WO2007148474A1 - トリテルペン酸を含む皮膚外用剤 - Google Patents
トリテルペン酸を含む皮膚外用剤 Download PDFInfo
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- WO2007148474A1 WO2007148474A1 PCT/JP2007/058781 JP2007058781W WO2007148474A1 WO 2007148474 A1 WO2007148474 A1 WO 2007148474A1 JP 2007058781 W JP2007058781 W JP 2007058781W WO 2007148474 A1 WO2007148474 A1 WO 2007148474A1
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- acid
- mass
- skin
- external preparation
- triterpenic
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- 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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—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
- A61K8/63—Steroids; Derivatives thereof
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
-
- 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
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- 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
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
Definitions
- the present invention relates to an external preparation for skin such as cosmetics and external preparations for skin containing triterpenic acid.
- Triterpenic acid typified by ursolic acid is known for its various physiological activities such as antioxidant, anti-inflammatory, melanin production-inhibiting, and collagen remodeling. Techniques used as components are already known (for example, Patent Document 1, Patent Document 2, Patent Document 3, and Patent Document 4). However, triterpenic acid is not sufficiently soluble in oily components and in aqueous components, causing problems such as precipitation of triterpenic acid during long-term storage of the preparation. Storage instability of a topical skin preparation containing triterpenic acid is undesirable because it reduces the above physiological activity.
- Patent Document 5 it has been studied to improve the solubility of triterpenic acid in oily components by derivatizing triterpenic acid into esters or ethers.
- Patent Document 6 a technique using an aliphatic saturated alcohol having 12 to 24 carbon atoms.
- Patent Document 6 a technique using an aliphatic saturated alcohol having 12 to 24 carbon atoms.
- the solubility of triterpenic acid is partly improved.For example, in a preparation containing triterpenic acid at a high concentration of 0.1% by mass or more, when it is stored for a long time under low temperature conditions. Sometimes produced crystals. That is, there has been a demand for means for further improving the solubility and storage stability of an external preparation for skin containing triterpenic acid.
- 4_n-butylresorcinol has a strong tyrosinase activity inhibitory action and is known to be a very useful whitening agent (Patent Document 7), and is used as a cosmetic raw material.
- Patent Document 7 a very useful whitening agent
- 4-alkylresorcinols such as 4-n-butylresorcinol have the effect of enhancing the long-term storage stability of triterpenic acid.
- topical skin preparations in combination with triterpenic acid was also not known.
- Patent Document 1 Japanese Patent Application Laid-Open No. 8-165231
- Patent Document 2 JP-A-8-208424
- Patent Document 3 Japanese Patent Laid-Open No. 11-12122
- Patent Document 4 Japanese Patent Laid-Open No. 2000-302659
- Patent Document 5 Japanese Unexamined Patent Publication No. 09-143050
- Patent Document 6 Japanese Unexamined Patent Application Publication No. 2004-331593
- Patent Document 7 Japanese Patent Laid-Open No. 02-49715
- the present invention refers to triterpenic acid and / or a derivative thereof (hereinafter also referred to as triterpenic acid or the like).
- the present inventors have prepared a topical skin preparation containing a relatively high concentration of triterpenic acid such as urzolic acid benzinole, etc., 4-alkylresorcinol such as 4_n-butylresorcinol and / or its
- triterpenic acid such as urzolic acid benzinole, etc.
- 4-alkylresorcinol such as 4_n-butylresorcinol and / or its
- 4_alkylresorcinol a salt
- the present invention relates to the following technique.
- a topical skin preparation containing (1) component 1) triterpenic acid and Z or a derivative thereof, and component 2) 4-alkylresorcinol and / or a salt thereof.
- Component 1 Power External preparation for skin according to (1), which is ursolic acid and Z or a derivative thereof.
- component 1) is benzyl triterpeneate.
- Branched fatty acid strength The external preparation for skin according to (7), which is S isostearic acid.
- Triterpenic acid and / or derivative thereof which is an essential component of the external preparation for skin of the present invention
- the skin external preparation of the present invention contains triterpenic acid and / or a derivative thereof (component 1).
- Triterpenic acid can be used without particular limitation as long as it is used in the field of external preparations for skin such as cosmetics.
