WO2013081193A1 - Produit cosmétique contenant un dérivé de cystéine et un alcool - Google Patents

Produit cosmétique contenant un dérivé de cystéine et un alcool Download PDF

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Publication number
WO2013081193A1
WO2013081193A1 PCT/JP2012/081728 JP2012081728W WO2013081193A1 WO 2013081193 A1 WO2013081193 A1 WO 2013081193A1 JP 2012081728 W JP2012081728 W JP 2012081728W WO 2013081193 A1 WO2013081193 A1 WO 2013081193A1
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Prior art keywords
alcohol
group
salt
cosmetic
cysteine derivative
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PCT/JP2012/081728
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English (en)
Japanese (ja)
Inventor
愼二 黒田
瀧野　嘉延
冬美恵 大倉
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味の素株式会社
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Priority to JP2013547267A priority Critical patent/JP5979155B2/ja
Publication of WO2013081193A1 publication Critical patent/WO2013081193A1/fr

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    • 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
    • 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
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • 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
    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • 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

Definitions

  • the present invention relates to a cosmetic containing (A) a specific cysteine derivative or a salt thereof, and (B) a specific alcohol. Furthermore, the present invention relates to (C) a cosmetic containing a specific amino acid in addition to the above (A) and (B).
  • Patent Document 1 describes that a cysteine derivative obtained by esterifying L-2-methylthiazolidine-2,4-dicarboxylic acid or a salt thereof is useful as a whitening agent.
  • Patent Document 2 describes that 2-methylthiazolidine-2,4-dicarboxylic acid or a derivative thereof has a whitening action.
  • these derivatives have not been put into practical use because they are easily decomposed and are not sufficiently stable.
  • An object of the present invention is to improve the solubility of a cysteine derivative and to provide a cosmetic having excellent usability and transdermal absorbability.
  • a cysteine derivative or a salt thereof is N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid, N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester, and their 2.
  • the cosmetic according to 1 above which is at least one selected from salts.
  • the cosmetic according to 1 or 2 wherein the alcohol is one or more selected from C 1-6 monohydric alcohol, polyhydric alcohol, C 8-22 monohydric alcohol, and aromatic alcohol. 4).
  • the alcohol is ethanol, propanol, isopropanol, butanol, glycerin, diglycerin, ethylene glycol, 1,3-butylene glycol, propylene glycol, dipropylene glycol, isoprene glycol, 1,2-pentanediol, 1,3- Pentanediol, 1,3-propanediol, 3-methyl-1,3-butanediol, ethylhexylglycerin, polyethylene glycol, cetyl alcohol, lauryl alcohol, isostearyl alcohol, stearyl alcohol, oleyl alcohol, myristyl alcohol, octyldodecanol, Behenyl alcohol, lanolin alcohol, cetostearyl alcohol, decyltetradecanol, hexyldecanol, phenoxyethanol and The cosmetic according to any one of the above 1 to 3, at least one selected from benzyl alcohol.
  • the alcohol is ethanol, isopropanol, 1,3-butylene glycol, propylene glycol, dipropylene glycol, 1,2-pentanediol, ethylhexylglycerin, polyethylene glycol, 3-methyl-1,3-butanediol, phenoxyethanol, and 5.
  • the amino acid is arginine, lysine, histidine, ornithine, glutamic acid, aspartic acid, pyrrolidone carboxylic acid, glutamine, asparagine, glycine, alanine, valine, leucine, isoleucine, serine, threonine, proline, hydroxyproline, tryptophan, phenylalanine, 7.
  • the cosmetic according to 6 above which is one or more selected from tyrosine and methionine.
  • the amino acid is one or more selected from arginine, glycine, pyrrolidone carboxylic acid, proline, alanine, histidine, lysine, serine, isoleucine, leucine, valine, phenylalanine, tryptophan, methionine, threonine 6.
  • Cosmetics according to 6. 8 The cosmetic according to 6 above, wherein the amino acid is at least one selected from arginine, lysine, histidine and ornithine. 9.
  • the cysteine derivative or a salt thereof is N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester or a salt thereof, (B) the alcohol is 1,3-butylene glycol, C) The cosmetic according to 6 above, wherein the amino acid is arginine. 10.
  • the present invention is a cosmetic containing (A) a specific cysteine derivative or a salt thereof and (B) a specific alcohol.
