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WO2024233155A1 - Compositions d'édulcorant - Google Patents

Compositions d'édulcorant Download PDF

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Publication number
WO2024233155A1
WO2024233155A1 PCT/US2024/026747 US2024026747W WO2024233155A1 WO 2024233155 A1 WO2024233155 A1 WO 2024233155A1 US 2024026747 W US2024026747 W US 2024026747W WO 2024233155 A1 WO2024233155 A1 WO 2024233155A1
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WIPO (PCT)
Prior art keywords
reb
composition
ppm
rebaudioside
beverage
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PCT/US2024/026747
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Daniel Scott GASPARD
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Cargill Inc
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Cargill Inc
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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A23L27/36—Terpene glycosides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/52—Adding ingredients
    • A23L2/60—Sweeteners

Definitions

  • Steviol glycosides are a class of sweet-tasting glycosylated diterpene compounds commonly obtained from the leaves of Stevia rebaudiana. Various such compounds are known, each having differing properties, taste profiles, and chemical structures. A typical steviol glycoside is characterized by a single steviol backbone and contains one or more carbohydrate residues at C13 and C19.
  • rebaudioside A contains a branched group of three glucosyl groups at C13 and a single ⁇ -glucosyl at C19, while rebaudioside D contains the same unit at C13 but a diglucosyl at C19.
  • Steviol glycosides can serve as powerful sweeteners even at low concentrations—providing a sweetening effect approximately 150 to 450 times greater than an equivalent amount of sugar. [0004] Steviol glycosides offer a non-caloric alternative to traditional caloric sweeteners such as sugar, glucose, sucrose, and/or fructose. However, in some cases, consumers may discern that the sensory and temporal taste profile of steviol glycosides differ somewhat from traditional caloric sweeteners.
  • steviol glycoside compositions may provide comparably reduced sweetness intensity, increased sweetness linger, increased bitterness, and unfamiliar sensory attributes, such as astringency and metallic tastes, when compared to traditional sweeteners.
  • These sensory attributes can limit the use of steviol glycosides in various consumer products, particularly those which seek to use steviol glycosides in the highest concentrations.
  • consumers have favored steviol glycosides as a low-calorie sweetener due, in part, to the fact that such compounds have the potential to be naturally obtained from botanical sources.
  • Further improvements to sweetener compositions are desired.
  • the present disclosure provides a sweetening amount of rebaudioside EE (Reb EE), wherein Reb EE may be a steviol glycoside compound of Formula I:
  • Reb EE may be present in the sweetener composition in an amount such that when the sweetener composition may be added to an aqueous solution at a concentration such that the solution includes 500 ppm Reb EE, the solution has a sweetness between 5.0 and 8.0 SEV, between 5.5 and 7.5 SEV, between 6.0 and 7.0 SEV, between 6.25 and 6.75, or about 6.5 SEV.
  • Reb EE may be present in the sweetener composition in an amount suitable to enhance sweetness of a food or beverage composition containing the sweetener composition.
  • the sweetener composition may include about 0.02 weight percent (wt%) to 100 wt%, about 0.04 wt% to 95 wt%, about 0.05 wt% to about 50 wt%, or about 0.05 wt% to about 10 wt% of Reb EE based on total weight of the composition.
  • the present disclosure provides a food or beverage product containing the sweetener composition described above.
  • the present disclosure provides a beverage product or concentrate including Reb EE having the structure of Formula I as shown above.
  • the beverage product or concentrate may include about 1 ppm to about 50,000 ppm of Reb EE.
  • the beverage product or concentrate may include about 50 ppm to about 500,000 ppm of total steviol glycosides.
  • the present disclosure provides a method for sweetening a food or beverage product.
  • the method includes adding Reb EE to the food or beverage product, wherein sweetness of the food or beverage may be higher than sweetness of the food or beverage prior to addition of Reb EE.
  • the present disclosure provides a method for sweetening a food or beverage product.
  • the method includes adding the sweetener composition described above to the food or beverage product, wherein sweetness of the food or beverage may be higher than sweetness of the food or beverage prior to addition of sweetener composition.
  • the present disclosure provides a use of the sweetener composition described above to increase the sweetness intensity in a food or beverage product.
  • the present disclosure provides an isolated and purified steviol glycoside compound (Reb EE), having the structure of Formula I as shown above.
  • the isolated and purified Reb EE compound may have a purity of about 95 % to about 99.9 %.
  • the present disclosure provides a composition including Reb EE and at least one additional steviol glycoside.
  • PT-974-WO-PCT BRIEF DESCRIPTION OF FIGURES [0015] The drawings illustrate generally, by way of example, but not by way of limitation, various embodiments discussed herein.
  • FIG.1 shows 1 H-NMR NMR spectra of a sample tested in Example 1.
  • FIG.2 shows 13 C-NMR NMR spectra of a sample tested in Example 1.
  • FIG.3 shows a summary of NMR results of a sample tested in Example 1.
  • DETAILED DESCRIPTION This disclosure relates to various compositions, such as sweetener compositions and other compositions, and in particular, steviol glycoside compositions which have improved sensory attributes, such as reduced bitterness and/or reduced off-taste(s).
  • All scientific and technical terms used herein have meanings commonly used in the art unless otherwise specified. The definitions provided herein are to facilitate understanding of certain terms used frequently herein and are not meant to limit the scope of the present disclosure.
  • a range of “about 0.1 % to about 5 %” or “about 0.1 % to 5 %” should be interpreted to include not just about 0.1 % to about 5 %, but PT-974-WO-PCT also the individual values (e.g., 1 %, 2 %, 3 %, and 4 %) and the sub-ranges (e.g., 0.1 % to 0.5 %, 1.1 % to 2.2 %, 3.3 % to 4.4 %) within the indicated range.
  • the statement “about X to Y” has the same meaning as “about X to about Y,” unless indicated otherwise.
  • compositions containing a steviol glycoside component or a mixture of a variety of steviol glycosides include rebaudioside EE (Reb EE).
  • the compositions may optionally include other steviol glycosides.
  • the compositions may optionally include other additional components.
  • the steviol glycoside component can include one or more steviol glycosides.
