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US20060083695A1 - Sweetener composition - Google Patents

Sweetener composition Download PDF

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Publication number
US20060083695A1
US20060083695A1 US11/249,629 US24962905A US2006083695A1 US 20060083695 A1 US20060083695 A1 US 20060083695A1 US 24962905 A US24962905 A US 24962905A US 2006083695 A1 US2006083695 A1 US 2006083695A1
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United States
Prior art keywords
monatin
salt
composition
beverage
radical scavenger
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US11/249,629
Inventor
Kenichi Mori
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Ajinomoto Co Inc
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Ajinomoto Co Inc
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Filing date
Publication date
Application filed by Ajinomoto Co Inc filed Critical Ajinomoto Co Inc
Priority to US11/249,629 priority Critical patent/US20060083695A1/en
Assigned to AJINOMOTO CO., INC. reassignment AJINOMOTO CO., INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MORI, KENICHI
Priority to US11/406,262 priority patent/US7781005B2/en
Publication of US20060083695A1 publication Critical patent/US20060083695A1/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
    • 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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/52—Adding ingredients
    • A23L2/60—Sweeteners
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • 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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
    • A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • the present invention relates to sweetener compositions comprising monatin or a salt thereof. More particularly, the present invention relates to a method for preserving monatin or a salt thereof.
  • Monatin is a natural amino acid derivative isolated from the root bark of a native plant ( Schierochiton ilicifolius ) of northern Transvaal of South Africa, and its structure has been reported by R. Vleggaar et al to be (2S,4S)-2-amino-4-carboxy-4-hydroxy-5-(3-indolyl)-pentanoic acid ((2S,4S)-4-hydroxy-4-(3-indolylmethyl)-glutamic acid) (R. Vleggaar et al., J. Chem. Soc. Perkin Trans ., pp. 3095-3098, (1992)).
  • monatin is described in, for example, ZA 87/4288, ZA 88/4220, U.S. Pat. No. 5,994,559, WO03/045914, WO03/059865, WO03/056026, WO04/067494, WO04/053125, C. W. Holzapfel et al., Synthetic Communication , vol. 24(22), pp. 3197-3211 (1994), K. Nakamura et al., Organic Letters , vol. 2, pp. 2967-2970 (2000), and the like.
  • Monatin is a superior sweetener which is 1400 times sweeter than sugar and contains no calories. It is stable to heat and expected to be applicable to various kinds of food.
  • the present inventor has first clarified at this time that monatin in the solution state tends to decompose when exposed to ultraviolet light, and that the tendency becomes particularly remarkable under acidic conditions (particularly at a pH of less than 5). As mentioned above, therefore, a means to use a superior sweetener, monatin, in a stable state irrespective of the condition it is placed in, becomes necessary.
  • the problem to be solved by the present invention solves the above-mentioned novel problem.
  • the problem of the present invention is to provide a method for preserving monatin or a salt thereof in a stable state even under ultraviolet light, and further, a sweetener composition, a beverage, a food, a pharmaceutical product and the like, which contain stable monatin or a salt thereof.
  • a preservation stabilizer for monatin or a salt thereof is also a problem of the present invention.
  • monatin and a salt thereof can be maintained in a stable state by maintaining monatin or a salt thereof in the co-presence of a radical scavenger.
  • the present invention provides the following:
  • a sweetener composition comprising monatin or a salt thereof and a radical scavenger.
  • radical scavenger is at least one member selected from the group consisting of ascorbic acid, ascorbate, ascorbic acid ester, erythorbic acid, erythorbic acid salt, erythorbic acid ester, uric acid, bilirubin, albumin, vitamin A, vitamin E, ubiquinol, carotenoid, histidine, tryptophan, 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4-hydroxyanisole, 3-tert-butyl-4-hydroxyanisole, propyl gallate, catechin, and mixtures thereof.
  • composition of (1) wherein the radical scavenger is at least one member selected from the group consisting of ascorbic acid, ascorbate, ascorbic acid ester, erythorbic acid, erythorbic acid salt, erythorbic acid ester, and mixtures thereof.
  • composition of any of (1)-(4) which is a liquid composition having a pH of not less than 2 and less than 7.
  • a beverage, a food, a mouth cavity composition, or a pharmaceutical product comprising a composition of any of (1)-(6).
  • a beverage comprising a composition of any of (1)-(6).
  • a method of preserving monatin or a salt thereof which comprises maintaining monatin or a salt thereof in the presence of a radical scavenger.
  • a method of preserving a sweetener composition, a beverage, a food, a mouth cavity composition, or a pharmaceutical product, comprising monatin or a salt thereof comprises maintaining monatin or a salt thereof in the presence of a radical scavenger.
  • a method of preserving a beverage comprising monatin or a salt thereof comprises maintaining monatin or a salt thereof in the presence of a radical scavenger.
  • a method of preserving monatin or a salt thereof which method comprises placing monatin or a salt thereof under a condition free of exposure to ultraviolet light.
  • a method of preserving a sweetener composition, a beverage, a food, a mouth cavity composition, or a pharmaceutical product comprising monatin or a salt thereof comprises placing monatin or a salt thereof under a condition free of exposure to ultraviolet light.
  • a method of preserving a beverage comprising monatin or a salt thereof comprises placing monatin or a salt thereof under a condition free of exposure to ultraviolet light.
  • a beverage comprising monatin or a salt thereof, which is enclosed in a container shielding ultraviolet light.
  • a beverage comprising monatin or a salt thereof and a radical scavenger, which is enclosed in a container shielding ultraviolet light.
  • a sweetener composition a food, a beverage, a mouth cavity composition, and a pharmaceutical product are provided, which contain monatin or a salt thereof, and which suppress decomposition of the monatin or salt thereof due to ultraviolet light, and provide a stable sweetness.
  • a preservation stabilizer for and a method of preserving monatin or a salt thereof are also provided.
  • the sweetener composition of the present invention contains monatin and a radical scavenger.
  • Monatin is a compound represented by the formula (I):
  • Monatin has an asymmetric moieties at the 2-position and the 4-position and includes the following 4 kinds of optical isomers.
  • the stereoisomer is not particularly limited.
  • (2R,4R)monatin, (2R,4S)monatin, (2S,4R)monatin, and (2S,4S)monatin, and any mixture of these can be used.
  • simple monatin means one without limitation on stereoisomerism.
  • the monatin used in the present invention may be used as a salt with an alkali metal, such as sodium, potassium, and the like; an alkaline earth metal such as magnesium and the like; and the like.
  • an alkali metal such as sodium, potassium, and the like
  • an alkaline earth metal such as magnesium and the like
  • the potassium salt is preferable, and monopotassium salt is more preferable.
  • (2S,4R)monatin and (2R,4S)monatin tend to be more easily decomposed by ultraviolet light than the other isomers.
  • Monatin is a known substance, and its production method is also known. For example, it can be produced by a method described in ZA 87/4288, ZA 88/4220, U.S. Pat. No. 5,994,559, WO03/045914, WO03/059865, WO03/056026, WO04/067494, WO04/053125, C. W. Holzapfel et al., Synthetic Communications , vol. 24(22), pp. 3197-3211(1994), K. Nakamura et al., Organic Letters , vol. 2, pp. 2967-2970(2000), and the like.
  • radical scavenger refers to a compound used to efficiently catch a radical (free group) produced during reaction and, for example, ascorbic acid, ascorbate, ascorbic acid ester, erythorbic acid (isoascorbic acid), erythorbic acid salt, erythorbic acid ester, uric acid, bilirubin, albumin, vitamin A, vitamin E, ubiquinol, carotenoid, histidine, tryptophan, 2,6-di-tert-butyl-4-methylphenol (BHT), 2-tert-butyl-4-hydroxyanisole, 3-tert-butyl-4-hydroxyanisole, propyl gallate, catechin, and the like can be mentioned.
  • radical scavenger in the present invention ascorbic acid, ascorbate, ascorbic acid ester, erythorbic acid, erythorbic acid salt, and erythorbic acid ester are preferable.
  • salt of ascorbate or erythorbic acid salt alkali metal salts (e.g., sodium salt, potassium salt, etc.) and the like can be mentioned. Particularly, a sodium salt is preferable.
  • as the ascorbic acid ester or erythorbic acid ester fatty acid esters (e.g., palmitic acid ester, stearic acid ester, and the like) are preferable.
  • particularly preferable radical scavenger is ascorbic acid.
  • ascorbic acid L-ascorbic acid (vitamin C) is more preferable.
  • the content of the radical scavenger in the sweetener composition of the present invention is not particularly limited as long as the effect of the present invention is afforded, and the content is generally not less than 1 mass part, preferably not less than 5 mass parts, more preferably not less than 10 mass parts, relative to 100 mass parts of monatin or a salt thereof.
  • the upper limit of the content is not particularly set and it is appropriately determined depending on the kind of radical scavenger to be used, and the kind of food on which a sweetener composition is used.
  • a radical scavenger is generally used in an amount of not more than 10000 mass parts, preferably not more than 5000 mass parts, relative to 100 mass parts of monatin or a salt thereof.
  • the sweetener composition of the present invention is preferably used as a sweetener, and may further contain other optional components such as a carrier, an extender, an excipient, an additive, a flavor, and the like as necessary.
  • the sweetener composition of the present invention may contain other sweeteners such as saccharides (e.g., sucrose, invert sugar, isomerized sugar, glucose, fructose, lactose, maltose, trehalose, xylose.
