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WO1999030578A1 - UTILISATION DE 1-METHYLESTER DE N-[N-3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]L-PHENYLALANINE DANS DES PRODUITS LAITIERS ET LEURS ANALOGUES - Google Patents

UTILISATION DE 1-METHYLESTER DE N-[N-3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]L-PHENYLALANINE DANS DES PRODUITS LAITIERS ET LEURS ANALOGUES Download PDF

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Publication number
WO1999030578A1
WO1999030578A1 PCT/US1998/027176 US9827176W WO9930578A1 WO 1999030578 A1 WO1999030578 A1 WO 1999030578A1 US 9827176 W US9827176 W US 9827176W WO 9930578 A1 WO9930578 A1 WO 9930578A1
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WO
WIPO (PCT)
Prior art keywords
ppm
aspartyl
phenylalanine
dimethylbutyl
methyl ester
Prior art date
Application number
PCT/US1998/027176
Other languages
English (en)
Inventor
Wanda M. Gaughan
Paula A. Gerlat
Jeanette G. Ziegler
Gale C. Walters
Lori Logli
Glenn Corliss
John Finley
Original Assignee
The Nutrasweet Company
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by The Nutrasweet Company filed Critical The Nutrasweet Company
Priority to AU19364/99A priority Critical patent/AU1936499A/en
Publication of WO1999030578A1 publication Critical patent/WO1999030578A1/fr

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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
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/346—Finished or semi-finished products in the form of powders, paste or liquids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING OR TREATMENT THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
    • A23C9/13—Fermented milk preparations; Treatment using microorganisms or enzymes using additives
    • A23C9/1307—Milk products or derivatives; Fruit or vegetable juices; Sugars, sugar alcohols, sweeteners; Oligosaccharides; Organic acids or salts thereof or acidifying agents; Flavours, dyes or pigments; Inert or aerosol gases; Carbonation methods
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING OR TREATMENT THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/152—Milk preparations; Milk powder or milk powder preparations containing additives
    • A23C9/156—Flavoured milk preparations ; Addition of fruits, vegetables, sugars, sugar alcohols or sweeteners
    • 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
    • A23G9/00—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
    • A23G9/52—Liquid products; Solid products in the form of powders, flakes or granules for making liquid products ; Finished or semi-finished solid products, frozen granules
    • 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
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G2200/00—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents
    • A23G2200/06—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents containing beet sugar or cane sugar if specifically mentioned or containing other carbohydrates, e.g. starches, gums, alcohol sugar, polysaccharides, dextrin or containing high or low amount of carbohydrate

