WO2007148832A1 - Agent d'éclaircissement de la peau contenant du zinc en tant que principe actif - Google Patents

Agent d'éclaircissement de la peau contenant du zinc en tant que principe actif Download PDF

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Publication number
WO2007148832A1
WO2007148832A1 PCT/JP2007/063051 JP2007063051W WO2007148832A1 WO 2007148832 A1 WO2007148832 A1 WO 2007148832A1 JP 2007063051 W JP2007063051 W JP 2007063051W WO 2007148832 A1 WO2007148832 A1 WO 2007148832A1
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WO
WIPO (PCT)
Prior art keywords
zinc
whitening
acid
amino acid
salt
Prior art date
Application number
PCT/JP2007/063051
Other languages
English (en)
Japanese (ja)
Inventor
Yoshinobu Takino
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 JP2008522638A priority Critical patent/JP5552741B2/ja
Publication of WO2007148832A1 publication Critical patent/WO2007148832A1/fr

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Classifications

    • 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
    • A61Q19/08—Anti-ageing preparations
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/27—Zinc; Compounds 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
    • A61K8/35—Ketones, e.g. benzophenone
    • A61K8/355—Quinones
    • 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
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • 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
    • A61K2800/70—Biological properties of the composition as a whole

Definitions

  • the present invention relates to a skin whitening agent and a cosmetic composition containing the same.
  • pyrrolidone carponate zinc salt which is a kind of organic zinc, is known to suppress UV-induced inflammatory factors such as AP-1 and NF- ⁇ .
  • organic zinc salts and inorganic zinc salts are known to be incorporated into cosmetic compositions for astringent, anti-inflammatory, white pigment, UV protection, deodorant, and bactericide applications. Use in the vicinity of a concentration range where high odors can be expected is difficult to use as a cosmetic because of irritation to the skin. In addition, when it is used at a low concentration, the above effectiveness on the skin is not found, and the compounding of zinc compounds into cosmetics has not progressed. Disclosure of the invention
  • the present inventors have introduced zinc into human melanocytes (melanocytes (melanocytes)), thereby promoting the expression of ascorbyllevate transposome. As a result, it was found that a whitening effect can be obtained.
  • the ascorbic acid transporation is a membrane protein that promotes the uptake of ascorbic acid into cells (see Hi roya a tsu tsukaguch i tec (199 9) Nat 399, 70-75). Increased expression of the ascorbic acid transporter promotes the uptake of ascorbic acid into cells in pupa pigment cells (melanin-producing cells (melanocytes)) and suppresses melanin production.
  • An object of the present invention is to obtain a whitening agent having an excellent whitening action and a cosmetic composition containing the same based on the above findings.
  • the present invention relates to a whitening composition comprising zinc as an active ingredient.
  • a practical method for introducing zinc is to make zinc a zinc salt and apply it to the skin at a certain concentration. Physically, it includes the following inventions.
  • a whitening agent containing zinc as an active ingredient (1) A whitening agent containing zinc as an active ingredient.
  • Zinc is selected from the group consisting of zinc pyrrolidone carboxylic acid, zinc dalconate, zinc sulfosulfate, zinc lactate, various amino acid zinc salts, acyl amino acid zinc salt, zinc sulfate, zinc chloride and zinc oxide.
  • the whitening agent according to (1) which is a selected compound.
  • Zinc is selected from the group consisting of zinc pyrrolidone carboxylic acid, zinc dalconate, zinc sulfosulfate, zinc lactate, various amino acid zinc salts, acyl amino acid zinc salt, zinc sulfate, zinc chloride and zinc oxide.
  • the whitening composition according to (5) which is a selected compound.
  • Zinc pyrrolidone carboxylic acid Zinc pyrrolidone carboxylic acid, zinc dalconate, zinc zinc sulfolime, zinc lactate, various amino acid zinc salts, acyl amino acid zinc salts, zinc sulfate, zinc chloride and oxidation for skin whitening Use of a zinc salt selected from the group consisting of zinc.
  • a whitening method comprising applying the composition according to any one of (5) to (11) to the skin.
  • FIG. 1 is a graph confirming the effect of enhancing the mRNA expression of ascorbic acid transpoment in melanocytes by pyrrolidone carboxylic acid zinc salt.
  • whitening means the concept that the skin is beautiful and white, and the whitening agent includes both those for therapeutic purposes and those for prevention purposes.
  • zinc used in the present invention needs to be made into zinc salt in a practical manner and applied to the skin at a constant concentration.
  • both an organic zinc salt and an inorganic zinc salt can be used.
  • the organic zinc salt include pyrrolidone carboxylic acid zinc salt, dalconic acid zinc salt, sulfocalcic acid zinc salt, zinc lactate salt, various amino acid zinc salts, and acyl amino acid zinc salt.
  • Inorganic zinc includes zinc sulfate, zinc chloride, zinc oxide, and the like.