  • sugar alcohols e.g., multitol, sorbitol, mannitol, erythritol, xylitol, lactitol, etc.
  • oligosaccharides e.g., multitol, sorbitol, mannitol, erythritol, xylitol, lactitol, etc.
  • oligosaccharides e.g., multitol, sorbitol, mannitol, erythritol, xylitol, lactitol, etc.
  • oligosaccharides e.g., multitol, sorbitol, mannitol, erythritol, xylitol, lactitol, etc.
  • oligosaccharides e.g., multitol, sorbitol, mannitol, erythritol, xylito
  • the form of the sweetener composition of the present invention is not particularly limited, and it is provided in various forms such as a freeze-dried product, a mixed and ground product, a liquid, an emulsion, and the like.
  • the sweetener composition as a freeze-dried product or a mixed and ground product may be granulated, where necessary, by a method known to those of ordinary skill in the art such as dry granulation, wet granulation and the like, to give granules.
  • a liquid sweetener water, alcohol, glycerol, propylene glycol, and the like can be used as a solvent to dissolve solute and, more preferably, water and alcohol can be used.
  • the amounts of the aforementioned composition and solvent to be added are adjusted according to methods known to those of ordinary skill in the art.
  • the sweetener composition of the present invention can be used for a wide variety of products including beverages, foods, pharmaceutical products, and the like.
  • various foods include powder juices, powder cocoas, instant coffee, chocolate, chewing gum, health foods, bread, cake, and the like, and various beverages such as coffee beverages, vegetable juice beverages, Japanese tea, Chinese tea, tea, milk beverages, soup beverages, carbonated beverages, sweet beverages, juice beverages, alcohol beverages, and the like.
  • various products that require a sweet taste such as toothpaste powders, pharmaceutical products and the like, and the like.
  • the present invention moreover provides a preservation stabilizer of monatin or a salt thereof.
  • the preservation stabilizer is characterized in that it contains a radical scavenger.
  • the radical scavenger is the same as those mentioned above.
  • decomposition of monatin and a salt thereof can be suppressed even under ultraviolet light, and they can be used for a stable sweetener composition and the like.
  • any other components such as the above-mentioned extenders, excipients, additives, flavors, sweeteners other than monatin, and the like can be added as long as the object of the present invention can be achieved.
  • the preservation stabilizer of the present invention is so used as to make the mass ratio of monatin or a salt thereof and radical scavenger the same as the mass ratio of the composition explained above.
  • the decomposition suppressive effect and preservation stabilization effect of the present invention is particularly remarkably exhibited in beverages containing monatin.
  • the decomposition suppressive effect and preservation stabilization effect can be exhibited in food and pharmaceutical products containing monatin in a liquid state, food and pharmaceutical products containing monatin together with a solvent in which monatin is dissolved, and food and pharmaceutical products in which monatin is used or preserved in a liquid state.
  • the decomposition suppressive effect and preservation stabilization effect can be exhibited in food and pharmaceutical products produced via a step comprising monatin in a liquid state during production thereof.
  • ultraviolet light refers to an electromagnetic wave having a shorter wavelength than visible light and a longer wavelength than X-ray, and the wavelength range thereof can be made to fall within the range of approximately 400 nm to 1 nm.
  • Ultraviolet light is divided according to wavelength range into near ultraviolet light 400 to 300 nm, deep ultraviolet light 300 to 200 nm, and vacuum ultraviolet light 200 to 1 nm. Since absorption due to oxygen is seen in a wavelength range of not more than 195 nm, a spectroscope for this wavelength range requires a special design such as vacuum optical path and the like. Ozone in the upper atmosphere absorbs not more than about 290 nm of the sunlight. (Tokyo Kagaku Dozin Co., Ltd., Encyclopedia of Chemistry, 1st ed.
  • the present invention when monatin is present in a liquid state, it is decomposed by ultraviolet light, namely, by the electromagnetic wave having a wavelength in the ultraviolet light region, and also decomposed by, for example, irradiation with sunlight. For example, when preserved in an ultraviolet shield, decomposition is hardly observed. Based on such finding, the present invention further provides a method of preserving monatin or a salt thereof, a method of preserving a sweetener composition containing monatin or a salt thereof, and a method of preserving a beverage, a food, a mouth cavity composition, or a pharmaceutical product containing monatin or a salt thereof.
  • a first preservation method includes maintaining monatin or a salt thereof in the presence of a radical scavenger.
  • decomposition of monatin is observed when monatin or a salt thereof is present in a liquid state.
  • monatin may also become partially liquid and may be decomposed when it is present in a solid state (e.g., a powder, etc.) due to moisture absorption and the like, the preservation method of the present invention is useful for the retention of quality.
  • any other component such as the above-mentioned extenders, excipients, additives, flavors, sweeteners other than monatin, and the like may be co-existent.
  • the preservation method of the present invention is so performed as to make the mass ratio of monatin or a salt thereof and radical scavenger similar to the mass ratio thereof in the composition explained earlier.
  • a second preservation method includes placing monatin or a salt thereof under a condition free of exposure to ultraviolet light.
  • any state may be employed as long as monatin and a salt thereof are not exposed to ultraviolet light and, for example, placing them in a container made from an ultraviolet light shielding material, such as aluminum and the like, wrapping them with a film and the like, which shield ultraviolet light, and the like can be mentioned.
  • the present invention also encompasses a means to prevent exposure of monatin or a salt thereof to ultraviolet light, for example, monatin or a salt thereof in a container, wherein monatin or a salt thereof is enclosed in a container that shields ultraviolet light, a sweetener composition, a beverage, a food, a mouth cavity composition, or a pharmaceutical product in a container, wherein monatin or a salt thereof is enclosed in a container that shields ultraviolet light, and the like.
  • a means to prevent exposure of monatin or a salt thereof to ultraviolet light for example, monatin or a salt thereof in a container, wherein monatin or a salt thereof is enclosed in a container that shields ultraviolet light, a sweetener composition, a beverage, a food, a mouth cavity composition, or a pharmaceutical product in a container, wherein monatin or a salt thereof is enclosed in a container that shields ultraviolet light, and the like.
  • monatin and the like are preserved under an ultraviolet light shield or monatin is enclosed in a container that shields ultraviolet light, it is still preferable to keep monatin in the presence of a radical scavenger, because consumer and the like may use or re-preserve monatin and the like under an ultraviolet light condition.
  • PET container Toyo Seikan Kaisha, Ltd. PET bottle (type: STHH350SA, maximum content: 376 ml, height: 157 mm, maximum diameter: 60 mm, liquid filled: 370 ml).
  • UV-B 0.006 mW/cm 2 .
  • Detection wavelength 210 nm.
  • Injection volume 10 ⁇ L.
  • pH meter type HM-30G, manufactured by DKK Toa Corporation.
  • Measurement method two-point calibration by automatic temperature calibration was performed and pH of the model drink was measured.
  • the pH of a beverage model solution a (citric acid 2 g, sodium benzoate 0.045 g)/L solution, was adjusted with 8N sodium hydroxide. (2R,4R)monatin potassium salt (25 mg) and various additives were dissolved in the adjusted beverage model solution (500 mL) and filled in PET containers.
  • L-Trp 25 mg was added instead of monatin.
  • the containers were left standing for about 165 hours in a constant temperature room controlled to room temperature 25° C. under a D65 fluorescence lamp adjusted to illuminance of about 3000 Lux.
  • the solution was simultaneously filled in a 20 ml screw cap vial and left standing for the same time in the same constant temperature room under a light shield.
  • the photodecomposition rate (%) (1 ⁇ (mass % concentration of monatin in light exposure solution/mass % concentration of monatin in light shield solution)) ⁇ 100
  • monatin is known to be present as an equilibrium of a lactone form of the formula (II) and a lactam form of the formula (III) in an aqueous solution, and the content ratio of the lactone form and lactam form tends to increase with lower pHs of the solution.
  • the monatin residual ratio (%) is shown in the upper line
  • the lactone present ratio (%) is shown in the lower left line
  • the lactam present ratio (%) is shown in the lower right line, all under light exposure and light shield.
  • the presence rates of lactone and lactam were calculated by the following formula:
  • the lactone and lactam presence rates (%) ((HPLC peak area of lactam or lactone after light exposure or light shield preservation)/(HPLC peak area of monatin immediately after sample preparation)) ⁇ 100
  • HPLC peak areas of lactone and lactam are not observed immediately after sample preparation.
  • Trp a solution having a concentration of 50 ppm was prepared (25° C.). The test solution was adjusted to a given pH with citrate buffer, and in the same manner as in Example 1, the photodecomposition rates of Trp and monatin were determined. The test conditions and results are shown in Table 8. From Table 8, it is clear that Trp tends to show photodecomposition in a neutral region rather than in an acidic region, and the photodecomposition behavior of monatin having an indole structure as does Trp is strikingly different from that of Trp, as evidenced by the tendency toward photodecomposition in an acidic region rather than in a neutral region, and the like. Therefore, the photodecomposition property of monatin cannot be predicted at all from the finding in the photodecomposition property of Trp.