Definitions

  • the invention relates to the use of the sweetener, N-[N-(3,3-dimethylbutyl)- L- ⁇ -aspartyl]-L-phenylalanine 1 -methyl ester (neotame), in dairy and dairy analogue products.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester is known as an extremely potent sweetening agent, as disclosed in U.S. Patent No. 5,480,668, the complete disclosure of which is incorporated by reference herein. Its sweetening potency, on a weight basis, is reported to be at least 40 times that of aspartame and about 8,000 times that of sucrose. N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester is a highly potent sweetener. It would be advantageous to be able to utilize its sweetener potency in dairy and dairy analogue products. Such use is not described or suggested by the prior art.
  • This invention relates to a dairy product comprising N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester in an amount effective to sweeten the dairy product.
  • the dairy products of this invention include, without limitation, milk (from various species and of various milkfat content), enzyme treated milk, filled milk, cream, creamers, cultured milk, milk concentrates, dry milk, fluid and dried whey, fluid and dry milk based desserts and beverages, and fluid and dry aerated desserts and toppings.
  • the dairy products of this invention also include frozen cultured milk products, such as frozen yogurt, and frozen fluid dairy products, such as ice cream, ice milk, sherbet, custards and french ice cream, mellorine, novelties, and the like. Most preferably, the dairy products of this invention are no-sugar added dairy products.
  • the invention also relates to a method of preparing a dairy product by incorporating an effective amount of N- [N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester in the dairy product to sweeten the product.
  • Another embodiment of this invention is related to a dairy analogue product comprising N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1 -methyl ester in an amount effective to sweeten the dairy analogue product.
  • the dairy analogue products of this invention include, without limitation, soy milk, soy powder, caseinates, and non-dairy coffee whiteners, as well as frozen products such as sorbet and non-dairy novelties.
  • the dairy analogue products of this invention are no-sugar added dairy analogue products.
  • the invention also relates to a method of preparing a dairy analogue product by incorporating an effective amount of N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester in the dairy analogue product to sweeten the product.
  • An additional embodiment of this invention is related to the use of N-[N-(3,3- dimethylbutyl)-L- -aspartyl]-L-phenylalanine 1-methyl ester blended with other natural or high intensity sweeteners in dairy and dairy analogue products.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester sweetener blends are added to dairy and dairy analogue products in an amount effective to sweeten the product.
  • this invention is directed to a method of sweetening dairy and dairy analogue products by the incorporation of N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with another sweetener in the dairy and dairy analogue products in an amount effective to sweeten these products.
  • This invention is related to dairy and dairy analogue products having N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester as a component.
  • neotame may be used in the dairy and dairy analogue products of this invention.
  • salts and metal complexes of neotame may be used, such as disclosed in U.S. Patent Application No. 09/146,963, U.S. Patent Application No. 09/146,964, U.S. Patent Application No. 09/148,134, and U.S. Patent Application No. 09/146,965, all filed September 4, 1998, and all of which are incorporated by reference herein.
  • Other exemplary forms of neotame that may be useful in this invention include cyclodextrin/neotame complexes such as disclosed in U.S. Provisional Patent Application No. 60/100,867 and cocrystallized neotame disclosed in U.S. Patent Application No. 09/154,568, both filed September 17, 1998, and the disclosure of both of which are incorporated by reference herein.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1- methyl ester will provide greater sweetener stability as compared to aspartame in the dairy and dairy analogue products of the present invention. It is also believed that use of N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1- methyl ester produces a higher quality dairy and dairy analogue product than other high intensity sweeteners.
  • the dairy products of this invention include, without limitation, milk (from various species and of various milkfat content), enzyme treated milk, filled milk, cream, creamers, cultured milk, milk concentrates, dry milk, fluid and dried whey, fluid and dry milk based desserts and beverages, and fluid and dry aerated desserts and toppings.
  • the dairy products of this invention may be liquids, gels, emulsions, powders, and mixtures thereof.
  • the dairy products also may be frozen fluid dairy products or frozen cultured milk products.
  • the dairy analogue products of this invention include, without limitation, soy milk, soy powder, caseinates and non-dairy coffee whiteners, as well as frozen products such as sorbet and non-dairy novelties.
  • the dairy and dairy analogue products of this invention may be prepared using ingredients and techniques well known to those skilled in the art.
  • the present invention includes incorporating N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester by heat processing, for example, high heat short time (HHST), ultra high temperature (UHT), batch, and vat processing.
  • HHST high heat short time
  • UHT ultra high temperature
  • vat processing for example, high heat short time (HHST), ultra high temperature (UHT), batch, and vat processing.
  • HHST high heat short time
  • UHT ultra high temperature
  • it is important to mix the ingredients properly for good content uniformity.
  • the N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester is added to dairy products in an amount effective to sweeten the product, typically at levels ranging from about 3 ppm to about 250 ppm, for no-sugar-added products.
  • the N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester is added to no-sugar-added dairy products at levels in the range between about 5 ppm to about 150 ppm, and most preferably from about 10 ppm to about 100 ppm.
  • lower levels may be used when an additional sweetener is present.
  • This invention is also related to non-reconstituted powdered dairy products, i.e., the powdered product prior to reconstitution, sweetened with N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester.
  • the N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester is present in these powdered dairy products in an amount effective to sweeten the product, typically at levels ranging from about 30 ppm to about 1,250 ppm for no-sugar added- products.
  • the N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester is added to these no-sugar added, non-reconstituted powdered dairy products in the range between about 60 ppm to about 1 ,000 ppm, and most preferably from about 90 ppm to about 835 ppm. Of course, lower levels may be used when an additional sweetener is present.
  • Still yet another embodiment of this invention is related to dairy analogue products sweetened with N-[N-(3,3-dimethylbutyl)-
  • N-[N-(3,3-dimethylbutyl)- L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester is present in the dairy analogue product in an amount effective to sweeten the product, typically at levels ranging from about 5 ppm to about 150 ppm for no-sugar added-products.
  • the N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester is added to these no-sugar added dairy analogue products in the range between about 10 ppm to about 100 ppm, and most preferably from about 12 ppm to about 50 ppm. Of course, lower levels may be used when an additional sweetener is present.
  • An additional embodiment of this invention is related to the use of N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with other natural or high intensity sweeteners in dairy and dairy analogue products.
  • Other 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.
  • Bulking agents may be used, as well, to replace the bulking functions of sugar; some of these bulking agents can provide added sweetness in and of themselves. For example, compared to sucrose, Raftilose P95TM ohgofructose is approximately 30% as sweet, isomalt is approximately 60% as sweet, and sorbitol is approximately 60%o as sweet.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester sweetener blends are added to dairy and dairy analogue products in an amount effective to sweeten the product.
