other nutritional supplements, such as vitamins (vitamin D) and minerals (e.g., calcium), to improve the nutritional composition of milk.

In a particularly desirable embodiment, a dairy composition comprises Reb DEMNO or a sweetener composition comprising Reb DEMNO in combination with a dairy product. In a specific embodiment, Reb DEMNO is present in the dairy composition in an amount in the range of about 200 ppm to about 20,000 ppm of the dairy composition, such as, for example, in the range of about 200 ppm to about 2,000 ppm, about 2,000 ppm to about 20,000 ppm.

Reb DEMNO or a sweetener composition comprising Reb DEMNO is also suitable for use in processed agricultural products, livestock products or seafood; processed meat products, such as sausages, etc.; steamed foods, pickled foods, preserves boiled in soy sauce, dishes, side dishes; soups; snacks, such as potato chips, sweet biscuits, etc.; as chopped fillings, leaves, stems, rods, homogenized pickled leaves and animal feed.

Tabletop Sweetener Composition

The present invention also contemplates a tabletop sweetener composition comprising Reb DEMNO.The tabletop composition may further include at least one bulking agent, additive, anticaking agent, functional ingredient, or a combination thereof.

Suitable " bulking agent " includes, but is not limited to maltodextrin (10DE, 18DE or 5DE), corn syrup solids (20 or 36DE), sucrose, fructose, glucose, invert sugar, sorbitol, xylose, ribulose, mannose, xylitol, mannitol, galactitol, erythritol, maltitol, lactitol, isomalt, maltose, tagatose, lactose, inulin, glycerol, propylene glycol, polyols, polydextrose, fructooligosaccharide, cellulose and cellulose derivative etc., and mixture thereof.In addition, according to still other embodiments of the present invention, granulated sugar (sucrose) or other caloric sweeteners, such as crystalline fructose, other carbohydrates or sugar alcohol, can be used as bulking agent, because they provide good content uniformity, and can not increase remarkable heat.

As used herein, phrases "anticaking agent" and "glidant" refer to any composition that helps content uniformity and uniform dissolution. According to specific embodiments, the limiting examples of anticaking agent include Tartar powder, calcium silicate, silicon dioxide, microcrystalline cellulose (Avicel, FMC BioPolymer, Philadelphia, Pa.) and tricalcium phosphate. In one embodiment, anticaking agent is with about 0.001% weight to about 3% weight of tabletop functional sweetener composition, such as about 0.001% weight to about 0.01% weight, about 0.01% weight to about 0.1% weight, about 0.1% weight to about 1% weight, about 1% weight to about 2% weight and about 2% weight to about 3% weight of tabletop functional sweetener composition is present in the tabletop sweetener composition.

The tabletop sweetener composition can be packaged in any form known in the art. Non-limiting forms include, but are not limited to, powder form, granular form, pouch, tablet, sachet, pill, cube, solid and liquid.

In one embodiment, the tabletop sweetener composition is a single serving (portion control) package comprising a dry blend. The dry blend formulation may typically comprise a powder or granules. Although the tabletop sweetener composition may be a pouch of any size, an exemplary non-limiting example of a conventional portion control tabletop sweetener pouch is about 2.5×1.5 inches and contains about 1 gram of a sweetener composition having a sweetness equal to 2 teaspoons of granulated sugar (~8 g). The content of Reb DEMNO in the dry blend tabletop sweetener formulation may vary. In specific embodiments, the dry blend tabletop sweetener formulation may contain Reb DEMNO in an amount from about 1% (w/w) to about 10% (w/w), such as, for example, from 1% (w/w) to about 2% (w/w), from about 2% (w/w) to about 4% (w/w), from about 4% (w/w) to about 6% (w/w), from about 6% (w/w) to about 8% (w/w), and from about 8% (w/w) to about 10% (w/w), of the tabletop sweetener composition.

Solid tabletop sweetener embodiments include cubes and tablets. A non-limiting example of a conventional cube is a standard cube equal in size to granulated sugar, which is about 2.2×2.2×2.2 cm ³ and weighs about 8 g. In one embodiment, the solid tabletop sweetener is in tablet form or any other form known to those skilled in the art.

Tabletop sweetener compositions can also be specifically liquid forms, wherein Reb DEMNO is mixed with a liquid carrier. Suitable non-limiting examples for carrier agents of liquid tabletop functional sweeteners include water, alcohol, polyols, glycerol bases or citric acid bases soluble in water, and mixtures thereof. For any form as described herein or known in the art, the sweetness equivalent of tabletop sweeteners can be changed to obtain desired sweetness characteristics. For example, tabletop sweetener compositions can include a sweetness suitable with the standard sugar of equal content. In another embodiment, tabletop sweetener compositions can include a sweetness up to 100 times of equal amount of sugar. In another embodiment, tabletop sweetener compositions can include a sweetness of 90 times, 80 times, 70 times, 60 times, 50 times, 40 times, 30 times, 20 times, 10 times, 9 times, 8 times, 7 times, 6 times, 5 times, 4 times, 3 times and 2 times of equal amount of sugar.

Beverages and beverage products

In one embodiment, the sweetened consumer's goods are beverage products. " Beverage products " as used herein are ready-to-drink beverages, beverage concentrates, beverage syrups or powdered beverages. Suitable ready-to-drink beverages include carbonated and non-carbonated beverages. Carbonated beverages include, but are not limited to, enhanced sparkling beverages, cola, lemon-lime flavored soda beverages, orange-flavored soda beverages, grape-flavored soda beverages, strawberry-flavored soda beverages, pineapple-flavored soda beverages, ginger ale, soft drinks and root beer. Non-carbonated beverages include, but are not limited to juice, fruit-flavored juice, juice beverages, nectar, vegetable juice, vegetable-flavored juices, sports drinks, energy drinks, fortified water beverages, vitamin-fortified water, beverages close to water (for example, water containing natural or synthetic flavoring agents), coconut water, tea-type beverages (for example, black tea (black tea), green tea, black tea (red tea), oolong tea), coffee, cocoa beverages, beverages containing milk components (for example, milk beverages, coffee containing milk components, latte, milk tea, fruit milk beverages), beverages containing cereal extracts, smoothies and combinations thereof.

Beverage concentrates and beverage syrups are prepared with an initial volume of a liquid matrix (e.g., water) and the desired beverage ingredients. Full-strength beverages are then prepared by adding more volume of water. Powdered beverages can be prepared by dry mixing all beverage ingredients in the absence of a liquid matrix. Full-strength beverages are then prepared by adding the total volume of water.

The beverage comprises a liquid matrix, i.e., a base component in which the ingredients including the sweetener or sweetener composition are dissolved. In one embodiment, the beverage comprises beverage-quality water as the liquid matrix, such as, for example, deionized water, distilled water, reverse osmosis water, carbon-treated water, purified water, demineralized water, soda water, and combinations thereof can be used. Additional suitable liquid matrices include, but are not limited to, phosphoric acid, phosphate buffers, citric acid, and citrate buffers.

In one embodiment, the beverage contains Reb DEMNO as the sole sweetener.

In another embodiment, a beverage contains a sweetener composition comprising Reb DEMNO.Any of the sweetener compositions comprising Reb DEMNO detailed herein can be used in a beverage.

In another embodiment, a method of preparing a beverage comprises mixing a liquid base and Reb DEMNO. The method may further comprise adding one or more sweeteners, additives and/or functional ingredients.

In yet another embodiment, a method of preparing a beverage includes mixing a liquid base and a sweetener composition comprising Reb DEMNO.

In one embodiment, the beverage contains Reb DEMNO in an amount ranging from about 1 ppm to about 10,000 ppm, such as, for example, from about 1 ppm to about 10 ppm, from about 10 ppm to about 100 ppm, from about 100 ppm to about 1,000 ppm, and from about 1,000 ppm to about 10,000 ppm. In another embodiment, Reb DEMNO is present in the beverage in an amount ranging from about 100 ppm to about 600 ppm. In still other embodiments, Reb DEMNO is present in the beverage in an amount ranging from about 100 to about 200 ppm, from about 100 ppm to about 300 ppm, from about 100 ppm to about 400 ppm, or from about 100 ppm to about 500 ppm. In still another embodiment, Reb DEMNO is present in the beverage in an amount ranging from about 300 to about 700 ppm, such as, for example, from about 400 ppm to about 600 ppm. In a specific embodiment, Reb DEMNO is present in the beverage in an amount ranging from about 500 ppm.

In another embodiment, a beverage contains a sweetener composition comprising Reb DEMNO, wherein Reb DEMNO is present in the beverage in an amount ranging from about 1 ppm to about 10,000 ppm, such as, for example, from about 1 ppm to about 10 ppm, from about 10 ppm to about 100 ppm, from about 100 ppm to about 1,000 ppm, and from about 1,000 ppm to about 10,000 ppm. In another embodiment, Reb DEMNO is present in the beverage in an amount ranging from about 100 ppm to about 600 ppm. In still other embodiments, Reb DEMNO is present in the beverage in an amount ranging from about 100 to about 200 ppm, from about 100 ppm to about 300 ppm, from about 100 ppm to about 400 ppm, or from about 100 ppm to about 500 ppm. In still another embodiment, Reb DEMNO is present in the beverage in an amount ranging from about 300 to about 700 ppm, such as, for example, from about 400 ppm to about 600 ppm. In a specific embodiment, Reb DEMNO is present in the beverage in an amount ranging from about 500 ppm.