- ursolic acid, oleanolic acid, belicic acid, asiatic acid, (2, 3, j3, 4) _ 2, 3, 23 trihydroxy-12-en-ursolic acid ((2, 3/3, 4 ⁇ ) -2,3,23-Trihydroxyurs-12-en-28-oic acid)) and the like can be preferably exemplified, and among these, ursolic acid can be particularly preferably exemplified.
- Triterpenic acid can be obtained by a conventional method, and plant strength may be extracted or a commercially available product may be used.
- ursolic acid is used for walrus, apple and cherry fruit and leaves of various plants
- oleanolic acid is used for olive leaves, apple bark, timber shoots, etc.
- belinic acid is used for dogwood bark, pomegranate peel and jujube.
- Asian acids are distributed in boxboxes, etc., so these plant extracts can be concentrated and purified for use.
- ursolic acid for example, Ursolic Acid (manufactured by Tokyo Chemical Industry)
- oleanolic acid for example, Oleanolic Acid (manufactured by Sigma_Aldrich)
- belic acid for example,
- Asiatic Acid manufactured by Sigma-Aldrich
- Betulic Acid manufactured by Sigma-Aldrich
- Asian acid Asian acid
- a derivative of triterpenic acid does not impair the physiological activity of the triterpenic acid. Just do it.
- Specific examples of the derivative of triterpenic acid include salts of triterpenic acid, esters of triterpenic acid, amides of triterpenic acid, ethers of triterpenic acid, and the like. Preferred examples are salts and esters of triterpenic acid.
- Esters include methyl ursolate, ethyl ursolate, propyl ursolate, butyl ursolate, benzyl ursolate, methyl oleanoate, ethyl oleanolate, propyl oleanolate, butyl oleanolate, benzyl oleanolate, Preference is given to methyl phosphate, ethyl ethyl phosphate, propyl belate, butyl belate, benzyl belate, methyl asiatic acid, ethyl ethyl acid, propyl diazate, butyl asiatic acid, benzyl asiatic acid, etc. It can be illustrated.
- benzyl ursolate is particularly preferred. This is because it has excellent storage stability and can obtain the high physiological activity of ursolic acid.
- any physiologically acceptable salt can be used without particular limitation.
- alkali metal salts such as sodium salt and potassium salt, calcium salt, and magnesium salt
- organic amine salts such as alkaline earth metal salts, ammonium salts, triethylamine salts and triethanolamine salts, and basic amino acid salts such as arginine salts and lysine salts.
- the derivative of triterpenic acid can be produced according to a conventional method.
- benzyl ester of triterbenic acid can be produced by converting triterpenic acid to triethylamine salt and reacting this with benzyl chloride.
- Triterpenic acid esters can be obtained by reacting triterpenic acid and alcohol in the presence of a mineral acid catalyst.
- the external preparation for skin of the present invention may contain one kind of triterpenic acid and derivatives thereof, or may contain two or more kinds in combination.
- the content of triterpenic acid and the like in the external preparation for skin of the present invention is not particularly limited as long as the physiological activity such as triterpenic acid is obtained. Since the external preparation for skin of the present invention contains triterpenic acid or the like in a total amount of 0.1% by mass or more, since precipitation of crystals is suppressed and high stability is exhibited, the total amount of triterpenic acid and the like is 0.1% by mass. % To 5% by mass, preferably 0.2% to 3% by mass, and more preferably 0.3% to 3% by mass. The excellent effects of the present invention can be obtained.
- the external preparation for skin of the present invention is characterized by containing 4-alkylresonoresinol and / or a salt thereof (component 2).
- the alkyl group in 4_alkylresorcinol is preferably an alkyl group having 3 to 10 carbon atoms, and an alkyl group having 3 to 8 carbon atoms is more preferable.
- n_propyl, isopropyl, n_butyl, isobutyl, sec-butyl, tert_butyl, aminole, n_hexyl, cyclohexyl, octyl, isooctyl Examples include groups.
- 4_n-butylresorcinol is particularly preferably used.
- 4_n-butylresorcinol and other 4_alkylresorcinols are known substances and can be prepared according to conventional methods.
- Eco, J .; Bitter, LA; Peiner, V. Trudy—Nauchono—Issledovatel skii I It can be produced according to the method described in nstitut Slantsev (1969), No. 18, 127-34.