  • the cysteine derivative of the present invention is a cysteine derivative represented by the general formula (I) or a salt thereof.
  • X and Y are each independently OR 1 , NHR 2 (wherein R 1 and R 2 each independently represents a hydrogen atom or a C 1-22 alkyl group); Z represents a hydrogen atom or a C 1-22 alkyl group; W represents a C 1-22 alkyl group, a C 1-22 alkoxy group or a C 1-22 alkylamino group. ]
  • C 1-22 alkyl group means a linear or branched hydrocarbon group having 1 to 22 carbon atoms, such as a methyl group, an ethyl group, an isopropyl group, a propyl group, a butyl group, Isobutyl group, sec-butyl group, tert-butyl group, pentyl group, sec-pentyl group, tert-pentyl group, isopentyl group, hexyl group, heptyl group, octyl group, 2-ethylhexyl group, tert-octyl group, nonyl group , Isononyl group, decyl group, isodecyl group, undecyl group, dodecyl group, tridecyl group, isotridecyl group, tetradecyl group, pentadecyl group, hexa
  • C 1-16 alkyl group examples include methyl group, ethyl group, isopropyl group, propyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, sec-pentyl group, tert-pentyl group.
  • C 1-6 alkyl group examples include methyl group, ethyl group, isopropyl group, propyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, sec-pentyl group, tert-pentyl group. Group, isopentyl group, hexyl group and the like.
  • the “C 1-22 alkoxy group” means a hydroxyl group substituted with the above “C 1-22 alkyl group”.
  • C 1-6 alkoxy group examples include methoxy group, ethoxy group, propoxy group, isopropyloxy group, butoxy group, isobutoxy group, tert-butoxy group, pentyloxy group, hexyloxy group and the like.
  • C 1-22 alkylamino group means an amino group substituted with the above “C 1-22 alkyl group”, and examples thereof include a methylamino group, an ethylamino group, a propylamino group, an isopropylamino group, and butyl.
  • Amino group isobutylamino group, tert-butylamino group, pentylamino group, hexylamino group, heptylamino group, octylamino group, nonylamino group, decylamino group, undecylamino group, dodecylamino group, tridecylamino group, tetra
  • Examples include decylamino group, pentadecylamino group, hexadecylamino group, heptadecylamino group, octadecylamino group, nonadecylamino group, eicosylamino group, heneicosylamino group, docosylamino group and the like.
  • C 1-6 alkylamino group examples include methylamino group, ethylamino group, propylamino group, isopropylamino group, butylamino group, isobutylamino group, tert-butylamino group, pentylamino group, and hexylamino group. Can be mentioned.
  • Halogen atom includes chlorine atom, bromine atom, fluorine atom and iodine atom.
  • X and Y are each independently OR 1 and NHR 2 (wherein R 1 and R 2 each independently represents a hydrogen atom or a C 1-22 alkyl group).
  • the “C 1-22 alkyl group” represented by R 1 or R 2 is preferably a C 1-6 alkyl group, more preferably a methyl group, an ethyl group or an isopropyl group, still more preferably an ethyl group. is there.
  • X is preferably OR 1 (wherein R 1 is as defined above); more preferably OR 1 ′ (wherein R 1 ′ is a hydrogen atom or a C 1-6 alkyl group (preferably Represents a methyl group, an ethyl group, or an isopropyl group); and more preferably a hydroxyl group, a methoxy group, an ethoxy group, or an isopropoxy group, and even more preferably a hydroxyl group or a methoxy group.
  • Y is preferably OR 1 (wherein R 1 is as defined above), more preferably OR 1 ′ (wherein R 1 ′ is as defined above), More preferred is a hydroxyl group, a methoxy group, an ethoxy group or an isopropoxy group, and even more preferred is a hydroxyl group or a methoxy group.
  • Z represents a hydrogen atom or a C 1-22 alkyl group.
  • the “C 1-22 alkyl group” represented by Z is preferably a C 1-6 alkyl group, and more preferably a methyl group.
  • Z is preferably a hydrogen atom or a C 1-6 alkyl group, more preferably a hydrogen atom or a methyl group.
  • W represents a C 1-22 alkyl group, a C 1-22 alkoxy group or a C 1-22 alkylamino group.
  • the “C 1-22 alkyl group” represented by W is preferably a C 1-16 alkyl group, more preferably a methyl group, a nonyl group, or a pentadecyl group, and still more preferably a methyl group.
  • the “C 1-22 alkoxy group” represented by W is preferably a C 1-6 alkoxy group, more preferably a tert-butoxy group.
  • the “C 1-22 alkylamino group” represented by W is preferably a C 1-6 alkylamino group.
  • W is preferably a C 1-22 alkyl group or a C 1-22 alkoxy group, more preferably a C 1-16 alkyl group or a C 1-6 alkoxy group, still more preferably a methyl group, a nonyl group, A pentadecyl group and a tert-butoxy group are preferable, and a methyl group and a tert-butoxy group are particularly preferable.
