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WO2000057726A1 - ALIMENTS FONCTIONNELS COMPRENANT UN ESTER DE 1-METHYLE N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE - Google Patents

ALIMENTS FONCTIONNELS COMPRENANT UN ESTER DE 1-METHYLE N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE Download PDF

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Publication number
WO2000057726A1
WO2000057726A1 PCT/US2000/008210 US0008210W WO0057726A1 WO 2000057726 A1 WO2000057726 A1 WO 2000057726A1 US 0008210 W US0008210 W US 0008210W WO 0057726 A1 WO0057726 A1 WO 0057726A1
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WIPO (PCT)
Prior art keywords
juice
composition
phenylalanine
aspartyl
group
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Ceased
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PCT/US2000/008210
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English (en)
Inventor
Subbarao V. Ponakala
Gale C. Walters
Paula A. Gerlat
Leora C. Hatchwell
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Nutrasweet Co
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Nutrasweet Co
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Priority to AU40388/00A priority Critical patent/AU4038800A/en
Publication of WO2000057726A1 publication Critical patent/WO2000057726A1/fr
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    • 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
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F3/00—Tea; Tea substitutes; Preparations thereof
    • A23F3/40—Tea flavour; Tea oil; Flavouring of tea or tea extract
    • A23F3/405—Flavouring with flavours other than natural tea flavour or tea oil
    • 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
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
    • 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
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their 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
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/13—Nucleic acids or derivatives thereof
    • 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
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/15—Vitamins
    • 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
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/175—Amino acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • This invention relates to the use of N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester (neotame) , as a sweetener or flavor modifier in nutraceuticals.
  • N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester (neotame) as a sweetener or flavor modifier in nutraceuticals.
  • nutritional supplements e.g., vitamins, minerals, amino acids, antioxidants, enzymes, natural food supplements, and herbs. It is estimated that there are approximately 850 nutritional supplement manufacturers in the United States. The combined influences of scientific discoveries, changes in insurance coverage towards an emphasis in disease prevention, and an aging population suggest increasing demand for nutritional supplements.
  • nutraceuticals are used for prevention or treatment of disease, compliance is inconsistent. It is believed that the main reason people avoid nutraceuticals is because of the unpleasant taste associated with them. For example, people may dislike the taste of nutritional supplements that contain cancer-preventive phytochemicals such as isothiocyanates and sulforaphanes (contained in cruciferous and leafy vegetables) , polyphenols and catechins (from tea and red wine) , isoflavones (in soy products) , and antioxidant flavonoids (found in citrus fruits) . These types of foods may possess bitter, astringent, or other unpleasant flavors which may render the nutritional supplements unpalatable.
  • cancer-preventive phytochemicals such as isothiocyanates and sulforaphanes (contained in cruciferous and leafy vegetables) , polyphenols and catechins (from tea and red wine) , isoflavones (in soy products) , and antioxidant flavonoids (found in citrus fruits) .
  • N- [N- (3 , 3-di ethylbuty1) -L- -asparty1] -L- phenylalanine 1-methyl ester is 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. Neotame also modifies the flavor and taste of mainstream foods and beverages, as disclosed in U.S. Patent Application 09/465,837, filed December 17, 1999, the complete disclosure of which is incorporated by reference.
  • the present invention provides nutraceuticals comprising N-[N-(3 , 3-dimethylbutyl) -L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester.
  • This invention also provides nutraceuticals comprising a blend of N-[N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester with another sweetener.
  • This invention also provides a method for preparing the nutraceuticals of this invention.
  • Nutraceuticals are food, botanicals and nutritional substances which are believed to have medicinal or health benefits, such as the prevention and treatment of disease. Nutraceuticals may refer to food in its natural state (e.g. broccoli or raspberry) , a processed and/or bioengineered food, or a food constituent or extract. Nutraceuticals include botanicals (such as herbs in all physical forms and extractives and plant acids) , antioxidants and phytochemicals (such as lycopenes, isoflavones, catechins, elegiac acid, etc.), vitamins and minerals, fatty acids and oils, as well as essential and non-essential amino acids, enzymes, lignin, stanol esters, and friendly bacteria.