  • the term steviol glycoside refers to rebaudioside A (Reb A) (CAS # 58543-16-1), rebaudioside B (Reb B) (CAS # 58543-17-2), rebaudioside C (Reb C) (CAS # 63550-99-2), rebaudioside D (Reb D) (CAS # 63279-13-0), rebaudioside E (Reb E) (CAS # 63279-14-1), rebaudioside EE (Reb EE), rebaudioside F (Reb F) (CAS # 438045-89-7), 1,3-stevioside (rebaudioside G or Reb G), rebaudioside I (Reb I) (MassBank Record: FU000332), rebaudioside J (Reb J) (CAS # 1313049-59-0), rebaudioside M (Reb M) (CAS # 1220616-44-3),
  • Steviol glycosides can be used in commercially available form, obtainable from Cargill, Inc. (Wayzata, MN). Rebaudiosides can be isolated and purified before use. [0032] Steviol glycosides are sometimes used as blends, such as blends of Reb D and Reb M. Such blends may be notated as “rebaudioside D/M” or “Reb D/M”, and may include the two rebaudiosides, their related isomers (e.g., natural or synthetic), and/or salts thereof.
  • steviol glycosides comprise a steviol backbone and differ by the presence and arrangement of carbohydrate residues at the C13 and C19 positions of the steviol backbone, according to the atom numbering on the base shown below.
  • the glucopyranosyl residues represent groups R1 and R2 in the following formula:
  • steviol glycosides differ structurally, but the various steviol glycosides also have differing physical and sensory properties.
  • Steviol is represented by the above formula when R 1 and R 2 are hydrogen.
  • Steviol glycosides generally have the formula shown above where steviol is the aglycone backbone and R1 and R2 can each be hydrogen or one or more sugar moieties. These sugar moieties are most commonly glucose, rhamnose, or xylose, but steviol glycosides have been reported that include fructose and deoxyglucose sugar moieties. Table 1 below shows the various steviol glycosides and the corresponding R 1 and R 2 groups: Table 1.
  • steviol glycosides differ structurally, but the various steviol glycosides can also differ in their sensory properties.
  • stevioside comprising three glucose units
  • rebaudioside A comprising four glucose units
  • Both stevioside and rebaudioside A add sweetness but can also be perceived as exhibiting bitterness attributes, especially at higher concentrations.
  • Rebaudioside A exhibits bitterness attributes that increase with concentration and that can limit its use at higher concentrations (e.g., greater than 400 ppm).
  • steviol glycosides can include increased numbers of glycosides and are found in much lower abundance in stevia extracts. Such compounds can sometimes be termed “minor” steviol glycosides, even when they are used as a primary component in a composition.
  • so-called minor steviol glycosides can include rebaudioside D and rebaudioside M, which are found in lower abundance in stevia extracts and comprise different sweetness attributes than the more abundant steviol glycosides. Some of the sweetness attributes of these minor steviol glycosides can be preferred over the major steviol glycosides. For example, rebaudioside D and rebaudioside M exhibit reduced bitterness attributes compared to rebaudioside A.
  • Rebaudioside EE [0037] In some embodiments, the present disclosure relates to an isolated and purified steviol glycoside compound Rebaudioside EE having the structure of Formula I:
  • the isolated and purified Reb EE may have a purity of 90 % or greater, 95 % or greater, or 99 % or greater.
  • the isolated and purified Reb EE may have a purity of 100 % or lower, 99.9 % or lower, 99.5 % or lower, 99 % or lower, 98 % or lower, or 95 % or lower.
  • the isolated and purified Reb EE may have a purity of about 95 % to about 99.9 %.
  • Compositions [0039]
  • the compositions discussed herein may be sweetener compositions or other compositions, such as foodstuffs, including Reb EE.
  • sucrose substitute refers to a low-calorie sweetener or a no-calorie sweetener.
  • low-calorie sweetener refers to sweeteners that have the same or lower intensity of sweetness per gram than sucrose but fewer calories.
  • suitable low- calorie sweeteners may include, but are not limited to, erythritol, arabitol, isomalt, tagatose, erythritol, maltitol, lactitol, sorbitol, mannitol, allulose, allose, sorbose, xylitol, hydrogenated starch hydrolysates, combinations thereof, and the like.
  • the low-calorie sweetener is a sugar alcohol or rare sugar.
  • no-calorie sweetener refers to sweeteners that have no calories, or do not add calories to the compositions to which they are added due to their low usage levels, but have higher intensity of sweetness per gram than sucrose.
  • No-calorie sweeteners may also be known in the art as high intensity sweeteners or high potency sweeteners.
  • No-calorie sweeteners may include, but are not limited to, steviol glycosides, mogrosides, sucralose, acesulfame potassium (acesulfame K), aspartame, saccharin, brazzein, combinations thereof, and the like.
  • Caloric sweeteners refer to ingredients that add both sweetness and calories to the compositions to which they are added.
  • Caloric sweeteners include, but are not limited to, trehalose, glucose, dextrose, fructose, galactose, sucrose, lactose, maltose, palatinose, isomaltulose, cane sugar, beet sugar, rice syrup, invert sugar, honey, agave syrup, maple syrup, high fructose corn syrup, combinations thereof, and the like.
  • sucrose as used herein includes sucrose in various forms including but not limited to standard (e.g., granulated or crystalline) table sugar, powdered sugar, caster sugar, icing sugar, sugar syrup, silk sugar, unrefined sugar, raw sugar cane, and molasses.
  • a composition or sweetener composition of the present disclosure includes rebaudioside EE (Reb EE).
  • the sweetener composition may include Reb EE with one or more additional steviol glycosides.
  • the one or more additional steviol glycosides may be selected from steviolmonoside, steviolbioside, stevioside, rebaudioside A (Reb A), rebaudioside B (Reb B), rebaudioside C (Reb C), rebaudioside D (Reb D), rebaudioside DG (Reb DG), rebaudioside E (Reb E), rebaudioside F (Reb F), rebaudioside J (Reb J), rebaudioside M (Reb M), rebaudioside N (Reb N), rebaudioside O (Reb O), rebaudioside V2 (Reb V2), rubusoside, dulcoside A, steviol-13-monoside, steviol-19-monoside, 13-[( ⁇ -D- PT-974-WO-PCT glucopyranosyl)oxy)kaur-16-en-18-oic acid 2-O- ⁇ -D-glucopyranosyl-p-
  • the sweetener composition including Reb EE has a sweetness level that is similar to sweeteners made with Reb A.
  • the sweetener composition has pleasing sensory attributes and reduced off-taste(s), reduced bitterness, or both reduced off- taste(s) and reduced bitterness.
  • the sweetener composition may be formulated as a concentrate, as a sweetener, or as part of a food product.