- 4-n-butylresorcinol can be produced by condensing resorcin and butanoic acid in the presence of zinc chloride and reducing with zinc amalgam / hydrochloric acid, or resorcin and n-butyl alcohol at 200 400 ° C.
- a method of condensing with C can be exemplified.
- 4-n xylrezonoresinol is commercially available from Aldrich, and can be purchased and used.
- the salt of 4 alkylresorcinol may be a physiologically acceptable salt usually used in cosmetics and the like.
- Preferred examples include alkali metal salts such as sodium and potassium, alkaline earth metal salts such as calcium and magnesium, organic amine salts such as ammonium salt, triethylamine and triethanolamine, and basic amino acid salts such as lysine and arginine.
- the external preparation for skin of the present invention may contain one of 4-alkylresorcinol and a salt thereof alone, or may contain two or more in combination.
- the content of 4 alkylresorcinol and the like in the external preparation for skin of the present invention is preferably 0.01% by mass or more in terms of the total amount with respect to the total amount of external preparation for skin. Is more preferably 0.1% by mass or more.
- the upper limit is preferably 3% by mass or less, more preferably 1% by mass or less, and even more preferably 0.5% by mass or less. This is because if the amount is too small, the effects of the present invention may not be exhibited, and if the amount is too large, the effect may reach its peak.
- the content ratio of triterpenic acid and / or a derivative thereof to 4_alkylresorcinol and / or a salt thereof is preferably 5 ::! To 1:10 5 ::! To 1: 5 is more preferable.
- the external preparation for skin of the present invention preferably further contains a branched fatty acid in addition to the essential components. This further improves the long-term storage stability of the external preparation for skin of the present invention.
- a branched fatty acid isostearic acid is preferred, which is preferably a branched fatty acid having 12 to 30 carbon atoms.
- the branched fatty acid may be contained as a free carboxylic acid or as a salt.
- the salt may be any salt that is usually used in cosmetics and is physiologically acceptable.
- Preferred examples include alkali metal salts such as sodium and potassium, alkaline earth metal salts such as calcium and magnesium, organic amine salts such as ammonium salt, triethylamine and triethanolamine, and basic amino acid salts such as lysine and arginine. .
- the content of the branched fatty acid is not particularly limited, but is 0.:! To 30% by mass, preferably :! to 10% by mass.
- the external preparation for skin of the present invention contains triterpenic acid or the like which is difficult to dissolve in water, it is an agent such as an oil agent type mainly composed of an oil agent or a polyhydric alcohol, or an essence agent type containing a large amount of polyhydric alcohols. Les, preferably in shape.
- 4-alkylresorcinol and the like are soluble in both oil and water, and therefore, it is also preferable to be an emulsified dosage form containing an oil and water-containing components including water.
- the external preparation for skin of the present invention can be applied to any preparation of cosmetics and external preparations for skin, but is particularly suitable for cosmetics.
- 4_n-butylresorcinol, etc. Is more desirable to apply to quasi drugs among cosmetics.
- the external preparation for skin of the present invention can be used for the purpose of treating, preventing or improving a specific skin disease or symptom according to various physiological activities possessed by triterpenic acid or the like.
- an external preparation for skin containing a derivative of ursolic acid such as benzyl ursolate can be used as an anti-wrinkle cosmetic because it has a function of reconstituting collagen fiber bundles.
- a skin external preparation containing lysine or a derivative thereof has an action of improving acne-prone skin, it can be used as a cosmetic for acne skin and oily skin.
- the external preparation for skin of the present invention may contain optional components that are usually used in external preparations for skin, in addition to the essential components.
- optional components can be used without particular limitation as long as they do not inhibit the effects of the present invention, and are hydrocarbons, silicones, esters, fatty acids, triglycerides, polyhydric alcohols, organics. Examples thereof include powders, inorganic powders, surfactants, thickeners, vitamins, steroids, preservatives, and UV absorbers.
- these optional components can be blended in a blending amount that does not impair the effects of the present invention.
- hydrocarbons examples include squalene, liquid paraffin, light liquid isoparaffin, heavy liquid isoparaffin, microcrystalline wax, solid paraffin, and the like.