The beverage may further include at least one additional sweetener.Any sweetener detailed herein may be used, including natural, non-natural or synthetic sweeteners.

In one embodiment, carbohydrate sweetener can be present in beverage with about 100ppm to about 140,000ppm, such as for example about 100ppm to about 1,000ppm, about 1,000ppm to about 10,000ppm, about 10,000ppm to about 100,000ppm and about 100,000ppm to about 140,000ppm concentration.Synthetic sweetener can be present in beverage with about 0.3ppm to about 3,500ppm, such as for example about 0.3ppm to about 3ppm, about 3ppm to about 30ppm, about 30ppm to about 300ppm, about 300ppm to about 3,000ppm and about 3,000ppm to about 3,500ppm concentration. The natural high potency sweetener may be present in the beverage at a concentration of about 0.1 ppm to about 3,000 ppm, such as, for example, about 0.1 ppm to about 1 ppm, about 1 ppm to about 10 ppm, about 10 ppm to about 100 ppm, about 100 ppm to about 1,000 ppm, about 1,000 ppm to about 3,000 ppm.

Beverages may further include additives, including but not limited to carbohydrates, polyols, amino acids and their corresponding salts, polyamino acids and their corresponding salts, sugar acids and their corresponding salts, nucleotides, organic acids, inorganic acids, organic salts (including organic acid salts and organic base salts), inorganic salts, bitter compounds, caffeine, flavoring agents and flavoring ingredients, astringent compounds, proteins or protein hydrolysates, surfactants, emulsifiers, weighting agents, juices, dairy products, cereals and other plant extracts, flavonoids, alcohols, polymers and combinations thereof. Any suitable additive described herein may be used.

In one embodiment, the polyol can be present in the beverage at a concentration of about 100 ppm to about 250,000 ppm, such as, for example, about 100 ppm to about 1,000 ppm, about 1,000 ppm to about 5,000 ppm, about 5,000 ppm to about 40,000 ppm, and about 40,000 ppm to about 100,000 ppm, and about 100,000 ppm to about 250,000 ppm.

In one embodiment, the amino acid can be present in the beverage at a concentration of about 10 ppm to about 50,000 ppm, such as, for example, about 1,000 ppm to about 10,000 ppm, about 2,500 ppm to about 5,000 ppm, or about 250 ppm to about 7,500 ppm.

In yet another embodiment, the nucleotides can be present in the beverage at a concentration of about 5 ppm to about 1,000 ppm, such as, for example, about 5 ppm to about 10 ppm, about 10 ppm to about 100 ppm, and about 100 ppm to about 1,000 ppm.

In yet another embodiment, the organic acid additive can be present in the beverage at a concentration of about 10 ppm to about 5,000 ppm, such as, for example, about 10 ppm to about 100 ppm, about 100 ppm to about 1,000 ppm, and about 1,000 ppm to about 5,000 ppm.

In yet another embodiment, the inorganic acid additive can be present in the beverage at a concentration of about 25 ppm to about 25,000 ppm, such as, for example, about 25 ppm to about 250 ppm, about 250 ppm to about 2,500 ppm, and about 2,500 ppm to about 25,000 ppm.

In yet another embodiment, the bitter compound can be present in the beverage at a concentration of about 25 ppm to about 25,000 ppm, such as, for example, about 25 ppm to about 250 ppm, about 250 ppm to about 2,500 ppm, and about 2,500 ppm to about 25,000 ppm.

In yet another embodiment, the flavoring agent can be present in the beverage at a concentration of about 0.1 ppm to about 4,000 ppm, such as, for example, about 0.1 ppm to about 1 ppm, about 1 ppm to about 10 ppm, about 10 ppm to about 100 ppm, about 100 ppm to about 1,000 ppm, and about 1,000 ppm to about 4,000 ppm.

In yet another embodiment, the polymer can be present in the beverage at a concentration of about 30 ppm to about 2,000 ppm, such as, for example, about 30 ppm to about 100 ppm, about 100 ppm to about 500 ppm, about 500 ppm to about 1,000 ppm, and about 1,000 ppm to about 2,000 ppm.

In one embodiment, the protein hydrolysate may be present in the beverage at a concentration of about 200 ppm to about 50,000 ppm, such as, for example, about 200 ppm to about 500 ppm, about 500 ppm to about 5,000 ppm, and about 5,000 ppm to about 50,000 ppm.

In yet another embodiment, the surfactant additive can be present in the beverage at a concentration of about 30 ppm to about 2,000 ppm, such as, for example, about 30 ppm to about 100 ppm, about 100 ppm to about 500 ppm, about 500 ppm to about 1,000 ppm, and about 1,000 ppm to about 2,000 ppm.

In yet another embodiment, the flavonoid additive can be present in the beverage at a concentration of about 0.1 ppm to about 1,000 ppm, such as, for example, about 0.1 ppm to about 1 ppm, about 1 ppm to about 10 ppm, about 10 ppm to about 100 ppm, and about 100 ppm to about 1,000 ppm.

In yet another embodiment, the alcohol additive can be present in the beverage at a concentration of about 625 ppm to about 10,000 ppm, such as, for example, about 625 ppm to about 1,000 ppm, about 1,000 ppm to about 5,000 ppm, and about 5,000 ppm to about 10,000 ppm.

In yet another embodiment, the astringent additive can be present in the beverage at a concentration of about 10 ppm to about 5,000 ppm, such as, for example, about 10 ppm to about 100 ppm, about 100 ppm to about 1,000 ppm, and about 1,000 ppm to about 5,000 ppm.

The beverage may further comprise one or more functional ingredients, as described in detail above. Functional ingredients include, but are not limited to, vitamins, minerals, antioxidants, preservatives, glucosamine, polyphenols, and combinations thereof. Any suitable functional ingredient described herein may be used.

It is contemplated that the pH of a sweetened consumer's product such as a beverage does not substantially or adversely affect the taste of the sweetener. The non-limiting example of the pH range of the composition that can be sweetened can be about 1.8 to about 10. A further example includes a pH range of about 2 to about 5. In a particular embodiment, the pH of the beverage can be about 2.5 to about 4.2. It will be appreciated by those skilled in the art that the pH of a beverage can vary based on the type of beverage. For example, a milk beverage can have a pH greater than 4.2.

The titratable acidity of a beverage including Reb DEMNO can range, for example, from about 0.01% to about 1.0% by weight of the beverage, such as, for example, from about 0.01% to 0.1%, and from about 0.1% to 1.0% by weight of the beverage.

In one embodiment, the sparkling beverage product has an acidity of about 0.01 to about 1.0% by weight of the beverage, such as, for example, about 0.01% to about 0.05%, about 0.05% to about 0.25%, about 0.25% to about 0.50%, and about 0.50% to about 1.0% by weight of the beverage.

Carbonation of the sparkling beverage product has 0 to about 2% (w/w) carbon dioxide or its equivalent, such as, for example, about 0.1% (w/w) to about 1.0% (w/w), and about 1.0% (w/w) to about 2.0% (w/w).

The temperature of a beverage containing Reb DEMNO can be, for example, in the range of about 4°C to about 100°C, such as about 4°C to about 25°C, about 25°C to about 50°C, about 50°C to about 75°C, and about 75°C to about 100°C.

The beverage may be a mid-calorie beverage having up to about 60 calories per 8 oz serving.

The beverage may be a low calorie beverage having up to about 40 calories per 8 oz serving.

The beverage may be a zero calorie beverage having less than about 5 calories per 8 oz serving.

In one embodiment, the beverage is included in Reb DEMNO between about 200ppm to about 500ppm, such as, for example, Reb DEMNO between about 200ppm to about 300ppm, about 300ppm to about 400ppm and about 400ppm to about 500ppm, wherein the liquid matrix of the beverage is selected from water, acidified water, phosphoric acid, phosphate buffer, citric acid, citrate buffer, carbon-treated water, and combinations thereof. The pH of the beverage can be about 2.5 to about 4.2, such as, for example, about 2.5 to about 3.0, about 3.0 to about 3.5, and about 3.5 to about 4.2. The beverage can further include additives, such as, for example, erythritol. The beverage can further include functional ingredients, such as, for example, vitamins.