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Abstract

Storing monatin or a salt thereof in the presence of a radical scavenger and/or in a UV light-shielding container is effective for preventing the decomposition of monatin or a salt thereof by exposure to ultraviolet light, particularly under acidic conditions. Sweetener compositions which contain monatin or a salt thereof and a radical scavenger and the like are resistant to decomposition by UV light.

Description

    CROSS REFERENCES TO RELATED APPLICATIONS
  • This application claims priority to U.S. Provisional Patent Application No. 60/618,979, filed on Oct. 18, 2004, and Japanese Patent Application No. 302120/2004, filed on Oct. 15, 2004, both of which are incorporated herein by reference in their entireties.
    • BACKGROUND OF THE INVENTION
  • 1. Field of the Invention
  • The present invention relates to sweetener compositions comprising monatin or a salt thereof. More particularly, the present invention relates to a method for preserving monatin or a salt thereof.
  • 2. Discussion of the Background
  • Monatin is a natural amino acid derivative isolated from the root bark of a native plant (Schierochiton ilicifolius) of northern Transvaal of South Africa, and its structure has been reported by R. Vleggaar et al to be (2S,4S)-2-amino-4-carboxy-4-hydroxy-5-(3-indolyl)-pentanoic acid ((2S,4S)-4-hydroxy-4-(3-indolylmethyl)-glutamic acid) (R. Vleggaar et al., J. Chem. Soc. Perkin Trans., pp. 3095-3098, (1992)). The synthesis of monatin is described in, for example, ZA 87/4288, ZA 88/4220, U.S. Pat. No. 5,994,559, WO03/045914, WO03/059865, WO03/056026, WO04/067494, WO04/053125, C. W. Holzapfel et al., Synthetic Communication, vol. 24(22), pp. 3197-3211 (1994), K. Nakamura et al., Organic Letters, vol. 2, pp. 2967-2970 (2000), and the like. Monatin is a superior sweetener which is 1400 times sweeter than sugar and contains no calories. It is stable to heat and expected to be applicable to various kinds of food.
    • SUMMARY OF THE INVENTION
  • The present inventor has first clarified at this time that monatin in the solution state tends to decompose when exposed to ultraviolet light, and that the tendency becomes particularly remarkable under acidic conditions (particularly at a pH of less than 5). As mentioned above, therefore, a means to use a superior sweetener, monatin, in a stable state irrespective of the condition it is placed in, becomes necessary.
  • Thus, the problem to be solved by the present invention solves the above-mentioned novel problem. Specifically, the problem of the present invention is to provide a method for preserving monatin or a salt thereof in a stable state even under ultraviolet light, and further, a sweetener composition, a beverage, a food, a pharmaceutical product and the like, which contain stable monatin or a salt thereof. In addition, provision of a preservation stabilizer for monatin or a salt thereof is also a problem of the present invention.
  • Accordingly, it is one object of the present invention to provide novel compositions which contain monatin or a salt thereof.
  • It is another object of the present invention to provide novel compositions which contain monatin or a salt thereof and which exhibit increased stability.
  • It is another object of the present invention to provide novel compositions which contain monatin or a salt thereof and which exhibit increased stability, even when exposed to ultraviolet light.
  • It is another object of the present invention to provide novel beverages, foods, pharmaceutical products, and the like, which contain stable monatin or a salt thereof.
  • These and other objects, which will become apparent during the following detailed description, have been achieved by the inventor's discovery that monatin and a salt thereof can be maintained in a stable state by maintaining monatin or a salt thereof in the co-presence of a radical scavenger.
  • Accordingly, the present invention provides the following:
  • (1) A sweetener composition, comprising monatin or a salt thereof and a radical scavenger.
  • (2) The composition of (1), wherein the radical scavenger is at least one member selected from the group consisting of ascorbic acid, ascorbate, ascorbic acid ester, erythorbic acid, erythorbic acid salt, erythorbic acid ester, uric acid, bilirubin, albumin, vitamin A, vitamin E, ubiquinol, carotenoid, histidine, tryptophan, 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4-hydroxyanisole, 3-tert-butyl-4-hydroxyanisole, propyl gallate, catechin, and mixtures thereof.
  • (3) The composition of (1), wherein the radical scavenger is at least one member selected from the group consisting of ascorbic acid, ascorbate, ascorbic acid ester, erythorbic acid, erythorbic acid salt, erythorbic acid ester, and mixtures thereof.
  • (4) The composition of (1), wherein the radical scavenger is ascorbic acid.
  • (5) The composition of any of (1)-(4), which is a liquid composition having a pH of not less than 2 and less than 7.
  • (6) The composition of any of (1)-(5), wherein the radical scavenger content is 1 to 10000 mass parts relative to 100 mass parts of monatin or a salt thereof.
  • (7) A beverage, a food, a mouth cavity composition, or a pharmaceutical product comprising a composition of any of (1)-(6).
  • (8) A beverage comprising a composition of any of (1)-(6).
  • (9) A preservation stabilizer for monatin or a salt thereof, which comprises a radical scavenger.
  • (10) A method of preserving monatin or a salt thereof, which comprises maintaining monatin or a salt thereof in the presence of a radical scavenger.
  • (11) A method of preserving a sweetener composition, a beverage, a food, a mouth cavity composition, or a pharmaceutical product, comprising monatin or a salt thereof, which method comprises maintaining monatin or a salt thereof in the presence of a radical scavenger.
  • (12) A method of preserving a beverage comprising monatin or a salt thereof, which method comprises maintaining monatin or a salt thereof in the presence of a radical scavenger.
  • (13) A method of preserving monatin or a salt thereof, which method comprises placing monatin or a salt thereof under a condition free of exposure to ultraviolet light.
  • (14) A method of preserving a sweetener composition, a beverage, a food, a mouth cavity composition, or a pharmaceutical product comprising monatin or a salt thereof, which method comprises placing monatin or a salt thereof under a condition free of exposure to ultraviolet light.
  • (15) A method of preserving a beverage comprising monatin or a salt thereof, which method comprises placing monatin or a salt thereof under a condition free of exposure to ultraviolet light.
  • (16) The method of (13)-(15), which comprises preservation in the presence of a radical scavenger.
  • (17) Monatin or a salt thereof, which is enclosed in a container shielding ultraviolet light.
  • (18) A sweetener composition, a beverage, a food, a mouth cavity composition, or a pharmaceutical product comprising monatin or a salt thereof, which is enclosed in a container shielding ultraviolet light.
  • (19) A beverage comprising monatin or a salt thereof, which is enclosed in a container shielding ultraviolet light.
  • (20) A sweetener composition, a beverage, a food, a mouth cavity composition, or a pharmaceutical product comprising monatin or a salt thereof and a radical scavenger, which is enclosed in a container shielding ultraviolet light.
  • (21) A beverage comprising monatin or a salt thereof and a radical scavenger, which is enclosed in a container shielding ultraviolet light.
  • According to the present invention, a sweetener composition, a food, a beverage, a mouth cavity composition, and a pharmaceutical product are provided, which contain monatin or a salt thereof, and which suppress decomposition of the monatin or salt thereof due to ultraviolet light, and provide a stable sweetness. According to the present invention, moreover, a preservation stabilizer for and a method of preserving monatin or a salt thereof are also provided.
    • DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
  • The sweetener composition of the present invention contains monatin and a radical scavenger. Monatin is a compound represented by the formula (I):
    Figure US20060083695A1-20060420-C00001
    Monatin has an asymmetric moieties at the 2-position and the 4-position and includes the following 4 kinds of optical isomers.
    Figure US20060083695A1-20060420-C00002
    In the present invention, the stereoisomer is not particularly limited. Where necessary, (2R,4R)monatin, (2R,4S)monatin, (2S,4R)monatin, and (2S,4S)monatin, and any mixture of these can be used. Unless otherwise specified, in the present specification, simple monatin means one without limitation on stereoisomerism. Moreover, the monatin used in the present invention may be used as a salt with an alkali metal, such as sodium, potassium, and the like; an alkaline earth metal such as magnesium and the like; and the like. In this case, the potassium salt is preferable, and monopotassium salt is more preferable.
  • According to the finding of the present inventor, of the 4 kinds of optical isomers, (2S,4R)monatin and (2R,4S)monatin tend to be more easily decomposed by ultraviolet light than the other isomers. Monatin is a known substance, and its production method is also known. For example, it can be produced by a method described in ZA 87/4288, ZA 88/4220, U.S. Pat. No. 5,994,559, WO03/045914, WO03/059865, WO03/056026, WO04/067494, WO04/053125, C. W. Holzapfel et al., Synthetic Communications, vol. 24(22), pp. 3197-3211(1994), K. Nakamura et al., Organic Letters, vol. 2, pp. 2967-2970(2000), and the like.
  • The term radical scavenger as used in the present invention refers to a compound used to efficiently catch a radical (free group) produced during reaction and, for example, ascorbic acid, ascorbate, ascorbic acid ester, erythorbic acid (isoascorbic acid), erythorbic acid salt, erythorbic acid ester, uric acid, bilirubin, albumin, vitamin A, vitamin E, ubiquinol, carotenoid, histidine, tryptophan, 2,6-di-tert-butyl-4-methylphenol (BHT), 2-tert-butyl-4-hydroxyanisole, 3-tert-butyl-4-hydroxyanisole, propyl gallate, catechin, and the like can be mentioned. As the radical scavenger in the present invention, ascorbic acid, ascorbate, ascorbic acid ester, erythorbic acid, erythorbic acid salt, and erythorbic acid ester are preferable. As the salt of ascorbate or erythorbic acid salt, alkali metal salts (e.g., sodium salt, potassium salt, etc.) and the like can be mentioned. Particularly, a sodium salt is preferable. As the ascorbic acid ester or erythorbic acid ester, fatty acid esters (e.g., palmitic acid ester, stearic acid ester, and the like) are preferable. In the present invention, particularly preferable radical scavenger is ascorbic acid. As the ascorbic acid, L-ascorbic acid (vitamin C) is more preferable.