  • the amount effective or effective amount of N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester necessary to sweeten the dairy and dairy analogue products of this invention is that amount necessary to provide a desired sweetness sensation in the mouth either alone or blended with other natural or high intensity sweeteners.
  • the blended N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester is present in an amount of about 0.1 ppm to about 100 ppm.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester employed will be dependent on the particular application.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester can be used to sweeten no sugar added orange sherbet in an amount between about 5 ppm to about 250 ppm, more preferably from about 20 ppm to about 150 ppm, and most preferably from about 30 ppm to about 75 ppm.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1 -methyl ester can be used to sweeten no sugar added strawberry frozen yogurt generally in an amount between about 5 ppm to about 150 ppm, more preferably from about 20 ppm to about 100 ppm, and most preferably from about 30 ppm to about 75 ppm.
  • the general range for adding N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester in an amount effective to sweeten no sugar added chocolate milk drink is from about 5 ppm to about 100 ppm, more preferably from about 20 ppm to about 75 ppm, and most preferably from about 25 ppm to about 40 ppm.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester can be used to sweeten no-sugar-added, low fat vanilla ice cream generally in an amount between about 5 ppm to about 75 ppm, more preferably from about 10 ppm to about 45 ppm, and most preferably from about 12 ppm to about 30 ppm.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester can be used to sweeten no-sugar-added, low fat chocolate ice cream generally in an amount between about 5 ppm to about 75 ppm, more preferably between about 10 ppm to about 45 ppm, and most preferably between about 12 ppm to about 30 ppm.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester can be used to sweeten strawberry yogurt generally in an amount between about 3 ppm to about 70 ppm, more preferably between about 5 ppm to about
  • N-[N- (3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester can be used to sweeten no sugar added chocolate pie filling generally in an amount between about 9 ppm to about 200 ppm, more preferably between about 20 ppm to 150 ppm, and most preferably 40 ppm to about 100 ppm.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]- L-phenylalanine 1-methyl ester can be used to sweeten reconstituted hot cocoa mix generally in an amount between about 7 ppm to about 13 ppm, preferably between about 8 ppm to about 12 ppm, and most preferably between about 9 ppm to about 11 ppm.
  • 1-methyl ester can be used to sweeten reconstituted whipped topping mix generally in an amount between about 5 ppm to about 75 ppm, more preferably between about 10 ppm to about 50 ppm, and most preferably between about 15 ppm and about 40 ppm.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester can be used to sweeten reconstituted vanilla flavored instant pudding mix generally in an amount between about 10 ppm and about 75 ppm, more preferably between about 15 ppm and about 60 ppm, and most preferably between 20 ppm and about 50 ppm.
  • (3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester can be used to sweeten hot cocoa mix (non-reconstituted) generally in an amount between about 90 ppm to about 170 ppm, preferably between about 100 ppm to about 150 ppm, and most preferably between about 115 ppm to about 140 ppm.
  • N-[N- (3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester can be used to sweeten whipped topping mix (non-reconstituted) generally in an amount between about 30 ppm to about 460 ppm, more preferably between about 60 ppm to about 300 ppm, and most preferably between about 90 ppm and about 245 ppm.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1- methyl ester can be used to sweeten vanilla flavored instant pudding mix (non- reconstituted) generally in an amount between about 170 ppm and about 1,250 ppm, more preferably between about 250 ppm and about 1,000 ppm, and most preferably between 335 ppm and about 835 ppm.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]- L-phenylalanine 1 -methyl ester can be used to sweeten no sugar added strawberry sorbet generally in an amount between 5 ppm to about 150 ppm, more preferably between about 20 ppm to about 100 ppm, and most preferably between about 25 ppm to about 50 ppm.
  • N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester can be used to sweeten this product generally in an amount between about 5 ppm and 75 ppm, more preferably between about 10 ppm and 45 ppm, and most preferably between about 12 ppm and 30 ppm.
  • dairy product formulations were made with different levels of N-[N- (3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester. These levels were selected to establish the levels that would be less sweet than acceptable and sweeter than acceptable.
  • dairy product formulations were made with N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with another sweetener, i.e. sugar, aspartame, acesulfame-K, saccharin, or cyclamate.
  • Bench screening was used to evaluate each of the different prototypes for each basic formulation using 100%) N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester. Also, bench screening was used to evaluate the formulations using N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1- methyl ester blended with another sweetener.
  • the tested examples included fluid, frozen fluid, cultured, and reconstituted powdered dairy products. These products covered a range of variables including: pH, processing, solids, fat levels, stabilizers, and flavors. The results from this bench screening established 3 ranges, going from a very general to a most preferred range for each application.
  • Example 1 No Sugar Added Orange Sherbet (24.4% total solids (TS), 1.4% butter fat (BF), 4.3% non-fat milk solids (NMS)).
  • Example 1 The constituents used to formulate the No Sugar Added Orange Sherbet of Example 1 are shown below in Table 1. TABLE 1 Example 1 Formulation No Sugar Added Orange Sherbet, 0 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester
  • the No Sugar Added Orange Sherbet of Example 1 was made by first blending all the dry ingredients. The dry ingredients were then added to water, cream, and skim milk. The mixture was mixed using medium shear forces. The mixture was then heated to 85°C (185°F) in a water bath and pasteurized for 5 minutes at 85°C (185°F). The pasteurized mixture was homogenized with a Silverson apparatus for 2 minutes at medium speed. The homogenized mixture was cooled to 21°C (70°F) in a water bath. The melted orange juice concentrate and vanilla were then added and blended well. The resulting mixture was cooled to 4°C (40°F) and held for 2-3 hours.
  • the mixture was next frozen in a Taylor Soft Serve Machine and packaged as 10-20 g servings which were hardened in a walk-in freezer at -32°C (-20°F) overnight. Before serving, the frozen product was tempered overnight at -14 to -12°C (6-10°F).
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1- methyl ester were prepared and evaluated to determine the general, preferred, and most preferred ranges.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester can be used to sweeten no sugar added orange sherbet generally in an amount between about 5 ppm to about 250 ppm, more preferably from about 20 ppm to about 150 ppm, and most preferably from about 30 ppm to about 75 ppm.
  • Examples 2-4 Orange Sherbet (N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester blended with other sweeteners).
  • Orange Sherbet was prepared in a manner substantially similar to Example 1, with the exception that Examples 2-4 were sweetened with N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with another sweetener, i.e., either aspartame (APM), acesulfame-K (Ace-K), or saccharin.
  • APM aspartame
  • Ace-K acesulfame-K
  • saccharin saccharin.
  • Example 2 N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with APM.
  • Various Orange Sherbet compositions having different concentrations of N-[N- (3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and APM were prepared.
  • a low level of one sweetener was combined with a high level of the other sweetener.
  • the general range for adding N-[N-(3,3-dimethylbutyl)-L- ⁇ - aspartyl]-L-phenylalanine 1-methyl ester blended with APM is from about 0.5 ppm to about 60 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about 20 ppm to about 1,300 ppm APM.
  • the preferred range is from about 1 ppm to about 50 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ - aspartyl]-L-phenylalanine 1-methyl ester and from about 100 ppm to about 650 ppm APM.
