WO2023079779A1 - アスコルビン酸誘導体含有組成物 - Google Patents
アスコルビン酸誘導体含有組成物 Download PDFInfo
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- WO2023079779A1 WO2023079779A1 PCT/JP2022/021724 JP2022021724W WO2023079779A1 WO 2023079779 A1 WO2023079779 A1 WO 2023079779A1 JP 2022021724 W JP2022021724 W JP 2022021724W WO 2023079779 A1 WO2023079779 A1 WO 2023079779A1
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- Prior art keywords
- ascorbic acid
- glucoside
- salt
- composition
- ascorbate
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23B2/00—Preservation of foods or foodstuffs, in general
- A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
- A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
- A23B2/729—Organic compounds; Microorganisms; Enzymes
- A23B2/771—Organic compounds containing hetero 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
- A61K8/67—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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/375—Ascorbic acid, i.e. vitamin C; Salts thereof
-
- 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
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/02—Antioxidant
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/06—Function of food ingredients pH modification agent
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2250/00—Food ingredients
- A23V2250/70—Vitamins
- A23V2250/708—Vitamin C
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/59—Mixtures
- A61K2800/591—Mixtures of compounds not provided for by any of the codes A61K2800/592 - A61K2800/596
Definitions
- the present invention relates to a composition with suppressed browning containing ascorbic acid 2-glucosides.
- Ascorbic acid acts as a reducing agent, a collagen synthesis promoter, and an antioxidant.
- ascorbic acid's excellent antioxidant effect suppresses melanin production in the skin and prevents pigmentation such as spots and freckles.
- Known as an ingredient it is widely used in pharmaceuticals, foods, cosmetics, and the like.
- ascorbic acid is a bulk powder and is unstable in a hygroscopic state or in alkalis, and an aqueous solution of ascorbic acid is strongly acidic and irritating. occurs, browning occurs, and the browning reaction proceeds.
- JP-A-04-099771 JP-A-04-099730 Japanese Patent Application Laid-Open No. 2001-199863 Japanese Patent Application Laid-Open No. 2002-265344 Japanese Patent Application Laid-Open No. 2005-220029 JP 2012-246248 A
- an object of the present invention is to provide a new means for suppressing browning of ascorbic acid 2-glucoside and a composition containing ascorbic acid 2-glucoside in which browning is suppressed.
- the present inventors conducted various studies on new means for suppressing the browning of ascorbic acid 2-glucoside.
- ascorbic acid is a sugar acid having an unsaturated lactone. Since sugars and amino acid-containing substances are conventionally susceptible to Maillard reaction, so-called browning, at room temperature or by heating, various amino acids, amino acid/sugar mixtures, amino acid/amino acid ester mixtures, peptides, 2-amino-2 are added to ascorbic acid.
- the present invention provides the following inventions [1] to [10].
- [1] A composition with suppressed browning containing an ascorbic acid 2-glucoside basic amino acid salt.
- Ascorbate 2-glucoside basic amino acid salt is selected from ascorbate 2-glucoside lysine salt, ascorbate 2-glucoside arginine salt, ascorbate 2-glucoside histidine salt, and ascorbate 2-glucoside tryptophan salt 1
- the composition according to [1] which is a species or two or more species.
- [3] The composition according to [1] or [2], wherein the pH of the composition is 5.0 or more and 7.5 or less.
- [5] A composition containing (a) ascorbic acid 2-glucoside basic amino acid salt and (b) ascorbic acid or a salt thereof.
- (b) The composition according to [5], wherein ascorbic acid or a salt thereof is one or more selected from ascorbic acid, alkali metal ascorbate, amino acid ascorbate and amine ascorbate. .
- the ascorbic acid 2-glucoside basic amino acid salt is from ascorbic acid 2-glucoside lysine salt, ascorbic acid 2-glucoside arginine salt, ascorbic acid 2-glucoside histidine salt, and ascorbic acid 2-glucoside tryptophan salt
- the composition according to [5] or [6] which is one or more selected.
- Powder of ascorbic acid 2-glucoside basic amino acid salt is from ascorbic acid 2-glucoside lysine salt, ascorbic acid 2-glucoside arginine salt, ascorbic acid 2-glucoside histidine salt, and ascorbic acid 2-glucoside tryptophan salt
- the composition according to [5] or [6] which is one or more selected.