- silicones include modified polysiloxanes such as dimethicone, femethicone, cyclomethicone, amodimethicone, and polyether-modified polysiloxane.
- esters examples include octyldodecyl oleate, cetyl isooctanoate, cetyl stearate, isopropyl myristate, hexyldecyl isostearate, neopentyl glycol disostearate, sorbitan sesquistearate, diisopropyl adipate , Di-2-ethyl hexyl sebacate, cetyl lactate, diisostearinoleate malate, ethylene glycol di-2-ethylhexanoate, neopentylglycone dicaprate, diglycerol _2_heptylundecanoate, tri-2-ethyl Glycerin xanthate, tri-2-ethylhexylhexamate trimethylolpropane, triisostearic acid trimethylolpropane, tetra_2-ethylhexanoi
- fatty acids examples include oleic acid, isostearic acid, lauric acid, myristic acid, palmitic acid, isopalmitic acid, stearic acid, behenic acid, undecylenic acid, and the like.
- triglycerides examples include castor oil, coconut oil, hydrogenated coconut oil, camellia oil, wheat germ oil, isostearic acid triglyceride, isooctanoic acid triglyceride, 2_ethylhexylic acid tridaleselide, olive oil, and the like.
- polyhydric alcohols examples include 1,3-butanediol, 1,2-butanediol, glycerin, diglycerin, dipropylene glycol, polyethylene glycol, 1,2_pentanediol, hexylene glycol, and isoprene glycol. Etc.
- organic powders examples include crystalline cellulose, cross-linked methylpolysiloxane, polyethylene powder, acrylic resin powder, and the like.
- Examples of the inorganic powders may include, for example, surface-treated talc, my strength, sericite, magnesium carbonate, calcium carbonate, titanium dioxide, iron oxide, bitumen, ultramarine, titanium my strength, titanium selenium. Site, silica and the like.
- Surfactants include, for example, fatty acid soap (sodium laurate, sodium palmitate, etc.), anionic surfactants such as potassium lauryl sulfate, alkylethanol triethanolamine ether, and salted stearyl trimethyl ammonium.
- Cationic surfactants such as benzanoreconium and laurylamine oxide, imidazoline amphoteric surfactants (2-cocoyl 2-imidazolinium hydroxide 1 carboxyethyloxy 2 sodium salt, etc.), betaines Surfactants (alkyl betaines, amide betaines, sulfobetaines, etc.), amphoteric surfactants such as isylmethyltaurine, sorbitan fatty acid esters (sorbitan monostearate, sorbitan sesquioleate, etc.), glycerin fatty acids ( Glycerin monoste Allate), propylene glycol fatty acid esters (propylene glycol monostearate, etc.), hardened castor oil derivatives, glycerin alkyl ether, P
- Examples of the thickener include acrylic acid 'alkyl methacrylate copolymer and / or salt thereof, carboxybule polymer and / or salt thereof, alginate, polyhydric alcohol ester of alginic acid, xanthan gum, hydroxypropyl cellulose, and the like. Can be mentioned.
- vitamins include retinol, retinoic acid, tocopherol, and riboflavin.
- steroids examples include steroids such as estradiol, echelle estradiol, and estriol.
- Examples of the ultraviolet absorber include preservatives such as phenoxyethanol, parabens, hibiten dalconate, and salt of benzalkonium salt, dimethylaminobenzoic acid esters, cinnamic acid esters, and benzophenone. Can be mentioned.
- Example 1 A cream of Example 1, which is an external preparation for skin of the present invention, was prepared according to the formulation shown below.
- (A) was mixed and dissolved by heating at 80 ° C.
- (A) was added to (B) while stirring (B), which was uniformly dissolved and heated at 80 ° C, and then cooled to 40 ° C while stirring with a homomixer. This was added with (C) heated to 40 ° C., and cooled to room temperature with stirring.
- Example 1 was prepared by substituting 4_n-butylresorcinol with water for Comparative Example 1, except that benzylursolate was removed and the amount of (C) pure water was increased to Comparative Example 2, and 4 Comparative Example 3 was obtained by removing both _n-butylresorcinol and benzylursolate and increasing the amount of (C) pure water accordingly.