  • botanicals such as herbs in all physical forms and extractives and plant acids
  • antioxidants and phytochemicals such as lycopenes, isoflavones, catechins, elegiac acid, etc.
  • vitamins and minerals such as lycopenes, isoflavones, catechins,
  • Herbs are plants or plant parts used for their medicinal, savory or aromatic qualities. Herbs are used not only to treat illness but also for their capacity to prevent illness.
  • Such herbs include but are not limited to, for example, acerola, augustifolia purpura, alfalfa, aloe vera, american leaf, angelica, astragalus, bilberry, black cohosh, black haw, brassica, broccoli, burdock, cascara sagrada, cat's claw, cayenne, chamomile, chasteberry, chicory, corn silk, crampbark, cranberry, dandelion, dong quai, echinacea, echinacea purpura, elderberry, evening primrose, eyebright, fennel seeds, fenugreek, feverfew, flax seed, garlic, gentian, ginger, ginkgo biloba, ginsengs, goldense
  • John's Wort salvia root, saw palmetto, schisandra berry, senna, soy, uva ursi, valerian root, wheat grass, willow bark, yerba mate, yerba santa, and yohimbe.
  • nutraceuticals include, but are not limited to, minerals such as calcium, iodine, magnesium, zinc, iron, selenium, manganese, chromium, copper, cobalt, molybdenum, or phosphorus; vitamins such as vitamin C (ascorbic acid) , vitamin A, vitamin B3, vitamin D (ergocalciferol), vitamin E (dl-alpha tocopherol) , thiamine (vitamin B-l) , riboflavin (vitamin B-2) , niacin, pyridoxine (vitamin B-6) , cyanocobalamin (vitamin B-12) , folic acid, biotin, pantothenic Acid, vitamin K; fatty acids such as the omega-3 unsaturated fatty acids (gamma-linoleic acid, ucospentaenoic acid, decosahexaenoic acid and the like) ; oils such as borage oil, high carotenoid canola
  • N- [N- (3 , 3-di ethylbuty1) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester may be used in nutraceuticals at both sweetening and subsweetening levels. At or above a given threshold amount, N-[N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester may function as a sweetener in the nutraceutical compositions of this invention. Below the threshold amount, N- [N- (3 , 3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester may function as a flavor modifier in the nutraceutical compositions of this invention.
  • N- [N- (3 , 3-dimethylbuty1) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester may be used alone or in a blend with other sweeteners.
  • Exemplary sweeteners which may be used in combination with N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester in the nutraceuticals of this invention include other high intensity sweeteners such as aspartame, acesulfame salts (e.g., acesulfame-K) , saccharin, sucralose, alitame, stevia derivatives, thaumatin and cycla ates, neohesperidine dihydrochalcone (NHDC) , and mono-, di- or tri derivatives of ammonium glycryrrhizin as well as natural sweeteners such as sucrose, fructose, dextrose,
  • N- [N- (3 , 3-dimethylbuty1) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester may be used as a sweetener or flavor modifier in a variety of nutraceutical products.
  • N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester or a sweetener blend of N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester may be blended with any of the above- mentioned nutraceuticals in a composition appropriate for consumption.
  • the nutraceutical compositions of this invention may be in solid or liquid form.
  • compositions of this invention may be formulated into tablets, capsules, or caplets using methods well known to those skilled in the art. Because of N-[N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester's superior sweetening effect, tablets made according to the present invention may be chewable tablets.
  • the nutraceutical compositions of this invention may also be delivered using physiologically acceptable fluids, such as water, milk, juice and the like.
  • physiologically acceptable fluids such as water, milk, juice and the like.
  • N-[N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl]- L-phenylalanine 1-methyl ester and a nutraceutical may be added to a milk-based or a fruit-based product (e.g., a juice) to provide a nutraceutically enhanced food product.
  • a fruit-based product includes products with a fruit or vegetable base.