In a specific embodiment, the beverage comprises Reb DEMNO; a polyol selected from erythritol, maltitol, mannitol, xylitol, glycerol, sorbitol, and combinations thereof; and optionally at least one additional sweetener and/or functional ingredient. In a specific embodiment, the polyol is erythritol. In one embodiment, Reb DEMNO and the polyol are present in the beverage in a weight ratio of about 1:1 to about 1:800, such as, for example, about 1:4 to about 1:800, about 1:20 to about 1:600, about 1:50 to about 1:300, or about 1:75 to about 1:150. In another embodiment, Reb DEMNO is present in the beverage in a concentration of about 1 ppm to about 10,000 ppm, such as, for example, about 1 ppm to about 10 ppm, about 10 ppm to about 100 ppm, about 100 ppm to about 1,000 ppm, and about 1,000 ppm to about 10,000 ppm. The polyol, such as, for example, erythritol, is present in the beverage at a concentration of about 100 ppm to about 250,000 ppm, such as, for example, about 200 ppm to about 100000 ppm, about 5,000 ppm to about 40,000 ppm, and about 1,000 ppm to about 35,000 ppm.

In a specific embodiment, beverage comprises the sweetener composition that comprises Reb DEMNO and erythritol as the sweetener component of sweetener composition.Usually, erythritol can account for about 0.1% to about 3.5% of sweetener component weight, such as for example about 0.1% to about 1%, about 1% to about 2% and about 2% to about 3.5%.Reb DEMNO is present in beverage with about 50ppm to about 600ppm, such as for example about 50ppm to about 100ppm, about 100ppm to about 300ppm and about 50ppm to about 100ppm concentration.Erythritol can account for about 0.1% to about 3.5% of sweetener component weight, such as for example about 0.1% to about 1%, about 1% to about 2% and about 2% to about 3.5%. In a specific embodiment, the concentration of Reb DEMNO in the beverage is about 300 ppm, and erythritol comprises 0.1% to about 3.5% by weight of the sweetener component, such as, for example, about 0.1% to about 1%, about 1% to about 2%, and about 2% to about 3.5%. The pH of the beverage is preferably between about 2.5 and about 4.2, such as, for example, between about 2.5 and about 3.0, about 3.0 and about 3.5, and about 3.5 to about 4.2.

In a specific embodiment, the beverage comprises Reb DEMNO; a carbohydrate sweetener selected from sucrose, fructose, glucose, maltose, and combinations thereof; and optionally at least one additional sweetener and/or functional ingredient. Reb DEMNO can be provided as a pure component or as part of a stevia extract or steviol glycoside mixture, as described above. Reb DEMNO can be present in the steviol glycoside mixture or stevia extract in an amount of about 5% by weight to about 99% by weight on a dry basis, such as, for example, about 5% by weight to about 25% by weight, about 25% by weight to about 50% by weight, about 50% by weight to about 75% by weight, and about 75% by weight to about 99% by weight. In a specific embodiment, Reb DEMNO and carbohydrate are present in the sweetener composition in a weight ratio of about 0.001:14 to about 1:0.01, such as, for example, about 0.001:14 to about 0.01:14, about 0.01:14 to about 0.1:14, about 0.1:14 to about 1:14, about 1:14 to about 1:10, about 1:10 to about 1:1, about 1:1 to about 1:0.1, and about 1:0.1 to about 1:0.01. In one embodiment, in another embodiment, Reb DEMNO is present in the beverage in a concentration of about 1 ppm to about 10,000 ppm, such as, for example, about 1 ppm to about 10 ppm, about 100 ppm to about 1000 ppm, about 100 ppm to about 1,000 ppm, and about 1,000 ppm to about 10,000 ppm. Carbohydrates such as, for example, sucrose are present in the beverage at a concentration of about 100 ppm to about 140,000 ppm, such as, for example, about 100 ppm to about 1,000 ppm, about 1,000 ppm to about 10,000 ppm, about 10,000 ppm to about 100,000 ppm, and about 100,000 ppm to about 140,000 ppm.

In a specific embodiment, the beverage comprises Reb DEMNO; an amino acid selected from the group consisting of glycine, alanine, proline, taurine, and combinations thereof; and optionally at least one additional sweetener and/or functional ingredient. In one embodiment, Reb DEMNO is present in the beverage at a concentration of about 1 ppm to about 10,000 ppm, such as, for example, about 1 ppm to about 10 ppm, about 10 ppm to about 100 ppm, about 100 ppm to about 1,000 ppm, and about 1,000 ppm to about 10,000 ppm. When present in a sweetened consumable, an amino acid such as, for example, glycine may be present in the beverage at a concentration of about 10 ppm to about 50,000 ppm, such as, for example, about 10 ppm to about 100 ppm, about 100 ppm to about 1,000 ppm, about 1,000 ppm to about 10,000 ppm, and about 10,000 ppm to about 50,000 ppm.

In a specific embodiment, the beverage comprises Reb DEMNO; a salt selected from sodium chloride, magnesium chloride, potassium chloride, calcium chloride, phosphate, and combinations thereof; and optionally at least one additional sweetener and/or functional ingredient. In one embodiment, Reb DEMNO is present in the beverage at a concentration of about 1 ppm to about 10,000 ppm, such as, for example, about 1 ppm to about 10 ppm, about 10 ppm to about 100 ppm, about 100 ppm to about 1,000 ppm, and about 1,000 ppm to about 10,000 ppm. An inorganic salt, such as, for example, magnesium chloride, is present in the beverage at a concentration of about 25 ppm to about 25,000 ppm, such as, for example, about 25 ppm to about 250 ppm, about 250 ppm to about 2,500 ppm, and about 2,500 ppm to about 25,000 ppm.

In another embodiment, a beverage includes a sweetener composition comprising Reb DEMNO and Reb B as sweetener components of the sweetener composition. When dried, the relative weight percentages of Reb DEMNO and Reb B can each vary from about 1% to about 99%, such as, for example, about 95% Reb DEMNO/5% Reb B, about 90% Reb DEMNO/10% Reb B, about 85% Reb DEMNO/15% Reb B, about 80% Reb DEMNO/20% Reb B, about 75% Reb DEMNO/25% Reb B, about 70% Reb DEMNO/30% Reb B, about 65% Reb DEMNO/35% Reb B, about 60% Reb DEMNO/40% Reb B, about 55% Reb DEMNO/45% Reb B, about 50% Reb DEMNO/50% Reb B, about 45% Reb DEMNO/55% Reb B, about 40% Reb DEMNO/60% Reb B, about 35% Reb DEMNO/40% Reb B, about 50% Reb DEMNO/50% Reb B, about 45% Reb DEMNO/55% Reb B, about 40% Reb DEMNO/60% Reb B, about 35% Reb DEMNO/40% Reb B, about DEMNO/65% Reb B, about 30% Reb DEMNO/70% Reb B, about 25% Reb DEMNO/75% Reb B, about 20% Reb DEMNO/80% Reb B, about 15% Reb DEMNO/85% Reb B, about 10% Reb DEMNO/90% Reb B or about 5% Reb DEMNO/95% Reb B. In a particular embodiment, Reb B comprises about 5% to about 40% by weight of the sweetener component, e.g., about 10% to about 30% or about 15% to about 25%. In another specific embodiment, Reb DEMNO is present in the beverage at a concentration of about 50 ppm to about 600 ppm, such as, for example, about 50 ppm to about 100 ppm, about 100 ppm to about 400 ppm, and about 400 ppm to about 600 ppm, and Reb B comprises about 5% to about 40% by weight of the sweetener component, such as, for example, about 5% to about 10%, about 10% to about 20%, about 20% to about 30%, and about 30% to about 40% by weight of the sweetener component. In another embodiment, Reb DEMNO is present at a concentration of about 50 ppm to about 600 ppm, such as, for example, about 50 ppm to about 100 ppm, about 100 ppm to about 300 ppm, and about 300 ppm to about 600 ppm, and Reb B is present at a concentration of about 10 ppm to about 150 ppm, such as, for example, about 10 ppm to about 50 ppm, about 50 ppm to about 100 ppm, and about 100 ppm to about 150 ppm. In a more specific embodiment, Reb DEMNO is present at a concentration of about 300 ppm and Reb B is present at a concentration of about 50 ppm to about 100 ppm. The pH of the beverage is preferably between about 2.5 to about 4.2, such as, for example, between about 2.5 to about 3.0, about 3.0 to about 3.5, about 3.5 to about 4.0, and about 4.0 to about 4.2.