- Cetyl isooctanoate 2. 0% by mass
- Canoleboxyvininole polymer 0.2% by mass Pure water 49. 0% by mass
- Low-temperature aging box (store at _10 ° C for 24 hours, then increase to 5 ° C over 24 hours, store at 5 ° C for 24 hours, cool to 10 ° C over 24 hours, Repeated as 1 cycle), let the sampnore left for 3 months return to room temperature, extract 0.1 g each of the creams of Example 1 and Comparative Examples:! ⁇ 3, spread on a black plate with a spatula,
- the fine precipitates contained in were observed under a microscope, and the number thereof was counted.
- the fine precipitate means a crystal of about 5 to 50 zm that can be observed under a microscope.
- Such fine precipitates are not at a level that gives a feeling to the skin when cosmetics are used, but such crystals may grow even larger. Therefore, it is important to suppress the precipitation of such fine precipitates in an external preparation for skin containing triterpenic acid.
- Example 1 In Example 1 containing benzylursolate and 4_n-butylresorcinol, no fine precipitate was observed. On the other hand, in Comparative Example 1 containing benzylursolate and not containing 4_n-butylresorcinol, many fine precipitates were observed. It does not contain benzylursolate and contains 4 n butylresorcinol No microprecipitates were observed in Comparative Example 2 containing sulfur and Comparative Example 3 containing neither benzyl ursolate nor 4 n-butylresorcinol.
- n-butylresorcinol was found to increase the dissolution stability of benzylursolate. That is, it was found that the external preparation for skin of the present invention is excellent in storage stability under low temperature conditions.
- a cream which is an external preparation for skin of the present invention was obtained in accordance with the formulation shown below, and it was designated as Example 2. That is, to (A) mixed and heated to 80 ° C, (B) mixed and heated and dissolved at 80 ° C was added, and (C) was further heated to 80 ° C. Was added and stirred. This was mixed with (D) at 40 ° C. and cooled with stirring.
- Example 2 4_n-butylresorcinol was replaced with water as Comparative Example 4. Further, Example 3 was obtained by substituting 4_n-butylresorcinol with 4_n_hexyl-resoronoresinol (purchased from Aldrich) in Example 2.
- Tri force prillic acid Z force purinate / myristic acid Z stearic acid
- Example 2 The creams of Example 2, Comparative Example 4, and Example 3 were stored in a low-temperature aging box for 3 months in the same manner as in Test Example 1, and then returned to room temperature and extended on a black flat plate. The number was counted. The results are shown in Table 2.
- Example 2 containing ursolic acid and 4 n-butylresorcinol, no fine precipitate was observed. On the other hand, a large amount of fine precipitates was observed in Comparative Example 4 containing ursolic acid and not 4-n butylresorcinol. In addition, no fine precipitate was observed in Example 3 containing ursolic acid and 4 n xyluresorcinol.
- Talyum which is an external preparation for skin of the present invention, was obtained in the same manner as in Example 1, and designated as Example 4.
- Example 4 n-butylresorcinol was replaced with water as Comparative Example 5.
- Example 5 Example 5 was obtained by removing (A) isostearic acid and increasing the amount of (C) pure water accordingly.
- SALACOS 334" manufactured by Nisshin OilliO Co., Ltd.
- Talyme which is an external preparation for skin of the present invention, was obtained in the same manner as in Example 1, and designated Example 6. Further, Example 7 was obtained by replacing belicic acid with oleanolic acid in Example 6. In Example 6 and Example 7, those in which 4-n-ol was replaced with water were designated as Comparative Example 6 and Comparative Example 7, respectively.
- Example 4 Contains benzylursolate, 4_n-butylresorcinol and isostearic acid
- Example 5 which contained ursolic acid benzil and isostearic acid and did not contain 4-n-butylresorcinol, many fine precipitates were observed.
- Example 5 containing ursolic acid and 4 n xyl-resorcinol and no isostearic acid, fine precipitates were observed.
- Example 6 containing berelic acid and 4_n-butylresorcinol, and Example 7 containing oleanolic acid and 41-n-butylresorcinol, fine precipitates were not observed.
- 4_n-butylresorcinol was removed, and in Comparative Examples 6 and 7, fine precipitates were observed.
- isostearic acid has the effect of enhancing the dissolution stability of triterpenic acid such as ursolic acid, belinic acid, and oleanolic acid, and enhances the storage stability of skin preparations containing triterpenic acid at high concentrations. I found out.