  • Exemplary fruit-based products that may be used in the present invention include fruit juices from the group consisting of apple, apricot, blackberry, blueberry, boysenberry, black, dark sweet or red sour cherry, cranberry, red or black currant, date elderberry, fig, concord, red, or white grape, grapefruit, kiwi, lemon, lime, loganberry, mango, nectarine, orange, papaya, passion fruit, peach, pear, pineapple, plum, pomegranate, prune, raisin, black or red raspberry, strawberry, tomato, or tomato sauce, tomato paste, watermelon, fruit juice blends, vegetable juice blends, and mixtures thereof.
  • the amount of N-[N- (3 , 3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester present in the nutraceutical compositions of this invention may vary considerably, depending upon the particular composition and the sweetness or flavor modification level desired. Because the sweetening potency of N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester is so high, the nutraceutical compositions of the present invention may be prepared using a very small amount of N-[N-(3,3- i ethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester.
  • the amount of N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester in the nutraceutical compositions of this invention is between about 10 ppb and about 1,000 ppm.
  • the amount of N-[N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester present preferably is between about 2 ppm and about 500 ppm, and most preferably between about 3 ppm and about 250 ppm, based upon the total amount of the composition.
  • the amount of N-[N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester present in the nutraceutical compositions of this invention preferably is between about 1 ppb and about 50 ppm, and most preferably between about 3 ppb and about 25 ppm, based upon the total amount of the composition.
  • the amount of the blend may be adjusted to provide a sweetness or flavor modification equivalent to the sweetness or flavor modification provided by N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester alone.
  • Example 1 A Chewable Vitamin C Tablet Containing N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester
  • a chewable tablet of vitamin C containing N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester is prepared by methods well known by those skilled in the art.
  • the chewable tablet has 0.01 percent by weight (100 ppm) N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester as well as sucrose, ascorbic acid, stearic acid, cellulose, silicon dioxide, magnesium stearate and starch.
  • a chewable multi-vitamin tablet containing N-[N- (3,3-dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- ethyl ester is prepared by methods well known by those skilled in the art.
  • the chewable multi- vitamin tablet has 0.01 percent by weight (100 ppm) N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester as well as vitamins A, B-1, B-2, B-6, B-12, C, D and E, folic acid, niacin, biotin and pantothenic acid.
  • a chewable zinc lozenge containing N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester is prepared by methods well known by those skilled in the art.
  • the chewable zinc lozenge has 0.005 percent by weight (50 ppm) N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester as well as sucrose, dried corn syrup, zinc gluconate, citric acid and malic acid.
  • amino acid supplement drink containing N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester is prepared by methods well known by those skilled in the art.
  • the amino acid drink has 0.006 percent by weight (60 ppm) N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester as well as water, whey protein, sorbitol, phosphoric acid, natural and artificial flavors, potassium benzoate, sodium citrate, sodium bisulfite, and the following amino acids: L- isoleucine, L-leucine, L-valine, L-lysine, L- methionine, L-cysteine, L-tyrosine, L-threonine, L- alanine, L-arginine, L-aspartic acid, L-glutamic acid, L-glycine, L-hist
  • Example 5 A Carbohydrate Drink Containing N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester
  • a carbohydrate drink containing N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester is prepared by methods well known by those skilled in the art.
  • the carbohydrate drink has 0.005 percent by weight (50 ppm) N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl ] -L-phenylalanine 1- methyl ester as well as water, glucose polymers, fructose, orange flavor, citric acid, potassium phosphate, magnesium succinate and ascorbic acid.
  • Example 6 A Protein Shake Containing N- [N- (3 , 3-dimethylbutyl) - L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester
  • a protein shake containing N- [N- (3 , 3-dimethylbutyl) - L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester is prepared by methods well known by those skilled in the art.
  • the protein shake has 0.0075 percent by weight (75 ppm) N-[N-( 3, 3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester as well as skim milk, calcium caseinate, egg albumin, whey protein concentrate, cellulose gel, potassium phosphate, carrageenan and artificial flavor.
  • Example 7 A Nutritional Drink Containing N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl ] -L-phenylalanine 1- methyl ester
  • a nutritional drink containing N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester is prepared by methods well known by those skilled in the art.