In another embodiment, the beverage includes a sweetener composition comprising Reb DEMNO and NSF-02 (available from PureCircle) as sweetener components of the sweetener composition. The relative weight percentages of Reb DEMNO and NSF-02 can each vary from about 1% to about 99%, such as, for example, about 95% Reb DEMNO/5% NSF-02, about 90% Reb DEMNO/10% NSF-02, about 85% Reb DEMNO/15% NSF-02, about 80% Reb DEMNO/20% NSF-02, about 75% Reb DEMNO/25% NSF-02, about 70% Reb DEMNO/30% NSF-02, about 65% Reb DEMNO/35% NSF-02, about 60% Reb DEMNO/40% NSF-02, about 55% Reb DEMNO/45% NSF-02, about 50% Reb DEMNO/50% NSF-02, about 45% Reb DEMNO/55% NSF-02, about 40% Reb DEMNO/50% NSF-02. In one embodiment, NSF-02 comprises about 5% to about 50% by weight of the sweetener component, such as, for example, about 10% to about 40% or about 20% to about 30%. In another specific embodiment, Reb DEMNO is present in the beverage at a concentration of about 50 ppm to about 600 ppm, such as, for example, about 50 ppm to about 100 ppm, about 100 ppm to about 400 ppm, and about 400 ppm to about 600 ppm, and NSF-02 comprises about 5 weight % to about 50 weight % of the sweetener component, such as, for example, about 5 weight % to about 10 weight %, about 10 weight % to about 20 weight %, about 20 weight % to about 30 weight %, about 30 weight % to about 40 weight %, and about 40 weight % to about 50 weight % of the sweetener component. In a more specific embodiment, Reb DEMNO is present at a concentration of about 50 ppm to about 600 ppm, such as, for example, about 50 ppm to about 100 ppm, about 100 ppm to about 400 ppm, about 400 ppm to about 600 ppm, and NSF-02 is present at a concentration of about 10 ppm to about 150 ppm, such as, for example, about 10 ppm to about 50 ppm, about 50 ppm to about 100 ppm, and about 100 ppm to about 150 ppm. In a more specific embodiment, Reb DEMNO is present at a concentration of about 300 ppm, and NSF-02 is present at a concentration of about 25 ppm to about 100 ppm, such as, for example, about 25 ppm to about 50 ppm, about 50 ppm to about 75 ppm, and about 75 ppm to about 100 ppm. The pH of the beverage is preferably between about 2.5 and about 4.2, such as, for example, between about 2.5 and about 3.0, about 3.0 and about 3.5, about 3.5 and about 4.0, and about 4.0 and about 4.2.

In yet another embodiment, a beverage includes a sweetener composition comprising Reb DEMNO and mogroside V as sweetener components of the sweetener composition. The relative weight percentages of Reb DEMNO and mogroside V can each vary from about 1% to about 99%, such as, for example, about 95% Reb DEMNO/5% mogroside V, about 90% Reb DEMNO/10% mogroside V, about 85% Reb DEMNO/15% mogroside V, about 80% Reb DEMNO/20% mogroside V, about 75% Reb DEMNO/25% mogroside V, about 70% Reb DEMNO/30% mogroside V, about 65% Reb DEMNO/35% mogroside V, about 60% Reb DEMNO/40% mogroside V, about 55% Reb DEMNO/45% mogroside V, about 50% Reb DEMNO/50% mogroside V, about 45% Reb DEMNO/55% mogroside V, about 40% Reb DEMNO/55% mogroside V, about 45% Reb DEMNO/50% mogroside V, about 46% Reb DEMNO/55% mogroside V, about 48% Reb DEMNO/50% mogroside V, about 49% Reb DEMNO/50% mogroside V, about 50% Reb DEMNO/50% mogroside V, about 51% Reb DEMNO/50% mogroside V, about 52% Reb DEMNO/50% mogroside V, about 53% Reb DEMNO/50% mogroside V, about 54% Reb DEMNO/50% mogroside V, about 56% Reb DEMNO/50% mogroside V, about 57% Reb DEMNO/50% mogroside V, about 58% Reb DEMNO/50% mogroside V, about 59% Reb DEMNO/50% mogroside V, about DEMNO/60% Mogroside V, about 35% Reb DEMNO/65% Mogroside V, about 30% Reb DEMNO/70% Mogroside V, about 25% Reb DEMNO/75% Mogroside V, about 20% Reb DEMNO/80% Mogroside V, about 15% Reb DEMNO/85% Mogroside V, about 10% Reb DEMNO/90% Mogroside V, or about 5% Reb DEMNO/95% Mogroside V. In a particular embodiment, mogroside V comprises about 5% to about 50% of the sweetener component, such as, for example, about 10% to about 40% or about 20% to about 30%. In another specific embodiment, Reb DEMNO is present in the beverage at a concentration of about 50 ppm to about 600 ppm, such as, for example, about 50 ppm to about 100 ppm, about 100 ppm to about 400 ppm, and about 400 ppm to about 600 ppm, and mogroside V comprises about 5% to about 50% by weight of the sweetener component, such as, for example, about 5% by weight to about 10% by weight, about 10% by weight to about 20% by weight, about 20% by weight to about 30% by weight, about 30% by weight to about 40% by weight, and about 40% by weight to about 50% by weight of the sweetener component. In a more specific embodiment, Reb DEMNO is present at a concentration of about 50 ppm to about 600 ppm, such as, for example, about 50 ppm to about 100 ppm, about 100 to about 400 ppm, about 400 ppm to about 600 ppm, and mogroside V is present at a concentration of about 10 ppm to about 250 ppm, such as, for example, about 10 ppm to about 100 ppm, about 100 ppm to about 200 ppm, and about 200 ppm to about 250 ppm. In a more specific embodiment, Reb DEMNO is present at a concentration of about 300 ppm, and mogroside is present at a concentration of about 100 ppm to about 200 ppm, such as, for example, about 100 ppm to about 125 ppm, about 125 ppm to about 175 ppm, and about 175 ppm to about 200 ppm. The pH of the beverage is preferably between about 2.5 to about 4.2, such as, for example, between about 2.5 to about 3.0, about 3.0 to about 3.5, about 3.5 to about 4.0, and about 4.0 to about 4.2.

In another embodiment, a beverage includes a sweetener composition comprising ReA DEMNO and Reb A as sweetener components of the sweetener composition. The relative weight percentages of Reb DEMNO and Reb A can each vary from about 1% to about 99%, such as, for example, about 95% Reb DEMNO/5% Reb A, about 90% Reb DEMNO/10% Reb A, about 85% Reb DEMNO/15% Reb A, about 80% Reb DEMNO/20% Reb A, about 75% Reb DEMNO/25% Reb A, about 70% Reb DEMNO/30% Reb A, about 65% Reb DEMNO/35% Reb A, about 60% Reb DEMNO/40% Reb A, about 55% Reb DEMNO/45% Reb A, about 50% Reb DEMNO/50% Reb A, about 45% Reb DEMNO/55% Reb A, about 40% Reb DEMNO/60% Reb A, about 35% Reb DEMNO/65% Reb A. In one embodiment, Reb DEMNO comprises about 30% Reb DEMNO/70% Reb A, about 25% Reb DEMNO/75% Reb A, about 20% Reb DEMNO/80% Reb A, about 15% Reb DEMNO/85% Reb A, about 10% Reb DEMNO/90% Reb A, or about 5% Reb DEMNO/95% Reb A. In one embodiment, Reb DEMNO comprises about 5% to about 40% of the sweetener component, such as about 10% to about 30% or about 15% to about 25%. In another embodiment, Reb DEMNO is present in a concentration of about 50 ppm to about 600 ppm, such as, for example, about 50 ppm to about 100 ppm, about 100 ppm to about 400 ppm, and about 400 ppm to about 600 ppm, and Reb A comprises about 5% to about 40% by weight of the sweetener component. In another embodiment, Reb DEMNO is present at a concentration of about 50 ppm to about 600 ppm, such as, for example, about 50 ppm to about 100 ppm, about 100 ppm to about 400 ppm, and about 400 ppm to about 600 ppm, and Reb A is present at a concentration of about 10 ppm to about 500 ppm, such as, for example, about 10 ppm to about 100 ppm, about 100 ppm to about 250 ppm, and about 250 ppm to about 500 ppm. In a more specific embodiment, Reb DEMNO is present at a concentration of about 300 ppm, and Reb A is present at a concentration of about 100 ppm. The pH of the beverage is preferably between about 2.5 to about 4.2, such as, for example, between about 2.5 to about 3.0, about 3.0 to about 3.5, about 3.5 to about 4.0, and about 4.0 to about 4.2.

Methods for improving timing and/or flavor profile

A method of imparting a more sugar-like temporal profile, flavor profile, or both to a sweetenable composition includes combining the sweetenable composition with Reb DEMNO or a sweetener composition of the present invention, ie, a sweetener composition comprising Reb DEMNO.

The method may further include adding other sweeteners, additives, functional ingredients, and combinations thereof. Any sweetener, additive, or functional ingredient described in detail herein may be used.

As used herein, "sugar-like" characteristics include any characteristics similar to sucrose, and include, but are not limited to, maximum response, flavor profile, temporal profile, adaptation behavior, mouthfeel, concentration/response function, tastant/ and flavor/sweetness interactions, spatial pattern selectivity, and temperature effects.

The flavor profile of a sweetener is a quantitative characteristic of the relative intensities of all the taste attributes exhibited.

These characteristics have dimensions in which the taste of sucrose differs from the taste of Reb DEMNO. Of these, however, the flavor profile and temporal profile are particularly important. In a single tasting of a sweet food or beverage, differences can be noted between those observed for sucrose and Reb DEMNO in (1) the attributes that make up the flavor profile of the sweetener, and (2) the speed at which the sweetness appears and dissipates, which makes up the temporal profile of the sweetener.