- each component was uniformly dissolved at 80 ° C., and then cooled to room temperature, to prepare an oil essence of Example 8. Further, a 4-n-butylresorcinol substituted with squalene was prepared as Comparative Example 8.
- Silicone KSG- 16 (Shin-Etsu Chemical Co., Ltd.) 10.0 mass% Decamethyl cyclopentane siloxane (manufactured by Shin-Etsu Chemical Co., Ltd.) 30.0 mass% isostearic acid 1.0 mass 0/0
- Example 8 The oil essence of Example 8 and Comparative Example 8 was stored in a low-temperature aging box for 3 months in the same manner as in Test Example 1, then returned to room temperature, extended onto a black flat plate, and the number of fine precipitates was counted. The results are shown in Table 4.
- Example 8 of the present invention containing 4_n-butylresorcinol, fine precipitates were not observed. On the other hand, in Comparative Example 8 containing no 4_n-butylresorcinol, many fine precipitates were observed. From this, it was found that 4_n-butylresorcinol enhances the dissolution stability of benzylursolate even in the oil essence dosage form for external use on the skin.
- the external preparation for skin containing triterpenic acid and the like of the present invention and 4 alkylresorcinol and the like is excellent in solubility of triterpenic acid and the like.
- a skin external preparation containing triterpenic acid or the like at a high concentration of 0.1% by mass or more is stored for a long time under low temperature conditions, the precipitation of triterbenic acid or the like does not occur.
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Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008522332A JP5166260B2 (ja) | 2006-06-19 | 2007-04-24 | トリテルペン酸を含む皮膚外用剤 |
AU2007262265A AU2007262265B2 (en) | 2006-06-19 | 2007-04-24 | Skin external preparation containing triterpenic acid |
EP07742216.0A EP2036565B1 (en) | 2006-06-19 | 2007-04-24 | Skin external preparation containing triterpenic acid |
BRPI0713746-0A BRPI0713746A2 (pt) | 2006-06-19 | 2007-04-24 | preparação externa para a pele |
US12/305,350 US8912172B2 (en) | 2006-06-19 | 2007-04-24 | Skin external preparation containing triterpenic acid |
CA2655788A CA2655788C (en) | 2006-06-19 | 2007-04-24 | Skin external preparation containing triterpenic acid |
CN200780022798.8A CN101472594B (zh) | 2006-06-19 | 2007-04-24 | 含有三萜酸的皮肤外用制剂 |
KR1020097000914A KR101389233B1 (ko) | 2006-06-19 | 2007-04-24 | 트리테르펜산을 포함하는 피부 외용제 |
HK09109407.9A HK1130696A1 (en) | 2006-06-19 | 2009-10-12 | Skin external preparation containing triterpenic acid |
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JP2006169113 | 2006-06-19 | ||
JP2006-169113 | 2006-06-19 |
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WO2007148474A1 true WO2007148474A1 (ja) | 2007-12-27 |
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PCT/JP2007/058781 WO2007148474A1 (ja) | 2006-06-19 | 2007-04-24 | トリテルペン酸を含む皮膚外用剤 |
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US (1) | US8912172B2 (ja) |
EP (1) | EP2036565B1 (ja) |
JP (1) | JP5166260B2 (ja) |
KR (1) | KR101389233B1 (ja) |
CN (1) | CN101472594B (ja) |
AU (1) | AU2007262265B2 (ja) |
BR (1) | BRPI0713746A2 (ja) |
CA (1) | CA2655788C (ja) |
HK (1) | HK1130696A1 (ja) |
RU (1) | RU2429829C2 (ja) |
WO (1) | WO2007148474A1 (ja) |
Cited By (3)