  • cysteine derivative represented by the general formula (I) include N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid and N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid.
  • Acid 2-ethyl ester is preferable, and N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester is more preferable.
  • Examples of the salt of the cysteine derivative of the present invention include a salt with an inorganic base and a salt with an organic base.
  • Examples of the salt with an inorganic base include sodium salt, potassium salt, calcium salt, magnesium salt, zinc salt, silver salt, ammonium salt and the like.
  • Examples of salts with organic bases include methylamine, diethylamine, trimethylamine, triethylamine, ethanolamine, diethanolamine, triethanolamine, ethylenediamine, tris (hydroxymethyl) methylamine, dicyclohexylamine, N, N′-dibenzylethylenediamine, and guanidine.
  • each salt can be obtained by reacting the cysteine derivative of the present invention with an inorganic base or an organic base.
  • cysteine derivative of the present invention can take various salt forms, but the effect of the present invention is great when the salt form is not taken.
  • the cysteine derivative of the present invention Since the cysteine derivative of the present invention has an inhibitory effect on black melanin production, it can be used as a whitening agent, or a preventive or therapeutic agent for spots. These uses utilize the property that the cysteine derivative of the present invention exhibits a stable dosage form, but is decomposed into cysteine relatively quickly by an enzyme such as acylase at the site of action after percutaneous absorption. Is.
  • the lower limit when the cysteine derivative of the present invention or a salt thereof is blended into a cosmetic is not particularly limited as long as the effect is exhibited, but 0.0001% by weight is preferably the lower limit. From the viewpoint that an effective effect can be exhibited, 0.001% by weight is more preferable, 0.01% by weight is more preferable, 0.1% by weight is more preferable, 0.5% by weight is more preferable, and 1% by weight. Is more preferable, and 2% by weight is more preferable.
  • the weight of the cysteine derivative portion (free body) is within the above range.
  • the upper limit when the cysteine derivative of the present invention or a salt thereof is blended into a cosmetic is not particularly limited as long as the effect is exhibited, but is preferably 20% by weight. 18% by weight is more preferred, 16% by weight is still more preferred, 12% by weight is even more preferred, 10% by weight is even more preferred, and 5% by weight is particularly preferred.
  • the weight of the cysteine derivative portion (free body) is within the above range.
  • cysteine derivative (I) is not particularly limited, and is produced by combining known methods. be able to. Specifically, it can be synthesized by the following method, but is not limited thereto.
  • Compound (IV) which is a precursor of cysteine derivative (I), can be synthesized by the following Step 1, and then cysteine derivative (I) can be synthesized by Step 2.
  • Compound (IV) may or may not be purified as necessary.
  • Step 1 Cysteine or a compound represented by general formula (II) obtained by esterification or amidation of cysteine in advance (hereinafter abbreviated as compound (II) and the same applies to compounds represented by other formulas). ) To form a ring by reacting with compound (III) to obtain compound (IV)
  • Compound (IV) can be obtained by reacting compound (II) with compound (III) in water or an alcohol such as methanol or ethanol for 5 to 24 hours.
  • an alcohol such as methanol or ethanol for 5 to 24 hours.
  • cysteine ethyl ester can be obtained, for example, by reacting cysteine in ethyl alcohol in the presence of hydrochloric acid or thionyl chloride at room temperature for about 5 to 24 hours.
  • cysteine amide is a protected cysteine and an amine in the presence of a dehydrating condensing agent such as EDCI.HCl (1-ethyl-3- (3-dimethylaminopropyl) -carbodiimide hydrochloride), methylene chloride, A compound obtained by reacting in a solvent such as N, N-dimethylformamide (DMF) at room temperature for 5 to 24 hours can be obtained by deprotection.
  • a dehydrating condensing agent such as EDCI.HCl (1-ethyl-3- (3-dimethylaminopropyl) -carbodiimide hydrochloride)
  • methylene chloride methylene chloride