  • The content of the radical scavenger in the sweetener composition of the present invention is not particularly limited as long as the effect of the present invention is afforded, and the content is generally not less than 1 mass part, preferably not less than 5 mass parts, more preferably not less than 10 mass parts, relative to 100 mass parts of monatin or a salt thereof. The upper limit of the content is not particularly set and it is appropriately determined depending on the kind of radical scavenger to be used, and the kind of food on which a sweetener composition is used. A radical scavenger is generally used in an amount of not more than 10000 mass parts, preferably not more than 5000 mass parts, relative to 100 mass parts of monatin or a salt thereof.
  • The sweetener composition of the present invention is preferably used as a sweetener, and may further contain other optional components such as a carrier, an extender, an excipient, an additive, a flavor, and the like as necessary. The sweetener composition of the present invention may contain other sweeteners such as saccharides (e.g., sucrose, invert sugar, isomerized sugar, glucose, fructose, lactose, maltose, trehalose, xylose. etc.); sugar alcohols (e.g., multitol, sorbitol, mannitol, erythritol, xylitol, lactitol, etc.); oligosaccharides; dietary fiber; aspartame; saccharin; acesulfame K; sucralose; and the like.
  • The form of the sweetener composition of the present invention is not particularly limited, and it is provided in various forms such as a freeze-dried product, a mixed and ground product, a liquid, an emulsion, and the like. The sweetener composition as a freeze-dried product or a mixed and ground product may be granulated, where necessary, by a method known to those of ordinary skill in the art such as dry granulation, wet granulation and the like, to give granules. For a liquid sweetener, water, alcohol, glycerol, propylene glycol, and the like can be used as a solvent to dissolve solute and, more preferably, water and alcohol can be used. For control of the specific gravity of each component, the amounts of the aforementioned composition and solvent to be added are adjusted according to methods known to those of ordinary skill in the art.
  • The sweetener composition of the present invention can be used for a wide variety of products including beverages, foods, pharmaceutical products, and the like. To be specific, various foods include powder juices, powder cocoas, instant coffee, chocolate, chewing gum, health foods, bread, cake, and the like, and various beverages such as coffee beverages, vegetable juice beverages, Japanese tea, Chinese tea, tea, milk beverages, soup beverages, carbonated beverages, sweet beverages, juice beverages, alcohol beverages, and the like. In addition, it can be used for various products that require a sweet taste such as toothpaste powders, pharmaceutical products and the like, and the like.
  • The present invention moreover provides a preservation stabilizer of monatin or a salt thereof. The preservation stabilizer is characterized in that it contains a radical scavenger. The radical scavenger is the same as those mentioned above. Using this preservation stabilizer, decomposition of monatin and a salt thereof can be suppressed even under ultraviolet light, and they can be used for a stable sweetener composition and the like. Where desired, any other components such as the above-mentioned extenders, excipients, additives, flavors, sweeteners other than monatin, and the like can be added as long as the object of the present invention can be achieved.
  • Generally, the preservation stabilizer of the present invention is so used as to make the mass ratio of monatin or a salt thereof and radical scavenger the same as the mass ratio of the composition explained above.
  • According to the findings of the present inventor, when monatin is present in a liquid state such as aqueous solution and the like, it tends to be decomposed by ultraviolet light, and a pronounced tendency is found in an acidic pH range (pH of 2 to 7). Decomposition is particularly remarkable when pH is not more than 6. In general, the pH of food is not less than 2, and the decomposition suppressive effect and preservation stabilization effect of monatin of the present invention become remarkable in sweetener compositions and food having a pH of not less than 2 and not more than 7, further not less than pH 2 and not more than 6, still further not less than pH 2 and not more than 5, and even further not less than pH 2 and not more than 4. Since decomposition of monatin due to ultraviolet light is observed when monatin is present in a liquid state such as aqueous solution and the like, the decomposition suppressive effect and preservation stabilization effect of the present invention is particularly remarkably exhibited in beverages containing monatin. In addition, the decomposition suppressive effect and preservation stabilization effect can be exhibited in food and pharmaceutical products containing monatin in a liquid state, food and pharmaceutical products containing monatin together with a solvent in which monatin is dissolved, and food and pharmaceutical products in which monatin is used or preserved in a liquid state. Furthermore, the decomposition suppressive effect and preservation stabilization effect can be exhibited in food and pharmaceutical products produced via a step comprising monatin in a liquid state during production thereof.
  • The term ultraviolet light refers to an electromagnetic wave having a shorter wavelength than visible light and a longer wavelength than X-ray, and the wavelength range thereof can be made to fall within the range of approximately 400 nm to 1 nm. Ultraviolet light is divided according to wavelength range into near ultraviolet light 400 to 300 nm, deep ultraviolet light 300 to 200 nm, and vacuum ultraviolet light 200 to 1 nm. Since absorption due to oxygen is seen in a wavelength range of not more than 195 nm, a spectroscope for this wavelength range requires a special design such as vacuum optical path and the like. Ozone in the upper atmosphere absorbs not more than about 290 nm of the sunlight. (Tokyo Kagaku Dozin Co., Ltd., Encyclopedia of Chemistry, 1st ed. 4th printing, 1998). As is clear from the Examples to be mentioned later, light irradiation from a lamp with a UV absorption film hardly decomposes monatin, but irradiation of sunlight, D65 lamp and near ultraviolet lamp (all having a wavelength in the ultraviolet light region) decomposes monatin. It is clear therefrom that the decomposition of monatin is attributable to an electromagnetic wave having a wavelength in the ultraviolet light region (assumed to be mainly 290 to 400 nm wavelength).
  • According to the findings of the present inventor, when monatin is present in a liquid state, it is decomposed by ultraviolet light, namely, by the electromagnetic wave having a wavelength in the ultraviolet light region, and also decomposed by, for example, irradiation with sunlight. For example, when preserved in an ultraviolet shield, decomposition is hardly observed. Based on such finding, the present invention further provides a method of preserving monatin or a salt thereof, a method of preserving a sweetener composition containing monatin or a salt thereof, and a method of preserving a beverage, a food, a mouth cavity composition, or a pharmaceutical product containing monatin or a salt thereof.
  • A first preservation method includes maintaining monatin or a salt thereof in the presence of a radical scavenger. Generally, decomposition of monatin is observed when monatin or a salt thereof is present in a liquid state. However, since monatin may also become partially liquid and may be decomposed when it is present in a solid state (e.g., a powder, etc.) due to moisture absorption and the like, the preservation method of the present invention is useful for the retention of quality. Moreover, any other component such as the above-mentioned extenders, excipients, additives, flavors, sweeteners other than monatin, and the like may be co-existent. Generally, the preservation method of the present invention is so performed as to make the mass ratio of monatin or a salt thereof and radical scavenger similar to the mass ratio thereof in the composition explained earlier.
  • A second preservation method includes placing monatin or a salt thereof under a condition free of exposure to ultraviolet light. To be specific, any state may be employed as long as monatin and a salt thereof are not exposed to ultraviolet light and, for example, placing them in a container made from an ultraviolet light shielding material, such as aluminum and the like, wrapping them with a film and the like, which shield ultraviolet light, and the like can be mentioned. Therefore, the present invention also encompasses a means to prevent exposure of monatin or a salt thereof to ultraviolet light, for example, monatin or a salt thereof in a container, wherein monatin or a salt thereof is enclosed in a container that shields ultraviolet light, a sweetener composition, a beverage, a food, a mouth cavity composition, or a pharmaceutical product in a container, wherein monatin or a salt thereof is enclosed in a container that shields ultraviolet light, and the like.
  • Even when monatin and the like are preserved under an ultraviolet light shield or monatin is enclosed in a container that shields ultraviolet light, it is still preferable to keep monatin in the presence of a radical scavenger, because consumer and the like may use or re-preserve monatin and the like under an ultraviolet light condition.
  • Other features of the invention will become apparent in the course of the following descriptions of exemplary embodiments which are given for illustration of the invention and are not intended to be limiting thereof.
    • EXAMPLES
  • Various conditions, light irradiation conditions, and HPLC analysis conditions employed for the following Examples, Comparative Examples and Reference Example are as described below.
  • Various Conditions:
  • Monatin used: (2R,4R)monatin potassium salt, (2S,4S)monatin potassium salt, and (2S,4R)monatin potassium salt.
  • Preservation PET container: Toyo Seikan Kaisha, Ltd. PET bottle (type: STHH350SA, maximum content: 376 ml, height: 157 mm, maximum diameter: 60 mm, liquid filled: 370 ml).
  • Light Irradiation Conditions:
  • Illuminance:
      • 2900-3100 LUX.
      • UV-A: 0.06 mW/cm2.
  • UV-B: 0.006 mW/cm2.
    TABLE 1
    UV-A(360 nm) UV-B(305 nm) illuminance
    place mW/cm2 lux
    outside 9:10 1.102 0.376 44,000
    outside 13:40 1.790 0.696 72,300
    outside 15:40 1.007 0.399 48,000
    near ultraviolet 0.597 0.053 23
    light lamp
    D65 lamp 0.06 0.006 2,900
    lamp with UV 0.001 0.001 2,700
    absorption film

