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WO2000015049A1 - UTILISATION DE CYCLODEXTRINE POUR STABILISER LE N-[N- (3,3-DIMETHYLBUTYL) -L-α- ASPARTYL] -L-PHENYLALANINE 1-ESTER METHYLIQUE - Google Patents

UTILISATION DE CYCLODEXTRINE POUR STABILISER LE N-[N- (3,3-DIMETHYLBUTYL) -L-α- ASPARTYL] -L-PHENYLALANINE 1-ESTER METHYLIQUE Download PDF

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Publication number
WO2000015049A1
WO2000015049A1 PCT/US1999/021471 US9921471W WO0015049A1 WO 2000015049 A1 WO2000015049 A1 WO 2000015049A1 US 9921471 W US9921471 W US 9921471W WO 0015049 A1 WO0015049 A1 WO 0015049A1
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WO
WIPO (PCT)
Prior art keywords
cyclodextrin
composition according
sweetener composition
aspartyl
dimethylbutyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1999/021471
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English (en)
Inventor
Ihab E. Bishay
Jim G. Fotos
Nitin Desai
Michael Cleary
Steve Schroeder
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Nutrasweet Co
Original Assignee
Nutrasweet Co
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Filing date
Publication date
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Priority to AU61504/99A priority Critical patent/AU6150499A/en
Publication of WO2000015049A1 publication Critical patent/WO2000015049A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A23G4/14—Chewing gum characterised by the composition containing organic or inorganic compounds containing peptides or proteins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/18—Chewing gum characterised by shape, structure or physical form, e.g. aerated products
    • A23G4/20—Composite products, e.g. centre-filled, multi-layer, laminated
    • 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
    • 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
    • A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
    • A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives
    • 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
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
    • A23L27/75—Fixation, conservation, or encapsulation of flavouring agents the flavouring agents being bound to a host by chemical, electrical or like forces, e.g. use of precursors

Definitions

  • This invention relates to a sweetener composition
  • a sweetener composition comprising N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester (neotame) and cyclodextrin.
  • the invention also relates to a process for stabilizing sweetener compositions. Further, this invention relates to a method of sweetening beverages, fluid dairy products, condiments, baked goods, frostings, bakery fillings, candies, chewing gum and table-top sweeteners, as well as to the compositions prepared by this method.
  • U.S. Patent No. 5,070,081 describes a process of forming inclusion complexes of cyclodextrin via agglomeration. This patent discloses the use of such inclusion complexes, for among other things, foods, pharmaceuticals, cosmetics and agriculture. Also disclosed are several advantages and uses of cyclodextrin complexes: controlled storage and release; improved physical and chemical stability of labile compounds; masking of off tastes or odors; enhanced bioavailability; stabilization of food flavors; easier tablet formation; separation, concentration and fractionation of substances. There is no disclosure or suggestion of cyclodextrin complexes of N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester.
  • European Patent Application 0 097 950 relates to stabilized compositions comprising aspartame in an aqueous medium such as aqueous foods containing aspartame.
  • the compositions further comprise a stabilizing agent (cyclodextrin, either alone or in combination with a sucrose fatty acid ester) which allows for long-term storage of the composition or food without significant deterioration of the aspartame.
  • cyclodextrin either alone or in combination with a sucrose fatty acid ester
  • EP 0 097 950 indicates that cyclodextrin complexation is useful in increasing stability and solubility of aspartame .
  • N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester is a high potency dipeptide sweetener (about 8000X sweeter than sucrose) that has the formula 3
  • N- [N- (3 , 3 -dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester is a uniquely stable high potency sweetener, it may degrade when used in foods under certain conditions, such as high pH, high temperature, or in the presence of reactive co- ingredients.
  • N- [N- (3 , 3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester containing products are examples of N- [N- (3 , 3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester containing products.
  • N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester is limited by the applications in which they can be used, as well as by their effectiveness.
  • Cyclodextrin inclusion is a molecular phenomenon in which one or more guest molecules interacts with the cavity of one or more cyclodextrin molecules to become entrapped, unlike encapsulation in which more than one guest molecule is entrapped in an encapsulation matrix.
  • guest molecules In order to form a cyclodextrin complex, guest molecules must come into contact with cyclodextrin cavities to form stable associations.
  • a variety of non-covalent forces such as van der Waal forces, hydrophobic interactions and other forces, are responsible for the formation of a stable complex.
  • Cyclodextrin can be used in combination with N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester (neotame) to add increased stability, dissolution and solubility of N- [N- (3 , 3 -dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester in various applications.