- an aqueous solution of ascorbic acid 2-glucoside basic amino acid salt is remarkably inhibited in browning, and has a pH ranging from weakly acidic to neutral. Therefore, it has a whitening effect and collagen production activity by inhibiting melanin production, which is a variety of functions of ascorbic acids. It has a wrinkle-improving effect due to oxidization and is useful as a compounding ingredient of safe foods, medicines or cosmetics without skin irritation.
- the ascorbic acid 2-glucoside basic amino acid salt can be obtained as a powder according to the present invention, the component can be stably stored for a long period of time and can be used in compositions such as cosmetics, foods, and pharmaceuticals at a high concentration. can be compounded. If ascorbic acid 2-glucoside basic amino acid salt and ascorbic acid or a salt thereof are contained, food compositions, pharmaceutical compositions, and cosmetic compositions that are excellent in storage stability and have a good feel during use can be obtained.
- FIG. 4 is a diagram showing the degree of browning of L-ascorbic acid by amino acid addition.
- FIG. 4 shows the FT/IR spectrum of powder of ascorbic acid 2-glucoside arginine salt. It is a figure which shows the result of having extract
- one aspect of the present invention is a composition with suppressed browning that contains an ascorbic acid 2-glucoside basic amino acid salt.
- Ascorbic acid in the present invention is a compound whose IUPAC name is (R)-3,4-dihydroxy-5-((S)-1,2-dihydroxyethyl)furan-2(5H)-one, and vitamin It is a substance also called C, L-ascorbic acid. Ascorbic acid, as described above, acts as a reducing agent, a collagen synthesis promoter, and an antioxidant. Known as an ingredient that prevents pigmentation, it is widely used in medicines, foods, and cosmetics.
- Ascorbic acid 2-glucoside is a substance in which glucose is bound to the carbon atom at the 2-position of ascorbic acid, and is metabolized to ascorbic acid in vivo, so it is regarded as a provitamin of ascorbic acid.
- the ascorbic acid 2-glucoside basic amino acid salt used in the present invention is a basic amino acid salt of ascorbic acid 2-glucoside.
- the ascorbic acid 2-glucoside basic amino acid is 1 selected from ascorbic acid 2-glucoside lysine salt, ascorbic acid 2-glucoside arginine salt, ascorbic acid 2-glucoside histidine salt, and ascorbic acid 2-glucoside tryptophan salt. species or two or more species.
- ascorbic acid 2-glucoside lysine salt and ascorbic acid 2-glucoside arginine salt are more preferable.
- the constituent molar ratio of ascorbic acid 2-glucoside and basic amino acid in the basic amino acid salt of ascorbic acid 2-glucoside is preferably 1:1.5 to 1.5:1, and 1:1.2 to 1.2. :1 is more preferred.
- Ascorbic acid 2-glucoside basic amino acid salt can be produced by reacting ascorbic acid 2-glucoside with a basic amino acid. Specifically, ascorbic acid 2-glucoside and a basic amino acid are added at 40 to 60°C in ion-exchanged water whose dissolved oxygen concentration has been reduced by ultrasonic treatment or the like, and the pH is adjusted to 5.22 to 5.55. By adjusting, the amount of basic amino acid to be added is adjusted and reacted. After completion of the reaction, ascorbic acid 2-glucoside basic amino acid salt can be isolated as a powder by freeze-drying, spray-drying, or the like.
- the obtained ascorbic acid 2-glucoside basic amino acid salt powder is stable for a long period of time and does not turn brown, so it is useful as a raw material for high-concentration formulation in cosmetics and pharmaceutical compositions. Since the solution is mixed with other bases, there is a limit to the upper limit of the concentration. In order to preserve the raw material in a liquid state, it is necessary to add a preservative, sterilize it by passing it through a filter, fill it in a sterile container, or store it at a low temperature. It becomes possible to store stably and compactly at room temperature without adding other components.
- compositions containing ascorbic acid 2-glucoside basic amino acids are useful as compositions such as foods, medicines, and cosmetics in which browning is suppressed.