  • Reb EE may be present in the sweetener composition at any suitable concentration.
  • Reb EE may be present in the sweetener composition suitable to enhance sweetness of a food or beverage composition containing the sweetener composition.
  • Reb EE may be present in the sweetener composition in an amount such that when the sweetener composition is added to an aqueous solution at a concentration such that the solution includes 500 ppm Reb EE, the solution has a sweetness of 4.0 SEV or greater, 4.5 SEV or greater, 5.0 SEV or greater, 5.5 SEV or greater, 6.0 or greater, 6.25 or greater, or about 6.5 SEV or greater.
  • Reb EE may be present in the sweetener composition such that the resulting solution that includes 500 ppm Reb EE has a sweetness of 8.0 SEV or lowers, 7.5 SEV or lower,7.0 SEV or lower, 6.75 or lower, or about 6.5 or lower.
  • Reb EE may be present in the sweetener composition such that the resulting solution that includes 500 ppm Reb EE has a sweetness between 5.0 and 8.0 SEV, between 5.5 and 7.5 SEV, between 6.0 and 7.0 SEV, between 6.25 and 6.75, or about 6.5 SEV.
  • the sweetener composition includes about 0.02 weight percent (wt%) or more, 0.04 wt% or more, 0.05 wt% or more, 0.1 wt% or more, 0.2 wt% or more, 0.5 wt% or more, or 1 wt% or more of Reb EE based on the total weight of the sweetener composition.
  • the sweetener composition may include about 100 wt% or less, 98 wt% or less, 95 wt% or less, 90 wt% or less, 80 wt% or less, 70 wt% or less, 60 wt% or less, 50 wt% or less, 40 wt% or less, 30 wt% or less, or 20 wt% or less of Reb EE based on the total weight of the sweetener composition.
  • the sweetener composition may include about 0.02 weight percent (wt%) to 100 wt%, about 0.04 wt% to 95 wt%, comprises about 0.05 wt% to about 50 wt%, or about 0.05 wt% to about 10 wt% of Reb EE based on the total weight of the sweetener composition.
  • the sweetener composition may include various amounts of additional steviol glycosides in addition to Reb EE. Steviol glycosides may be present in the composition in any amount desired for the intended use or for an intended or desired flavor profile, taste profile (e.g., off tastes or lack thereof, bitterness, sourness, umami, etc.), or sweetness profile (e.g., level of sweetness, temporal aspects of sweetness).
  • Examples of additional steviol glycoside compounds PT-974-WO-PCT that may be included in the sweetener composition in addition to Reb EE include steviolmonoside, steviolbioside, stevioside, rebaudioside A (Reb A), rebaudioside B (Reb B), rebaudioside C (Reb C), rebaudioside D (Reb D), rebaudioside DG (Reb DG), rebaudioside E (Reb E), rebaudioside F (Reb F), rebaudioside J (Reb J), rebaudioside M (Reb M), rebaudioside N (Reb N), rebaudioside O (Reb O), rebaudioside V2 (Reb V2), rubusoside, dulcoside A, steviol-13-monoside, steviol-19- monoside, 13-[( ⁇ -D-glucopyranosyl)oxy)kaur-16-en-18-oic acid 2-O- ⁇ -D-glu
  • the sweetener composition includes Reb EE in combination with one or more additional steviol glycoside compounds selected from the group consisting of Reb A, Reb D, Reb DG, Reb J, Reb M, Reb N, Reb O, Reb V2, and combinations thereof.
  • the sweetener composition includes Reb EE in combination with one or more additional steviol glycoside compounds selected from the group consisting of Reb D, Reb J, Reb M, Reb O, and Reb V2.
  • the sweetener composition includes Reb EE in combination with one or more additional steviol glycoside compounds selected from the group consisting of Reb D, Reb M, and combinations thereof.
  • Reb EE makes up the entire steviol glycoside content of the sweetener composition.
  • Reb EE is present in an amount of about 0.5 wt% or greater, 1 wt% or greater, 2 wt% or greater, 5 wt% or greater, 10 wt% or greater, 25 wt% or greater, or 50 wt% or greater based on the total amount of steviol glycosides in the sweetener composition.
  • Reb EE may be present in an amount of about 100 wt% or less, 90 wt% or less, 80 wt% or less, 70 wt% or less, 60 wt% or less, 50 wt% or less, 40 wt% or less, 30 wt% or less, 20 wt% or less, 10 wt% or less, or 5 wt% or less based on the total amount of steviol glycosides in the sweetener composition.
  • Reb EE may be present in an amount of is present in an amount of about 0.5 wt% to 100 wt% or about 0.5 wt% to about 10 wt% based on the total amount of steviol glycosides in the sweetener composition.
  • the one or more additional steviol glycosides may be present in an amount of 0.1 wt% or greater, 0.2 wt% or greater, 0.5 wt% or greater, 1 wt% or greater, 2 wt% or greater, 5 wt% or greater, 10 wt% or greater, 25 wt% or greater, 30 wt% or greater, 40 wt% or greater, 50 wt% or greater, 60 wt% or greater, 70 wt% or greater, 80 wt% or greater, or 90 wt% or greater based on the total amount of steviol glycosides in the sweetener composition.
  • the one or more additional steviol glycosides may be present in an amount of 99.5 wt% or less, 98 wt% or less, 95 wt% or less, 90 wt% or less, 80 wt% or less, 70 wt% or less, 60 wt% or less, 50 wt% or less, 40 wt% or less, 30 wt% or less, 20 wt% or less, 10 wt% or less, or 5 wt% or less based on the total PT-974-WO-PCT amount of steviol glycosides in the sweetener composition.
  • the one or more additional steviol glycosides may be present in an amount of 0.1 wt% to about 99.5 wt% based on the total amount of steviol glycosides in the sweetener composition.
  • the total amount of steviol glycosides in the sweetener composition may be 0.5 wt% or greater, 1 wt% or greater, 2 wt% or greater, 5 wt% or greater, 10 wt% or greater, 20 wt% or greater, 30 wt% or greater, 40 wt% or greater, 50 wt% or greater, 60 wt% or greater, 70 wt% or greater, 80 wt% or greater, 90 wt% or greater, or 95 wt% or greater based on the weight of the sweetener composition.
  • the total amount of steviol glycosides in the sweetener composition may be about 100 wt% or less, 90 wt% or less, 80 wt% or less, 70 wt% or less, 60 wt% or less, 50 wt% or less, 40 wt% or less, 30 wt% or less, 20 wt% or less, 10 wt% or less, or 5 wt% or less based on the weight of the sweetener composition.