  • the more preferred range is from about 7 ppm to about 30 ppm N-
  • Example 3 N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with Ace-K.
  • the general range for adding N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with Ace- K is from about 1 ppm to about 60 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ - aspartyl]-L-phenylalanine 1-methyl ester and from about 20 ppm to about 400 ppm Ace-K.
  • the preferred range is from about 1 ppm to about 50 ppm N-[N- (3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about
  • Ace-K 50 ppm to 340 ppm Ace-K.
  • the most preferred range is from about 7 ppm to about 30 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about 80 ppm to about 150 ppm Ace-K.
  • the amount of Ace-K is limited by its bitter character and an impression of greasiness or slickness at high concentration levels.
  • Example 4 N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with saccharin.
  • the general range for adding N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with saccharin is from about 10 ppm to about 60 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester and from about 20 ppm to about 200 ppm saccharin.
  • the preferred range is from about 15 ppm to about 50 ppm N-[N-
  • Example 5 No Sugar Added Strawberry Frozen Yogurt (25.1% TS, 1.3% BF, 10.5% NMS).
  • the No Sugar Added Strawberry Frozen Yogurt of Example 5 was made by first blending the dry ingredients listed in Part 1 of Table 2 to form a dry blend.
  • the dry blend was added to the milk and the cream in a mixer while using medium shear force.
  • the mixture was then heated to 60-71°C (140-160°F), followed homogenization in a Silverson apparatus at medium speed for 4 minutes.
  • the mixture was then pasteurized at 85°C (185°F) for 4 minutes and cooled to 4°C (40°F).
  • the Part 2 ingredients were next blended in to the cooled mixture. Again the mixture was cooled to 4°C (40°F) and then frozen in a soft serve machine to form the frozen yogurt.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester were prepared and evaluated to determine the general, preferred, and most preferred ranges.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester can be used to sweeten strawberry frozen yogurt generally in an amount between about 5 ppm to about 150 ppm, more preferably from about 20 ppm to about 100 ppm, and most preferably from about 30 ppm to about 75 ppm.
  • Example 6 No Sugar Added Chocolate Milk Drink (12.4% TS, 1.1% fat, 10.3% NMS).
  • the No Sugar Added Chocolate Milk Drink of Example 6 was made by first blending the dry ingredients together to form a dry blend. The milk was then added while the mixture was being mixed by a mixer at a high shear force. The mixture was then pasteurized at 88°C (190°F) for 2 minutes, followed by being homogenized in a Silverson apparatus for 4 minutes at low speed. The mixture was next cooled to 21°C (70°F) while stirring and packaged. The packaged Chocolate Milk Drink was refrigerated.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1- methyl ester were prepared and evaluated to determine the general, preferred, and most preferred ranges.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester can be used to sweeten no sugar added chocolate milk drink generally in an amount between about 5 ppm to about 100 ppm, more preferably from about 20 ppm to about 75 ppm, and most preferably from about 25 ppm to about 40 ppm.
  • Example 7 No Sugar Added, Low Fat Vanilla Ice Cream (29.56% TS, 2.74% fat, 4.12% protein solids, 10.41% NMS).
  • the No Sugar Added, Low Fat Vanilla Ice Cream of Example 7 was made by first adding the skim milk to a mixer and stirring. The stabilizer was gradually adding through a tri-blender. To this mixture, the N-[N-(3,3-dimethylbutyl)-L- ⁇ - aspartyl]-L-phenylalanine 1-methyl ester, malodextrin, nonfat dry milk, polydextrose, and cream were added. The mixture was heated to 60-71 °C (140- 160°F), followed by homogenization in a Turrax apparatus at medium speed for 4 minutes. The homogenized mixture was then pasteurized at 85°C (185°F) for 30 minutes and rapidly cooled to 4°C (40°F). The vanilla then was blended in to the mixture to form the No Sugar Added, Low Fat Vanilla Ice Cream, which was then frozen in a soft serve machine.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester were prepared and evaluated to determine the general, preferred, and most preferred ranges.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ - aspartyl]-L-phenylalanine 1-methyl ester can be used to sweeten no sugar added, low fat vanilla ice cream generally in an amount between about 5 ppm to about 75 ppm, more preferably from about 10 ppm to about 45 ppm, and most preferably from about 12 ppm to about 30 ppm.
  • Examples 8-11 Low Fat Vanilla Ice Cream (N-[N-(3,3-dimethylbutyl)-L- ⁇ - aspartyl]-L-phenylalanine 1-methyl ester blended with other sweeteners).
  • Low Fat Vanilla Ice Cream was prepared in a manner substantially similar to Example 7, with the exception that Examples 8-11 were sweetened with N-[N- (3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with another sweetener, i.e., either aspartame (APM), acesulfame-K (ace-K), saccharin, or sucrose.
  • APM aspartame
  • ace-K acesulfame-K
  • saccharin or sucrose.
  • Example 8 N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with APM.
  • the general range for adding N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with APM is from about 1 ppm to about 75 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester and from about 100 ppm to about 1,000 ppm APM.
  • the preferred range is from about 1 ppm to about 45 ppm N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about 130 ppm to about 800 ppm APM.
  • the more preferred range is from about 2 ppm to about 30 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about 200 ppm to about 600 ppm APM.
  • the most preferred blend is about 3 ppm N-[N-(3,3-dimethylbutyl)-L- -aspartyl]-L-phenylalanine 1- methyl ester and about 500 ppm APM.
  • Example 9 N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with Ace-K.
  • the general range for adding N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with Ace-K is from about 1 ppm to about 75 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester and from about 100 ppm to about 550 ppm Ace-K.
  • the preferred range is from about 1 ppm to about 45 ppm N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about 150 ppm to about 500 ppm Ace-K.
  • the more preferred range is from about 2 ppm to about 30 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1- methyl ester and from about 200 ppm to about 400 ppm Ace-K.
  • the most preferred blend is about 9 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester and about 270 ppm Ace-K.
  • Example 10 N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with saccharin.
  • Various Vanilla Low Fat Ice Cream compositions having different concentrations of N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and saccharin were prepared. A low level of one sweetener was combined with a high level of the other sweetener.
  • the general range for adding N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with saccharin is from about 1 ppm to about 75 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ - aspartyl]-L-phenylalanine 1-methyl ester and from about 100 ppm to about 450 ppm saccharin.
  • the preferred range is from about 1 ppm to about 45 ppm N- [N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about 150 ppm to about 400 ppm.
  • the more preferred range is from about 2 ppm to about 30 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1- methyl ester and from about 200 ppm to about 350 ppm saccharin.
  • the most preferred blend is about 3 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester and about 300 ppm saccharin.
  • Example 11 N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with sucrose.
  • compositions having different concentrations of N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and sucrose were prepared. A low level of one sweetener was combined with a high level of the other sweetener.
  • the general range for adding N-[N-(3, 3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with sucrose is from about 1 ppm to about 75 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ - aspartyl]-L-phenylalanine 1-methyl ester and from about 0.5%> (w/w) to about 15% (w/w) sucrose.
  • the preferred range is from about 1 ppm to about 45 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about 1.5% (w/w) to about 13% (w/w) sucrose.
  • the more preferred range is from about 2 ppm to about 30 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester and from about 3% (w/w) to about 12%> (w/w) sucrose.