    (ref.: illuminance about 700-1000 lux on indoor desk)
  • Temperature: 25° C. constant temperature room (forced circulation).
  • Apparatus:
      • Luminance meter: Tokyp Koden Ltd.
      • Digital luminance meter ANA-F11.
      • UV Radiometer: Topcon Corporation UV Radiometer UVR-3036/S.
      • (light receiver: UV-A (365 nm), UV-B (305 nm)).
      • Lamp: manufactured by Toshiba Corporation, tube diameter 32.5 mm,
      • tube length 580 mm, 20 W (common).
      • D65 fluorescence lamp type: FL20S.D-EDL-D65.
      • Near ultraviolet light lamp type: FL20S.BLB.
      • Fluorescence lamp with UV absorption film type: FL20S.N-SDL-NU.
      • (the light emmitted by D65 fluorescence lamp has similar spectrum as sunlight).
        HPLC Analysis Used:
  • Instruments used:
      • Pump: LC-9A manufactured by Shimadzu Corporation.
      • Column oven: CTO-10A manufactured by Shimadzu Corporation.
      • Detector: SPD-10A manufactured by Shimadzu Corporation.
      • Autosampler: SIL-9A manufactured by Shimadzu Corporation.
      • Gradient: LPG-1000 manufactured by Tokyo Rikakikai Co., Ltd.
  • Column: CAPCELL PAK C18 TYPE MG 5 μm
      • 4.6 mm×250 mm manufactured by Shiseido Company, Limited.
  • Column temperature: 40° C.
  • Detection wavelength: 210 nm.
  • Mobile liquid composition:
      • Solution A 20 mm KH2PO4/acetonitrile=100/5.
      • Solution B acetonitrile alone.
  • Gradient pattern: (shown in Table 2).
    TABLE 2
    Time (min) Solution A (%) Solution B (%)
    0 100 0
    15 100 0
    40 63 37
    45 63 37
  • Injection volume: 10 μL.
  • Analysis cycle: 70 min/1 sample.
  • pH Measurement Conditions:
  • pH meter: type HM-30G, manufactured by DKK Toa Corporation.
  • PH standard solution: phosphate pH standard equimolal solution (JIS Z 8802) pH=7, manufactured by Junsei Chemical Co., Ltd.
  • Phthalate pH standard solution (JIS Z 8802) pH=4 manufactured by Junsei Chemical Co., Ltd.
  • Measurement method: two-point calibration by automatic temperature calibration was performed and pH of the model drink was measured.
  • Preservation of Monatin by Addition of Radical Scavenger.
    • EXAMPLES 1-9, COMPARATIVE EXAMPLES 1-5, REFERENCE EXAMPLE 1
  • The pH of a beverage model solution, a (citric acid 2 g, sodium benzoate 0.045 g)/L solution, was adjusted with 8N sodium hydroxide. (2R,4R)monatin potassium salt (25 mg) and various additives were dissolved in the adjusted beverage model solution (500 mL) and filled in PET containers. In Reference Example 1, L-Trp (25 mg) was added instead of monatin. The containers were left standing for about 165 hours in a constant temperature room controlled to room temperature 25° C. under a D65 fluorescence lamp adjusted to illuminance of about 3000 Lux. The solution was simultaneously filled in a 20 ml screw cap vial and left standing for the same time in the same constant temperature room under a light shield. These light exposure solutions and light shield solutions were subjected to HPLC analysis, and photodecomposition rates were calculated by the following formula:
    The photodecomposition rate (%)=(1−(mass % concentration of monatin in light exposure solution/mass % concentration of monatin in light shield solution))×100
  • The pH, monatin used, and additives used for each solution were as shown in Table 3. The results are shown in Table 3. From Table 3, it is clear that the decomposition of monatin was remarkably suppressed by the presence of a radical scavenger under light irradiation including ultraviolet light by D65 lamp.
  • As described in ZA 87/4288 and ZA 88/4220, monatin is known to be present as an equilibrium of a lactone form of the formula (II) and a lactam form of the formula (III) in an aqueous solution, and the content ratio of the lactone form and lactam form tends to increase with lower pHs of the solution.
    Figure US20060083695A1-20060420-C00003
  • In the following Tables, the monatin residual ratio (%) is shown in the upper line, the lactone present ratio (%) is shown in the lower left line, and the lactam present ratio (%) is shown in the lower right line, all under light exposure and light shield.
  • The monatin residual ratio was calculated by the following formula:
    The monatin residual ratio (%)=((monatin mass % concentration after light exposure or light shield preservation)/(monatin mass % concentration before light exposure or light shield preservation))×100
  • The presence rates of lactone and lactam were calculated by the following formula:
    The lactone and lactam presence rates (%)=((HPLC peak area of lactam or lactone after light exposure or light shield preservation)/(HPLC peak area of monatin immediately after sample preparation))×100
  • The HPLC peak areas of lactone and lactam are not observed immediately after sample preparation.
  • Difference in photodecomposition rate of monatin due to pH difference.
    • COMPARATIVE EXAMPLES 6-11
  • In the same manner as in Example 1, except that additives were not added, the photodecomposition rate of monatin was determined. The pH and monatin used for each solution are shown in Table 4. The results are shown in Table 4.From Table 4, it is clear that decomposition of monatin due to ultraviolet light tends to increase with lower pHs.
  • Decomposition rate of monatin with ultraviolet light shield.
    • EXAMPLES 10-12
  • In the same manner as in Example 1, except that a fluorescence lamp with a UV absorption film (exposure time 73 hours) was used instead of a D65 lamp, the photodecomposition rate of monatin was determined. The pH, monatin, and additives used for each solution are shown in Table 5. The results are shown in Table 5. From Table 5, it is clear that decomposition of monatin was markedly suppressed when ultraviolet light was shielded.
    • EXAMPLE 13 AND COMPARATIVE EXAMPLES 12-13
  • In the same manner as in Example 1, except that sunlight (exposure time 14 hours) was used instead of a D65 lamp, the photodecomposition rate of monatin was determined. The pH, monatin, and additives used for each solution are shown in Table 6. The results are shown in Table 6. From Table 6, it is clear that the decomposition of monatin due to sunlight including ultraviolet light was markedly suppressed when a radical scavenger was present.
    • EXAMPLE 14 AND COMPARATIVE EXAMPLES 14-15
  • In the same manner as in Example 1, except that a near ultraviolet light lamp (exposure time 73 hour) was used instead of a D65 lamp, the photodecomposition rate of monatin was determined. The pH, monatin, and additives used for each solution are shown in Table 7. The results are shown in Table 7. From Table 7, it is clear that the decomposition of monatin due to ultraviolet light was markedly suppressed when a radical scavenger was present.
  • pH dependency of photodecomposition behavior of Trp and monatin.
    • EXPERIMENTAL EXAMPLE
  • The pH dependency of the photodecomposition behavior of tryptophan (Trp) and monatin was examined.
  • For Trp, a solution having a concentration of 50 ppm was prepared (25° C.). The test solution was adjusted to a given pH with citrate buffer, and in the same manner as in Example 1, the photodecomposition rates of Trp and monatin were determined. The test conditions and results are shown in Table 8. From Table 8, it is clear that Trp tends to show photodecomposition in a neutral region rather than in an acidic region, and the photodecomposition behavior of monatin having an indole structure as does Trp is strikingly different from that of Trp, as evidenced by the tendency toward photodecomposition in an acidic region rather than in a neutral region, and the like. Therefore, the photodecomposition property of monatin cannot be predicted at all from the finding in the photodecomposition property of Trp.
  • Furthermore, it was surprisingly found that addition of ascorbic acid to monatin afforded an effect comparable to shading over a wide pH range.
    TABLE 3
    Light source D65 lamp illuminance 3000 lux exposure time 165 hr
    photo-
    decom-
    light light position
    pH monatin additive exposure shielding rate
    Ex. 1 3.1 (2R,4R) ascorbic acid 25 71.3% 64.0% −11.5%
    mg (50 ppm) (25.7%, 1.2%) (23.2%, 1.7%)
    Ex. 2 3.1 (2R,4R) ascorbic acid 54.6% 76.9% 29.1%
    0.25 mg (16.6%, 0.1%) (20.8%, 1.0%)
    (0.5 ppm)
    Ex. 3 3.1 (2R,4R) ascorbic acid 75.0% 74.4% −0.9%
    2.5 mg (5 ppm) (21.2%, 0.9%) (25.1%, 1.8%)
    Ex. 4 3.1 (2R,4R) ascorbic acid 72.8% 68.8% −5.7%
    250 mg (26.2%, 1.7%) (25.1%, 1.8%)
    (500 ppm)
    Ex. 5 3.1 (2R,4R) BHT 25 mg 67.4% 76.6% 12.0%
    (50 ppm) (19.4%, 0.9%) (21.3%, 1.0%)
    Ex. 6 3.1 (2R,4R) catechin 74.9% 77.3% 3.1%
    25 mg (50 ppm) (21.2%, 0.5%) (21.6%, 1.0%)
    Ex. 7 3.1 (2S,4S) ascorbic acid 75.5% 73.1% −3.3%
    25 mg (50 ppm) (12.2%, 0.7%) (19.9%, 0.9%)
    Ex. 8 3.1 (2S,4R) ascorbic acid 63.3% 62.6% −1.1%
    25 mg (50 ppm) (13.2%, 1.4%) (36.3%, 1.6%)
    Ex. 9 3.1 (2S,4S) ascorbic acid 75.3% 72.3% −4.1%
    (2R,4R) 25 mg (50 ppm) (13.2%, 1.4%) (20.9%, 0.9%)
    Com. Ex. 1 3.1 (2R,4R) none 42.4% 77.3% 45.1%
    (12.5%, 0.6%) (21.6%, 0.9%)
    Com. Ex. 2 3.1 (2S,4S) none 41.0% 77.9% 47.4%
    (12.2%, 0.7%) (21.1%, 1.1%)
    Com. Ex. 3 3.1 (2S,4R) none  7.9% 63.6% 87.6%
    (5.5%, 0.0%) (39.5%, 1.7%)
    Com. Ex. 4 3.1 (2S,4S) none 46.6% 80.8% 42.3%
    (2R,4R) (14.1%, 0.8%) (22.2%, 0.1%)
    Com. Ex. 5 3.1 (2R,4R) trehalose 42.1% 77.0% 45.3%
    25 mg (12.3%, 0.8%) (21.3%, 1.0%)
    Ref. Ex. 1 3.1 L-Trp none 94.0% 100.0%  6.0%
  • TABLE 4
    Light source D65 lamp illuminance 3000 lux exposure time 165 hr
    photo-
    light light decomposition
    pH monatin additive exposure shielding rate
    Com. Ex. 6 2.8 (2R,4R) none 36.8%  77.4% 52.5%
    (13.0%, 0.9%) (25.5%, 13%)
    Com. Ex. 7 3.5 (2R,4R) none 63.4%  87.6% 27.6%
    (11.5%, 0.5%) (14.7%, 0.5%)
    Com. Ex. 8 4.0 (2R,4R) none 79.8%  94.8% 15.9%
    (6.5%, 0.0%) (7.1%, 0.0%)
    Com. Ex. 9 4.5 (2R,4R) none 89.8% 100.0% 10.2%
    (2.6%, 0.0%) (2.7%, 0.0%)
    Com. Ex. 10 5.5 (2R,4R) none 96.9% 101.8%  4.8%
    (0.0%, 0.0%) (0.0%, 0.0%)
    Com. Ex. 11 6.5 (2R,4R) none 97.3% 101.7%  4.3%
    (0.0%, 0.0%) (0.0%, 0.0%)
  • TABLE 5
    Light source fluorescence lamp with UV absorption film 73 hr
    photo-
    light decomposition
    pH monatin additive exposure light shielding rate
    Ex. 10 3.1 (2R,4R) ascorbic acid 76.7% 74.2% −3.4%
    25 mg (21.1%, 0.6%) (20.0%, 0.5%)
    (50 ppm)
    Ex. 11 3.1 (2R,4R) K2SO3 74.4% 76.0% 2.1%
    25 mg (20.0%, 0.5%) (20.0%, 0.5%)
    (50 ppm)
    Ex. 12 3.1 (2R,4R) none 75.2% 76.8% 2.1%
    (20.9%, 1.4%) (20.9%, 0.5%)
  • TABLE 6
    Light source: sunlight, 14 hr
    photo-
    light light decomposition
    pH monatin additive exposure shielding rate
    Ex. 13 3.1 (2R,4R) ascorbic acid 77.3% 74.2% −4.2%
    25 mg (22.2%, 0.6%) (20.1%, 0.5%)
    (50 ppm)
    Com. Ex. 12 3.1 (2R,4R) K2SO3  2.2% 76.0% 97.2%
    25 mg (0.7%, 0.0%) (20.0%, 0.5%)
    (50 ppm)
    Com. Ex. 13 3.1 (2R,4R) none 41.9% 76.8% 45.4%
    (13.3%, 0.9%) (20.9%, 0.5%)
  • TABLE 7
    Light source: near ultraviolet light lamp; 73 hr
    photo-
    light light decomposition
    pH monatin additive exposure shielding rate
    Ex. 14 3.1 (2R,4R) ascorbic 76.2% 74.2% −2.7%
    acid (21.0%, 0.6%) (20.1%, 0.5%)
    25 mg
    (50 ppm)
    Com. Ex. 14 3.1 (2R,4R) K2SO3  3.9% 76.0% 94.8%
    25 mg (0.8%, 0.0%) (20.0%, 0.5%)
    (50 ppm)
    Com. Ex. 15 3.1 (2R,4R) none 16.3% 76.8% 78.8%
    (6.3%, 1.4%) (20.9%, 0.5%)
  • TABLE 8
    Light source: D65 lamp illuminance
    3000 lux, exposure time 165 hr
    photodecomposition rate
    Trp monatin monatin (50 ppm) +
    pH (50 ppm) (50 ppm) ascorbic acid (50 ppm)
    2.8 7.3% 52.5% not measured
    3.1 6.0% 45.1% −2%
    3.5 6.2% 27.6% not measured
    4 5.5% 15.9% not measured
    4.5 5.4% 10.2% −1%
    5.5 12.5% 4.8% not measured
    6.5 55.1% 4.3%  0%
  • Obviously, numerous modifications and variations of the present invention are possible in light of the above teachings. It is therefore to be understood that, within the scope of the appended claims, the invention may be practiced otherwise than as specifically described herein.
  • All patents and other references mentioned above are incorporated in full herein by this reference, the same as if set forth at length.

