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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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US
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
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English (en)
Inventor
Kenichi Mori
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ajinomoto Co Inc
Original Assignee
Ajinomoto Co Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 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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Classifications

    • 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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US7781005B2 (en) 2010-08-24
US20060257550A1 (en) 2006-11-16
KR20070064672A (ko) 2007-06-21
CN101035442B (zh) 2012-04-11
JP4858171B2 (ja) 2012-01-18
BRPI0517419A (pt) 2008-10-07
CN101035442A (zh) 2007-09-12
KR101205568B1 (ko) 2012-11-27

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