  • the most preferred blend is about 9 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and about 4.2% (w/w) sucrose.
  • Example 12 No Sugar Added, Low Fat Chocolate ice cream (31.3% TS, 2.6% fat, 3.9% protein solids, 9.8% NMS).
  • Cream of Example 12 are shown in Table 8.
  • the No Sugar Added, Low Fat Chocolate Ice Cream of Example 12 was made by adding the skim milk to a jacketed kettle.
  • the sorbitol powder and the stabilizer were dry blended. While rapidly mixing, the dry blend was added to the skim milk. The mixing was slowed and the maltodextrin, nonfat dry milk, polydextrose, cocoa, and cream were added.
  • the mixture was then heated to 60- 71°C (140-160°F), followed by being homogenized in a Turrax Apparatus at medium speed for 4 minutes.
  • the homogenized mixture was then pasteurized at 82°C (180°F); the heat was held at 82°C (180°F) for 30 minutes.
  • the mixture was then rapidly cooled to 15°C (60°F).
  • vanilla and the N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester were added to the mixture.
  • the blended mixture was frozen in a soft serve machine.
  • the Chocolate Ice Cream was tempered at -14 to -12°C (6-10°F) before serving.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester were prepared and evaluated to determine the general, preferred, and most preferred ranges.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ - aspartyl]-L-phenylalanine 1-methyl ester can be used to sweeten no sugar added, low fat chocolate ice cream generally in an amount between about 5 ppm to about 75 ppm, more preferably from about 10 ppm to about 45 ppm, and most preferably from about 12 ppm to about 30 ppm.
  • Example 13 Strawberry Yogurt.
  • the Strawberry Yogurt of Example 13 was made by adding the yogurt white mass to a Hobart mixing bowl.
  • the N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester was added to the white mass and mixed with a spatula until it was dispersed throughout the product.
  • the strawberry fruit prep was added to the sweetened white mass and mixed with a paddle for about 10 minutes.
  • the resulting mixture was packaged in plastic deli cups.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester were prepared and evaluated to determine the general, preferred, and most preferred ranges.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester can be used to sweeten strawberry yogurt generally in an amount between about 3 ppm to about 70 ppm, more preferably from about 5 ppm to about 60 ppm, and most preferably from about 25 ppm to about 50 ppm.
  • Example 14-18 was sweetened with N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with another sweetener, i.e., either aspartame (APM), acesulfame-K (ace-K), saccharin, sucralose, or sucrose.
  • APM aspartame
  • ace-K acesulfame-K
  • saccharin sucralose, or sucrose.
  • Example 14 N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with APM.
  • the general range for adding N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with APM is from about 3 ppm to about 50 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1- methyl ester and from about 100 ppm to about 425 ppm APM.
  • the preferred range is from about 5 ppm to about 25 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ - aspartyl]-L-phenylalanine 1-methyl ester and from about 125 ppm to about 400 ppm APM.
  • the most preferred range is from about 6 ppm to about 15 ppm N- [N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about 125 ppm to about 375 ppm APM.
  • Example 15 N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with Ace-K.
  • the general range for adding N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with Ace-K is from about 3 ppm to about 50 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1- methyl ester and from about 100 ppm to about 500 ppm Ace-K.
  • the preferred range is from about 5 ppm to about 25 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ - aspartyl]-L-phenylalanine 1-methyl ester and from about 100 ppm to about 450 ppm Ace-K.
  • the most preferred range is from about 6 ppm to about 15 ppm N- [N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about 125 ppm to about 375 ppm Ace-K.
  • Example 16 N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with saccharin.
  • the general range for adding N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with saccharin is from about 3 ppm to about 50 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ - aspartyl]-L-phenylalanine 1-methyl ester and from about 30 ppm to about 300 ppm saccharin.
  • the preferred range is from about 5 ppm to about 45 ppm N- [N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about 50 ppm to about 250 ppm saccharin.
  • the most preferred range is from about 9 ppm to about 30 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester and from about 55 ppm to about 175 ppm saccharin.
  • Example 17 N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with sucralose.
  • the general range for adding N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with sucralose is from about 3 ppm to about 25 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ - aspartyl]-L-phenylalanine 1-methyl ester and from about 40 ppm to about 200 ppm sucralose.
  • the preferred range is from about 5 ppm to about 20 ppm N-[N- (3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about 45 ppm to about 150 ppm sucralose.
  • the most preferred range is from about 6 ppm to about 15 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1- methyl ester and from 50 ppm to about 125 ppm sucralose.
  • Example 18 N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with sucrose.
  • the general range for adding N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with sucrose is from about 3 ppm to about 50 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1- methyl ester and from about 1.5% (w/w) to about 9%> (w/w) sucrose.
  • the preferred range is from about 5 ppm to about 45 ppm N-[N-(3,3-dimethylbutyl)- L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about 2% (w/w) to about 7%> (w/w) sucrose.
  • the most preferred range is from about 9 ppm to about 30 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about 2.25% (w/w) to about 6%> (w/w) sucrose.
  • Example 19 No Sugar Added Chocolate Pie Filling.
  • Example 19 The constituents used to formulate the No Sugar Added Chocolate Pie Filling of Example 19 are shown below in Table 10.
  • Example 19 The No Sugar Added Chocolate Pie Filling of Example 19 was made by first whisking together the milk, cream, eggs, starch and salt. The resulting mixture was brought to a boil, whisking almost constantly. The heat was reduced and the mixture was cooked for approximately two minutes. The mixture was removed from the heat. N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1 -methyl ester, chocolate, and vanilla were added and the mixture was whisked until smooth. The resulting mixture was poured into an 8 or 9 inch (20.3 or 22.9 cm) pie shell and refrigerated before serving.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1- methyl ester were prepared and evaluated to determine the general, preferred, and most preferred ranges.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester can be used to sweeten no sugar added chocolate pie filling generally in an amount between about 9 ppm to about 200 ppm, more preferably from about 20 ppm to about 150 ppm, and most preferably from about 40 ppm to about 100 ppm.
  • Example 20 No Sugar Added Hot Cocoa Mix.
  • Example 11 The constituents used to formulate the No Sugar Added Hot Cocoa Mix of Example 20 are shown in Table 11.
  • Example 20 The No Sugar Added Hot Cocoa Mix of Example 20 was made by adding all ingredients, through a sieve, to a mixing bowl and mixing thoroughly on low for approximately 5 minutes. Hot Cocoa can then be prepared from the mix by adding hot water and stirring vigorously.
  • compositions having different concentrations of N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester were prepared and evaluated to determine the general, preferred, and most preferred.
  • L-phenylalanine 1-methyl ester can be used to sweeten no sugar added hot cocoa mix (reconstituted) generally in an amount between about 7 ppm to about 13 ppm, more preferably from about 8 ppm to about 12 ppm, and most preferably from about 9 ppm to about 11 ppm.
  • Hot Cocoa Mix was prepared in a manner substantially similar to Example 20, with the exception that Examples 21-26 were sweetened with N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with another sweetener, i.e., either sucrose, aspartame (APM), acesulfame K (Ace-K), saccharin, or cyclamate.
  • APM aspartame
  • Ace-K acesulfame K
  • saccharin or cyclamate.
  • Example 21 N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with sucrose.