  • cyclodextrin due to its formation of a molecular complex, provides the best opportunity for stabilization of N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester than other, less specific methods, such as encapsulation.
  • Cyclodextrin can be ⁇ , ⁇ or ⁇ , and may be substituted or unsubstituted.
  • This complex can be used in a variety of applications. Complex formation can be accomplished by a variety of methods, such as co-precipitation, slurry complexation, paste complexation, mixing and heating, extrusion, dry mixing, or other methods known in the art.
  • This invention is directed to a sweetener composition
  • a sweetener composition comprising N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester and cyclodextrin.
  • the compositions of this invention can be used, for example, as a sweetener for incorporation in processed foods and beverages or as a table-top sweetener.
  • the sweetener composition comprises cyclodextrin which is selected from the group consisting of ⁇ -cyclodextrin, ⁇ -cyclodextrin, ⁇ cyclodextrin, or a mixture thereof.
  • the cyclodextrin may be substituted or unsubstituted.
  • the sweetener composition has a molar ratio of cyclodextrin to N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester in the range from about 200:1 to about 1:50.
  • the molar ratio of cyclodextrin to neotame is in the range from about 10:1 to about 1:4.
  • composition of this invention may comprise N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester inclusion complexes of cyclodextrin.
  • composition of this invention may comprise agglomerates of N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester inclusion complexes of cyclodextrin.
  • compositions such as beverages, fluid dairy products, condiments, baked goods, frostings, bakery fillings, candy and chewing gum containing the sweetener composition of this invention in an amount effective to sweeten the composition, as well as to a method of making such compositions .
  • the invention also includes table-top sweeteners comprised of the sweetener composition of this invention.
  • the sweetener composition of this invention may comprise N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester in combination with another high intensity or natural sweetener.
  • Yet another embodiment of the invention is directed to a process for stabilizing a sweetener composition comprising the step of contacting cyclodextrin with N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester to form a mixture.
  • the invention also includes a process for stabilizing a sweetener composition comprising adding cyclodextrin to a composition containing N- [N- (3 , 3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester.
  • the process may also include the step of agitating the mixture sufficiently to cause interpenetration of the components and inclusion complex formation.
  • Methods used to stabilize the sweetener compositions of this invention include co-precipitation, slurry complexation, paste complexation, damp mixing and heating, extrusion, and dry mixing.
  • agitation may be continued until agglomerates form and then agglomerates of the N- [N-
  • Particularly preferred techniques include agglomeration and wet pelletization.
  • N- [N- (3, 3-dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester (neotame) used in the present invention has the formula
  • the N- [N- (3, 3-dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester may be prepared through various methods.
  • One such method comprises the steps of (i) treating a mixture of aspartame and 3,3- dimethylbutyraldehyde in an organic solvent with hydrogen in the presence of a hydrogenation catalyst at a temperature and pressure effective to form an organic solvent solution of N- [N- (3 , 3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester; (ii) filtering the organic solvent solution to remove the hydrogenation catalyst; and (iii) forming an aqueous/organic solvent solution from the organic solvent solution to precipitate the N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester from the aqueous/organic solvent solution.
  • the aqueous/organic solvent solution has an amount of organic solvent of about 17% to about 30% by weight of the aqueous/organic solvent solution.
  • a particularly preferred organic solvent for use in this method is methanol .
  • the precipitate is recovered using standard filtration techniques to provide highly purified N- [N-3 , 3-dimethylbutyl) - L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester. This method of preparation is described in U.S. Patent No. 5,728,862, the entire disclosure of which is incorporated by reference herein. Further, the entire disclosures of U.S.
  • Patents 5,480,668 and 5,510,508 also related to the synthesis and purification of N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester, are incorporated by reference herein.
  • the cyclodextrin used in the present invention is a cyclic oligosaccharide homolog that is also known as cycloamylose . It consists of 6 to 10 D-glucopyranose groups bonded through ⁇ - (1 , 4) -glucoside bonds to form a cyclic structure. It is named ⁇ -cyclodextrin, ⁇ - cyclodextrin, or ⁇ -cyclodextrin according to the degree of polymerization (6, 7 or 8 glucose units) .
  • the interior of the ring contains C-H bonds or ether bonds and is hydrophobic, while the exterior of the ring is interspersed with OH groups and is highly hydrophilic.
  • cyclodextrin is capable of entrapping N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester in its interior.