An expert sensory panel that tasted compositions comprising sugar and compositions comprising Reb DEMNO (both with and without additives) determined whether the profile was more sugar-like, and provided their impression of the similarity of the profiles of the sweetener compositions (both with and without additives) to those comprising sugar. A suitable process for determining whether a composition has a more sugar-like taste is described in the embodiments described below.

In a specific embodiment, a group of assessors is used to measure the reduction of sweetness lingering. In short, a group of assessors (usually 8 to 12 individuals) are trained to evaluate the sweetness perception and measure the sweetness at several time points from when the sample is initially placed in the mouth until 3 minutes after it is coughed out. Using statistical analysis, the results between samples containing additives and samples not containing additives are compared. The reduction in the score at the time point measured after the sample has been cleared from the mouth indicates the presence of a reduction in sweetness perception.

The evaluation panelists can be trained by using methods well known to those of ordinary skill in the art. In a specific embodiment, the evaluation panelists can be trained by using Spectrum ^TM descriptive analysis methods (Meilgaard et al., Sensory Evaluation Techniques, 3rd edition, Chapter 11). Desirably, the focus of the training should be to identify and measure basic tastes; in particular, sweetness. In order to ensure the accuracy and repeatability of the result, each evaluation member should repeat the measurement of about 3 to about 5 times of the sweetness of each sample to reduce, stop at least 5 minutes between each repetition and/or sample, and rinse well with water to clean the mouth.

Typically, the method for measuring sweetness includes taking 10 mL of sample into the mouth, holding the sample in the mouth for 5 seconds and gently turning the sample in the mouth, rating the sweetness intensity perceived in 5 seconds, expectorating the sample (no swallowing after expectorating the sample), rinsing with a mouthful of water (e.g., vigorously moving the water in the mouth, as with a mouthwash) and expectorating the rinse water, rating the sweetness intensity perceived immediately after expectorating the rinse water, waiting for 45 seconds, while during the waiting period of that 45 seconds, identifying the time of maximum perceived sweetness intensity and rating the sweetness intensity at that time (normal movement of the mouth and swallowing when necessary), rating the sweetness intensity after another 10 seconds, rating the sweetness intensity after another 60 seconds (accumulated 120 seconds after rinsing), and rating the sweetness intensity after another 60 seconds (accumulated 180 seconds after rinsing). Take a 5-minute interval between samples and rinse well with water to clean the mouth.

Delivery System

Reb DEMNO and sweetener compositions comprising Reb DEMNO can also be formulated into various delivery systems with improved ease of handling and dissolution rate. Non-limiting examples of suitable delivery systems include sweetener compositions co-crystallized with sugars or polyols, agglomerated sweetener compositions, compacted sweetener compositions, dried sweetener compositions, granular sweetener compositions, spheronized sweetener compositions, granulated sweetener compositions, and co-dried sweetener compositions.

Co-crystallized sugar/polyol and Reb DEMNO compositions

In a specific embodiment, the sweetener composition is co-crystallized with sugar or polyols in various ratios to prepare a substantially water-soluble sweetener that is substantially free of dust problems. Sugar as used herein generally refers to sucrose (C ₁₂ H ₂₂ O ₁₁ ). Polyol as used herein is synonymous with sugar alcohol, generally referring to molecules containing more than one hydroxyl group, erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, isomalt, propylene glycol, glycerol (glycerol), threitol, galactitol, palatinose, reduced isomaltose-oligosaccharides, reduced wood-oligosaccharides, reduced gentio-oligosaccharides, reduced maltose syrup, reduced glucose syrup, and sugar alcohols or any other carbohydrates that can be reduced that adversely affect the taste of the sweetener composition.

In another embodiment, a method for preparing a sugar or polyol co-crystallized Reb DEMNO sweetener composition is provided. Such methods are well known to those of ordinary skill in the art and are discussed in more detail in U.S. Patent No. 6,214,402. According to some embodiments, a method for preparing a sugar or polyol co-crystallized Reb DEMNO sweetener composition may include the steps of preparing a supersaturated sugar or polyol syrup, adding a predetermined amount of a premix containing a desired ratio of Reb DEMNO sweetener composition and sugar or polyol to the syrup, while vigorously mechanically stirring, removing the sugar or polyol syrup mixture by heating, and rapidly cooling the sugar or polyol syrup mixture during crystallization and coagulation, while vigorously stirring. During processing, the Reb DEMNO sweetener composition is introduced as an integral part of the sugar or polyol matrix, thereby preventing the sweetener composition from separating or settling out of the mixture during handling, packaging or storage. The resulting product can be granular, free-flowing, non-caking and can be easily and evenly dispersed or dissolved in water.

In a specific embodiment, the sugar or polyol syrup may be commercially available or obtained by effectively mixing a sugar or polyol with water. The sugar or polyol syrup may be supersaturated by removing water from the syrup to produce a syrup having a solids content ranging from about 95% to about 98% by weight of the syrup. Typically, water may be removed from the sugar or polyol syrup by heating and stirring the sugar or polyol syrup while maintaining the sugar or polyol syrup at a temperature of not less than about 120° C. to prevent premature crystallization.

In another specific embodiment, a dry premix is prepared by mixing the Reb DEMNO sweetener composition and a sugar or a polyol in the desired amounts. According to certain embodiments, the weight ratio of the Reb DEMNO sweetener composition to the sugar or polyol is in the range of about 0.001:1 to about 1:1, such as, for example, in the range of about 0.001:1 to about 0.01:1, about 0.01:1 to about 0.1:1, and about 0.1:1 to about 1:1. Other components, such as flavorings or other high-potency sweeteners, may also be added to the dry premix as long as the amount does not adversely affect the overall taste of the sugar co-crystallized sweetener composition.

The amounts of the premix and the supersaturated syrup can be varied in order to produce products with different sweetness levels. In particular embodiments, the Reb DEMNO sweetener composition is present in an amount from about 0.001% to about 50% by weight of the final product, such as, for example, from about 0.001% to about 0.01%, from about 0.01% to about 0.1%, from about 0.1% to about 1%, from about 1% to about 2.5%, from about 2.5% to about 10%, from about 10% to about 20%, from about 20% to about 30%, from about 30% to about 40%, and from about 40% to about 50%.

The sweetener composition of sugar or polyol co-crystallization of the present invention is applicable to any composition that can be sweetened, to replace conventional caloric sweeteners and other types of low-caloric or non-caloric sweeteners. In addition, the sweetener composition of sugar or polyol co-crystallization as herein described can be combined with a bulking agent in certain embodiments, and its non-limiting examples include dextrose, maltodextrin, lactose, inulin, polyol, polydextrose, cellulose and cellulose derivatives. Such a product can be particularly suitable for use as a desktop sweetener.

Agglomerated sweetener compositions

In certain embodiments, a coacervate of a Reb DEMNO sweetener composition is provided. As used herein, "sweetener coacervate" refers to a plurality of sweetener particles that are aggregated and held together. Examples of sweetener coacervates include, but are not limited to, coacervates, extrudates, and granules held by a binder.

Adhesive-retained aggregates

According to certain embodiments, a method for preparing a coagulum of a Reb DEMNO sweetener composition, a binder, and a carrier is provided. Methods for preparing a coagulum are well known to those of ordinary skill in the art and are disclosed in more detail in U.S. Patent No. 6,180,157. Generally described, according to certain embodiments, the method for preparing a coagulum comprises the steps of preparing a premix solution comprising a Reb DEMNO sweetener composition and a binder in a solvent, heating the premix to a temperature sufficient to effectively form a mixture of the premix, applying the premix to a fluidized carrier by a fluidized bed agglomerator, and drying the resulting coagulum. The sweetness level of the resulting coagulum can be adjusted by varying the amount of the sweetener composition in the premix solution.

In a specific embodiment, the premix solution comprises a Reb DEMNO sweetener composition and a binder that are dissolved in a solvent. The binder can have enough bond strength to promote cohesion. Non-limiting examples of suitable binders include maltodextrin, sucrose, gellan gum, gum arabic, hydroxypropyl methylcellulose, carboxymethylcellulose, polyvinyl pyrrolidone, cellobiose, protein and mixtures thereof. The Reb DEMNO sweetener composition and the binder can be dissolved in the same solvent or in two different solvents. In embodiments where different solvents are used to dissolve the sweetener composition and the binder, before being merged into a single solution, the solvents can be the same or different. Any solvent that dissolves the Reb DEMNO sweetener composition and/or the binder can be used. Desirably, the solvent is a food grade solvent, and its non-limiting examples include ethanol, water, isopropanol, methanol and mixtures thereof. To achieve complete mixing of the premix, the premix may be heated to a temperature in the range of about 30° C. to about 100° C., such as, for example, in the range of about 30° C. to about 50° C., about 50° C. to about 75° C., and about 75° C. to about 100° C. The term “achieving mixing” as used herein refers to a mixture that is sufficient to form a mixture.