  • the nutritional drink has 0.0075 percent by weight (75 ppm) N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl ] -L-phenylalanine 1- methyl ester as well as milk protein isolate, caseinate, glutamine, whey protein concentrate, albumin, maltodextrin, potassium citrate, vitamins A, B-1, B-2, B-6, B-12, C, D and E, folic acid, niacin, biotin and pantothenic acid.
  • a chewable herb tablet containing N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl ] -L-phenylalanine 1- methyl ester is prepared by methods well known by those skilled in the art.
  • the chewable herb tablet has 0.005 percent by weight (50 ppm) N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl ] -L-phenylalanine 1- methyl ester as well as microcrystalline cellulose, corn starch, ginkgo biloba extract, magnesium stearate and silicon dioxide.
  • Example 9 A Valerian Solution Containing N- [N- (3 , 3-dimethylbuty1) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester
  • valerian solution containing 0.2 weight percent (2 mg per gram) valerian was prepared.
  • the valerian solution was separated into two separate samples which were then prepared with 0.0002 weight percent (2 ppm) and 0.001 weight percent (10 ppm) respectively of N-[N-(3, 3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester.
  • Both the 0.0002 weight percent and 0.001 weight percent samples of N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester were sufficient to remove the peroxide notes in the control sample of the control solution.
  • the 0.001 weight percent N-[N- (3 , 3-dimethylbuty1) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester solution removed the astringency from the control sample.
  • a chamomile solution containing 0.1 weight percent (1 mg per gram) chamomile was prepared.
  • the chamomile solution was separated into two separate samples which were then prepared with 0.0002 weight percent (2 ppm) and 0.001 weight percent (10 ppm) respectively of N-[N- (3 , 3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester.
  • Both the 0.0002 weight percent and 0.001 weight percent samples of N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester were sufficient to remove the peroxide notes in the control sample of the chamomile solution.
  • Example 11 A Saw Palmetto Solution Containing N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester
  • a saw palmetto solution containing 0.32 weight percent (3.2 mg per gram) saw palmetto was prepared.
  • the saw palmetto solution was separated into two separate samples which were then prepared with 0.0002 weight percent (2 ppm) and 0.001 weight percent (10 ppm) respectively of N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester.
  • a gingko biloba solution containing 0.12 weight percent (1.2 mg per gram) gingko biloba was prepared.
  • the gingko biloba solution was separated into two separate samples which were then prepared with 0.0002 weight percent (2 ppm) and 0.001 weight percent (10 ppm) respectively of N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- ethyl ester.
  • N-[N-(3,3- dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester solution reduced the astringency, while the 0.001 weight percent solution removed the astringency, when compared to the control sample of gingko biloba solution.
  • Both N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester solutions reduced bitterness and removed the prune flavor present in the control sample.
  • Example 13 A Siberian Ginseng Solution Containing N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester
  • a Siberian ginseng solution containing 0.5 weight percent (5 mg per gram) Siberian ginseng was prepared.
  • the Siberian ginseng solution was separated into two separate samples which were then prepared with 0.0002 weight percent (2 ppm) and 0.001 weight percent (10 ppm) respectively of N-[N- (3, 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester.
  • the 0.0002 weight percent sample of N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester accentuated the flavors found in the control sample of the Siberian ginseng.
  • Example 14 A Green Tea Solution Containing N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester
  • a green tea solution containing 0.25 weight percent (2.5 mg per gram) green tea was prepared.
  • the green tea solution was separated into two separate samples which were then prepared with 0.0002 weight percent (2 ppm) and 0.001 weight percent (10 ppm) respectively of N-[N-( 3, 3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester.
  • Both the 0.0002 weight percent and 0.001 weight percent samples of N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester diminished astringency and bitterness when compared to the control sample.
  • the 0.001 weight percent sample provided complex flavors like malt, caramel and raisin-prune .