  • the total amount of steviol glycosides in the sweetener composition may be 0.5 wt% to 100 wt%, 1 wt% to 90 wt%, or 1 wt% to 50 wt% based on the weight of the sweetener composition.
  • the sweetener composition is an aqueous solution containing Reb EE.
  • the amount of Reb EE in the sweetener composition may be 1 ppm or greater, 5 ppm or greater, 10 ppm or greater, 50 ppm or greater, 100 ppm or greater, 500 ppm or greater, 1,000 ppm or greater, 5,000 ppm or greater, or 10,000 ppm or greater.
  • the amount of Reb EE in the sweetener composition may be 100,000 ppm or less, 50,000 ppm or less, 30,000 ppm or less, 20,000 ppm or less, 10,000 ppm or less, 8,000 ppm or less, 5,000 ppm or less, 2,000 ppm or less, or 1,000 ppm or less.
  • the composition may include Reb EE at a concentration of 1 ppm to 100,000 ppm, 1 ppm to 50,000 ppm, 1 ppm to 30,000 ppm, or 5 ppm to 10,000 ppm.
  • the sweetener composition is an aqueous solution containing one or more steviol glycosides and including Reb EE.
  • the total amount of steviol glycosides in the sweetener composition may be 1 ppm or greater, 5 ppm or greater, 10 ppm or greater, 50 ppm or greater, 100 ppm or greater, 500 ppm or greater, 1,000 ppm or greater, 5,000 ppm or greater, 10,000 ppm or greater, 50,000 ppm or greater, 100,000 ppm or greater, or 200,000 ppm or greater.
  • the amount of steviol glycosides in the sweetener composition may be 500,000 ppm or less, 400,000 ppm or less, 300,000 ppm or less, 200,000 ppm or less, 100,000 ppm or less, 50,000 ppm or less, 30,000 ppm or less, 20,000 ppm or less, 10,000 ppm or less, 8,000 ppm or less, 5,000 ppm or less, 2,000 ppm or less, or 1,000 ppm or less.
  • the composition may include steviol glycosides at a concentration of 1 ppm to 500,000 ppm, 1 ppm to 300,000 ppm, 1 ppm to 100,000 ppm, 1 ppm to 50,000 ppm, 1 ppm to 30,000 ppm, or 5 ppm to 10,000 ppm.
  • the sweetener composition is added to an aqueous solution at a concentration such that the solution comprises 400 ppm Reb EE, the solution has i) reduced bitterness relative to an equivalent solution prepared with Reb A; ii) reduced metallic notes relative to an equivalent solution prepared with Reb M; and/or iii) reduced sweetness linger relative to an equivalent solution prepared with a combination of Reb D and Reb M.
  • the sweetener composition may exhibit reduced bitterness compared to equivalent compositions prepared with Reb A.
  • the sweetener composition may exhibit reduced metallic notes compared to equivalent compositions prepared with Reb M.
  • the sweetener composition may exhibit reduced sweetness linger compared to equivalent compositions prepared with a combination of Reb D and Reb M.
  • the sweetener composition when the sweetener composition is added to an aqueous solution at a concentration such that the aqueous solution includes 400 ppm Reb EE, the solution has i) reduced bitterness relative to an equivalent compositions prepared with Reb A; ii) reduced metallic notes relative to an equivalent compositions prepared with Reb M; and/or iii) reduced sweetness linger relative to an equivalent compositions prepared with a combination of Reb D and Reb M.
  • Additional Components [0056]
  • the sweetener composition may additionally include one or more bulking agents, plasticizers, emulsifiers, flavorings, or combinations thereof.
  • Suitable bulking agents include oligosaccharides (such as fructo-oligosaccharides (kestose, nystose, and the like), nigero-oligosaccharides, xylo-oligosaccharides (xylotriose, xylobiose and the like), gentio-oligosaccharides (gentiobiose, gentiotriose, gentiotetraose, and the like), galacto-oligosaccharides, tetrasaccharides, mannan-oligosaccharides, malto- oligosaccharides (maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose, and the like), soybean oligosaccharides, and the like), polysaccharides (such as starch and starch- derivatives including maltodextrin
  • the bulking agent may include vegetable fibers, dextrin, maltodextrin, polydextrose, inulin, dehydrated grain syrups (such as dried rice syrup), pectin, sugar alcohols, or a combination of two or more thereof.
  • the bulking agent is a sugar alcohol.
  • Bulking agents may be added to the sweetener composition in an amount of up to 75 %, up to PT-974-WO-PCT 70 %, up to 65 %, up to 60 %, up to 55 %, up to 50 %, up to 45 %, up to 40 %, up to 35 %, up to 30 %, up to 25 %, up to 20 %, up to 15 %, or up to 10 % by weight of the sweetener composition.
  • the sweetener composition may include a bulking agent in an amount of 0.5 % to 75 %, 1 % to 60 %, 2 % to 55 %, or 3 % to 50 % by weight.
  • an ingredient may function as both a sweetener and a bulking agent in a sweetener composition.
  • bulking agents include erythritol, maltitol, lactitol, sorbitol, mannitol, xylitol, allulose, and tagatose.
  • the sweetener composition also contains one or more additional non-steviol glycoside sweetener compounds.
  • the sweetener composition may include only non- caloric sweeteners. Alternatively, the sweetener composition may include a combination of non- caloric and caloric sweeteners.
  • the additional non-steviol glycoside sweetener compounds can be any type of sweetener, for example, a sweetener obtained from a plant or plant product, or a physically or chemically modified sweetener obtained from a plant, or a synthetic sweetener.
  • exemplary non-steviol glycoside sweeteners that may be included in the sweetener composition include sucrose, fructose, glucose, erythritol, maltitol, lactitol, sorbitol, mannitol, xylitol, tagatose, trehalose, galactose, rhamnose, cyclodextrin (e.g., ⁇ -cyclodextrin, ⁇ -cyclodextrin, and ⁇ - cyclodextrin), ribulose, threose, arabinose, xylose, lyxose, allose, altrose, mannose, idose, lactose, maltose,
  • Non-steviol glycoside sweeteners and aspects thereof are also described in PCT International Publication Nos. WO 2019/071220 and WO 2019/071182 and in US Patent Application Publication Nos. 2019/0223481 and 2019/0223483, each of which is incorporated by reference herein in its entirety.