The content of adhesive in the solution can change according to various factors, including the bonding strength of the specific adhesive selected and the specific solvent. Adhesive is usually present in the premix solution in an amount of about 1% weight to about 50% weight of the premix solution, such as about 1% weight to about 5% weight, about 5% weight to about 15% weight, about 15% weight to about 25% weight, about 25% weight to about 35% weight, about 35% weight to about 45% weight and about 45% weight to about 50% weight. The weight ratio of adhesive and Reb DEMNO sweetener composition in the premix solution can be from as low as about 1:10 to as high as about 10:1 changes, such as for example about 1:10 to about 1:5, about 1:5 to about 1:1, about 1:1 to about 5:1 and about 5:1 to about 10:1. The weight ratio of adhesive and Reb DEMNO sweetener composition can also be changed to about 2:1 from about 0.5:1.0.

After the premix solution is prepared, the premix solution is applied to a fluidized carrier using a fluidized bed agglomerator. Preferably, the premix is applied to the fluidized carrier by spraying the premix onto the fluidized carrier to form an agglomerate of the Reb DEMNO sweetener composition and the carrier. The fluidized bed agglomerator can be any suitable fluidized bed agglomerator known to those of ordinary skill in the art. For example, the fluidized bed agglomerator can be a batch, continuous or continuous turbulent agglomerator.

The carrier is fluidized and its temperature is adjusted to between about 20°C and about 50°C, or between about 35°C and about 45°C. In some embodiments, the carrier is heated to about 40°C. The carrier can be placed in a removable bowl of a fluidized bed agglomerator. After the bowl is fixed to the fluidized bed agglomerator, the carrier is fluidized and heated by adjusting the inlet air temperature as needed. The inlet air temperature can be maintained between about 50°C and about 100°C, such as, for example, between about 50°C and about 60°C, about 60°C and about 70°C, about 70°C and about 80°C, about 80°C and about 90°C, and about 90°C and about 100°C. For example, in order to heat the fluidized carrier to about 40°C, the inlet air temperature can be adjusted to between about 70°C and about 75°C.

Once the fluidized carrier reaches the desired temperature, the premix solution can be applied through the nozzle of the fluidized bed agglomerator. The premix solution can be sprayed onto the fluidized carrier at any speed that effectively produces a coagulum with a desired particle size distribution. Those skilled in the art will recognize that many parameters can be adjusted to obtain a desired particle size distribution. After the spraying is complete, the coagulum can be allowed to dry. In certain embodiments, the coagulum is dried until the outlet air temperature reaches about 35 to about 40°C.

The amount of Reb DEMNO sweetener composition, carrier, and binder in the resulting agglomerate can vary depending on various factors, including the choice of binder and carrier, and the desired sweetening efficacy of the agglomerate. It will be appreciated by one of ordinary skill in the art that the amount of Reb DEMNO sweetener composition present in the agglomerate can be controlled by varying the amount of Reb DEMNO sweetener composition added to the premix solution. The amount of sweetness is particularly important when attempting to match the sweetness delivered by other natural and/or synthetic sweeteners in various products.

In one embodiment, the weight ratio of carrier to Reb DEMNO sweetener composition is between about 1:10 and about 10:1, such as, for example, between about 1:10 and about 1:5, about 1:5 and about 1:1, about 1:1 and about 5:1, and about 5:1 and about 10:1. In one embodiment, the Reb DEMNO sweetener composition is present in the agglomerate in an amount in the range of about 0.1% to about 99.9% by weight, such as, for example, between about 0.1% to about 1%, about 1% to about 10%, about 10% to about 50%, about 50% to about 90%, about 90% to about 99%, and about 99% to 99.9% by weight, the carrier is present in the agglomerate in an amount in the range of about 50% to about 99.9% by weight, such as, for example, in the range of about 50% to about 60%, about 60% to about 70%, about 70% to about 80%, about 80% to about 90%, and about 90% to 99.9% by weight, and the binder is present in the agglomerate in an amount in the range of about 0.1 to about 15% by weight, such as, for example, in the range of about 0.1% to about 1%, about 1% to about 5%, about 5% to about 10%, and about 10% to about 15%, based on the total weight of the agglomerate. In another embodiment, the Reb DEMNO sweetener composition is present in the agglomerate in an amount ranging from about 50% to about 99.9% by weight, such as, for example, in the ranges of about 50% to about 60%, about 60% to about 70%, about 70% to about 80%, about 80% to about 90%, and about 90% to 99.9% by weight, the carrier is present in the agglomerate in an amount ranging from about 75 to about 99% by weight, such as, for example, in the ranges of about 75% to about 80%, about 80% to about 85%, about 85% to about 90%, about 90% to about 95%, and about 95% to about 99% by weight, and the binder is present in the agglomerate in an amount ranging from about 1% to about 7% by weight, such as, for example, in the ranges of about 1% to about 2%, about 2% to about 4%, about 4% to about 6%, and about 6% to about 7%.

The particle size distribution of the agglomerate can be determined by screening the agglomerate through screens of various sizes. If desired, the product can also be screened to produce a narrower particle size distribution. For example, a 14 mesh screen can be used to remove large particles and produce a particularly good appearance product, particles smaller than 120 mesh can be removed to obtain an agglomerate with improved flowability, or if desired for a particular application, a narrower particle size distribution can be obtained.

It will be appreciated by those skilled in the art that the particle size distribution of the agglomerates can be controlled by various factors, including the choice of binder, the concentration of the binder in the solution, the spray speed of the spray solution, the atomizing air pressure, and the specific carrier used. For example, increasing the spray speed can increase the average particle size.

In certain embodiments, the coagulants provided herein can be mixed with a mixing agent. As used herein, the mixing agent includes a large number of ingredients commonly used in food or beverages, including but not limited to those used as adhesives, carriers, bulking agents and sweeteners. For example, the coagulants of the present invention can be used to prepare tabletop sweeteners or powdered beverage mixtures by dry mixing the coagulants with the mixing agents commonly used to prepare tabletop sweeteners or powdered beverage mixtures using methods well known to those of ordinary skill in the art.

Extrudate

Also provided in embodiments herein is the extrudate of substantially dust-free and substantially free-flowing Reb DEMNO sweetener composition or the coagulum of extrusion.According to certain embodiments, such granules can use or not use adhesive, use extrusion and spheronization process to form.As used herein, " extrudate " or " sweetener composition of extrusion " refer to the cylindrical, free-flowing, relatively non-dusty, mechanically strong granules of Reb DEMNO sweetener composition.As used herein, term " ball " or " sweetener composition of spheronization " refer to relatively spherical, smooth, free-flowing, relatively non-dusty, mechanically strong granules.Although ball generally has smoother surface, and can be stronger/harder than extrudate, extrudate provides cost advantage owing to needing less processing.If desired, ball of the present invention and extrudate can be further processed to form various other granules, as for example, by grinding or chopping.

In another embodiment, a method of preparing an extrudate of a Reb DEMNO sweetener composition is provided. Such methods are well known to those of ordinary skill in the art and are described in more detail in U.S. Patent No. 6,365,216. Generally described, a method of preparing a sweetener extrudate of a Reb DEMNO sweetener composition comprises the steps of: mixing the Reb DEMNO sweetener composition, a plasticizer, and an optional binder to form a wet mass; extruding the wet mass to form an extrudate; and drying the extrudate to obtain particles of the Reb DEMNO sweetener composition.

Non-limiting examples of suitable plasticizers include, but are not limited to, water, glycerol, and mixtures thereof. According to certain embodiments, the plasticizer is typically present in the wet mass in an amount of about 4% to about 45% by weight, such as, for example, about 4% to about 15%, about 15% to about 25%, about 25% to about 35%, and about 35% to about 45% by weight.

The limiting examples of suitable adhesives include but are not limited to polyvinylpyrrolidone (PVP), maltodextrin, microcrystalline cellulose, starch, hydroxypropyl methylcellulose (HPMC), methylcellulose, hydroxypropyl cellulose (HPC), gum arabic, gelatin, xanthan gum, and mixtures thereof. Adhesives are usually present in wet mass in an amount of about 0.01% to about 45% by weight, such as, for example, about 0.01% to about 0.5%, about 0.5% to about 1%, about 1% to about 10%, about 10% to about 20%, about 20% to about 30%, about 30% to about 40%, and about 40% to about 45%.

In a particular embodiment, the binder can be dissolved in the plasticizer to form a binder solution, which is then added to the Reb DEMNO sweetener composition and other optional ingredients. The use of a binder solution provides better distribution of the binder through the wet mass.

Other optional ingredients that may be included in the wet mass include carriers and additives. One of ordinary skill in the art will readily appreciate that carriers and additives may comprise any typical food ingredient and will readily determine the appropriate amount of a given food ingredient to obtain a desired flavor, taste or functionality.

Methods of extruding a wet mass to form an extrudate are well known to those of ordinary skill in the art. In a specific embodiment, the extrudate is formed using a low pressure extruder equipped with a die. The extrudate can be cut to length using a cutting device connected to the discharge end of the extruder to form an extrudate that is substantially cylindrical in shape and can have the form of noodles or pellets. The shape and size of the extrudate can vary depending on the shape and size of the die opening and the use of the cutting device.