Claims (21)

1. A sweetener composition, comprising monatin or a salt thereof and a radical scavenger.
2. The composition of claim 1, wherein said radical scavenger is at least one member selected from the group consisting of ascorbate acid, ascorbate, an ascorbic acid ester, erythorbic acid, erythorbic acid salt, an erythorbic ester, uric acid, bilirubin, albumin, vitamin A, vitamin E, ubiquinol, carotenoid, histidine, tryptophan, 2,6-d-tert-butyl-4-methylphenol, 2-tert-butyl-4-hydroxyanisole, 3-tert-butyl-4-hydroxyanisole, propyl gallate, catechin, and mixtures thereof.
3. The composition of claim 1, wherein said radical scavenger is at least one member selected from the group consisting of ascorbic acid, ascorbate, an ascorbic acid ester, erythorbic acid, erythorbic acid salt, an erythorbic acid ester, and mixtures thereof.
4. The composition of claim 1, wherein said radical scavenger is ascorbic acid.
5. The composition of claim 1, which is a liquid composition having a pH of not less than 2 and less than 7.
6. The composition of claim 1, wherein said radical scavenger is present in an amount of 1 to 10000 mass parts relative to 100 mass parts of said monatin or a salt thereof.
7. A beverage, a food, a mouth cavity composition, or a pharmaceutical product, which comprises a composition according to claim 1.
8. A beverage comprising a composition according to claim 1.
9. A preservation stabilizer for monatin or a salt thereof, which comprises a radical scavenger.
10. A method of preserving monatin or a salt thereof, said method comprising maintaining monatin or a salt thereof in the presence of a radical scavenger.
11. A method of preserving a sweetener composition, a beverage, a food, a mouth cavity composition, or a pharmaceutical product, which comprises monatin or a salt thereof, said method comprising maintaining said monatin or a salt thereof in the presence of a radical scavenger.
12. A method of preserving a beverage, which comprises monatin or a salt thereof, said method comprising maintaining said monatin or a salt thereof in the presence of a radical scavenger.
13. A method of preserving monatin or a salt thereof, said method comprising placing monatin or a salt thereof under a condition free of exposure to ultraviolet light.
14. A method of preserving a sweetener composition, a beverage, a food, a mouth cavity composition, or a pharmaceutical product, which comprises monatin or a salt thereof, said method comprising placing monatin or a salt thereof under a condition free of exposure to ultraviolet light.
15. A method of preserving a beverage, which comprises monatin or a salt thereof, said method comprising placing monatin or a salt thereof under a condition free of exposure to ultraviolet light.
16. The method of claim 13, which further comprises preserving said monatin or salt thereof in the presence of a radical scavenger.
17. Monatin or a salt thereof, which is enclosed in a container shielding ultraviolet light.
18. A sweetener composition, a beverage, a food, a mouth cavity composition, or a pharmaceutical product, which comprises monatin or a salt thereof, wherein said sweetener composition, beverage, food, mouth cavity composition, or pharmaceutical product is enclosed in a container shielding ultraviolet light.
19. A beverage, which comprises monatin or a salt thereof, wherein said beverage is enclosed in a container shielding ultraviolet light.
20. A sweetener composition, a beverage, a food, a mouth cavity composition, or a pharmaceutical product, which comprises monatin or a salt thereof and a radical scavenger, wherein said sweetener composition, beverage, food, mouth cavity composition, or pharmaceutical product is enclosed in a container shielding ultraviolet light.
21. A beverage, which comprises monatin or a salt thereof and a radical scavenger, wherein said beverage is enclosed in a container shielding ultraviolet light.
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Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050106305A1 (en) * 2003-08-25 2005-05-19 Cargill, Inc. Beverage compositions comprising monatin and methods of making same
US20050112260A1 (en) * 2003-08-01 2005-05-26 Cargill, Inc. Monatin tabletop sweetener compositions and methods of making same
US20050221455A1 (en) * 2003-10-21 2005-10-06 Cargill, Inc. Production of monatin and monatin precursors
US20050282260A1 (en) * 2002-04-23 2005-12-22 Cargill, Incorporated Polypeptides and biosynthetic pathways for the production of monatin and its precursors
US20060252135A1 (en) * 2005-04-26 2006-11-09 Cargill, Incorporated Polypeptides and biosynthetic pathways for the production of stereoisomers of monatin and their precursors
US20070072277A1 (en) * 2001-12-27 2007-03-29 Ajinomoto Co., Inc. Process for producing glutamate derivatives
US20070099277A1 (en) * 2005-04-20 2007-05-03 Cargill, Incorporated Products and methods for in vivo secretion of monatin
US20070105938A1 (en) * 2005-04-20 2007-05-10 Cargill, Incorporated Products and Methods for In Vivo Secretion of Monatin
US20080015361A1 (en) * 2006-05-24 2008-01-17 Cargill, Incorporated Methods And Systems For Increasing Production of Equilibrium Reactions
US20080020434A1 (en) * 2005-04-26 2008-01-24 Cargill, Incorporated Polypeptides and biosynthetic pathways for the production of stereoisomers of monatin and their precursors
US20080020435A1 (en) * 2006-03-07 2008-01-24 Cargill, Incorporated Aldolases, nucleic acids encoding them and methods for making and using them
US20080193984A1 (en) * 2004-10-05 2008-08-14 Ajinomoto Co., Inc. Process For Producing Amino Acid Derivative From Hydroxyimino Acid
US20080318290A1 (en) * 2002-08-26 2008-12-25 Ajinomoto Co., Inc. Novel aldolase and production process of substituted alpha-keto acids
US20090088577A1 (en) * 2007-10-01 2009-04-02 Subash Buddoo Production of monatin enantiomers
US20090087829A1 (en) * 2007-10-01 2009-04-02 Dean Brady Production of monatin enantiomers
US20090087888A1 (en) * 2007-10-01 2009-04-02 Subash Buddoo Production of monatin stereoisomers
US20090117625A1 (en) * 2002-04-23 2009-05-07 Cargill, Incorporated Polypeptides and Biosynthetic Pathways for the Production of Monatin and Its Precursors
US20090198072A1 (en) * 2006-05-24 2009-08-06 Cargill, Incorporated Methods and systems for increasing production of equilibrium reactions
US20100075005A1 (en) * 2008-09-24 2010-03-25 Pepsico, Inc. Beverage composition and method of reducing degradation of monatin
US20100105924A1 (en) * 2001-12-27 2010-04-29 Ajinomoto Co. Inc. Processes of producing glutamic acid compounds and production intermediates therefore and novel intermediate for the processes
US20100184165A1 (en) * 2004-06-07 2010-07-22 Ajinomoto Co., Inc. Novel aldolase, and method for producing optically active ihog and monatin
US20100255548A1 (en) * 2002-12-09 2010-10-07 Ajinomoto Co., Inc. Mutated d-aminotransferase and method for producing optically active glutamic acid derivatives using the same
US20100330245A1 (en) * 2001-11-30 2010-12-30 Ajinomoto Co., Inc. Crystals of non-natural-type stereoisomer salt of monatin and use thereof
US7973070B2 (en) 2008-03-11 2011-07-05 Ajinomoto Co., Inc. Monatin hydrate crystals
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
US9101160B2 (en) 2005-11-23 2015-08-11 The Coca-Cola Company Condiments with high-potency sweetener
US9371317B2 (en) 2013-02-19 2016-06-21 Senomyx, Inc. Sweet flavor modifier
US9382196B2 (en) 2008-07-31 2016-07-05 Senomyx, Inc. Processes and intermediates for making sweet taste enhancers
US9420814B2 (en) 2012-08-06 2016-08-23 Senomyx, Inc. Sweet flavor modifier
US9603848B2 (en) 2007-06-08 2017-03-28 Senomyx, Inc. Modulation of chemosensory receptors and ligands associated therewith
US11945813B2 (en) 2018-08-07 2024-04-02 Firmenich Incorporated 5-substituted 4-amino-1H-benzo[c][1,2,6]thiadiazine 2,2-dioxides and formulations and uses thereof