  • Cysteine derivative (I) can be synthesized by reacting compound (IV) with compound (V) or compound (V ′) in the presence or absence of a solvent and in the presence or absence of a base.
  • the solvent include THF (tetrahydrofuran), ethyl acetate, isopropyl acetate, acetonitrile, acetone, ethanol, methanol, dichloromethane, water, or a mixture thereof, preferably THF, ethyl acetate, isopropyl acetate, acetonitrile, acetone, Dichloromethane, water, or a mixture thereof.
  • the base examples include organic bases such as triethylamine, diisopropylethylamine, pyridine, N-methylmorpholine, and inorganic bases such as lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate, and potassium acetate.
  • organic bases such as triethylamine, diisopropylethylamine, pyridine, N-methylmorpholine
  • inorganic bases such as lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate, and potassium acetate.
  • the amount of compound (V) or compound (V ′) to be used is 1.0 to 5.0 mol, preferably 1.2 to 3.0 mol, per 1 mol of compound (IV).
  • the amount of base used is 1.0 to 5.0 mol, preferably 1.2 to 4.0 mol, per 1 mol of compound (IV).
  • the reaction temperature is ⁇ 10 to 100 ° C., preferably 0 to 90 ° C.
  • the reaction time is 1 hour to 48 hours, preferably 3 hours to 20 hours. Further, this may be converted to other cysteine derivatives (I) by esterification, amidation, hydrolysis or acid anhydride.
  • [(B) alcohol] C 1-6 monohydric alcohol such as ethanol, propanol, isopropanol, butanol as the alcohol which is the component (B) present invention; glycerin, diglycerin, ethylene glycol, 1,3-butylene glycol, propylene glycol, dipropylene glycol Polyhydric alcohols such as isoprene glycol, 1,2-pentanediol, 1,3-pentanediol, 1,3-propanediol, 3-methyl-1,3-butanediol, ethylhexylglycerin, polyethylene glycol; cetyl alcohol; Lauryl alcohol, isostearyl alcohol, stearyl alcohol, oleyl alcohol, myristyl alcohol, octyldodecanol, behenyl alcohol, lanolin alcohol, cetostearyl alcohol, de C 8-22 monohydric alcohols such as siltetradecanol and he
  • it is at least one selected from C 1-6 monohydric alcohol, polyhydric alcohol, and aromatic alcohol, more preferably ethanol, propanol, isopropanol, butanol, glycerin, diglycerin, ethylene glycol, 1 , 3-butylene glycol, propylene glycol, dipropylene glycol, isoprene glycol, 1,2-pentanediol, 1,3-pentanediol, 1,3-propanediol, 3-methyl-1,3-butanediol, ethylhexylglycerin , Polyethylene glycol, phenoxyethanol and benzyl alcohol, more preferably ethanol, isopropanol, 1,3-butylene glycol, propylene glycol, dipropylene glycol.
  • C 1-6 monohydric alcohol, polyhydric alcohol, and aromatic alcohol more preferably ethanol, propanol, isopropanol, butanol, glycerin
  • the lower limit when blending the component (B) in the cosmetic is not particularly limited as long as the effect is exhibited, but 0.0001% by weight is preferably the lower limit. From the viewpoint that an effective effect can be exhibited, 0.001% by weight is more preferable, 0.01% by weight is further preferable, 0.1% by weight is still more preferable, 0.5% by weight is even more preferable, and 1% by weight. % Is particularly preferred.
  • the upper limit when blending the component (B) in the cosmetic is not particularly limited as long as the effect is exhibited, but is preferably 20% by weight. 18% by weight is more preferred, 16% by weight is still more preferred, 14% by weight is even more preferred, 12% by weight is even more preferred, and 10% by weight is particularly preferred.
  • A) / (B) 1/30000 to 20/1 (g / g), preferably 1/10000 to 5/1 (g / g), more preferably 1/10000 to 1/1 (g / g), and even more preferably 1/1000 to 1. / 10 (g / g).
  • the above ratio is calculated based on the weight of the cysteine derivative portion (free body).
  • the cosmetic of the present invention preferably further contains an amino acid that is component (C).
  • component (C) arginine, lysine, histidine, ornithine, glutamic acid, aspartic acid, pyrrolidonecarboxylic acid, glutamine, asparagine, glycine, alanine, valine, leucine, isoleucine, serine, threonine, proline, hydroxyproline, tryptophan, phenylalanine , Tyrosine and methionine.
  • L form or D form optically active form
  • DL form racemic form
  • Acidic amino acids may be used as free acidic amino acids or as salts.
  • the salt is not particularly limited as long as it is a salt that can be usually used in cosmetics, but metal salts such as sodium salt, potassium salt, calcium salt, magnesium salt, zinc salt, silver salt; ammonium salt, ethanolamine salt, etc.
  • Amine salts; basic amino acid salts such as lysine and arginine; and alkali metal salts are preferred.
  • Basic amino acids may be used as free basic amino acids or as salts.