After extruding the extrudate, the extrudate is dried by using methods well known to those of ordinary skill in the art. In a specific embodiment, a fluidized bed dryer is used to dry the extrudate.

Optionally, in a specific embodiment, the extrudate is formed into a sphere before the drying step. The spheres are formed by loading the extrudate into a spherical pelletizer, which consists of a vertical hollow cylinder (bowl) with a horizontal rotating disc (friction plate) therein. The rotating disc surface can have various textures suitable for specific purposes. For example, a grid pattern corresponding to the desired particle size can be used. The extrudate is formed into a sphere by contact with the rotating disc and by collisions between the bowl wall and the particles. During ball formation, excess moisture can be transferred to the surface or thixotropic behavior can be exhibited by the extrudate, requiring a slight dusting of a suitable powder to reduce the probability that the particles will stick together.

As previously mentioned, the extrudate of the Reb DEMNO sweetener composition may be formed with or without a binder. It is desirable to form an extrudate without a binder because it reduces costs and improves product quality. In addition, the number of additives in the extrudate is reduced. In embodiments where a binder is not used to form an extrudate, the method for forming the granules further comprises the steps of heating the wet mass and plasticizer of the Reb DEMNO sweetener composition to promote the wet mass to combine. Desirably, the wet mass is heated to a temperature of about 30°C to about 90°C, such as, for example, about 30°C to about 40°C, about 40°C to about 50°C, about 50°C to about 60°C, about 60°C to about 70°C, about 70°C to about 80°C, and about 80°C to about 90°C. According to certain embodiments, the method for heating the wet mass includes, but is not limited to, an oven, a kneader with a heating jacket, or an extruder with mixing and heating capabilities.

Granules

In one embodiment, a granular form of the Reb DEMNO sweetener composition is provided. As used herein, the terms "granules," "granular form," and "particulate form" are synonymous and refer to a free-flowing, substantially non-dusty, mechanically strong agglomerate of the Reb DEMNO sweetener composition.

In another embodiment, a method of preparing a granular form of a Reb DEMNO sweetener composition is provided. Granulation methods are well known to those of ordinary skill in the art and are described in more detail in PCT Publication WO 01/60842. In certain embodiments, such methods include, but are not limited to, spray granulation with a wet binder, powder compaction, pulverization, extrusion, and tumbling agglomeration with or without fluidization. Due to its simplicity, a preferred method of forming granules is powder compaction. Also provided herein is a compacted form of a sweetener Reb DEMNO composition.

In one embodiment, a method of forming granules of a Reb DEMNO sweetener composition comprises the steps of compacting the Reb DEMNO sweetener composition to form compacts; fracturing the compacts to form granules; and optionally screening the granules to obtain granules of the Reb DEMNO sweetener composition having a desired particle size.

Any known compacting technique can be used to achieve the method of compacting the Reb DEMNO sweetener composition. The limiting examples of such technology include roller compacting, tableting, pre-tabletting, hammer extrusion (ram extrusion), plunger pressing, roller briquetting, reciprocating piston processing, molding and micronization. Compacting can take any form that can subsequently experience size reduction, and its limiting examples include thin slices, sheets, small pieces, blocks and pellets. It should be understood by those of ordinary skill in the art that the shape and appearance of the compacted object will change according to the shape and surface characteristics of the device used in the compacting step. Therefore, the compaction can be smooth, wrinkled, grooved or pillowcase-like, etc. In addition, the actual size and characteristics of the compaction will depend on the type of equipment and operating parameters adopted during the compaction.

In particularly desirable embodiments, the Reb DEMNO sweetener composition is compacted into thin sheets or sheets using a roller compactor. Conventional roller compacting devices typically include a hopper and a pair of rotating rollers for feeding the sweetener composition to be compacted, one or both of which are fixed on their axles, and a roller is optionally slightly movable. The Reb DEMNO sweetener composition is supplied to the device by gravity or force-feeding screw through the hopper. The actual size of the compacted object obtained depends on the size of the device used, such as the roller width and the hardness, density and thickness of the compacted object. Factors such as the pressure, rolling speed, feed rate and feed screw amplifier used during the compacting process.

In a specific embodiment, prior to the compacting step, the sweetener composition is degassed, resulting in more efficient compaction and formation of stronger compacts and resulting granules. Degassing can be achieved by any known means, non-limiting examples of which include screw feeding, vacuum degassing, and combinations thereof.

In another specific embodiment, before compacting, a dry binder is mixed with the Reb DEMNO sweetener composition. Using a dry binder can improve granule strength and assist their dispersion in liquid. Suitable dry binders include, but are not limited to, pregelatinized corn starch, microcrystalline cellulose, hydrophilic polymers (e.g., methylcellulose, hydroxypropyl methylcellulose, hydroxypropyl cellulose, polyvinyl pyrrolidone, alginate, xanthan gum, gellan gum and gum arabic) and mixtures thereof. According to certain embodiments, the dry binder is generally present in an amount of about 0.1% to about 40% by weight based on the gross weight of the mixture of the Reb DEMNO sweetener composition and the dry binder, such as, for example, about 0.1% to about 1%, about 1% to about 5%, about 5% to about 10%, about 10% to about 20%, about 20% to about 30%, and about 30% to about 40% by weight.

After the compacting step, the compacts are broken to form granules. Any suitable means of breaking the compacts can be used, including grinding. In a specific embodiment, breaking the compacts is achieved in multiple steps using various grinding opening sizes. In certain embodiments, breaking the compacts is achieved in two steps: a breaking step and a subsequent grinding step. The breaking step of the compacts is reduced to "exceed" the number of times in the granular sweetener sweetener composition. "Exceeding" as used herein refers to a material larger than the maximum desired particle size.

Fracturing the compacts generally results in granules of varying sizes. Therefore, it may be desirable to screen the granules to obtain granules having a desired particle size range. Any conventional means for screening granules may be used to screen the granules, including sifters and screens. After screening, the "fines" may optionally be recycled through a compactor. As used herein, "fines" refers to material that is smaller than the minimum desired particle size.

Co-dried sweetener compositions

Also provided herein is a co-dried Reb DEMNO sweetener composition comprising a Reb DEMNO sweetener composition and one or more auxiliary agents. As used herein, auxiliary agents include any composition that is desired to be used with and compatible with the product to be prepared. It will be appreciated by those skilled in the art that one or more functionalities will be selected based on the desired product application for which the sweetener composition will be used. A large number of ingredients are compatible with the sweetener composition and can be selected for this functional property. In one embodiment, one or more auxiliary agents include at least one additive of the sweetener composition described below herein. In another embodiment, one or more auxiliary agents include a bulking agent, a flow agent, an encapsulating agent, or a mixture thereof.

In another embodiment, a method of co-drying a Reb DEMNO sweetener composition and one or more adjuvants is provided. Such methods are well known to those of ordinary skill in the art and are described in more detail in PCT Publication WO 02/05660. The Reb DEMNO sweetener composition and one or more adjuvants may be co-dried using any conventional drying apparatus or technique known to those of ordinary skill in the art. Suitable drying methods include, but are not limited to, spray drying, convection drying, vacuum drum drying, freeze drying, pan drying, and high speed paddle drying.

In a particularly desirable embodiment, the Reb DEMNO sweetener composition is spray dried. A solution of the Reb DEMNO sweetener composition and one or more desired adjuvants is prepared. The solution may be prepared using any suitable solvent or solvent mixture, depending on the solubility characteristics of the Reb DEMNO sweetener composition and one or more adjuvants. According to certain embodiments, suitable solvents include, but are not limited to, water, ethanol, and mixtures thereof.

In one embodiment, the solution of the Reb DEMNO sweetener composition and one or more adjuvants may be heated prior to spray drying. The temperature may be selected based on the solubility properties of the dry ingredients and the desired viscosity of the spray drying feed.

In another embodiment, a non-reactive, non-flammable gas (e.g., carbon dioxide) may be added to a solution of the Reb DEMNO sweetener composition and one or more adjuvants prior to atomization. The non-reactive, non-flammable gas may be added in an amount effective to reduce the bulk density of the resulting spray-dried product and to produce a product comprising hollow spheres.

Spray drying methods are well known to those of ordinary skill in the art. In one embodiment, a solution of the Reb DEMNO sweetener composition and one or more adjuvants is fed through a spray dryer at an air inlet temperature in the range of about 150°C to about 350°C, such as, for example, about 150°C to about 200°C, about 200°C to about 250°C, about 250°C to about 300°C, and about 300°C to about 350°C. Increasing the air inlet temperature with a constant air flow can produce a product with a reduced bulk density. According to certain embodiments, the air outlet temperature can be at about 70°C to about 140°C, such as, for example, about 70°C to about 80°C, about 80°C to about 90°C, about 90°C to about 100°C, about 100°C to about 110°C, about 110°C to about 120°C, about 120°C to about 130°C, and about 130°C to about 140°C. Lowering the gas outlet temperature can result in a product with a higher moisture content, which allows for easy agglomeration in a fluid bed dryer, resulting in a sweetener composition with better dissolution properties.