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JPWO2023149442A1 (en) * 2022-02-03 2023-08-10

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5994559A (en) * 1998-08-06 1999-11-30 The Board Of Governors For Higher Education, State Of Rhode Island And Providence Plantations Synthesis of monatin-A high intensity natural sweetener
US20050004394A1 (en) * 2001-12-27 2005-01-06 Ajinomoto Co. In Processes of producing glutamic acid compounds and production intermediates therefore and novel intermediate for the processes
US20050009153A1 (en) * 2001-12-27 2005-01-13 Ajinomoto Co., Inc. Process of producing glutamate derivatives
US20050020508A1 (en) * 2001-11-30 2005-01-27 Ajinomoto Co., Inc. Crystals of non-natural-type stereoisomer salt of monatin and use thereof
US20050272939A1 (en) * 2004-06-04 2005-12-08 Ajinomoto Co. Inc Crystals of free (2R, 4R)-monatin and use thereof
US20060106305A1 (en) * 2003-10-17 2006-05-18 Jan Lau Heart valve leaflet locator

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002275468A (en) * 2001-03-21 2002-09-25 Nikken Kasei Kk Antioxidant containing dihydrochalcone
JP4301003B2 (en) * 2001-12-27 2009-07-22 味の素株式会社 Method for producing glutamic acid derivative
JP2003292484A (en) * 2002-04-01 2003-10-15 Ajinomoto Co Inc METHOD FOR PRODUCING gamma-HYDROXYAMINO ACID DERIVATIVE AND MONATINS
JP2004002544A (en) 2002-05-31 2004-01-08 Soda Aromatic Co Ltd Antioxidant
EP2557160A3 (en) 2002-12-09 2013-03-27 Ajinomoto Co., Inc. Mutated D-aminotransferase and method for producing optically active glutamic acid derivatives using the same
WO2004067494A1 (en) 2003-01-09 2004-08-12 Ajinomoto Co., Inc. Processes for producing glutamic acid derivative and pyroglutamic acid derivative and novel intermediate for production
BRPI0413241A (en) * 2003-08-01 2006-10-03 Cargill Inc monatin table sweetener compositions and methods of making the same
ATE360370T1 (en) * 2003-08-14 2007-05-15 Cargill Inc CHEWING GUM COMPOSITIONS CONTAINING MONTH AND METHOD FOR THE PRODUCTION THEREOF
BRPI0413931A (en) * 2003-08-25 2006-10-24 Cargill Inc beverage compositions comprising monatin and methods for their manufacture
KR101216575B1 (en) * 2004-07-14 2012-12-31 아지노모토 가부시키가이샤 Crystal of (2R,4R)-monatin potassium salt and sweetener composition containing same

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5994559A (en) * 1998-08-06 1999-11-30 The Board Of Governors For Higher Education, State Of Rhode Island And Providence Plantations Synthesis of monatin-A high intensity natural sweetener
US20050020508A1 (en) * 2001-11-30 2005-01-27 Ajinomoto Co., Inc. Crystals of non-natural-type stereoisomer salt of monatin and use thereof
US20050004394A1 (en) * 2001-12-27 2005-01-06 Ajinomoto Co. In Processes of producing glutamic acid compounds and production intermediates therefore and novel intermediate for the processes
US20050009153A1 (en) * 2001-12-27 2005-01-13 Ajinomoto Co., Inc. Process of producing glutamate derivatives
US20060106305A1 (en) * 2003-10-17 2006-05-18 Jan Lau Heart valve leaflet locator
US20050272939A1 (en) * 2004-06-04 2005-12-08 Ajinomoto Co. Inc Crystals of free (2R, 4R)-monatin and use thereof