  • the preferred range is from about 1 ppm to about 10 ppm N-[N-(3,3-dimethylbutyl)- L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about 2.0% (w/w) to about 8.0% (w/w) sucrose.
  • the more preferred range is from about 1 ppm to about 6.3 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about 4%> (w/w) to about 7.5% (w/w) sucrose.
  • the most preferred blend is about 5 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester and about 4% (w/w) sucrose.
  • Example 22 N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with APM.
  • the general range for adding N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with APM is from about 0.5 ppm to about 15 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]- L-phenylalanine 1-methyl ester and from about 20 ppm to about 850 ppm APM.
  • the preferred range is from about 1 ppm to about 12 ppm N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about 30 pm to about 700 ppm APM.
  • the most preferred range is from about 1 ppm to about 10 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about 40 ppm to about 600 ppm APM.
  • Example 23 N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with Ace-K.
  • the general range for adding N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with Ace- K is from about 0.5 ppm to about 12 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester and from about 20 ppm to about 360 ppm Ace-K.
  • the preferred range is from about 1 ppm to about 15 ppm N-[N-
  • Example 24 N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with saccharin.
  • Various hot cocoa mix compositions having different concentrations of N-[N- (3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and saccharin were prepared.
  • a low level of one sweetener was combined with a high level of the other sweetener.
  • the general range for adding N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with saccharin is from about
  • the preferred range is from about 1 ppm to about 12 ppm N-[N- (3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about 15 ppm to about 180 ppm saccharin.
  • the more preferred range is from about 2 ppm to about 10 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about 20 ppm to about 150 ppm saccharin.
  • the most preferred blend is about 5 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester and about 100 ppm saccharin.
  • the amount of saccharin used is limited by its bitter and metallic character at higher concentrations.
  • Example 25 N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with cyclamate.
  • the general range for adding N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester blended with cyclamate is from about 0.5 ppm to about 13 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester and from about 70 ppm to about 2,400 ppm cyclamate.
  • the preferred range is from about 1 ppm to about 12 ppm N-[N- (3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester and from about 130 ppm to about 1,300 ppm cyclamate.
  • the more preferred range is from about 1.8 ppm to about 9 ppm N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester and from about 130 ppm to about 1,000 ppm cyclamate.
  • the most preferred blends are about 8 ppm to about 9.5 ppm N-[N- (3, 3 -dimethylbutyl)-L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester and from about 130 ppm to about 500 ppm cyclamate.
  • the amount of cyclamate used is limited by its sourness at higher concentrations.
  • Example 26 No Sugar Added Whipped Topping Mix.
  • Example 26 The No Sugar Added Whipped Topping Mix of Example 26 was made by adding all dry ingredients together in a suitable size jar with a screw top. With the lid screwed on tightly, the jar was shaken until the dry mix was well blended, approximately 5 minutes. Milk was added to a bowl and the dry mix was gradually added to the milk. Using a mechanical mixer, the mixture was blended and then whipped until the topping formed and held peaks. The resulting whipped topping was refrigerated.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester were prepared and evaluated to determine the general, preferred, and most preferred ranges.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester can be used to sweeten no sugar added whipped topping mix (reconstituted) generally in an amount between about 5 ppm to about 75 ppm, more preferably from about 10 ppm to about 50 ppm, and most preferably from about 15 ppm to about 40 ppm.
  • Example 27 No Sugar Added Vanilla Flavored Instant Pudding Mix.
  • Example 27 The No Sugar Added Vanilla Flavored Instant Pudding Mix of Example 27 was made by adding the Staley starch through a sieve into a suitable size jar with a screw top lid. The rest of the dry ingredients were added. The jar was shaken until the dry mix was well blended, approximately 5 minutes. The milk was added to a bowl and the dry mix was added gradually to the milk. Using a mechanical mixer, the mixture was blended on medium for 30 seconds. The resulting pudding was refrigerated.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester were prepared and evaluated to determine the general, preferred, and most preferred ranges.
  • N-[N-(3,3- dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester can be used to sweeten no sugar added vanilla flavored instant pudding mix (reconstituted) generally in an amount between about 10 ppm to about 75 ppm, more preferably from about 15 ppm to about 60 ppm, and most preferably from about 20 ppm to about 50 ppm.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester were selected to establish the levels that would be less sweet than acceptable and sweeter than acceptable.
  • Bench screening was used to evaluate each of the different prototypes for each basic formulation using 100%> N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester.
  • the tested examples were frozen dairy analogue products.
  • the results from this bench screening established 3 ranges, going from a very general to a most preferred range for each application.
  • Example 28 No Sugar Added Strawberry Sorbet (20.9% TS).
  • the No Sugar Added Strawberry Sorbet of Example 28 was made by first blending the dry ingredients together to form a dry blend. The dry blend was added to water in a mixer while using medium shear. Next, the strawberry puree and the lemon juice concentrate were added to the mixture and pasteurized at 85°C (185°F) for 4 minutes. The pasteurized mixture was then homogenized in a Silverson apparatus at low speed for 2 minutes. The mixture was next cooled to 4°C (40°F) and stored in a refrigerator. The cool mixture was frozen in a soft serve machine and packaged in 10-20 g servings. The individual servings were hardened in a walk-in freezer overnight at -7°C (20°F). The Strawberry Sorbet was tempered at -14 to -12°C (6-10°F) before serving.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L-phenylalanine 1- methyl ester were prepared and evaluated to determine the general, preferred, and most preferred ranges.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester can be used to sweeten no sugar added strawberry sorbet generally in an amount between about 5 ppm to about 150 ppm, more preferably from about 20 ppm to about 100 ppm, and most preferably from about 25 ppm to about 50 ppm.
  • Example 29 No Sugar Added Non-Dairy Vanilla Frozen Dessert based on Soy Milk and Soy Protein (28.32% TS, 2.81% fat, 3.94% protein solids).
  • the constituents used to formulate the No Sugar Added Non-Dairy Vanilla Frozen Dessert are shown in Table 15.
  • Example 29 The No Sugar Added Non-Dairy Vanilla Frozen Dessert of Example 29 was made by adding the soy beverage to a jacketed kettle. The sorbitol powder and the stabilizer were dry blended. With rapid agitation, the dry blend was gradually added to the soy beverage. The stirring was slowed and then the maltodextrin, polydextrose, wiptreme, and isolated soy protein were added. The resulting mixture was heated to 65 °C (150°F) and mixed in a Turrax high shear mixer for approximately 3 minutes to simulate homogenization. The mixture was then heated to 70°C (160°F) and held at that temperature for 30 minutes. Then the mixture was cooled to 15°C (60°F). The N-[N-(3,3-dimethylbutyl)-L- -aspartyl]-L-phenylalanine 1-methyl ester and Vanilla Flavor were added and the resulting mixture was frozen in a soft serve freezer.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester were prepared and evaluated to determine the general, preferred, and most preferred ranges.
  • N-[N-(3,3-dimethylbutyl)-L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester can be used to sweeten no sugar added non-dairy vanilla frozen dessert generally in an amount between about 5 ppm to about 75 ppm, more preferably from about 10 ppm to about 45 ppm, and most preferably from about 12 ppm to about 30 ppm.