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JP2014040383A (ja) * | 2012-08-21 | 2014-03-06 | Pola Chem Ind Inc | 皮膚外用組成物 |
JP2014040382A (ja) * | 2012-08-21 | 2014-03-06 | Pola Chem Ind Inc | 皮膚外用組成物 |
JP2015003888A (ja) * | 2013-06-24 | 2015-01-08 | ポーラ化成工業株式会社 | 皮膚外用剤 |
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JP5539224B2 (ja) * | 2008-01-11 | 2014-07-02 | シャンハイ・インスティチュート・オブ・ファーマシューティカル・インダストリー(エスアイピーアイ) | アジアティック酸(asiaticacid)及びその選択される塩に基づく治療用製剤 |
US8440237B2 (en) | 2009-04-27 | 2013-05-14 | Mary Kay Inc. | Botanical anti-acne formulations |
US8084504B2 (en) | 2009-10-02 | 2011-12-27 | Johnson & Johnson Consumer Companies, Inc. | High-clarity aqueous concentrates of 4-hexylresorcinol |
US8906432B2 (en) | 2009-10-02 | 2014-12-09 | Johnson & Johnson Consumer Companies, Inc. | Compositions comprising an NFκB-inhibitor and a non-retinoid collagen promoter |
US20110081430A1 (en) | 2009-10-02 | 2011-04-07 | Simarna Kaur | COMPOSITIONS COMPRISING AN NFkB-INHIBITOR AND A TROPOELASTIN PROMOTER |
CA2859419C (en) | 2011-12-19 | 2018-10-16 | Mary Kay Inc. | Cosmetic composition comprising an aqueous extract of navy-bean |
US20140086859A1 (en) | 2012-09-24 | 2014-03-27 | Johnson & Johnson Consumer Companies, Inc. | Low oil compositions comprising a 4-substituted resorcinol and a high carbon chain ester |
RU2664694C2 (ru) * | 2013-09-17 | 2018-08-21 | Джонсон Энд Джонсон Конзьюмер Компаниз, Инк. | Композиции с низким содержанием масел, включающие 4-замещенный резорцин и сложный эфир с длинной углеродной цепью |
WO2015138237A1 (en) | 2014-03-10 | 2015-09-17 | Mary Kay Inc. | Skin lightening compositions |
EP3565518A4 (en) * | 2016-12-28 | 2020-06-03 | L'Oreal | SOLID WATER-FREE COMPOSITION FOR CARE AND / OR TREATMENT OF KERATIN MATERIALS |
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- 2007-04-24 US US12/305,350 patent/US8912172B2/en not_active Expired - Fee Related
- 2007-04-24 BR BRPI0713746-0A patent/BRPI0713746A2/pt not_active IP Right Cessation
- 2007-04-24 KR KR1020097000914A patent/KR101389233B1/ko not_active IP Right Cessation
- 2007-04-24 RU RU2009101326/15A patent/RU2429829C2/ru not_active IP Right Cessation
- 2007-04-24 AU AU2007262265A patent/AU2007262265B2/en not_active Ceased
- 2007-04-24 CN CN200780022798.8A patent/CN101472594B/zh active Active
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JP2014040383A (ja) * | 2012-08-21 | 2014-03-06 | Pola Chem Ind Inc | 皮膚外用組成物 |
JP2014040382A (ja) * | 2012-08-21 | 2014-03-06 | Pola Chem Ind Inc | 皮膚外用組成物 |
JP2015003888A (ja) * | 2013-06-24 | 2015-01-08 | ポーラ化成工業株式会社 | 皮膚外用剤 |
Also Published As
Publication number | Publication date |
---|---|
US20090253663A1 (en) | 2009-10-08 |
CA2655788A1 (en) | 2007-12-27 |
BRPI0713746A2 (pt) | 2012-11-06 |
EP2036565A1 (en) | 2009-03-18 |
RU2429829C2 (ru) | 2011-09-27 |
CN101472594A (zh) | 2009-07-01 |
US8912172B2 (en) | 2014-12-16 |
AU2007262265B2 (en) | 2012-06-07 |
AU2007262265A1 (en) | 2007-12-27 |
CA2655788C (en) | 2014-03-18 |
JPWO2007148474A1 (ja) | 2009-11-12 |
KR20090021387A (ko) | 2009-03-03 |
EP2036565A4 (en) | 2013-01-02 |
JP5166260B2 (ja) | 2013-03-21 |
KR101389233B1 (ko) | 2014-04-24 |
RU2009101326A (ru) | 2010-07-27 |
EP2036565B1 (en) | 2014-04-16 |
CN101472594B (zh) | 2014-06-25 |
HK1130696A1 (en) | 2010-01-08 |
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