  • Cyclodextrin is usually produced from starch by treating it with an amylase or a similar enzyme produced from Bacillus macerans or an alkali-resistant bacterium. There are no particular limitations on the cyclodextrin that can be used in the present invention with respect to the conditions for producing it or other factors.
  • ⁇ -cyclodextrin, ⁇ -cyclodextrin and ⁇ cyclodextrin may be used either independently or as a mixture, and either substituted or unsubstituted, although the intended object of the present invention may be achieved with any type of cyclodextrin.
  • cyclodextrin may be substituted with alkyl, hydroxyalkyl , acetyl, amine, sulphate, or a mixture thereof.
  • dimethyl cyclodextrin, trimethyl cyclodextrin, tertiary amine cyclodextrin, carboxymethyl cyclodextrin, acetylated cyclodextrin, hydroxypropyl cyclodextrin, hydroxyethyl cyclodextrin and sulphated cyclodextrin may be suitable for use in the present invention.
  • Stabilization of N- [N- (3 , 3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester may be effected through simply using it together with the cyclodextrin, i.e., adding cyclodextrin to a composition containing N- [N- (3 , 3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester.
  • increased solubility and dissolution are better attained using a complexation technique.
  • N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester inclusion complexes of cyclodextrin Factors such as the amount of complex to be formed, limitations imposed by the stability of N- [N- (3 , 3-dimethylbutyl ) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester, and ease of recovery of the complex determine the plausibility of using individual techniques .
  • Co-precipitation is one method.
  • cyclodextrin is dissolved in water, and the N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester is added with stirring.
  • concentration of cyclodextrin is limited by the fact that N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester can tolerate higher temperatures for only a short time. Higher concentrations can be achieved, however, with more soluble cyclodextrin. Certain substituted cyclodextrins tend to have greater solubility.
  • the concentration is chosen to be sufficiently high so that the solubility of the cyclodextrin/N- [N- (3 , 3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester complex will be exceeded as the complexation reaction proceeds or as the reaction cools.
  • the molar ratio of cyclodextrin to neotame is generally in the range of about 200:1 to about 1:50. Preferably, this range is from about 10:1 to about 1:4.
  • the temperature range is not critical but generally is from about 35°C to about 80 °C. Preferably, the temperature does not go above 80°C.
  • the cyclodextrin complex is retrieved by collection of precipitate after cooling or by freeze drying.
  • the precipitate formed can be collected by decantation, centrifugation or filtration.
  • the precipitate may be washed with a small amount of water or other water miscible solvent such as cold ethyl alcohol, cold methanol or cold acetone.
  • slurry complexation paste complexation, damp mixing and heating, extrusion and dry mixing techniques can also be used to form the sweetener compositions of the present invention. These methods are outlined in "Cyclodextrin Complexation" by MaryJane Buehne of Cerestar USA, Inc.
  • Complexation may also be effected through an agglomeration method, such as that disclosed in U.S. Patent No. 5,070,081.
  • an agglomeration method such as that disclosed in U.S. Patent No. 5,070,081.
  • the cyclodextrin in solid form and the N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester are contacted in the presence of a small amount of water sufficient to serve as an agglomeration binding liquid to form a mixture.
  • the mixture is agitated sufficiently to cause interpenetration of the components and inclusion complex formation to occur. Agitation is continued until agglomerates form, and agglomerates are then recovered.
  • Wet pelletization techniques known in the art, including a severe agitation may also be used to form agglomerates .
  • Cyclodextrin is an expensive component, the use of which may result in flavor masking and other adverse conditions, such as off-taste notes or incompatability with other flavors, at high levels.
  • cyclodextrin need only be employed in relatively small amounts to stabilize the neotame according to the present invention.
  • the use of cyclodextrin becomes cost-effective and the adverse effects of cyclodextrin at high levels are avoided.
  • the molar ratio of cyclodextrin to N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester in the present invention ranges from about 200:1 to about 1:50.
  • the molar ratio of cyclodextrin to neotame is in the range from about 10:1 to about 1:4.
  • Temperature has more than one effect upon cyclodextrin complexes of this invention. While heating can increase the solubility of these complexes, it can also destabilize the complexes. Accordingly, it is necessary many times to balance these effects in preparation of the complexes of this invention.
  • One of ordinary skill in the art can readily determine such a balance without undue experimentation.
  • heating may be used to form the complexes of this invention.
  • Heat can be used to increase the solubility of the cyclodextrin and the N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester to put individual molecules into solution so that the complexes of this invention can be formed.