  • the salt is not particularly limited as long as it is a salt that can be usually used in cosmetics.
  • inorganic acid salts such as hydrochloride and sulfate; organic acid salts such as acetate and citrate; glutamic acid and aspartic acid and the like Examples thereof include acidic amino acid salts, and hydrochloride is preferable.
  • the lower limit when the component (C) is blended into the cosmetic is not particularly limited as long as the effect is exhibited, but is preferably 0.0001% by weight. From the viewpoint that an effective effect can be exhibited, 0.001% by weight is more preferable, 0.01% by weight is further preferable, 0.1% by weight is still more preferable, 0.5% by weight is even more preferable, and 1% by weight. % Is particularly preferred.
  • the upper limit when the component (C) is blended into the cosmetic is not particularly limited as long as the effect is exhibited, but is preferably 20% by weight. 18% by weight is more preferred, 16% by weight is still more preferred, 14% by weight is even more preferred, 12% by weight is even more preferred, and 10% by weight is particularly preferred.
  • A) / (C) 1/30000 to 20/1 (g / g), preferably 1/10000 to 5/1 (g / g), more preferably 1/10000 to 1/1 (g / g), and even more preferably 1/1000 to 1. / 10 (g / g).
  • the above ratio is calculated based on the weight of the cysteine derivative portion (free body).
  • the cosmetic of the present invention usually contains various components that can be used in cosmetics (including pharmaceutical external preparations and quasi drugs). You may mix
  • examples include inhibitors, preservatives, emulsifiers, fats and waxes, silicone compounds, perfume oils and the like.
  • the cosmetic of the present invention can be obtained by appropriately mixing and stirring the constituent components. It can also be appropriately heated to 40 ° C to 90 ° C.
  • cosmetics is a concept including quasi drugs.
  • It can take arbitrary forms, such as liquid form, paste form, gel form, solid form, and powder form.
  • N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid N-acetyl-cysteinylpyruvic acid; hereinafter sometimes abbreviated as N-Ac-CP
  • N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester obtained by the same operation as in Synthesis Example 1 was dissolved in a mixed solvent of methanol (120 ml) and water (120 ml), and 2N NaOH. (182.4 ml) was added. The reaction was heated with stirring at 100 ° C. for 4 hours and at 80 ° C. overnight under an argon atmosphere. After allowing the reaction solution to cool to room temperature, AMBERLITEIR 120B H AG (about 250 g) was added to adjust the pH of the solution to 1 to 2.
  • cysteine derivatives selected from ethanol, propylene glycol, dipropylene glycol, polyethylene glycol, phenoxyethanol, 3-methyl-1,3-butanediol, benzyl alcohol, 1,2-pentanediol, 1,3-butylene glycol, and ethylhexyl glycerin. It was found that more cysteine derivatives can be added to the cosmetic when one or more of the above are used.
  • compositions of Examples and Comparative Examples were prepared at the ratios shown in Tables 2 to 5 and added at the top of the cup of a three-dimensional skin model placed in a 12-well plate at 200 ⁇ l / cup, and at the bottom at 1 ml / well of PBS ( phosphate-buffered saline) was added, and the mixture was allowed to stand at 37 ° C. for 5 hours. After standing, the lower solution was collected, and the cysteine derivative concentration (T 1 ) was measured using HPLC.
  • PBS phosphate-buffered saline
  • the transdermal absorbability was evaluated according to the following criteria in comparison with the obtained cysteine derivative concentration (T 0 ) by adding an aqueous solution (Comparative Example 3 or 5) to the upper part of the skin model cup and conducting the same experiment. Note that an EPI-200X three-dimensional skin model manufactured by Kurabo Industries Co., Ltd. was used for this transdermal absorbability evaluation.
  • the cosmetics containing the (A) component, the (B) component, and the (C) component have good solubility (thus, the poor feeling of use due to the solubility is remarkably improved). It can also be seen that a composition having good transdermal absorbability can be obtained.
  • BG 1,3 butylene glycol
  • PG propylene glycol
  • DPG dipropylene glycol
  • PEG polyethylene glycol
  • PPG polypropylene glycol
  • PVP polyvinylpyrrolidone
  • VA vinyl acetate
  • the cosmetics of the present invention were found to be excellent in use feeling and transdermal absorbability. As a result, it has become possible to provide cosmetics that are more effective than conventional whitening cosmetics.