- the content of ascorbic acid 2-glucoside basic amino acid salt in the composition of the present invention is 1 to 40% by mass from the viewpoint of the effect of suppressing browning and the functional performance of ascorbic acid 2-glucoside basic amino acid salt as ascorbic acid. is preferred, 2 to 35 mass % is more preferred, and 5 to 30 mass % is even more preferred.
- compositions containing ascorbic acid 2-glucoside basic amino acid salts include food compositions, pharmaceutical compositions, and cosmetic compositions. Forms of these compositions include liquid compositions, emulsified compositions, powder compositions, and solid compositions.
- Food compositions include functional foods and foods for specified health uses.
- Pharmaceutical compositions include tablets, granules, syrups and other oral preparations, creams, ointments, liquids and other transdermal preparations, eye drops, injections, and the like.
- the cosmetic composition may be a liquid cosmetic, an emulsified cosmetic, a powdery cosmetic, a solid cosmetic, or the like.
- these cosmetics include water, oils, surfactants, moisturizing ingredients, alcohols, polyols, UV absorbers, UV protection agents, various powders, and various cosmetics. Ingredients, antioxidants, antimicrobials, fragrances, etc. are preferably included.
- the cosmetic of the present invention is more preferably a skin cosmetic from the viewpoint of sufficiently obtaining the function of ascorbic acid 2-glucoside basic amino acid salt.
- the form thereof is preferably an aqueous liquid cosmetic, an oil-in-water emulsified cosmetic, or a water-in-oil emulsified cosmetic.
- the pH of the composition of the present invention is preferably 5.0 to 7.5, more preferably 5.0 to 6.5, more preferably 5.0, from the viewpoint of the effect of suppressing browning and reducing irritation when applied to the skin. ⁇ 6.0 is more preferred.
- composition containing the ascorbic acid 2-glucoside basic amino acid salt of the present invention By further blending ascorbic acid or a salt thereof with the composition containing the ascorbic acid 2-glucoside basic amino acid salt of the present invention, it is possible to obtain a composition, particularly a cosmetic, with excellent usability. Accordingly, another aspect of the present invention is a composition containing (a) ascorbic acid 2-glucoside basic amino acid salt and (b) ascorbic acid or a salt thereof.
- the salt of ascorbic acid may be a salt of ascorbic acid and a basic substance, and examples thereof include one or more selected from alkali metal ascorbate, amino acid ascorbate and amine ascorbate salts. be done.
- Alkali metal salts of ascorbic acid include sodium, potassium and lithium ascorbic acid salts.
- Ascorbic acid amino acid salts include ascorbic acid glycine, alanine, valine, leucine, isoleucine, lysine, arginine, histidine, serine, threonine, cysteine, methionine, asparagine, glutamine salts, proline salts, phenylalanine salts, tyrosine salts, tryptophan salts and the like.
- Amine salts of ascorbic acid include ammonium salts, alkylamine salts and alkanolamine salts of ascorbic acid. Among these, alkali metal ascorbates are more preferred.
- the molar ratio of ascorbic acid to the basic substance in the salt of ascorbic acid is preferably 1:1.5 to 1.5:1, more preferably 1:1.2 to 1.2:1.
- the content molar ratio (a/b) of component (a) and component (b) in the composition of the present invention is the effect of suppressing browning of the composition, the effect of exhibiting functions as ascorbic acid, and the feeling of use such as stickiness. Therefore, it is preferably 0.2 to 5.0, more preferably 0.3 to 3.0, and still more preferably 0.5 to 2.0.
- the pH of the composition of the present invention is preferably 5.0 to 7.5, more preferably 5.0 to 6.5, and even more preferably 5.0 to 6.0.
- compositions containing ascorbic acid 2-glucoside basic amino acid salt and ascorbic acid or a salt thereof include food compositions, pharmaceutical compositions, and cosmetic compositions as described above. Forms of these compositions include liquid compositions, emulsified compositions, powder compositions, and solid compositions. Food compositions include functional foods and foods for specified health uses. Pharmaceutical compositions include tablets, granules, syrups and other oral preparations, creams, ointments, liquids and other transdermal preparations, eye drops, injections, and the like.
- the cosmetic composition may be a liquid cosmetic, an emulsified cosmetic, a powdery cosmetic, a solid cosmetic, or the like.