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Abstract

Selon cette invention, des produits laitiers et leurs analogues sont édulcorés avec 1-méthylester de N-[N-3,3-diméthylbutyl)-L-α-aspartyl]L-phénylalanine. Lesdits produits laitiers comprennent le lait (fabriqué par différentes espèces et possédant diverses teneurs en matière grasse), le lait traité avec des enzymes, le lait imitation, la crème, la crème en poudre, le lait de culture, les concentrés de lait, le lait en poudre, le lactosérum liquide et en poudre, des desserts et des boissons à base de lait liquide et en poudre ainsi que des nappages et des desserts gazéifiés, liquides et en poudre. Les produits laitiers comprennent également des produits surgelés à base de lait de culture, tels que le yaourt glacé, et des produits laitiers surgelés à base de lait liquide, par exemple, les glaces, le lait glacé, les sorbets, les flans et les glaces aux oeufs, la mellorine et les friandises. Les produits analogues comprennent le lait de soja, le soja en poudre, les caséinates et les colorants à café non laitiers, ainsi que des produits surgelés tels que les sorbets et les friandises exemptes de lait.
PCT/US1998/027176 1997-12-17 1998-12-17 UTILISATION DE 1-METHYLESTER DE N-[N-3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]L-PHENYLALANINE DANS DES PRODUITS LAITIERS ET LEURS ANALOGUES WO1999030578A1 (fr)

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AU19364/99A AU1936499A (en) 1997-12-17 1998-12-17 Use of n-{n-(3,3-dimethylbutyl)-l-alpha-aspartyl}-l-phenylalanine 1-methyl esterin dairy and dairy analogue products