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Abstract

La présente invention s'attaque au problème de proposer un produit cosmétique qui a une solubilité améliorée d'un dérivé de cystéine et qui présente une sensation de peau supérieure et une absorbabilité transdermique supérieure. A cet effet, selon l'invention, un produit cosmétique est proposé qui contient (A) un dérivé de cystéine spécifique ou un sel de celui-ci et (B) un alcool.
PCT/JP2012/081728 2011-11-30 2012-11-30 Produit cosmétique contenant un dérivé de cystéine et un alcool WO2013081193A1 (fr)

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JP2013547267A JP5979155B2 (ja) 2011-11-30 2012-11-30 システイン誘導体およびアルコールを含有する化粧料

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JP2011-262161 2011-11-30

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2013081192A1 (ja) * 2011-11-30 2015-04-27 味の素株式会社 システイン誘導体および界面活性剤を含有する化粧料
CN109715128A (zh) * 2016-10-05 2019-05-03 荷兰联合利华有限公司 毛发处理组合物
CN109715129A (zh) * 2016-10-05 2019-05-03 荷兰联合利华有限公司 毛发处理组合物

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004517063A (ja) * 2000-11-17 2004-06-10 ロレアル ２−オキソチアゾリジン−４−カルボン酸誘導体の剥離促進剤としての使用
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