Cited By (77)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110189368A1 (en) * 2001-11-30 2011-08-04 Ajinomoto Co., Inc. Crystals of non-natural-type stereoisomer salt of monatin and use thereof
US20100330245A1 (en) * 2001-11-30 2010-12-30 Ajinomoto Co., Inc. Crystals of non-natural-type stereoisomer salt of monatin and use thereof
US7951835B2 (en) 2001-11-30 2011-05-31 Ajinomoto Co., Inc. Crystals of non-natural-type stereoisomer salt of monatin and use thereof
US20110189738A1 (en) * 2001-12-27 2011-08-04 Ajinomoto Co., Inc. Process for producing glutamate derivatives
US8202711B2 (en) 2001-12-27 2012-06-19 Ajinomoto Co., Inc. Process for producing glutamate derivatives
US20070072277A1 (en) * 2001-12-27 2007-03-29 Ajinomoto Co., Inc. Process for producing glutamate derivatives
US20100261234A1 (en) * 2001-12-27 2010-10-14 Ajinomoto Co., Inc. Process for producing glutamate derivatives
US8563278B2 (en) 2001-12-27 2013-10-22 Ajinomoto Co., Inc. Process of producing glutamate derivatives
US8535920B2 (en) 2001-12-27 2013-09-17 Ajinomoto Co., Inc. Process for producing glutamate derivatives
US20100105924A1 (en) * 2001-12-27 2010-04-29 Ajinomoto Co. Inc. Processes of producing glutamic acid compounds and production intermediates therefore and novel intermediate for the processes
US20100323411A1 (en) * 2001-12-27 2010-12-23 Ajinomoto Co., Inc. Process of producing glutamate derivatives
US9034610B2 (en) 2002-04-23 2015-05-19 Cargill, Incorporated Polypeptides and biosynthetic pathways for the production of monatin and its precursors
US20050282260A1 (en) * 2002-04-23 2005-12-22 Cargill, Incorporated Polypeptides and biosynthetic pathways for the production of monatin and its precursors
US8440434B2 (en) 2002-04-23 2013-05-14 Cargill, Incorporated Polypeptides and biosynthetic pathways for the production of monatin and its precursors
US8435765B2 (en) 2002-04-23 2013-05-07 Cargill, Incorporated Polypeptides and biosynthetic pathways for the production of monatin and its precursors
US8372989B2 (en) 2002-04-23 2013-02-12 Cargill, Incorporated Polypeptides and biosynthetic pathways for the production of monatin and its precursors
US20080274518A1 (en) * 2002-04-23 2008-11-06 Cargill, Incorporated Polypeptides and Biosynthetic Pathways for the Production of Monatin and its Precursors
US20090117625A1 (en) * 2002-04-23 2009-05-07 Cargill, Incorporated Polypeptides and Biosynthetic Pathways for the Production of Monatin and Its Precursors
US7572607B2 (en) 2002-04-23 2009-08-11 Cargill, Incorporated Polypeptides and biosynthetic pathways for the production of monatin and its precursors
US8058038B2 (en) 2002-08-26 2011-11-15 Ajinomoto Co., Inc. Aldolase and production process of substituted α-keto acids
US8273556B2 (en) 2002-08-26 2012-09-25 Ajinomoto Co., Inc. Aldolase and production process of substituted α-keto acids
US8697416B2 (en) 2002-08-26 2014-04-15 Ajinomoto Co., Inc. Recombinant polynucleotide, host cells containing the same and a process for producing a protein having aldolase activity
US20080318290A1 (en) * 2002-08-26 2008-12-25 Ajinomoto Co., Inc. Novel aldolase and production process of substituted alpha-keto acids
US20100279365A1 (en) * 2002-08-26 2010-11-04 Ajinomoto Co., Inc. Novel aldolase and production process of substituted alpha-keto acids
US8058034B2 (en) 2002-12-09 2011-11-15 Ajinomoto Co., Inc. Mutated D-aminotransferase and method for producing optically active glutamic acid derivatives using the same
US20100255548A1 (en) * 2002-12-09 2010-10-07 Ajinomoto Co., Inc. Mutated d-aminotransferase and method for producing optically active glutamic acid derivatives using the same
US8669080B2 (en) 2002-12-09 2014-03-11 Ajinomoto Co., Inc. Mutated D-aminotransferase and method for producing optically active glutamic acid derivatives using the same
US20050112260A1 (en) * 2003-08-01 2005-05-26 Cargill, Inc. Monatin tabletop sweetener compositions and methods of making same
US20090130285A1 (en) * 2003-08-25 2009-05-21 Abraham Timothy W Beverage Compositions Comprising Monatin and Methods of Making Same
US20050106305A1 (en) * 2003-08-25 2005-05-19 Cargill, Inc. Beverage compositions comprising monatin and methods of making same
US20050221455A1 (en) * 2003-10-21 2005-10-06 Cargill, Inc. Production of monatin and monatin precursors
US8206955B2 (en) 2003-10-21 2012-06-26 Cargill, Incorporated Production of monatin and monatin precursors
US8048647B2 (en) 2004-06-07 2011-11-01 Ajinomoto Co., Inc. Aldolase, and method for producing optically active IHOG and monatin
US20100184165A1 (en) * 2004-06-07 2010-07-22 Ajinomoto Co., Inc. Novel aldolase, and method for producing optically active ihog and monatin
US20080193984A1 (en) * 2004-10-05 2008-08-14 Ajinomoto Co., Inc. Process For Producing Amino Acid Derivative From Hydroxyimino Acid
US8043836B2 (en) 2004-10-05 2011-10-25 Ajinomoto Co., Inc. Process for producing amino acid derivative from hydroxyimino acid
US8158389B2 (en) 2005-04-20 2012-04-17 Cargill, Incorporated Products and methods for in vivo secretion of monatin
US8153405B2 (en) 2005-04-20 2012-04-10 Cargill, Incorporated Products and methods for in vivo secretion of monatin
US20070099277A1 (en) * 2005-04-20 2007-05-03 Cargill, Incorporated Products and methods for in vivo secretion of monatin
US20070105938A1 (en) * 2005-04-20 2007-05-10 Cargill, Incorporated Products and Methods for In Vivo Secretion of Monatin
US7582455B2 (en) 2005-04-26 2009-09-01 Cargill, Incorporated Polypeptides and biosynthetic pathways for the production of stereoisomers of monatin and their precursors
US20080020434A1 (en) * 2005-04-26 2008-01-24 Cargill, Incorporated Polypeptides and biosynthetic pathways for the production of stereoisomers of monatin and their precursors
US20060252135A1 (en) * 2005-04-26 2006-11-09 Cargill, Incorporated Polypeptides and biosynthetic pathways for the production of stereoisomers of monatin and their precursors
US8975046B2 (en) 2005-04-26 2015-03-10 Cargill, Incorporated Polypeptides and biosynthetic pathways for the production of stereoisomers of monatin and their precursors
US8076108B2 (en) 2005-04-26 2011-12-13 Cargill, Incorporated Polypeptides and biosynthetic pathways for the production of stereoisomers of monatin and their precursors
US9101160B2 (en) 2005-11-23 2015-08-11 The Coca-Cola Company Condiments with high-potency sweetener
US20080020435A1 (en) * 2006-03-07 2008-01-24 Cargill, Incorporated Aldolases, nucleic acids encoding them and methods for making and using them
US9518280B2 (en) 2006-03-07 2016-12-13 Cargill, Incorporated Aldolases, nucleic acids encoding them and methods for making and using them
US9005938B2 (en) 2006-03-07 2015-04-14 Cargill, Incorporated Aldolases, nucleic acids encoding them and methods for making and using them
US8043837B2 (en) 2006-03-07 2011-10-25 Cargill, Incorporated Aldolases, nucleic acids encoding them and methods for making and using them
US7888081B2 (en) 2006-05-24 2011-02-15 Cargill, Incorporated Methods and systems for increasing production of equilibrium reactions
US20090198072A1 (en) * 2006-05-24 2009-08-06 Cargill, Incorporated Methods and systems for increasing production of equilibrium reactions
US20080015361A1 (en) * 2006-05-24 2008-01-17 Cargill, Incorporated Methods And Systems For Increasing Production of Equilibrium Reactions
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
US9603848B2 (en) 2007-06-08 2017-03-28 Senomyx, Inc. Modulation of chemosensory receptors and ligands associated therewith
US20090087888A1 (en) * 2007-10-01 2009-04-02 Subash Buddoo Production of monatin stereoisomers
US8003361B2 (en) 2007-10-01 2011-08-23 Cargill Incorporated Production of monatin enantiomers
US8367847B2 (en) 2007-10-01 2013-02-05 Cargill, Incorporated Production of monatin enantiomers
US20090088577A1 (en) * 2007-10-01 2009-04-02 Subash Buddoo Production of monatin enantiomers
US20090087829A1 (en) * 2007-10-01 2009-04-02 Dean Brady Production of monatin enantiomers
US8076107B2 (en) 2007-10-01 2011-12-13 Cargill, Incorporated Production of monatin stereoisomers
US20110218227A1 (en) * 2008-03-11 2011-09-08 Ajinomoto Co., Inc Hydrate crystals
US7973070B2 (en) 2008-03-11 2011-07-05 Ajinomoto Co., Inc. Monatin hydrate crystals
US9382196B2 (en) 2008-07-31 2016-07-05 Senomyx, Inc. Processes and intermediates for making sweet taste enhancers
US9732052B2 (en) 2008-07-31 2017-08-15 Senomyx, Inc. Processes and intermediates for making sweet taste enhancers
US10570105B2 (en) 2008-07-31 2020-02-25 Firmenich Incorporated Processes and intermediates for making sweet taste enhancers
US10308621B2 (en) 2008-07-31 2019-06-04 Senomyx, Inc. Processes and intermediates for making sweet taste enhancers
US10087154B2 (en) 2008-07-31 2018-10-02 Senomyx, Inc. Processes and intermediates for making sweet taste enhancers
US20100075005A1 (en) * 2008-09-24 2010-03-25 Pepsico, Inc. Beverage composition and method of reducing degradation of monatin
US8142829B2 (en) 2008-09-24 2012-03-27 Pepsico, Inc. Beverage composition and method of reducing degradation of monatin
US9420814B2 (en) 2012-08-06 2016-08-23 Senomyx, Inc. Sweet flavor modifier
US9745293B2 (en) 2012-08-06 2017-08-29 Senomyx, Inc. Sweet flavor modifier
US9687015B2 (en) 2012-08-06 2017-06-27 Senomyx, Inc. Sweet flavor modifier
US9695162B2 (en) 2013-02-19 2017-07-04 Senomyx, Inc. Sweet flavor modifier
US9475803B2 (en) 2013-02-19 2016-10-25 Senomyx, Inc. Sweet flavor modifier
US9371317B2 (en) 2013-02-19 2016-06-21 Senomyx, Inc. Sweet flavor modifier
US11945813B2 (en) 2018-08-07 2024-04-02 Firmenich Incorporated 5-substituted 4-amino-1H-benzo[c][1,2,6]thiadiazine 2,2-dioxides and formulations and uses thereof

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US7781005B2 (en) 2010-08-24
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EP1808083B1 (en) 2012-12-05

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