  • This temperature is generally in the range of 35°-80°C.
  • Cooling of the solution is usually necessary to crystallize or precipitate the complexes in order to allow formation of a stable complex and to decrease the solubility of this soluble complex.
  • the solution is generally cooled to a temperature in the range of 0°- 10°C. It is important to note that it may be desirable to leave some complex in solution, as opposed to completely crystallizing all complex out of solution, when recovering the inclusion complexes of the present invention.
  • the solvent of choice should be a solvent which does not complex well with cyclodextrin, which is easily removed, for example, by evaporation and in which N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester is highly soluble so that only a small amount of solvent is required. Further, the more soluble the cyclodextrin is in the solvent, the more molecules that are available for complexation. Water, ethanol, diethyl ether, methanol and isopropanol are examples of suitable solvents. In the present invention, water is the most commonly used solvent.
  • N- [N- (3 , 3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester in the cyclodextrin solution a small amount of solvent may be added or the N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester may be dispersed as a fine precipitate.
  • the amount of cyclodextrin and the amount of N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester that can be solubilized increases so that more of these molecules exist in a molecular form that provides for complexation.
  • the cyclodextrin and N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester may become sufficiently dilute so that they do not come into contact with each other as frequently as in a more concentrated solution.
  • the size of agglomerates can be varied by controlling the amount of solvent added and to a lesser degree by controlling the agitation. Increasing the amount of solvent tends to increase the agglomerate size. Increasing the agitation tends to decrease the agglomerate size.
  • the amount of solvent added when forming agglomerates normally will be within about 10 to about 100% by weight based on the cyclodextrin, preferably about 25- 50%. Added solvent has been found necessary for formation of the complex and for agglomeration.
  • drying of the complexes of this invention should be carefully controlled to avoid the loss of N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester. Drying can be accomplished by a variety of methods. Oven drying, drum drying, fluid bed drying, spray drying, low temperature drying, freeze drying, etc., may be used.
  • the cyclodextrin stabilized N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester compositions of this invention can be analyzed by a variety of techniques . The method or methods selected depend upon the desired information (whether complexation has occurred, how much complexation has occurred, which portions of the molecules are involved in complexation, etc. ) .
  • NMR nuclear magnetic resonance spectroscopy
  • FTIR Fourier transform infrared spectroscopy
  • DSC differential scanning calorimetry
  • HPLC high pressure liquid chromatography
  • compositions of this invention are suitable for use in any food to replace natural sweeteners, as well as other high intensity sweeteners, normally used as sweeteners.
  • food as used herein includes, for example, beverages, fluid dairy products, condiments, baked goods, frostings, bakery fillings, candies and chewing gum.
  • Beverages include, without limitation, carbonated soft drinks, including cola, lemon-lime, root beer, heavy citrus ("dew type") / fruit flavored and cream sodas; powdered soft drinks, as well as liquid concentrates such as fountain syrups and cordials; coffee and coffee-based drinks, coffee substitutes and cereal - based beverages; teas, including dry mix products as well as ready-to-drink teas (herbal and tea-leaf based) ; fruit and vegetable juices and juice flavored beverages as well as juice drinks, nectars, concentrates, punches and "ades” ; sweetened and flavored waters, both carbonated and still; sport/energy/health drinks; alcoholic beverages plus alcohol -free and other low-alcohol products including beer and malt beverages, cider, and wines (still, sparkling, fortified wines and wine coolers) ; other beverages processed with heating (infusions, pasteurization, ultra high temperature, ohmic heating or commercial aseptic sterilization) and hot-filled packaging; and cold-filled products made through
  • Fluid dairy products include, without limitation, non- frozen, partially frozen and frozen fluid dairy products such as, for example, milks, ice creams, sorbets and yogurts.
  • Condiments include, without limitation, ketchup, mayonnaise, salad dressing, Worcestershire sauce, fruit -flavored sauce, chocolate sauce, tomato sauce, chili sauce, and mustard.
  • Baked goods include, without limitation, cakes, cookies, pastries, breads, donuts and the like.
  • Bakery fillings include, without limitation, low or neutral pH fillings, high, medium or low solids fillings, fruit or milk based (pudding type or mousse type) fillings, hot or cold make-up fillings and nonfat to full-fat fillings.
  • the present invention is particularly effective for enhancing the stability of N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester in the above-named foods and beverages which are canned, bottled, pouched, packaged or otherwise packed in manners suitable for shipping and display at room temperature or in a chilled state.