  • PT-974-WO-PCT [0059]
  • the sweetener composition may further optionally include a liquid carrier, binder matrix, additional additives, and/or the like.
  • the sweetener composition contains one or more additives including 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, flavorants and flavoring ingredients, astringent compounds, proteins or protein hydrolysates, surfactants, emulsifiers, weighing agents, gums, antioxidants, colorants, flavonoids, alcohols, polymers or combinations thereof.
  • additives including 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, flavorants and flavoring ingredients, astringent compounds, proteins or protein hydrolysates, surfactants, emulsifiers,
  • the additives act to improve the temporal and flavor profile of the sweetener to provide a sweetener composition with a favorable taste, such as a taste similar to sucrose.
  • a favorable taste such as a taste similar to sucrose.
  • ingredients and aspects thereof are described, for example, in PCT International Publication Nos. WO 2019/071220 and WO 2019/071182 and in US Patent Application Publication Nos.2019/0223481 and 2019/0223483, each of which is incorporated by reference herein in its entirety.
  • the sweetener composition may be incorporated in or used to prepare any known edible material or other composition intended to be ingested and/or contacted with the mouth of a human or animal, such as, for example, pharmaceutical compositions, supplement compositions (e.g., gummy, tablet, etc.), edible gel mixes and compositions, dental and oral hygiene compositions, foodstuffs (e.g., confections, condiments, chewing gum, cereal compositions, baked goods, baking goods, cooking adjuvants, dairy products, and tabletop sweetener compositions), and beverage products (e.g., beverages, beverage mixes, beverage concentrates, etc.). Examples of such compositions and aspects thereof are set forth in PCT International Publication Nos.
  • the sweetener composition may be a beverage product or can be used to prepare a beverage product.
  • a “beverage product” may be a ready-to-drink beverage, a beverage concentrate, a beverage syrup, frozen beverage, a powdered beverage, or the like.
  • 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 sparkling beverage, orange flavored sparkling beverage, grape flavored sparkling beverage, strawberry flavored sparkling beverage, pineapple flavored sparkling beverage, ginger- ale, soft PT-974-WO-PCT drinks and root beer.
  • Non-carbonated beverages include, but are not limited to fruit juice, fruit- flavored juice, juice drinks, nectars, vegetable juice, vegetable-flavored juice, sports drinks, energy drinks, enhanced water drinks, enhanced water with vitamins, near water drinks (e.g., water with natural or synthetic flavorants), coconut water, tea type drinks (e.g. black tea, green tea, red tea, oolong tea), coffee, cocoa drink, beverage containing milk components (e.g.
  • frozen beverages include, but are not limited to, icees, frozen cocktails, daiquiris, pina coladas, margaritas, milk shakes, frozen coffees, frozen lemonades, granitas, and slushees.
  • Beverages may be alcoholic (e.g., a liqueur or cream liqueur) or non-alcoholic beverages.
  • the beverage may be a brewed for fermented beverage, for example, beer or kombucha.
  • Beverage concentrates and beverage syrups can be prepared with an initial volume of liquid matrix (e.g., water) and the desired beverage ingredients.
  • the sweetener composition can be a food product or can be used to prepare a food product.
  • the food product may be any caloric or non-caloric food product suitable for human consumption.
  • Suitable food products include, but are not limited to, confectionary products (e.g., candies, candied nuts, candy bars, caramels, chocolates, chocolate bars, chocolate drops, chocolate in the form of hollow figures or any desired shape, filled chocolate bars, pralines, truffles, cereal bars, chewing gum, and pastillage), condiments, chewing gum, cereal compositions, baked goods, bakery products (e.g., breads such as bagels, buns, rolls, biscuits and loaf breads; cookies; brownies; muffins; desserts such as cakes, cheesecakes and pies; snack cakes; sweet goods such as doughnuts, Danish pastries, sweet rolls, cinnamon rolls, and coffee cakes), cooking adjuvants, dairy products (e.g., ice cream, yogurt, chilled desserts, pudding, mousse, custard, milk shakes, malts, cream cheeses, cheeses, fudge), dairy-alternatives, frozen desserts (e.g., ice cream, sorbet, frozen yoghurt, and the like), tabletop sweeten
  • compositions described herein may be used in food products in any form, such as melted or mixed into the recipe of the end product, in the form of a filling, inclusions, toppings, or coatings, molded around other discrete ingredients such as nuts, fruit, dried fruit, biscuits, candy pieces or shapes, PT-974-WO-PCT combinations thereof, and the like.
  • the composition may be used as a coating, inclusion (chunks, flakes, or ripples), topping, or core (soft or solid).
  • the Reb EE is included in a beverage product or concentrate. That is, a beverage product or concentrate may include Reb EE (having the structure of Formula I as shown above).
  • the beverage product or concentrate may include total steviol glycosides at a concentration of 50 ppm or greater, 100 ppm or greater, 500 ppm or greater, 1,000 ppm or greater, 5,000 ppm or greater, 10,000 ppm or greater, 50,000 ppm or greater, 100,000 ppm or greater, or 200,000 ppm or greater.
  • the amount of steviol glycosides in the beverage product or concentrate may be 500,000 ppm or less, 400,000 ppm or less, 300,000 ppm or less, 200,000 ppm or less, 100,000 ppm or less, 50,000 ppm or less, 30,000 ppm or less, 20,000 ppm or less, 10,000 ppm or less, 8,000 ppm or less, 5,000 ppm or less, 2,000 ppm or less, or 1,000 ppm or less.
  • the beverage product or concentrate may include steviol glycosides at a concentration of 1 ppm to 500,000 ppm, 1 ppm to 300,000 ppm, 1 ppm to 100,000 ppm, 1 ppm to 50,000 ppm, 1 ppm to 30,000 ppm, or 5 ppm to 10,000 ppm.
  • a method of preparing a beverage provided herein includes adding a sweetener composition as described herein to a liquid matrix (e.g., water or an aqueous solution). The method can further comprise adding one or more sweeteners, additives and/or functional ingredients to the beverage or to the composition before adding it to the liquid matrix.
  • a method of sweetening a food or beverage product may include adding Reb EE to the food or beverage product, where the sweetness of the food or beverage is higher than the sweetness of the food or beverage prior to addition of Reb EE.
  • the method of sweetening the food or beverage product may include adding a sweetener composition containing Reb EE to the food or beverage product, where the sweetness of the food or beverage is higher than the sweetness of the food or beverage prior to addition of the sweetener composition.