- these cosmetics include water, oils, surfactants, moisturizing ingredients, alcohols, polyols, UV absorbers, UV protection agents, It preferably contains various powders, various cosmetic ingredients, antioxidants, antibacterial agents, fragrances, and the like.
- the cosmetic of the present invention is more preferably a skin cosmetic from the viewpoint of sufficiently obtaining the functions of ascorbic acid 2-glucoside basic amino acid salt and ascorbic acid or a salt thereof.
- the form thereof is preferably an aqueous liquid cosmetic, an oil-in-water emulsified cosmetic, or a water-in-oil emulsified cosmetic.
- FIG. 2 shows the FT/IR spectrum of the obtained ascorbic acid 2-glucoside arginine salt powder.
- 1720 cm -1 nonionic COOH, antisymmetric stretching vibration
- a specific band at 1400 cm -1 were observed, confirming introduction of ionic bond of arginine.
- Example 1 (Effect of addition of ascorbic acid 2-glucoside arginine salt on change in degree of browning (coloration) of ascorbic acid due to addition of amino acid) Take 100 ml of water, dissolve 1.5% of ascorbic acid (ASA), and adjust the pH to 5.0 with 1M sodium hydroxide solution to prepare a test solution.
- Ascorbic acid 2-glucoside arginine salt (ASA2-G.Arg) is prepared by dissolving the product of Production Example 1 at 1.5% in 100 ml of water to prepare a test solution. 0.2% of glycine was added to each of the test solutions, dissolved and prepared, and stored (at room temperature) for 20 months. This test solution was sampled every designated month, and the absorption spectrum (wavelength 480 nm) was measured to evaluate the degree of browning (coloration). The results are shown in FIG.
- Example 2 Changes in degree of browning (coloration) in ascorbic acid and ascorbic acid 2-glucoside lysine salt (manufacturing example 2) by addition of amino acid mixture].
- 4% ascorbic acid (ASA) is dissolved in 200 ml of water and adjusted to pH 5.0 with 1 M sodium hydroxide solution to prepare a test solution.
- 4% of ascorbic acid 2-glucoside lysine salt (ASA2-G ⁇ Lys) (Production Example 2) is similarly dissolved to prepare a test solution.
- An amino acid mixture histidine 1.5%, alanine 1.2%, leucine 2.6%) was added and dissolved in each of the test solutions and stored (at room temperature) for 20 months. Each test solution was sampled every designated month, and the absorption spectrum (wavelength: 480 nm) was measured to evaluate the degree of browning (degree of coloration). The results are shown in FIG.
- Example 3 A blending example and a manufacturing method example in the case of blending 10% by mass of ascorbic acid 2-glucoside arginine salt (ASA2-G.Arg) to produce a beauty essence are shown below.
- Composition (unit is % by mass) 1. Water 67.98% 2. Propanediol 17.0% 3. ASA2-G Arg 10.0% 4. Glycerin 3.9% 5. Sodium citrate 0.5% 6. 1,3-BG 0.30% 7. Glycosphingolipid 0.15% 8. Xanthan gum 0.12% 9. Sodium Hyaluronate 0.02% 10. Citric acid 0.02% 11. Acetyl hydroxyproline 0.01% 12. Hydrolyzed Collagen 0.001% 13.
- Example (stability comparison between ASG and ASA2-G Arg) A beauty essence containing 5% by mass of ASA2-G ⁇ Arg and ascorbic acid 2-glucoside (ASG) was prepared in the same manner as in the above examples and used as a sample. The solution was filled in a transparent 30 mL capped glass bottle and stored at room temperature under illumination of 30,000 lux. Absorbance at 420 nm was measured at 0, 1, 2, 3, 4, 5 and 6 months. Samples were diluted 100-fold with water at the time of measurement. Water was used for the blank.
- Example (Mixing of ASA2-G Arg and Na Ascorbate) A beauty essence was prepared by mixing ASA2-G Arg and sodium ascorbate (ASNa) (the total concentration of these ingredients was 30% by mass), and was applied to the face of 6 subjects. ) obtained the results of the questionnaire. Scores on a 5-point scale from good to bad were averaged.