  • Amino acid zinc salts include glycine zinc salt, alanine zinc salt, valine zinc salt, oral icin zinc salt, isoleucine zinc salt, phenylalanine zinc salt, thionine zinc salt, tributofan zinc salt, asparagine zinc salt, glutamine zinc salt, Examples include various amino acid zinc salts such as serine zinc salt, threonine zinc salt, cysteine zinc salt, tyrosine zinc salt, zinc aspartate, zinc glutamate, lysine zinc salt, arginine zinc salt, or histidine zinc salt. '
  • the acyl amino acid zinc salt is a zinc salt of a compound in which an acyl group is bonded to an amino group of an amino acid.
  • Examples of the acyl amino acid include compounds having the following structural formula.
  • R 1 is an acyl group having 2 to 22 carbon atoms
  • R 2 is a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms
  • R 3 is an amino acid, palin. , Leucine, iso mouth Isine, phenylalanine, methionine, tributofan, asparagine, glutamine, serine, threonine, cysteine, tyrosine, aspartic acid, glutamic acid, lysine, arginine, histidine, alanine side chain or hydrogen atom
  • n is 0 or 1 Represents an integer.
  • pyrrolidone carboxylic acid zinc salt which has a blood flow promoting effect, is expected to collect useful substances such as ascorbic acid in the blood vessels at the application site. It is a zinc salt in which the expression promoting effect is more remarkably reflected in the whitening effect.
  • Pyrididone carboxylic acid zinc salt is a zinc salt of 2-pyrrolidone and 5-power ruponic acid, and may be various hydrates. Hereinafter, it is also simply referred to as “PCA zinc salt” or “PCAZn salt”.
  • PCA zinc salt or “PCAZn salt”.
  • the pyrrolidone carboxylic acid zinc salt used in the examples is a dihydrate and has the following structure.
  • any of D-form, L-form and DL-form may be used.
  • L—PC A zinc salt or DL—PC A zinc salt can be used. These can be used alone or in combination, and when the DL form is used, the ratio of the D form and the L form is not particularly limited.
  • the whitening agent of the present invention is used by blending it with a composition such as a cosmetic or an external preparation for skin. At this time, the blending amount is 1 M to 10 OmM (0.000035 wt% as PCA zinc salt). ⁇ 3.5 wt%), preferably 1 ⁇ ⁇ 50 ⁇ (?
  • a further aspect of the present invention relates to a composition
  • a composition comprising zinc and one or more selected from the group consisting of ascorbic acid, N-acyl acidic amino acid ester, amino acid and amino acid derivative at the same time.
  • ascorbic acid is preferably added in an amount of about 5 to 60 O mM, preferably about 5 to 30 O mM simultaneously with zinc, from the viewpoint of the whitening effect.
  • ascorbic acid may be various derivatives as long as it is in a form that can be blended in cosmetics.
  • N-ascorbic acid ester (6-cortisyl stearate, 6-ascorbyl palmitate, 2,6-dipalmitate ascorbyl, 2, 3, 5, 6-tetrahexyldecanoate ascorbyl And various derivatives such as tocopheryl ascorbic acid) may be used.
  • the N-acyl acidic amino acid ester used in the present invention is represented by the following structure. OO
  • X and Y may be the same or different, but X and Y are ester-forming residues of sterol, linear or branched liquid higher alkyl alcohol or alkenyl alcohol having 8 to 30 carbon atoms, or carbon number.
  • 1 is at least one selected from ester-forming residues of solid straight-chain or branched higher alcohols having 2 to 38.
  • COR bonded to the nitrogen atom is a straight-chain acyl group having 8 to 22 carbon atoms.
  • N is 1 or 2.
  • a, b is 0 to 1.0, and b is 0 to 1 0.
  • N-acyl acid diesters particularly preferred are N-acyl acid diesters, and preferred examples thereof include, for example, N-lauroyl glutamate di (cholesteryl benyloctyldodecyl), N-lauroyl glutamate di (cholesteryloctyldodecyl), N-lauroyl Di-glutamate (phytosteryl 2-year-old cutyldodecyl), N-lauroylglutamate di-octyldodecyl phytosteryl behenyl), etc., from Ajinomoto Co., Inc., respectively. It is marketed under the trade names of Erdeyu CL-2020, Erdeyu PS-2203, and Eldeyu PS-304.
  • this N-acyl acidic amino acid ester contributes to the improvement of the moisturizing power and skin conditioning properties, and also contributes to the improvement of stability.
  • the blending amount is preferably 0.1% by weight or more, more preferably 0.1% by weight or more, still more preferably 0.5% by weight or more, and N-acyl acidic amino acid If the blending amount of the ester is increased more than necessary, there is a risk of stickiness, so it is preferably 20% by weight or less, more preferably 10% by weight or less, and 5% by weight or less. More preferably.
  • An amino acid or amino acid derivative is incorporated in the composition to contribute to the improvement of the moisturizing effect.
  • amino acid examples include alanine, arginine, asparagine, Aspartic acid, citrulline, cystine, cystine, glutamine, glutamic acid, darlicin, histidine, oxyproline, isoleucine, leucine, lysine, methionine, ornithine, riggalanine, proline, serine, threonine, triftophan, tyrosin, etc. Any of those L-forms, D-forms or DL-forms may be used, or a salt thereof. Examples of such salts include sodium salt, potassium salt, triethanolamine salt and the like. .