  • Sensory Attributes [0066]
  • the sweetener composition may be formulated to provide desirable sensory attributes, such as perceived sweetness, little or no bitterness, minimal or no off-taste(s), and temporal profiles of the same, including, for example, sweetness linger.
  • Sensory attributes may be evaluated, for example, by a sensory panel.
  • taste refers to sensory perception on the tongue.
  • the 5 basic tastes are sweet, sour, salty, bitter, and umami.
  • aroma refers to the orthonasal perception in the nasal cavity.
  • PT-974-WO-PCT As used herein, “flavor” refers to the taste and retronasal perception in the nasal cavity.
  • off-taste(s) refer to a taste or flavor attribute profile that is not characteristic or usually associated with a substance or composition as described herein and/or a characteristic taste or flavor associated with a substance or composition that is undesirable.
  • the off-taste may be an undesirable taste such as bitterness, undesirable mouthfeel such as astringency, mouth drying, undesirable flavor such as rancid, cardboard, aftertaste, inconsistent flavor (e.g., a flavor with an uneven onset or intensity, a flavor that may be perceived too early or too late), and the like.
  • Sweetness of a compound or composition may be determined by measuring sucrose equivalent values (SEV) using methods and processes well known to those skilled in the art.
  • SEV may be determined by measuring sweetness equivalence to a reference sucrose solution or to another compound with a known sweetness level. For example, sweetness may also be measured or observed relative to other steviol glycosides, such as rebaudioside D, rebaudioside M, or rebaudioside A.
  • taste panelists are trained to detect and scale sweetness of reference sucrose solutions containing between 10 g to 150 g/kg sucrose. The sweetener compositions containing the glycosides are then tasted at a series of dilutions to determine the concentration of the sweetener composition that is as sweet as a given sucrose reference.
  • sweetener composition is as sweet as 50 g/kg of sucrose solution in a citric acid buffer, pH 3.1, then the sweetener composition is assigned a SEV of 5.
  • sweetness value is used interchangeably herein with “SEV”.
  • bitterness of a compound or composition may be determined by measuring caffeine equivalent values using methods and processes well known to those skilled in the art. For example, bitterness may be determined by measuring bitterness equivalence to a reference caffeine solution or to another compound with a known bitterness level. Bitterness may also be measured or observed relative to other steviol glycosides, such as rebaudioside D, rebaudioside M, or rebaudioside A .
  • taste panelists are trained to detect and scale bitterness of reference caffeine solutions containing between 0.1 g to 0.8 g/kg caffeine.
  • the sweetener compositions containing the glycosides are then tasted at a series of dilutions to determine the concentration of the sweetener composition that is as bitter as a given caffeine reference. For example, if a sweetener composition is as bitter as 0.3 g/kg of caffeine solution, then the sweetener composition is assigned a bitterness of 5.
  • minor steviol glycosides including Reb EE, may exhibit specific sensory attributes related to sweetness intensity. Perceived sweetness intensity can be reported as PT-974-WO-PCT SEV.
  • the sweetener composition may include sensory modifiers that may be used to increase the perceived sweetness intensity of minor steviol glycosides. Sensory modifiers are further discussed in PCT/US2020/026524, published as WO2020210118. [0074] A sensory panel may be used to determine the magnitude of, for example, sweetness intensity, reduction in bitterness, or shifts in their temporal profiles. A sensory panel may be used to quantify the amounts of specific steviol glycosides to achieve a desired sensory profile. Sensory panels are a scientific and reproducible method that is essential to the food and beverage industry.
  • a sensory panel involves a group of two or more individual panelists. Panelists are instructed according to industry-recognized practices to avoid the influence of personal subjectivity and strengthen reproducibility. For example, panelists may objectively evaluate sensory attributes of a tested product but may not provide subjective attributes such as personal preference.
  • the sensory panel can be conducted with two, three, four, five, six, or more panelists, in which the panelists identify and agree on a lexicon of sensory attributes for a given set of samples. After evaluating a specific sample, the panelists can assign a numerical intensity score for each attribute using an intensity scale.
  • the panel may use a roundtable consensus approach, or the panelists may score and evaluate the sensory attribute(s) individually.
  • Either format can further involve a panel leader who directs the discussion regarding terminology and directs the panel to evaluate particular products and attributes.
  • a trained sensory panel can be utilized to assess specific attributes using descriptive analysis or time intensity methodologies.
  • panelist refers to a highly trained expert taster, such as those commonly used for sensory methodologies such as descriptive analysis, and/or an experienced taster familiar with the sensory attribute(s) being tested.
  • the panelist may be a trained panelist.
  • a trained panelist has undergone training to understand the terms and sensory phenomenon associated with those sensory attributes relevant to the tested product and are aligned on the use of common descriptors for those sensory attributes of interest (i.e., a sensory lexicon).
  • a trained panelist testing a given composition will understand the terms and sensory attributes associated with said composition, e.g., saltiness, sourness, bitterness, astringency, mouthfeel, acidity, and the like.
  • the trained panelist will have been trained against reference samples corresponding to the sensory attributes being tested and thus have calibrated to recognize and quantitatively assess such criteria.
  • the panelist may be an experienced taster.
  • roundtable consensus approach refers to the sensory panel assay methodology wherein panelists discus sensory attributes and intensities before mutually agreeing on an intensity score and attribute characterization for the particular sensory attribute(s) being assayed.
  • a sensory panel using a roundtable consensus approach may include 2, 3, 4, 5, 6, or more panelists.
  • the panelists will identify and agree on a lexicon of sensory attribute, including, if applicable, reference or standardized samples (also referred to as sensory anchors) for a particular sensory attribute.
  • the reference sample(s) used for a given sensory attribute(s) will depend on the samples being assayed and the lexicon of sensory attributes determined by the panel.
  • One of skill in the art will recognize the appropriate lexicon and reference or standard samples necessary for sensory assessment of a given sample(s).
  • the samples are scored and evaluated by panelists independently after panelists have agreed upon or been instructed in a lexicon of sensory attributes and intensity scores including, if applicable, assay specific calibration on reference samples (also referred to as sensory anchors) for a particular sensory attribute. Examples of common reference samples are described below. Panelists may evaluate samples in replicate and may be blinded to the samples they are testing. Samples being tested may be provided to the panelists randomly or in a sequential order. In some aspects, samples may be tested by panelists using a randomized balanced sequential order. Scores from individual panelists are then assessed using standard statistical analysis methods to determine an average sensory intensity score.