  • Example 15 An Aloe Vera Solution Containing N- [N- ( 3 , 3-dimethylbuty1) -L- ⁇ -aspartyl ] -L- phenylalanine 1-methyl ester
  • aloe vera solution containing 1.5 weight percent (15 mg per gram) aloe vera was prepared.
  • the aloe vera solution was separated into two separate samples which were then prepared with 0.0002 weight percent (2 ppm) and 0.001 weight percent (10 ppm) respectively of N- [N-(3, 3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester.
  • Both the 0.0002 weight percent and 0.001 weight percent samples of N-[N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester dampened the aloe vera flavor when compared to the control sample.
  • Example 16 An Astragalus Solution Containing N- [N- (3 , 3-dimethylbuty1) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester
  • An astragalus solution containing 1.0 weight percent (10 mg per gram) astragalus was prepared.
  • the astragalus solution was separated into two separate samples which were then prepared with 0.0002 weight percent (2 ppm) and 0.001 weight percent (10 ppm) respectively of N-[N- (3 , 3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester.
  • Both the 0.0002 weight percent and 0.001 weight percent samples of N-[N-(3 , 3-dimethylbutyl) -L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester dampened the flavor when compared to the control sample.
  • a black cohosh solution containing 0.8 weight percent (8 mg per gram) black cohosh was prepared.
  • the black cohosh solution was separated into two separate samples which were then prepared with 0.0002 weight percent (2 ppm) and 0.001 weight percent (10 ppm) respectively of N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester.
  • Both the 0.0002 weight percent and 0.001 weight percent samples of N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester brought out pleasant vanilla, citrus, caramel notes not present in the control sample
  • a dong quai solution containing 0.6 weight percent (6 mg per gram) dong quai was prepared.
  • the dong quai solution was separated into two separate samples which were then prepared with 0.0002 weight percent (2 ppm) and 0.001 weight percent (10 ppm) respectively of N- [N- (3 , 3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester.
  • Both the 0.0002 weight percent and 0.001 weight percent samples of N- [N-(3, 3-dimethylbutyl) -L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester reduced or eliminated the green leafy flavors present in the control sample.
  • the 0.001 weight percent sample reduced the strong bitter notes present in the control sample.
  • echinacea solution containing 0.25 weight percent (2.5 mg per gram) echinacea was prepared.
  • the echinacea solution was separated into two separate samples which were then prepared with 0.0002 weight percent (2 ppm) and 0.001 weight percent (10 ppm) respectively of N-[N- (3 , 3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester.
  • Both the 0.0002 weight percent and 0.001 weight percent samples of N- [N- (3, 3-dimethylbuty1) -L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester eliminated the green leafy flavors present in the control sample. Both samples furthermore brought out pleasant flavors not present in the control sample.
  • vitamin C ascorbic acid
  • biotin biotin, calcium pantothenate, niacinamide, pyridoxine hydrochloride (vitamin B-6) , riboflavin (vitamin B-2) , thiamine mononitrate (vitamin B-1) , vitamin A, cyanocobalamin (vitamin B- 12), vitamin D3 (ergocalciferol), dl-alpha tocopherol (vitamin E) and vitamin K was sweetened with 0.0018 weight percent (18 ppm) of N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester.
  • the 0.0018 weight percent (18 ppm) milk solution of N-[N-(3, 3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester suppressed inherent vitamin flavor and bitterness when compared to the unsweetened multivitamin control sample.
  • N- [N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester sweetened tablet suppressed objectionable flavor and bitterness when compared to an unsweetened chewable vitamin tablet.
  • a soy drink was prepared with 0.000045 weight percent (450 ppb) of 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 reduced the bitterness and beany oxidized flavors present in the control sample and also brought out dairy flavors not present in the control sample.
  • Example 25 A Grapefruit Juice Containing N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- ethyl ester and a Nutritional Supplement
  • a grapefruit juice sample containing a nutritional supplement (MetaForm Technically Advanced Nutrition®, by Great American Nutrition, Salt Lake City, UT) was separated into two samples which were then prepared with 0.0002 weight percent (2 ppm) and 0.001 weight percent (10 ppm) respectively of N-[N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester.