  • This invention is also directed to a sweetened food composition, such as described above, containing an effective amount of the sweetener composition of this invention to sweeten the food composition.
  • Determination of the amount of sweetener composition to be added to the food composition, in order to effectively sweeten the food composition, can be readily determined by one of ordinary skill in the art.
  • the sweetener composition of the present invention can be used as a table-top sweetener.
  • the sweetener composition of the present invention can be used for this purpose alone or in combination with known bulking agents. Suitable bulking agents include, but are not limited to, dextrose, maltodextrin, lactose, inulin, polyols, polydextrose, cellulose and cellulose derivatives.
  • a table-top sweetener comprising the present sweetener composition may also include any other ingredients commonly present in table-top sweeteners in order to tailor the taste of the product to a specific end use.
  • a table-top sweetener comprising the present sweetener composition may take any known form.
  • Suitable forms include, but are not limited to, sachets including the sweetener in powder or granular form, tablets, liquid sweeteners, and jar, pouches, pocket or other forms in which the sweetener may be measured in, for example, spoon for spoon form.
  • the sweetener composition of this invention can also include known natural sweeteners as well as other high intensity sweeteners.
  • Sweeteners that may be employed include, without limitation, aspartame, acesulfame-K, sucralose, saccharin, alitame, cyclamates, stevia derivatives, thaumatin, sucrose (liquid and granulated) , high fructose corn syrup, high conversion corn syrup, crystalline fructose, glucose (dextrose) , polyol sugar alcohols, invert sugar and mixtures thereof .
  • ⁇ -cyclodextrin 34.02 g, 0.03 mol
  • a solution of 350 ml water and 75 ml ethanol was heated using a hot plate.
  • a separate N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester (10.95 g, 0.03 mol) solution dissolved in 75 ml of ethanol was added.
  • the clear solution was allowed to cool to 40°C (approximately 0.5 hr) then vacuum distilled until 230 ml of condensate was collected (approximately .75 hr) .
  • the solution was cooled under atmospheric conditions to 3°C (approximately 10 min). No precipitate had formed, so the product was freeze dried to collect complex.
  • Sample was analyzed using differential scanning calorimetry and compared with DSC scans of N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester, ⁇ -cyclodextrin, and a dry blend of ⁇ -cyclodextrin and N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester.
  • the data indicated the formation of the desired complex.
  • ⁇ -cyclodextrin (28.35 g, 0.025 mol) was slurried in a solution of 350 ml water and 75 ml ethanol, and the solution was heated using a hot plate. Once the ⁇ - cyclodextrin/water/ethanol solution reached 50°C (approximately 1 hr) , a separate N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester (3.7846 g, 0.010 mol) solution dissolved in 75 ml of ethanol was added.
  • ⁇ -cyclodextrin (28.35 g, 0.025 mol) was slurried in a solution of 350 ml water and 75 ml ethanol, and the solution was heated using a hot plate. Once the ⁇ - cyclodextrin/water/ethanol solution reached 53 °C (approximately 0.5 hr) , a separate N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester (1.8923 g, 0.0052 mol) solution dissolved in 75 ml of ethanol was added.
  • the clear solution was allowed to cool to 42 °C (approximately 1 hr) then vacuum distilled (28" Hg) until a precipitate formed (approximately 2.5 hr) , which was suspected to be uncomplexed cyclodextrin.
  • the vacuum was discontinued, after 180 ml of condensate was collected.
  • the solution was freeze dried to collect complex.
  • Sample was analyzed using differential scanning calorimetry and compared with DSC scans of N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester, ⁇ - cyclodextrin, and a dry blend of ⁇ -cyclodextrin and N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester.
  • the data indicated formation of the desired complex.
  • ⁇ -cyclodextrin (28.35 g, 0.025 mol) was slurried in a solution of 350 ml water and 75 ml ethanol, and the solution was heated using a hot plate. Once the ⁇ - cyclodextrin/water/ethanol solution reached 50°C (approximately 40 min), a separate N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester (0.94615 g, 0.0026 mol) solution dissolved in 75 ml of ethanol was added.
  • the clear solution was allowed to cool to 43°C (approximately 0.5 hr) then vacuum distilled (28" Hg) until a precipitate formed (approximately 3 hr) .
  • the vacuum was discontinued, after 140 ml of condensate was collected.
  • the solution was freeze dried to collect complex.
  • Sample was analyzed using differential scanning calorimetry and compared with DSC scans of N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester, ⁇ - cyclodextrin, and a dry blend of ⁇ -cyclodextrin and N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester.