  • a sensory attribute(s) of a given composition may be evaluated in comparison to one or more reference or anchor samples.
  • sodium chloride solutions can be used by experienced panelists as saltiness anchors to assess the relative intensity of saltiness for a given composition
  • sucrose solutions can be used by experienced panelists as sweetness anchors to PT-974-WO-PCT assess the relative intensity of sweetness for a given composition
  • citric acid solutions can be used by experienced panelists as sourness anchors to assess the relative intensity of sourness for a given composition
  • caffeine solutions can be used by experienced panelists as bitterness anchors to assess the relative intensity of bitterness for a given composition
  • monosodium glutamate (MSG) solutions can be used by experienced panelists as umami anchors to assess the relative intensity of umami for a given composition.
  • panelists can be presented with a solution to assess sensory attributes, e.g., 10-20 mL of a sample. Panelists will dispense approximately 3- 4 mL of each solution into their own mouths, disperse the solution by moving their tongues, and record a value for the particular sensory attribute being tested. If multiple solutions are to be tested in a session, the panelists may cleanse their palates with water between samples.
  • sensory attributes e.g. 10-20 mL of a sample.
  • Panelists will dispense approximately 3- 4 mL of each solution into their own mouths, disperse the solution by moving their tongues, and record a value for the particular sensory attribute being tested. If multiple solutions are to be tested in a session, the panelists may cleanse their palates with water between samples.
  • Equivalent scales and methodologies can be used for sweet, bitter, sour, and umami sensory attributes.
  • the panelists can use a standard range of 0.035 % (wt), 0.05 % (wt), 0.07 % (wt), 0.15 % (wt), and 0.2 % (wt) citric acid solutions in water corresponding to a sourness intensity value of 2, 3, 5, 10, and 15, respectively.
  • a sourness intensity value of 2, 3, 5, 10, and 15, respectively.
  • the number and range of standard solutions may be changed (e.g., using only the solutions corresponding to the 2 and 7 sourness intensity values).
  • the panelists For each test composition, the panelists dispense each composition (approximately 2-5 mL of liquid compositions or solutions prepared with water, or 5-10 g of solid compositions) into their own mouths, disperses the composition by moving their tongues/chewing, and records a sourness intensity value between 0 and 15 for each composition based on comparison to the aforementioned standard citric acid solutions. Between tasting compositions, the panelists are able to cleanse their palates with water. The panelists also can taste the standard 0.035 %, 0.05 %, 0.07 %, 0.15 %, and 0.2 % citric acid solutions ad libitum between tasting test solutions to ensure recorded sourness intensity values are accurate against the scale of the standard citric acid solutions.
  • the temperature at which the test is conducted may be specific to the sample beginning tested, e.g., samples may be tested at 22 oC (e.g., room temperature), at 0 °C (e.g., for frozen samples), or between 60-80 °C (e.g., a cooked sample served warm).
  • 22 oC e.g., room temperature
  • 0 °C e.g., for frozen samples
  • 60-80 °C e.g., a cooked sample served warm.
  • PT-974-WO-PCT [0080]
  • Bitterness of a composition can be tested by a panel of at least two panelists.
  • the panelists can use a standard range of 0.0125 % (wt), 0.01875 % (wt), 0.025 % (wt), 0.031 % (wt), 0.07 % (wt), and 0.12 % (wt) caffeine solutions in water corresponding to a bitterness intensity value of 2, 3, 4, 5, 10, and 15, respectively.
  • the number and range of standard solutions may be changed (e.g., using only the solutions corresponding to the 2, 3, and 5 bitterness intensity values).
  • the panelists For each test composition, the panelists dispense each composition (approximately 2-5 mL of liquid compositions or solutions prepared with water, or 5-10 g of solid compositions) into their own mouths, disperses the composition by moving their tongues/chewing, and records a bitterness intensity value between 0 and 15 for each composition based on comparison to the aforementioned standard caffeine solutions. Between tasting compositions, the panelists are able to cleanse their palates with water. The panelists also can taste the standard 0.0125 %, 0.01875 %, 0.025 %, 0.031 %, 0.07 %, and 0.12 % caffeine solutions ad libitum between tasting test solutions to ensure recorded bitterness intensity values are accurate against the scale of the standard caffeine solutions.
  • the temperature at which the test is conducted may be specific to the sample beginning tested, e.g., samples may be tested at 22 oC (e.g., room temperature), at 0 °C (e.g., for frozen samples), or between 60-80 °C (e.g., a cooked sample served warm).
  • 22 oC e.g., room temperature
  • 0 °C e.g., for frozen samples
  • 60-80 °C e.g., a cooked sample served warm.
  • sweetness of a composition can be tested by a panel of at least two panelists.
  • the panelists can use a standard range of 2 % (wt), 5 % (wt), 8 % (wt), 10 % (wt), and 15 % (wt) sucrose solutions corresponding to a sweetness intensity value of 2, 5, 8, 10, and 15, respectively.
  • a standard range of 2 % (wt), 5 % (wt), 8 % (wt), 10 % (wt), and 15 % (wt) sucrose solutions corresponding to a sweetness intensity value of 2, 5, 8, 10, and 15, respectively e.g., the number and range of standard solutions may be changed (e.g., using only the solutions corresponding to the 2, 5, and 8 sweetness intensity values).
  • the panelists For each test composition, the panelists dispense each composition (approximately 2-5 mL of liquid compositions or solutions prepared with water, or 5-10 g of solid compositions) into their own mouths, disperses the composition by moving their tongues/chewing, and records a sweetness intensity value between 0 and 15 for each composition based on comparison to the aforementioned standard sucrose solutions. Between tasting compositions, the panelists are able to cleanse their palates with water. The panelists also can taste the standard 2 %, 5 %, 8 %, 10 %, and 15 % sucrose solutions ad libitum between tasting test solutions to ensure recorded sweetness intensity values are accurate against the scale of the standard sucrose solutions.
  • the temperature at which the test is conducted PT-974-WO-PCT may be specific to the sample beginning tested, e.g., samples may be tested at 22 °C (e.g., room temperature), at 0 °C (e.g., for frozen samples), or between 60-80 °C (e.g., a cooked sample served warm).
  • samples may be tested at 22 °C (e.g., room temperature), at 0 °C (e.g., for frozen samples), or between 60-80 °C (e.g., a cooked sample served warm).
  • This test is referred to herein as the “Standardized Sweetness Intensity Test.”