  • the 0.001 weight percent N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester sample also provided sweetness to the control sample.
  • Example 26 A Tomato Juice Containing N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl ] -L-phenylalanine 1-methyl ester and a Nutritional Supplement
  • a tomato juice containing a nutritional supplement (MetaForm Technically Advanced Nutrition®, by Great American Nutrition, Salt Lake City, UT) were separated into two samples which were then prepared with 0.0002 weight percent (2 ppm) and 0.001 weight percent (10 ppm) respectively of N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl ] -L-phenylalanine 1- methyl ester. Both the 0.0002 weight percent and 0.001 weight percent N-[N- (3 , 3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester samples reduced the bitterness and cardboard whey flavor when compared to the tomato juice control containing only the nutritional supplement.
  • a commercial orange juice (Tropicana Pure Premium®, by Tropicana, Brandenton, FL) was fortified with 350 mg per cup calcium and then prepared with 0.0001 (1 ppm) of N-[N- (3, 3-dimethylbuty1) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester.
  • the N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester orange juice sample reduced bitterness when compared to the calcium-fortified control sample, and had a more syrupy mouthfeel.
  • Example 28 A Cat's Claw Tea Containing N-[N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L- phenylalanine 1-methyl ester
  • a cat's claw tea was prepared with 0.0002 weight percent (2 ppm) and 0.005 weight percent (50 ppm) respectively of N- [N- (3 , 3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester. Both the 0.0002 weight percent and 0.005 weight percent N-[N- (3 , 3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester cat's claw samples reduced the bitterness and green grassy flavor when compared to control sample.
  • Example 29 A Feverfew Tea Containing N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester and Other Sweeteners
  • Samples of feverfew tea were prepared containing 0.0005 weight percent (5 ppm) N-[N-(3,3- dimethylbuty1) -L- ⁇ -aspartyl] -L-phenylalanine 1- methyl ester plus either 0.02 weight percent (200 ppm) aspartame, 0.026 weight percent (260 ppm) acesulfame-K, 0.016 weight percent (160 ppm) sucralose, or 5 weight percent (50,000 ppm) sucrose. On a sweetening level, samples of feverfew tea were sweetened with 0.00075 weight percent (7.5 ppm) N-
  • the feverfew teas containing N-[N-(3 , 3-dimethylbutyl) -L- ⁇ -aspartyl]-L- phenylalanine 1-methyl ester brought out an increase of mint flavors that were not present in the control sample.

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Abstract

La présente invention concerne des aliments fonctionnels comprenant un ester de 1-méthyle N-[N-(3,3-diméthylbutyl)-L-α-aspartyl]-L-phénylalanine. La présente invention concerne également des aliments fonctionnels comprenant un mélange d'ester de 1-méthyle N-[N-(3,3-diméthylbutyl)-L-α-aspartyl]-L-phénylalanine avec un autre édulcorant. L'invention concerne en outre une méthode de préparation des aliments fonctionnels selon l'invention.
PCT/US2000/008210 1999-03-29 2000-03-29 ALIMENTS FONCTIONNELS COMPRENANT UN ESTER DE 1-METHYLE N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE Ceased WO2000057726A1 (fr)

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AU40388/00A AU4038800A (en) 1999-03-29 2000-03-29 Nutraceuticals having

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AR (1) AR023208A1 (fr)
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WO2002030404A3 (fr) * 2000-10-12 2003-04-03 Bioriginal Food & Science Corp Therapie combinee destinee aux symptomes premenstruels
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WO2006074881A1 (fr) * 2005-01-14 2006-07-20 Nutrinova Nutrition Specialties & Food Ingredients Gmbh Melange de sirop de mais a forte teneur en fructose (hfcs 42 ou hfcs 55) et edulcorant a gout intense ayant le profil de gout du sucre pur
FR2897754A1 (fr) * 2006-02-24 2007-08-31 Hachmi Graia Utilisation d'extraits de trigonella foenum graecum pour attenuer le gout sucre dans une preparation destinee a etre avalee et ayant une saveur sucree.