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US6995297P 1997-12-17 1997-12-17
US60/069,952 1997-12-17

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WO1999030578A1 true WO1999030578A1 (fr) 1999-06-24

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PCT/US1998/027176 WO1999030578A1 (fr) 1997-12-17 1998-12-17 UTILISATION DE 1-METHYLESTER DE N-[N-3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]L-PHENYLALANINE DANS DES PRODUITS LAITIERS ET LEURS ANALOGUES

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Cited By (11)

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Publication number Priority date Publication date Assignee Title
WO2000043416A1 (fr) * 1999-01-25 2000-07-27 The Nutrasweet Company MELANGES D'EDULCORANT SYNERGIQUES A BASE DE N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER
WO2000056176A1 (fr) * 1999-03-25 2000-09-28 The Nutrasweet Company GELS COMESTIBLES EDULCORES AVEC N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER
WO2000057726A1 (fr) * 1999-03-29 2000-10-05 The Nutrasweet Company ALIMENTS FONCTIONNELS COMPRENANT UN ESTER DE 1-METHYLE N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE
WO2000069282A1 (fr) * 1999-05-13 2000-11-23 The Nutrasweet Company Modification du gout et des proprietes physico-chimiques de neotame, a l'aide d'additifs d'acide hydrophobe
WO2001010236A1 (fr) * 1999-08-11 2001-02-15 The Nutrasweet Company PRODUITS DE CONFISERIE EDULCORES AU MOYEN DE N-[N-(3,3-DIMETHYBUTYL)-1-α-ASPARTYL]-L-PHENYLALANINE METHYL ESTER
WO2002085130A1 (fr) * 2001-04-20 2002-10-31 The Coca-Cola Company Boisson carbonatee congelee non calorique ou pauvre en calories
WO2006097947A3 (fr) * 2005-03-14 2007-09-20 Leaf Italia S R L Composition edulcorante solide a base de lait
US7579032B2 (en) 2001-04-27 2009-08-25 Pepsico, Inc. Use of erythritol and D-tagatose in zero-or low-calorie beverages
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
US8367138B2 (en) 2005-11-23 2013-02-05 The Coca-Cola Company Dairy composition with high-potency sweetener
US9101160B2 (en) 2005-11-23 2015-08-11 The Coca-Cola Company Condiments with high-potency sweetener

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CA1267030A (fr) * 1988-08-30 1990-03-27 Hans T. Christiansen Methode de production d'une boisson lactee edulcoree a l'aspartame
US5093137A (en) * 1990-10-17 1992-03-03 Shazer Jr William H Reduced calorie frozen dairy desserts and processes for producing them
WO1995030689A1 (fr) * 1994-05-09 1995-11-16 Claude Nofre Procede perfectionne de preparation d'un compose derive de l'aspartame utile comme agent edulcorant
US5480668A (en) * 1992-11-12 1996-01-02 Nofre; Claude N-substituted derivatives of aspartame useful as sweetening agents
WO1998039979A1 (fr) * 1997-03-10 1998-09-17 Ajinomoto Co., Inc. Composition d'edulcorant au goût ameliore

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US5093137A (en) * 1990-10-17 1992-03-03 Shazer Jr William H Reduced calorie frozen dairy desserts and processes for producing them
US5480668A (en) * 1992-11-12 1996-01-02 Nofre; Claude N-substituted derivatives of aspartame useful as sweetening agents
WO1995030689A1 (fr) * 1994-05-09 1995-11-16 Claude Nofre Procede perfectionne de preparation d'un compose derive de l'aspartame utile comme agent edulcorant
WO1998039979A1 (fr) * 1997-03-10 1998-09-17 Ajinomoto Co., Inc. Composition d'edulcorant au goût ameliore

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000043416A1 (fr) * 1999-01-25 2000-07-27 The Nutrasweet Company MELANGES D'EDULCORANT SYNERGIQUES A BASE DE N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER
WO2000056176A1 (fr) * 1999-03-25 2000-09-28 The Nutrasweet Company GELS COMESTIBLES EDULCORES AVEC N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER
WO2000057726A1 (fr) * 1999-03-29 2000-10-05 The Nutrasweet Company ALIMENTS FONCTIONNELS COMPRENANT UN ESTER DE 1-METHYLE N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE
WO2000069282A1 (fr) * 1999-05-13 2000-11-23 The Nutrasweet Company Modification du gout et des proprietes physico-chimiques de neotame, a l'aide d'additifs d'acide hydrophobe
WO2001010236A1 (fr) * 1999-08-11 2001-02-15 The Nutrasweet Company PRODUITS DE CONFISERIE EDULCORES AU MOYEN DE N-[N-(3,3-DIMETHYBUTYL)-1-α-ASPARTYL]-L-PHENYLALANINE METHYL ESTER
US8465786B2 (en) 2001-04-20 2013-06-18 The Coca-Cola Company Non caloric frozen carbonated beverage
WO2002085130A1 (fr) * 2001-04-20 2002-10-31 The Coca-Cola Company Boisson carbonatee congelee non calorique ou pauvre en calories
US7579032B2 (en) 2001-04-27 2009-08-25 Pepsico, Inc. Use of erythritol and D-tagatose in zero-or low-calorie beverages
WO2006097947A3 (fr) * 2005-03-14 2007-09-20 Leaf Italia S R L Composition edulcorante solide a base de lait
US8367138B2 (en) 2005-11-23 2013-02-05 The Coca-Cola Company Dairy composition with high-potency sweetener
US9101160B2 (en) 2005-11-23 2015-08-11 The Coca-Cola Company Condiments with high-potency sweetener
US9149051B2 (en) 2005-11-23 2015-10-06 The Coca-Cola Company Dairy composition with high-potency sweetener
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

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