  • the data indicated formation of the desired complex.
  • a carbonated soft drink was formulated by adding to 978.50 g of distilled water, in the order specified, 1.00 g sodium benzoate, 0.10 g N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester, 3.20 g cola acid and 17.20 g cola flavor.
  • a carbonated soft drink was formulated by adding to 978.20 g of distilled water, in the order specified, 1.00 g sodium benzoate, 0.10 g N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester, 0.31 g cyclodextrin, 3.20 g cola acid and 17.20 g cola flavor.
  • a carbonated soft drink was formulated by adding to 978.20 g of distilled water, in the order specified, 1.00 g sodium benzoate, 0.408 g premix (comprised of 0.102 g N- [N- (3, 3-dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester and 0.306 g cyclodextrin), 3.20 g cola acid and 17.20 g cola flavor.
  • a carbonated soft drink was formulated by adding to 978.194 g of distilled water, in the order specified, 1.00 g sodium benzoate, 0.408 g 1:1 cyclodextrin/N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester complex, 3.20 g cola acid and 17.20 g cola flavor.
  • a carbonated soft drink was formulated by adding to 977.700 g of distilled water, in the order specified, 1.00 g sodium benzoate, 0.867 g 2.5:1 cyclodextrin/N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester complex, 3.20 g cola acid and 17.20 g cola flavor.
  • a carbonated soft drink was formulated by adding to 977.000 g of distilled water, in the order specified, 1.00 g sodium benzoate, 1.632 g 5:1 cyclodextrin/N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester complex, 3.20 g cola acid and 17.20 g cola flavor.
  • a carbonated soft drink was formulated by adding to 975.400 g of distilled water, in the order specified, 1.00 g sodium benzoate, 3.158 g 10:1 cyclodextrin/N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester complex, 3.20 g cola acid and 17.20 g cola flavor.
  • Sorbitol powder (1661.6 g) was divided into two equal portions. To one portion, 525 g of lycasin was added. Into an Aaron Process Mixer, 945 g gum base was placed and heated to about 115 C -140°C. Hand mixed with the other portion of sorbitol powder was 0.900 g N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester. The speed on the mixer was set to #80 and the neotame/sorbitol mixture was gradually added.
  • the lycasin/sorbitol mixture 210 g glycerin, 105 g mannitol and 52.5 g peppermint flavor were added in that order.
  • the temperature control was shut off and the product left to sit for 10 minutes.
  • the product was then divided into four equal portions and dusted with mannitol. Each portion was rolled with a rolling pin to a thickness of 0.2" (0.51 cm) and cut into 1.5" x 0.5" (3.81 cm x 1.27 cm) strips.
  • Sorbitol powder (1658.87 g) was divided into two equal portions. To one portion, 525 g of lycasin was added. Into an Aaron Process Mixer, 945 g gum base was placed and heated to about 115°-140°C. Hand mixed with the other portion of sorbitol powder was 3.629 g 1:1 cyclodextrin/N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester complex. The speed on the mixer was set to #80 and the neotame complex/sorbitol mixture was gradually added.
  • the lycasin/sorbitol mixture 210 g glycerin, 105 g mannitol and 52.5 g peppermint flavor were added in that order.
  • the temperature control was shut off and the product left to sit for 10 minutes.
  • the product was then divided into four equal portions and dusted with mannitol. Each portion was rolled with a rolling pin to a thickness of 0.2" (0.51 cm) and cut into 1.5" x 0.5" (3.81 cm x 1.27 cm) strips
  • Sorbitol powder (1634.29 g) was divided into two equal portions. To one portion, 525 g of lycasin was added. Into an Aaron Process Mixer, 945 g gum base was placed and heated to about 115°-140°C. Hand mixed with the other portion of sorbitol powder was 28.213 g 10:1 cyclodextrin/N- [N- (3 , 3 -dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester complex. The speed on the mixer was set to #80 and the neotame complex/sorbitol mixture was gradually added.
  • Table 2 shows that the long-term stability of the N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester was improved by using ⁇ -cyclodextrin.
  • Table 3 illustrates the increase in half life achieved by cyclodextrin stabilized N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester. Table 3 was generated using the data from Table 2. TABLE 3. Half Life.