EP1552838A4 (fr) * 2002-05-31 2007-12-12 Suntory Ltd Composition contenant du glycoside de rubrobusarine
WO2001028590A3 (fr) * 1999-10-19 2008-01-03 Nutrasweet Co COMPOSITIONS PHARMACEUTIQUES RENFERMANT UN ESTER N-[N-(3,3-DIMETHYLBUTYL)-1-α-ASPARTYL]-L-PHENYLALANINE METHYL
WO2008057963A3 (fr) * 2006-11-02 2008-09-04 Coca Cola Co Composition édulcorante très puissante renfermant du phytoestrogène et compositions sucrées par cette composition
EP2132994A1 (fr) * 2008-06-11 2009-12-16 Ludwig Manfred Jacob Fermentation de solutions contenant du jus de grenade à l'aide de sacchatomyces boulardii et de lactobaciles, produits de fermentation ainsi obtenus et leur utilisation
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US10856563B2 (en) 2012-03-30 2020-12-08 Givaudan S.A. N-acyl-amino acid derivatives for improvement of the flavor profile of edible compositions
US10913922B2 (en) 2012-03-30 2021-02-09 Givaudan S.A. N-acylated methionine derivatives as food flavoring compounds
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WO2001028590A3 (fr) * 1999-10-19 2008-01-03 Nutrasweet Co COMPOSITIONS PHARMACEUTIQUES RENFERMANT UN ESTER N-[N-(3,3-DIMETHYLBUTYL)-1-α-ASPARTYL]-L-PHENYLALANINE METHYL
WO2002030404A3 (fr) * 2000-10-12 2003-04-03 Bioriginal Food & Science Corp Therapie combinee destinee aux symptomes premenstruels
WO2002080704A1 (fr) * 2001-04-03 2002-10-17 Michigan Biotechnology Institute Composition permettant d'ameliorer les caracteristiques gustatives et les caracteristiques de teneur en sucre de boissons contenant des edulcorants puissants
US7063865B2 (en) * 2002-05-10 2006-06-20 Jeremy Park Jones Composition and method for substantially reducing the deleterious effects of alcohol on the body
EP1552838A4 (fr) * 2002-05-31 2007-12-12 Suntory Ltd Composition contenant du glycoside de rubrobusarine
FR2859603A1 (fr) * 2003-09-11 2005-03-18 Christian Fenioux Utilisation de la neohesperidine dihydrochalcone dans des compositions orales comprenant des vitamines et/ou des mineraux
EP1514481A1 (fr) * 2003-09-11 2005-03-16 Christian Fenioux Utilisation de la néohespéridine dihydrochalcone dans des comprimés à croquer comprenant des vitamines et/ou minéraux
US8790734B2 (en) 2003-09-12 2014-07-29 Tropicana Products, Inc. Reduced sugar citrus juice beverage
US8440248B2 (en) 2003-09-12 2013-05-14 Tropicana Products, Inc. Reduced sugar citrus juice beverage
DE102004061309A1 (de) * 2004-12-20 2006-06-22 Roland Glaser Nahrungsergänzungsmittel
EP1681061A1 (fr) * 2005-01-11 2006-07-19 Jobes Vital GmbH Composition pour le traitement de l'apnée, du ronflement et des troubles du sommeil
WO2006074881A1 (fr) * 2005-01-14 2006-07-20 Nutrinova Nutrition Specialties & Food Ingredients Gmbh Melange de sirop de mais a forte teneur en fructose (hfcs 42 ou hfcs 55) et edulcorant a gout intense ayant le profil de gout du sucre pur
US9101160B2 (en) 2005-11-23 2015-08-11 The Coca-Cola Company Condiments with high-potency sweetener
FR2897754A1 (fr) * 2006-02-24 2007-08-31 Hachmi Graia Utilisation d'extraits de trigonella foenum graecum pour attenuer le gout sucre dans une preparation destinee a etre avalee et ayant une saveur sucree.