- test product 1 some subjects had the impression that it was sticky after application.
- Test products 2-6 had almost the same feeling when used. It was found that when ASNa is mixed in an amount of 20% or more, the feeling of use is greatly improved. Furthermore, these test products 1 to 5 showed the same degree of browning when stored at 40°C, and there was no difference.
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Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2023557617A JPWO2023079779A1 (https=) | 2021-11-07 | 2022-05-27 | |
| US18/706,232 US20250017841A1 (en) | 2021-11-07 | 2022-05-27 | Compound containing ascorbic acid derivative |
| KR1020247017809A KR20240104126A (ko) | 2021-11-07 | 2022-05-27 | 아스코르브산 유도체 함유 조성물 |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021181546 | 2021-11-07 | ||
| JP2021-181546 | 2021-11-07 |
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| WO2023079779A1 true WO2023079779A1 (ja) | 2023-05-11 |
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| PCT/JP2022/021724 Ceased WO2023079779A1 (ja) | 2021-11-07 | 2022-05-27 | アスコルビン酸誘導体含有組成物 |
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|---|---|
| US (1) | US20250017841A1 (https=) |
| JP (1) | JPWO2023079779A1 (https=) |
| KR (1) | KR20240104126A (https=) |
| WO (1) | WO2023079779A1 (https=) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006045080A (ja) * | 2004-08-02 | 2006-02-16 | Pola Chem Ind Inc | 医薬部外品に好適な皮膚外用剤 |
| JP2006188461A (ja) * | 2005-01-06 | 2006-07-20 | Kose Corp | 化粧料 |
| WO2013065705A1 (ja) * | 2011-10-31 | 2013-05-10 | 興和株式会社 | 粉末化粧料 |
| JP2014129278A (ja) * | 2012-12-28 | 2014-07-10 | Kao Corp | 皮膚外用組成物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2997303B2 (ja) | 1990-08-19 | 2000-01-11 | 三栄源エフ・エフ・アイ株式会社 | 褐変防止剤 |
| JP3016835B2 (ja) | 1990-08-19 | 2000-03-06 | 三栄源エフ・エフ・アイ株式会社 | アスコルビン酸の褐変防止方法 |
| JP2001199863A (ja) | 2000-01-18 | 2001-07-24 | Fancl Corp | 化粧料 |
| JP4666792B2 (ja) | 2001-03-07 | 2011-04-06 | 花王株式会社 | 化粧料 |
| JP4247133B2 (ja) | 2004-02-03 | 2009-04-02 | 花王株式会社 | 水中油型乳化組成物 |
| JP2012246248A (ja) | 2011-05-27 | 2012-12-13 | Kracie Home Products Ltd | 化粧料 |
| JP6115086B2 (ja) * | 2012-11-13 | 2017-04-19 | 味の素株式会社 | アミノ酸化合物の酢酸塩を含有する化粧料組成物 |
| WO2018075810A1 (en) * | 2016-10-18 | 2018-04-26 | Somahultion, Llc | Dermatological compositions for providing nutrients to skin and methods thereof |
-
2022
- 2022-05-27 WO PCT/JP2022/021724 patent/WO2023079779A1/ja not_active Ceased
- 2022-05-27 US US18/706,232 patent/US20250017841A1/en active Pending
- 2022-05-27 JP JP2023557617A patent/JPWO2023079779A1/ja active Pending
- 2022-05-27 KR KR1020247017809A patent/KR20240104126A/ko active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006045080A (ja) * | 2004-08-02 | 2006-02-16 | Pola Chem Ind Inc | 医薬部外品に好適な皮膚外用剤 |
| JP2006188461A (ja) * | 2005-01-06 | 2006-07-20 | Kose Corp | 化粧料 |
| WO2013065705A1 (ja) * | 2011-10-31 | 2013-05-10 | 興和株式会社 | 粉末化粧料 |
| JP2014129278A (ja) * | 2012-12-28 | 2014-07-10 | Kao Corp | 皮膚外用組成物 |
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| Publication number | Publication date |
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| JPWO2023079779A1 (https=) | 2023-05-11 |
| KR20240104126A (ko) | 2024-07-04 |
| US20250017841A1 (en) | 2025-01-16 |
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