  • Ex. 11 1 1 complex of cyclodextrin and N- [N (3,3' dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester (Example 1) added to chewing gum formulation

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Inorganic Chemistry (AREA)
  • Peptides Or Proteins (AREA)
  • Seasonings (AREA)

Abstract

On combine du N-[N-(3,3-diméthylbutyl)-L-α-aspartyl]-L-phénylalanine 1-ester méthylique et de la cyclodextrine pour former des compositions présentant une stabilité et une solubilité accrues. La cyclodextrine peut être de la cyclodextrine α, β ou η, ou bien un mélange de ces dernières et peut être substituée ou non substituée. Ce complexe stabilisé peut être utilisé dans une grande diversité d'applications. Pour former ledit complexe on peut utiliser divers procédés, tels que la co-précipitation, la complexation de pâtes épaisses, la complexation de pâtes, le mélange et le chauffage, l'extrusion, le mélange à sec, la formation de billes à l'état humide, l'agglomération et d'autres procédés connus par les hommes et les femmes de l'art.
PCT/US1999/021471 1998-09-17 1999-09-16 UTILISATION DE CYCLODEXTRINE POUR STABILISER LE N-[N- (3,3-DIMETHYLBUTYL) -L-α- ASPARTYL] -L-PHENYLALANINE 1-ESTER METHYLIQUE Ceased WO2000015049A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU61504/99A AU6150499A (en) 1998-09-17 1999-09-16 The use of cyclodextrin to stabilize n-(n- (3,3-dimethylbutyl) -1-alpha- aspartyl) -l-phenylalanine 1-methyl ester

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US10086798P 1998-09-17 1998-09-17
US60/100,867 1998-09-17

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Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000049036A1 (fr) * 1999-02-18 2000-08-24 The Nutrasweet Company AGGLOMERAT DE N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER
WO2000057725A1 (fr) * 1999-03-26 2000-10-05 The Nutrasweet Company PARTICULES DE N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER
WO2000069283A1 (fr) * 1999-05-13 2000-11-23 The Nutrasweet Company UTILISATION D'ADDITIFS POUR MODIFIER LES CARACTERISTIQUES GUSTATIVES DE N-NEOHEXYL $G(a)-ASPARTYL-L-PHENYLALANINE METHYLESTER
WO2005020716A1 (fr) * 2003-08-28 2005-03-10 Ajinomoto Switzerland Ag Solution d'aspartame
EP1576891A1 (fr) * 2004-03-16 2005-09-21 Kraft Foods Holdings, Inc. Méthode de séchage de néotame avec des co-agents
US7014876B2 (en) * 2001-09-28 2006-03-21 Kao Corporation Packaged beverage
US7326430B2 (en) 2000-07-18 2008-02-05 The Nutrasweet Company Method of preparing liquid compositions for delivery of N-[N- (3,3-dimethylbutyl-L-α-aspartyl]-L-phenylalanine 1-methyl ester in food and beverage systems
WO2008147723A1 (fr) * 2007-05-22 2008-12-04 The Coca-Cola Company Systèmes d'administration pour compositions édulcorantes naturelles très puissantes, procédés de préparation et utilisations
EP1656031A4 (fr) * 2003-07-11 2011-02-09 Cadbury Adams Usa Llc Compositions de gomme a macher et de confiserie contenant un complexe d'elimination des taches et procedes de fabrication et d'utilisation associes
US20110195161A1 (en) * 2010-02-08 2011-08-11 Coca Cola Company Solubility enhanced terpene glycoside(s)
US8017168B2 (en) 2006-11-02 2011-09-13 The Coca-Cola Company High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith
US8162176B2 (en) 2007-09-06 2012-04-24 The Coca-Cola Company Method and apparatuses for providing a selectable beverage
US9101160B2 (en) 2005-11-23 2015-08-11 The Coca-Cola Company Condiments with high-potency sweetener
US20150366253A1 (en) * 2014-06-20 2015-12-24 Epc (Beijing) Natural Products Co., Ltd. Stevia sweetener with improved solubility with a cyclodextrin
US20180146700A1 (en) * 2011-06-03 2018-05-31 Purecircle Sdn Bhd Stevia composition
US10631558B2 (en) 2006-03-06 2020-04-28 The Coca-Cola Company Methods and apparatuses for making compositions comprising an acid and an acid degradable component and/or compositions comprising a plurality of selectable components

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EP0097950A1 (fr) * 1982-06-28 1984-01-11 Ajinomoto Co., Inc. Composition stabilisée d'aspartame, procédé pour sa production et denrée alimentaire aqueuse