WO2008057963A3 (fr) * 2006-11-02 2008-09-04 Coca Cola Co Composition édulcorante très puissante renfermant du phytoestrogène et compositions sucrées par cette composition
US9101161B2 (en) 2006-11-02 2015-08-11 The Coca-Cola Company High-potency sweetener composition with phytoestrogen and compositions sweetened therewith
EP2132994A1 (fr) * 2008-06-11 2009-12-16 Ludwig Manfred Jacob Fermentation de solutions contenant du jus de grenade à l'aide de sacchatomyces boulardii et de lactobaciles, produits de fermentation ainsi obtenus et leur utilisation
US9788562B2 (en) 2008-08-29 2017-10-17 Tropicana Products, Inc. Naturally sweetened juice beverage products
WO2012142678A1 (fr) * 2011-04-21 2012-10-26 Fit-Bioceuticals Limited Composition pour la perte de poids
US20130224169A1 (en) * 2011-08-02 2013-08-29 Walter Joe FORD, JR. Composition and method for recovery from mild traumatic brain injury
US8840937B2 (en) * 2011-08-02 2014-09-23 Walter Joe FORD, JR. Composition and method for recovery from mild traumatic brain injury
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US20130323350A1 (en) * 2011-10-17 2013-12-05 Allen Seligson Orally dispersible multi-micronutrient dietary supplement composition and methods of using same
WO2013149008A3 (fr) * 2012-03-30 2013-11-28 Givaudan, S.A. Améliorations apportées à des composés organiques ou se rapportant à ceux-ci
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US10856563B2 (en) 2012-03-30 2020-12-08 Givaudan S.A. N-acyl-amino acid derivatives for improvement of the flavor profile of edible compositions
US10836712B2 (en) 2012-03-30 2020-11-17 Givaudan S.A. Organic compounds
US10711230B2 (en) 2012-03-30 2020-07-14 Givaudan Sa N-acyl proline derivatives as food flavoring compounds
US10201175B2 (en) 2012-03-30 2019-02-12 Givaudan Sa N-acylated 1-aminocycloalkyl carboxylic acids as food flavouring compounds
US10645955B2 (en) 2012-03-30 2020-05-12 Givaudan Sa N-acyl derivatives of gamma amino-butyric acid and beta alanine as food flavouring compounds
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US10674755B2 (en) 2013-10-02 2020-06-09 Givaudan S.A. Organic Compounds
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CN103549434A (zh) * 2013-11-15 2014-02-05 哈尔滨艾克尔食品科技有限公司 一种玉米须泡腾片的制作方法
US10525007B2 (en) * 2014-01-31 2020-01-07 Pocket Tea, Llc Tea composition for oral administration
JP2016005443A (ja) * 2014-06-20 2016-01-14 株式会社ノエビア 容器詰め飲料
WO2016187643A1 (fr) * 2015-05-25 2016-12-01 Arborvitae Health And Wellbeing Pty. Ltd. Composition et ses utilisations
CN107735099A (zh) * 2015-05-25 2018-02-23 崖柏健康与福利私人有限公司 组合物和其用途
EP3302513A4 (fr) * 2015-05-25 2019-01-23 Arborvitae Health And Wellbeing Pty. Ltd. Composition et ses utilisations
CN105166044A (zh) * 2015-08-07 2015-12-23 河南行知专利服务有限公司 一种含水果的健胃润肠风味酸乳及其制备方法
JP2021510493A (ja) * 2017-10-23 2021-04-30 シムライズ アーゲー 芳香組成物
JP7003249B2 (ja) 2017-10-23 2022-01-20 シムライズ アーゲー 芳香組成物
CN108175104A (zh) * 2018-01-18 2018-06-19 广东健林生物科技有限公司 一种高维生素c含量咀嚼片及其制作方法
CN116268178A (zh) * 2023-03-27 2023-06-23 广西壮族自治区农业科学院 一种酶解百香果皮的制备方法及用途
IT202300012270A1 (it) * 2023-06-15 2024-12-15 Azienda Agricola Officinalis Di Nicola Dalla Grana Integratore alimentare liquido a base di estratto ad elevata concentrazione di sostanza attiva, nonché metodo di preparazione di tale integratore alimentare liquido

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