  • amino acid derivatives include those obtained by cyclization, acylation or esterification of the above-mentioned amino acids, such as acetyl glutamic acid, acetyl methionine, acetyl cysteine, N, N-diacetyl L-cystine dimethyl. And esters, acyl glutamate, acylglycine, acylalanine, and acyl arginine ester salts. However, N-acyl acidic amino acid ester is not included. In addition to these components, components generally used as cosmetics or external preparations for skin can be added within a range that does not impair the effects of the present invention.
  • Ingredients commonly used in cosmetics or topical skin preparations include antioxidants, anti-inflammatory agents, UV absorbers, cell activators, humectants, metal chelators, oily raw materials, surfactants, solvents, high Examples include molecular substances, powder substances, pigments, fragrances, transdermal absorption enhancers, and steroid hormones.
  • antioxidants anti-inflammatory agents
  • UV absorbers cell activators
  • humectants metal chelators
  • oily raw materials such as sodium bicarbonate
  • surfactants such as sodium bicarbonate
  • solvents high
  • molecular substances powder substances, pigments, fragrances, transdermal absorption enhancers, and steroid hormones.
  • composition of the present invention comprises oil, lotion, cream, emulsion, gel, shampoo, hair rinse, hair conditioner, enamel, foundation, lipstick, funny, pack, ointment, tablet, injection solution, granule, capsule , Perfume, powder, eau de cologne, toothpaste, sarcophagus, aerosol, cleansing foam, skin aging prevention improver, skin inflammation preventive improver, bath preparation, hair nourishing agent, skin cosmetic, sunscreen, pigmented dryness Prevention / amelioration of photosensitivity such as dermatosis / sunlight urticaria, prevention / amelioration of photoallergy, prevention of photoimmune suppression, or improvement / prevention / antibacterial of anti-rough skin due to trauma, redness, cracks, etc.
  • Insecticide pest control agent, keratolytic agent, epidermis stripping agent, anti-acne prevention agent, keratosis It can be used to prevent improving agent of various skin diseases such as Uroko ⁇ -psoriasis.
  • the other conventional components in the composition are added to the composition containing zinc. Can be added in a range that does not inhibit the above.
  • Other commonly used ingredients in the composition include preservatives, anti-fading agents, buffers, acne agents, anti-dandruff and itching agents, antiperspirant deodorants, burn agents, anti-ticks, lice agents, keratin softeners, dryness Drugs for dermatoses, antiviral agents, hormones, vitamins, amino acids / peptides, proteins, astringents, refreshing / stimulating agents, animal and plant-derived components, antibiotics, antifungal agents, hair restorers, etc. be able to.
  • DL-PCA zinc salt is prepared by reacting DL-PCA and zinc oxide in water at 100 ° C for 2 hours, followed by stirring at room temperature for 5 hours, followed by precipitation of crystals. Was synthesized by filtration.
  • PCAZn salt and other Zn salts were confirmed from the blood flow promoting effect (increase in blood volume).
  • a Zn salt and an Na salt for each sample were prepared and applied to a human forearm, and the blood flow promoting effect was visually evaluated.
  • Samples used were (1) PCAZn salt, (2) PC ANa salt, (3) Zn salt of darconic acid, (4) Na salt of darconic acid, (5) Zn salt of sulfuric acid, and (6) Sulfate Na 2 salt.
  • the concentration was 5 wt% and the pH was adjusted between 5.5 and 6.5.
  • the above sample was 801, semi-occluded patch on the forearm, and after 30 minutes, the patch was removed for visual evaluation. Further, visual observation was performed after 30 minutes and 50 minutes, and a score was assigned according to Table 1. The results are shown in Table 2. The result is the average of the scores obtained. 5 flat points
  • P C A Zn salt is expected to enhance whitening compared to other Zn salts.
  • Glycine zinc salt 0.0 0 0 5% Cuenic acid 1.0% Urea 4.0% Salicylic acid 2. 0% Lactic acid 2. 0% Glycerin 2. 0% Betaine 2.0% Hyaluronic acid 0.1% Ethanol 1 5.0% Buffer 0.1% Fragrance 0.2% Preservative Mm.
  • Dalconic acid zinc salt 0.02% Resorcinol 0.1% Kojic acid 1.0% Stearic acid 2. 0% Boroxyethylene (25) Cetyl ether-3.0% Glyceryl monostearate 2.0% Octyl Dodecanol 10.0% Cetanol 6.0% Reduced lanolin 4.0% Scran 9.0%
  • Dalconic acid zinc salt 0.02% Resorcinol 0.1% Ascorbic acid 5.0% Stearic acid 2. 0% Polyoxyethylene (25) Cetyle 3.0% Glyceryl monostearate 2.0% Octyldodecanol 10. 0% cetanol 6.0% reduced lanolin 4.0% squalene 9.0%
  • Zinc sulfate salt 0.0 1% Lactic acid 2.0% Stearyl alcohol 0.5% Hardened palm oil 3.0% Liquid paraffin 35.0% Dipropylene glycol 6.0% Polyethylene glycol (400) 4.0% sorbitan sesquioleate 1.6% polyoxyethylene (20) oleyl ether 2.4% strength lupoxyvinyl polymer 1.5% hydroxylated lithium Rum 0.1% chelating agent appropriate amount preservative Appropriate amount Fragrance Appropriate amount Purified water The remaining formulation example 16 Essence
  • Zinc lactate salt 0 005% Fluic acid 0 5% Dipropylene dallicol 50 0% Polyethylene glycol (400) 5.0% Ethanol 1 0.0% Forced l-poxyvinyl polymer 0.5% Sodium alginate 0.5% Hydroxyl hydroxide 0 • 2% Polyoxyethylene monostearate (20) Sorbene 1.0% Sorbite monooleate 0.5% Ololeic alcohol 0.5% Bracenta extract 0.2% Acetic acid d 1 _ ⁇ -Tocopherol 0.2% Fragrance Appropriate amount Preservative Appropriate amount Anti-fading agent Appropriate amount Purified water The remaining formulation example 1 9 packs
  • the present invention can be used in the field of cosmetics.