US5070081A (en) * 1988-04-20 1991-12-03 National Research Council Of Canada Inclusion complexes of cyclodextrins by agglomeration
US5480668A (en) * 1992-11-12 1996-01-02 Nofre; Claude N-substituted derivatives of aspartame useful as sweetening agents

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EP0097950A1 (fr) * 1982-06-28 1984-01-11 Ajinomoto Co., Inc. Composition stabilisée d'aspartame, procédé pour sa production et denrée alimentaire aqueuse
US5070081A (en) * 1988-04-20 1991-12-03 National Research Council Of Canada Inclusion complexes of cyclodextrins by agglomeration
US5480668A (en) * 1992-11-12 1996-01-02 Nofre; Claude N-substituted derivatives of aspartame useful as sweetening agents

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000049036A1 (fr) * 1999-02-18 2000-08-24 The Nutrasweet Company AGGLOMERAT DE N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER
WO2000057725A1 (fr) * 1999-03-26 2000-10-05 The Nutrasweet Company PARTICULES DE N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER
US6365216B1 (en) 1999-03-26 2002-04-02 The Nutrasweet Company Particles of N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester
WO2000069283A1 (fr) * 1999-05-13 2000-11-23 The Nutrasweet Company UTILISATION D'ADDITIFS POUR MODIFIER LES CARACTERISTIQUES GUSTATIVES DE N-NEOHEXYL $G(a)-ASPARTYL-L-PHENYLALANINE METHYLESTER
US7326430B2 (en) 2000-07-18 2008-02-05 The Nutrasweet Company Method of preparing liquid compositions for delivery of N-[N- (3,3-dimethylbutyl-L-α-aspartyl]-L-phenylalanine 1-methyl ester in food and beverage systems
US7014876B2 (en) * 2001-09-28 2006-03-21 Kao Corporation Packaged beverage
EP1656031A4 (fr) * 2003-07-11 2011-02-09 Cadbury Adams Usa Llc Compositions de gomme a macher et de confiserie contenant un complexe d'elimination des taches et procedes de fabrication et d'utilisation associes
WO2005020716A1 (fr) * 2003-08-28 2005-03-10 Ajinomoto Switzerland Ag Solution d'aspartame
EP1576891A1 (fr) * 2004-03-16 2005-09-21 Kraft Foods Holdings, Inc. Méthode de séchage de néotame avec des co-agents
US9101160B2 (en) 2005-11-23 2015-08-11 The Coca-Cola Company Condiments with high-potency sweetener
US10631560B2 (en) 2006-03-06 2020-04-28 The Coca-Cola Company Methods and apparatuses for making compositions comprising an acid and an acid degradable component and/or compositions comprising a plurality of selectable components
US10631558B2 (en) 2006-03-06 2020-04-28 The Coca-Cola Company Methods and apparatuses for making compositions comprising an acid and an acid degradable component and/or compositions comprising a plurality of selectable components
US8017168B2 (en) 2006-11-02 2011-09-13 The Coca-Cola Company High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith
WO2008147723A1 (fr) * 2007-05-22 2008-12-04 The Coca-Cola Company Systèmes d'administration pour compositions édulcorantes naturelles très puissantes, procédés de préparation et utilisations
US8162176B2 (en) 2007-09-06 2012-04-24 The Coca-Cola Company Method and apparatuses for providing a selectable beverage
US8814000B2 (en) 2007-09-06 2014-08-26 The Coca-Cola Company Method and apparatuses for providing a selectable beverage
US10046959B2 (en) 2007-09-06 2018-08-14 The Coca-Cola Company Method and apparatuses for providing a selectable beverage
US8434642B2 (en) 2007-09-06 2013-05-07 The Coca-Cola Company Method and apparatus for providing a selectable beverage
US20110195161A1 (en) * 2010-02-08 2011-08-11 Coca Cola Company Solubility enhanced terpene glycoside(s)
US20180146700A1 (en) * 2011-06-03 2018-05-31 Purecircle Sdn Bhd Stevia composition
US11825867B2 (en) 2011-06-03 2023-11-28 Purecircle Sdn Bhd Stevia composition
US20150366253A1 (en) * 2014-06-20 2015-12-24 Epc (Beijing) Natural Products Co., Ltd. Stevia sweetener with improved solubility with a cyclodextrin
EP3157940A4 (fr) * 2014-06-20 2018-01-10 EPC (Beijing) Natural Products Co., Ltd. Édulcorant à base de stevia, à solubilité améliorée, mélangé avec une cyclodextrine
US10485256B2 (en) * 2014-06-20 2019-11-26 Sweet Green Fields International Co., Limited Stevia sweetener with improved solubility with a cyclodextrin

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