Any suitable spray drying device can be used to co-dry the Reb DEMNO sweetener composition and one or more auxiliary agents. It will be appreciated by those of ordinary skill in the art that the device selection can be customized to obtain a product with a specific physical property. For example, a foam spray drying can be used to produce a low bulk density product. Alternatively, a fluidized bed can be connected to the outlet of a spray dryer to produce a product with an enhanced dissolution rate for an instant product. Examples of spray dryers include, but are not limited to, a downstream nozzle tower spray dryer, a downstream rotary atomizer spray dryer, a countercurrent nozzle tower spray dryer, and a mixed flow fountain nozzle spray dryer.

The resulting co-dried Reb DEMNO sweetener composition can be further processed or separated using techniques well known to those of ordinary skill in the art. For example, a screening technique can be used to obtain a desired particle size distribution. Alternatively, the resulting co-dried Reb DEMNO sweetener composition can be further processed, such as agglomeration.

Spray drying uses atomizable liquid feeds (e.g., slurries, solutions, and suspensions). Alternative drying methods can be selected depending on the feed type. For example, freeze drying and pan drying can handle not only liquid feeds, as described above, but also wet cakes and pastes. Paddle dryers, such as high-speed paddle dryers, can accept slurries, suspensions, gels, and wet cakes. Vacuum drum drying methods, although primarily used with liquid feeds, have great flexibility in handling feeds with a wide range of viscosities.

The resulting co-dried Reb DEMNO sweetener compositions have surprising functionality for use in a variety of systems. Significantly, the co-dried Reb DEMNO sweetener compositions are believed to have superior taste properties. Additionally, the co-dried Reb DEMNO sweetener compositions may have improved stability in low-moisture systems.

The present invention is further described by the following examples, which cannot be interpreted as limiting its scope in any way. On the contrary, it should be clearly understood that various other embodiments, modifications and equivalents thereof can be adopted, which are after reading this specification, without departing from the spirit of the present invention and/or the scope of the appended claims, those skilled in the art can think of.

Example

Example 1

Preparation of Reb DEMNO Compositions from Commercially Available Stevia Extracts

A polymer resin was used in the preparation of the Reb DEMNO composition. The resin was a copolymer of N-vinyl pyrrolidone (NVP) and ethylene glycol dimethacrylate (EGDMA) having an average particle size (volume weighted average) of 60 microns. The resin was prepared by stirring an aqueous suspension of N-vinyl pyrrolidone (NVP) and ethylene glycol dimethacrylate (EGDMA) in a 50:50 mass ratio of NVP:EGDMA at 75°C using lauroyl peroxide as a polymerization initiator and in the presence of cyclohexanol and 1-dodecanol. The feed material used was a commercial Stevia extract "SGD" containing (wt/wt, dry basis) 23.78% Reb D, 2.58% Reb E, 11.31% Reb M, 6.88% Reb N, 5.53% Reb O, 9.29% Reb A, 3.25% steviol glycosides, 0.28% Reb F, 1.75% Reb C, 0.11% dulcoside A, 0.77% rubusoside, 0.36% Reb B, 0.07% steviolbioside. The polymer resin (2 g, free flowing) was mixed with ethanol (about 20 mL) to obtain a slurry and loaded into a glass column to obtain a packed column with a bed volume of 12 mL. The column was connected to a peristaltic pump and 99% ethanol (20 mL) was pumped through the resin at 54 mL/hr. The resin was then washed with water (40 mL) at 54 mL/hr. A feed of a commercial stevia sample "SGD" (150 mg dry sample dissolved in 16 mL water) was loaded onto the resin at 54 mL/hr. The resin was then eluted (flow rate 54 mL/hr) with 64 mL of water, 96 mL of 15% ethanol, 96 mL of 40% ethanol, and 80 mL of 99% ethanol, collecting fractions according to each eluent used. The fractions were evaporated on a rotary evaporator and vacuum oven (overnight, 40°C, <1 mbar) to obtain a dry product. The feed and RebDEMNO/T13SG ratios of the various fractions are shown in Table 1.

Table 1.

Example 2

Beverage preparations

Cola-flavored carbonated drinks:

Carbonated cola beverage samples were prepared using Reb DEMNO prepared according to Example 1 as the sole sweetener. Regular and diet cola beverages were prepared using the ingredients listed in Table 2. The diet beverages were sweetened using different stevia extracts (containing either 99.7% Reb DEMNO/T13SG ratio or 98% Reb A/T13SG ratio). The concentration of the stevia composition used was 500 ppm.

Table 2.

A 5-member trained panelist evaluated the samples for seven characteristics - sweetness, bitterness, sweetness linger, bitterness linger, astringency, brown spice, and vanilla notes in duplicate. The sugar-free beverage containing Reb DEMNO showed significantly higher sweetness and directed higher spice notes compared to the control beverage containing HFCS and the sugar-free beverage containing Reb A. There was no difference in vanilla notes and unfavorable attributes such as bitterness, sweetness linger, bitterness linger, astringency compared to the control beverage containing HFCS. The overall taste of the formulation containing Reb DEMNO was superior in terms of unfavorable attributes such as bitterness, sweetness linger, bitterness linger, astringency compared to the sugar-free beverage containing Reb A.

Claims (9)

1. A method for preparing a steviol glycoside composition, the method comprising the steps of: (a) passing an initial mixture of steviol glycosides through a column packed with a polymer resin, the initial mixture of steviol glycosides further comprising a solvent selected from alcohol, water, an aqueous acid solution or a combination thereof, wherein Reb D, Reb E, Reb M, Reb N and Reb O are weakly retained in the column; and (b) eluting a fraction having a high content of Reb D, Reb E, Reb M, Reb N and Reb O with an initial elution solvent selected from pure water, aqueous acid, alcohol-water or an alcohol-aqueous acid mixture having less than 40% by volume of alcohol to obtain a solution having a high content of Reb D, Reb E, Reb M, Reb N and Reb O, wherein the Reb DEMNO/T13SG ratio in the solution is higher than the Reb DEMNO/T13SG ratio of the initial mixture of steviol glycosides, The polymer resin is a copolymer of N-vinyl pyrrolidone and ethylene glycol dimethacrylate, Wherein "Reb DEMNO/T13SG ratio" is the ratio of "Reb DEMNO content" to "T13SG content" on a dry basis according to the following formula: {Reb DEMNO content/T13SG content}×100%, Wherein “Reb DEMNO content” refers to the sum of the contents of Reb D, Reb E, Reb M, Reb N and Reb O on a dry basis, and “T13SG content” refers to the sum of the contents of the following 13 steviol glycosides on a dry basis: Reb A, Reb B, Reb C, Reb D, Reb E, Reb F, Reb M, Reb N, Reb O, steviol glycosides, steviolbiosides, dulcoside A and rubusoside. 2. The process of claim 1 further comprising removing the initial elution solvent to obtain a dry solid having a higher Reb DEMNO/T13SG ratio than the dry solid of the initial mixture. 3. The method of claim 1, further comprising: one or more steps of eluting a fraction using one or more alcohol-water mixtures or one or more alcohol-aqueous acid mixtures having a higher alcohol volume percentage than the initial elution solvent by 5-99%, wherein the fraction has a low content of Reb D, Reb E, Reb M, Reb N and Reb O, to obtain an elution solution having a low content of Reb D, Reb E, Reb M, Reb N and Reb O, wherein the Reb DEMNO/T13SG ratio is lower than the Reb DEMNO/T13SG ratio of the initial mixture of steviol glycosides. 4. The method of claim 3, further comprising removing the solvent mixture from the elution solution to obtain a dry solid or dry solids having a lower Reb DEMNO/T13SG ratio than the dry solids of the initial mixture of steviol glycosides. 5. The method of claim 1, further comprising the step of regenerating the column with a regeneration solvent for subsequent steviol glycoside loading, wherein the regeneration solvent is selected from the group consisting of pure water, aqueous acid, water with less than 5% alcohol by volume, aqueous acid with less than 5% alcohol by volume, and combinations thereof. 6. The method of claim 1, wherein the polymer resin has the following characteristics: (a) Particle size of 1 μm to 1200 μm; (b) A nitrogen content of 0% to 99% by mass. 7. The method of claim 1 wherein the polymer resin is prepared in the presence of lauroyl peroxide. 8. The method of claim 1, wherein the polymer resin is prepared in the presence of the following substances, which are then removed by washing the resin prior to use: a) cyclohexanol, b) 1-dodecanol, c) toluene, d) methyl isobutyl ketone, e) calcium chloride dihydrate, f) sodium phosphate dodecahydrate, g) calcium lignin sulfonate, h) polyvinyl alcohol, i) hydrochloric acid, j) methanol, k) ethyl acetate, 1) sodium chloride, m) water, n) Sodium lauryl sulfate. 9. The method of claim 1, wherein the polymer resin is prepared by stirred aqueous suspension polymerization, spray polymerization, or emulsion polymerization.