Abstract

La présente invention concerne un agent d'éclaircissement de la peau ayant un toucher agréable à l'usage. De manière spécifique, l'invention concerne un agent d'éclaircissement de la peau constitué d'un sel pyrrolidone carboxylate de zinc. L'invention concerne également une composition pour la peau et une préparation à usage externe pour la peau, qui se caractérisent en ce qu'elles contiennent l'agent d'éclaircissement de la peau.
PCT/JP2007/063051 2006-06-23 2007-06-21 Agent d'éclaircissement de la peau contenant du zinc en tant que principe actif WO2007148832A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2008522638A JP5552741B2 (ja) 2006-06-23 2007-06-21 亜鉛を有効成分として含有する美白剤

Applications Claiming Priority (12)

Application Number Priority Date Filing Date Title
JP2006-173918 2006-06-23
JP2006173918 2006-06-23
JP2006-223941 2006-08-21
JP2006223941 2006-08-21
US86649906P 2006-11-20 2006-11-20
US86650306P 2006-11-20 2006-11-20
US60/866,503 2006-11-20
US60/866,499 2006-11-20
JP2006329172 2006-12-06
JP2006-329172 2006-12-06
US87184506P 2006-12-26 2006-12-26
US60/871,845 2006-12-26

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WO2007148832A1 true WO2007148832A1 (fr) 2007-12-27

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PCT/JP2007/062958 WO2007148831A1 (fr) 2006-06-23 2007-06-21 Promoteur de synthèse du collagene contenant un sel de zinc en tant qu'ingrédient actif
PCT/JP2007/063051 WO2007148832A1 (fr) 2006-06-23 2007-06-21 Agent d'éclaircissement de la peau contenant du zinc en tant que principe actif

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JP2018138525A (ja) * 2017-02-24 2018-09-06 株式会社ディーエイチシー ビタミンｃトランスポーター産生促進剤及びビタミンｃ吸収促進用組成物
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EP3192493B1 (fr) * 2014-09-10 2023-07-12 Ajinomoto Co., Inc. Produit hydratant et produit cosmétique contenant celui-ci
FR3030273B1 (fr) * 2014-12-23 2018-07-13 Laboratoires Lea Composition comprenant un extrait de lotus, un extrait d'hamamelis et du zinc, et son utilisation cosmetique
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CN109053529A (zh) * 2018-08-09 2018-12-21 吴文君 L-焦谷氨酸金属配合物及其制备方法和应用
JP7400727B2 (ja) 2018-10-10 2023-12-19 味の素株式会社 細胞外マトリックス分解酵素阻害剤
CN110613648A (zh) * 2019-10-22 2019-12-27 花安堂生物科技集团有限公司 一种具有改善皮肤屏障的皮肤护理组合物及其应用
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