  • Temporal aspects of taste, flavor, and/or aromatic properties of compositions described herein may be evaluated by any suitable means known in the art.
  • Temporal aspects also referred to as time attributes, may include, but are not limited to, time to taste/flavor/aroma onset, time at max taste/flavor/aroma, and taste/flavor/aroma linger.
  • Time to taste/flavor/aroma onset refers to the time (in seconds) it takes from the time the sample is put in the mouth until the given taste/flavor/aroma is perceived.
  • Time to taste/flavor/aroma onset may be measured by putting a sample in the mouth and swallowing (not holding in the mouth or spitting), starting a timer when the sample is put in the mouth, and noting the time when the given taste/flavor/aroma is perceived.
  • Time at max flavor/taste/aroma is defined as the time (in seconds) the sample remains at the highest intensity of the given taste/flavor/aroma.
  • Time at max taste/flavor/aroma may be measured by putting a sample in the mouth and swallowing (not holding in the mouth or spitting), starting a timer when peak intensity of the taste/flavor/aroma begins and noting the time when the taste/flavor/aroma intensity begins to decline.
  • Taste/flavor/aroma linger is defined as the time (in seconds) from when the taste/flavor/aroma starts to drop from peak intensity until the given taste/flavor/aroma is no longer discerned.
  • Taste/flavor/aroma linger may be measured by putting a sample in the mouth and swallowing (not holding in the mouth or spitting), starting a timer when the peak intensity of the taste/flavor/aroma begins to decline, and noting the time when the taste/flavor/aroma is no longer perceived.
  • a control sample is typically used as a reference point or for comparison purposes.
  • a control sample can be used to qualify the sensory perception (e.g., sweetness or other sensory attribute) of Reb EE.
  • the control sample can be a composition such as a sweetener composition as described herein, but without the presence of Reb EE.
  • control sample is otherwise the same, and it should contain the same component(s) and other ingredients at the same relative concentrations.
  • Other standard samples are commonly used in sensory panels, for example standard samples used to evaluate intensity of sensory attributes as outlined above.
  • control sample may be a modified control sample which contains a different sweetener, such as another steviol glycoside with a known sweetness profile.
  • exemplary sweeteners used as control samples include Reb A and Reb D/M.
  • PT-974-WO-PCT [0084] This disclosure is not limited to sensory testing by experienced or trained panelists. For example, it is possible to utilize untrained and inexperienced panelists.
  • Table 2 lists the tested materials and source of various components. Table 2.
  • Component Ingredients Source [0088] Assays were carried out to characterize the sensory attributes, e.g., sweetness profile, of aqueous solutions of samples. Sensory attributes of the compositions were tested by a panel of individuals that are experienced in sensory testing. The experienced panelists assessed sensory attributes such as, but not limited to, bitterness, metallic notes, mouth drying, sweetness intensity, and sweetness linger. The panelists compared the sweeteners against Reb A and Reb D/M.
  • Example 1 – Reb EE [0089] Reb EE was isolated and its structure was determined using high resolution accurate mass (HRAM) and nuclear magnetic resonance (NMR). [0090] Reb EE was extracted from dried stevia leaf using hot water. The hot water extract was then freeze-dried to a powder.
  • HRAM high resolution accurate mass
  • NMR nuclear magnetic resonance
  • the powder was then solubilized with 50 % ethanol and purified using a C18 prep column via Prep LC, utilizing a water and methanol gradient.
  • the resulting fractions for each steviol glycoside were pooled from multiple injections and evaporated in a rotary evaporator to remove methanol.
  • the low methanol solution was then freeze-dried to a powder.
  • the pooled fraction powder was then solubilized with 50 % ethanol and purified further using Prep LC until the desired purity (> 95 %) was reached (usually taking 3 - 5 iterations, depending on the steviol glycoside). Finally, the pooled fraction powder was freeze-dried three consecutive times to ensure no residual solvent is present in the powder.
  • the sample was prepared by dissolving the sample in 0.6 mL dimethylsulfoxide DMSO-d6.
  • a set of 1- and 2-dimensional 1 H-NMR and 13 C-NMR spectra were recorded to characterize the sample.
  • the NMR spectra are shown in FIGS.1 ( 1 H-NMR) and 2 ( 13 C-NMR) and FIG.2 shows a summary of the NMR data used to confirm the structure of Reb EE.
  • the 1 H and 13 C NMR spectral data indicated the presence of a steviol core structure containing three (3) ⁇ -glucose moieties, one (1) ⁇ -rhamnose moiety and one (1) ⁇ -xylose moiety.

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Abstract

L'invention concerne une composition d'édulcorant comprenant une quantité édulcorante de glycoside de stéviol rébaudioside EE (Reb EE). Le Reb EE peut être présent à une concentration de 0,02 à 100 % en poids de la composition. Le Reb EE peut être inclus dans un aliment ou des boissons ou un concentré. Un produit ou concentré de boisson peut comprendre environ 1 ppm à environ 50 000 ppm de Reb EE. Le produit ou concentré de boisson peut comprendre environ 50 ppm à environ 500 000 ppm de glycosides de stéviol totaux. Un composé de Reb EE isolé et purifié peut avoir une pureté d'environ 95 % à environ 99,9 %. L'invention concerne également des procédés d'adoucissement d'un produit alimentaire ou de boisson à l'aide de Reb EE.
PCT/US2024/026747 2023-05-09 2024-04-29 Compositions d'édulcorant Pending WO2024233155A1 (fr)

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WO2016100689A1 (fr) 2014-12-17 2016-06-23 Cargill, Incorporated Composés de glycoside de stéviol, compositions pour l'ingestion par voie orale ou utilisation, et procédé permettant d'améliorer la solubilité du glycoside de stéviol
WO2019071182A1 (fr) 2017-10-06 2019-04-11 Cargill, Incorporated Amplificateurs de solubilité de glycoside de stéviol
WO2020210118A1 (fr) 2019-04-06 2020-10-15 Cargill, Incorporated Modificateurs sensoriels
US20210000960A1 (en) * 2013-06-07 2021-01-07 Purecircle Sdn Bhd Stevia extract containing selected steviol glycosides as flavor, salty and sweetness profile modifier
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WO2016100689A1 (fr) 2014-12-17 2016-06-23 Cargill, Incorporated Composés de glycoside de stéviol, compositions pour l'ingestion par voie orale ou utilisation, et procédé permettant d'améliorer la solubilité du glycoside de stéviol
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