EP1267822A2 - Utilisation d'acide 3,4-dihydroxymandelique pour la protection contre des dommages oxydatifs dus a la lumiere ultraviolette - Google Patents

Utilisation d'acide 3,4-dihydroxymandelique pour la protection contre des dommages oxydatifs dus a la lumiere ultraviolette

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Publication number
EP1267822A2
EP1267822A2 EP01923646A EP01923646A EP1267822A2 EP 1267822 A2 EP1267822 A2 EP 1267822A2 EP 01923646 A EP01923646 A EP 01923646A EP 01923646 A EP01923646 A EP 01923646A EP 1267822 A2 EP1267822 A2 EP 1267822A2
Authority
EP
European Patent Office
Prior art keywords
acid
mixtures
stereoisomers
dihydroxyphenyl
weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP01923646A
Other languages
German (de)
English (en)
Inventor
Jakob Peter Ley
Roland Langner
William Johncock
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Symrise AG
Original Assignee
Haarmann and Reimer GmbH
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 Haarmann and Reimer GmbH filed Critical Haarmann and Reimer GmbH
Publication of EP1267822A2 publication Critical patent/EP1267822A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • 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
    • A23B2/742—Organic compounds containing oxygen
    • A23B2/754—Organic compounds containing oxygen containing carboxyl groups
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
    • 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
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • 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
    • 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

Definitions

  • the invention relates to the use of 2- (3,4-dihydroxyphenyl) -2-hydroxyacetic acid, hereinafter referred to as 3,4-dihydroxymandelic acid, as an antioxidant and / or radical scavenger for protection against ultraviolet light-induced oxidative damage.
  • Ultraviolet light in particular ultraviolet light in the range from 290 to 400 nm, dissolves photooxidative processes on or in the skin e.g. from mammals or humans, different reactive oxygen compounds or radicals being formed starting from oxygen. These can e.g. Damage or destroy intracellular molecules and thus weaken the cell's vitality or even kill it.
  • Radicals can also damage the intracellular molecules or structures.
  • the lipid layer and the sebum which serve as a barrier against the environment, can be destroyed by oxidative processes.
  • a major component of the essential sebum is squalene, which is highly unsaturated and very sensitive to oxidation.
  • Antioxidants or radical scavengers which support the natural defense mechanisms against free radicals and reactive oxygen compounds in physiological systems, protect the lipid layer of the skin from oxidative processes. They also protect the oxidation-sensitive components of cosmetics, pharmaceuticals or foods from autoxidation.
  • Antioxidants are substances that significantly delay or completely prevent oxidation in small concentrations compared to the oxidizable substrate. Many antioxidants act as radical scavengers and / or at the same time
  • the object of the present invention is to develop active substances which, on account of their strong specific radical-catching and / or antioxidative action, can protect cells and tissues of the skin of mammals from the harmful effects of free radicals and oxidative processes.
  • the invention therefore relates to the use of 3,4-dihydroxymandelic acid including its stereoisomers or mixtures thereof as antioxidants and / or radical scavengers for protecting the mammalian skin, but in particular the human skin, from oxidative processes which are induced by ultraviolet light.
  • 3,4-dihydroxymandelic acid is applied to the skin and / or hair in an effective amount in the form of topically administrable preparations, preferably in the form of cosmetic or dermatological preparations.
  • 3,4-dihydroxymandelic acid including its stereoisomers or mixtures thereof particularly well suppresses the harmful effects of free radicals and oxidative processes which are induced by UV light on or in the skin and the natural antioxidative ones Processes supported.
  • the use of 3,4-dihydroxymandelic acid including its stereoisomers or mixtures thereof in combination with other antioxidants particularly well suppresses the harmful effects of free radicals and oxidative processes which are induced by UV light on or in the skin and supports the natural antioxidants
  • 3,4-dihydroxymandelic acid has been proposed in US Pat. No. 5,834,510 as an agent for skin, nail and hair care.
  • ⁇ -hydroxycarboxylic acids among which 3,4-dihydroxy-mandelic acid is not mentioned, are used in concentrations of greater than or equal to 2% by weight, preferably greater than or equal to 7% by weight, based on the total volume of the formulation. It is not described in US Pat. No. 5,834,510 that 3,4-dihydroxy-mandelic acid, including its stereoisomers and mixtures thereof, have an anti-oxidative or radical-scavenging effect.
  • 3,4-dihydroxymandelic acid including its stereoisomers and their mixtures in concentrations of less than 1% by weight, preferably 0.001 to 0.5% by weight, based on the total weight of a formulation is an extremely strong antioxidant and has a radical-catching effect. Even at a concentration of 0.1% by weight, based on the total weight of a formulation, their extremely protective effect of the oxidation of the sebum of human skin initiated by ultraviolet light was not foreseeable.
  • antioxidants which are suitable or customary for cosmetic and / or dermatological applications can be used as further antioxidants.
  • the antioxidants are advantageously selected from the group of imidazoles (eg urocanic acid) and their derivatives, carotenoids, carotenes (eg ⁇ -carotene, ⁇ -carotene, lycopene) and their derivatives, chlorogenic acid and their derivatives, lipoic acid and their derivatives, aurothioglucose, propylthiouracil and other thiols (e.g. thioredoxin, glutathione, cysteine, cystine, cystamine and their
  • Glycosyl and N-acyl derivatives or their alkyl esters as well as their salts, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and their derivatives as well as phenolic acid amides of phenolic benzylamines (eg homovanillic acid, 3,4-dihydroxyphenylacetic acid, ferulic acid, caffeic acid, sinapic acid, sinapic acid, sinapinic acid, sinapinic acid, sinapinic acid, sinapinic acid, sinapinic acid, sinapinic acid, sinapinic acid, sinapinic acid, sinapinic acid, sinapic acid, - Ferulic acid or dihydro coffee acid of 3,4-dihydroxybenzyl-, 2,3,4-trihydroxy-benzyl- or 3,4,5-trihydroxybenzylamine), catecholoximes or catecholoxime ether (eg 3,4-dihydroxybenzaldoxime, 3,4-dihydroxy
  • Ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives e.g. vitamin E acetate
  • vitamin A and derivatives e.g. vitamin A palmetto
  • rutinic acid and its derivatives e.g. quercetin, ⁇ -glucosylrutin
  • flavonoids e.g. quercetin, ⁇ -glucosylrutin
  • phenolic acids e.g. gallic acid, ferulic acid
  • derivatives e.g. propyl, ethyl, octyl
  • furfurylidene glucitol butylated hydroxytoluene
  • zinc and its derivatives e.g. ZnO, ZnSO 4
  • selenium and its derivatives e.g. selenomethionine
  • stilbenes and their derivatives e.g. stilbene oxide, resveratrol
  • the 3,4-dihydroxymandelic acid including its stereoisomers or mixtures thereof can be incorporated into conventional cosmetic or dermatological preparations.
  • the amount of 3,4-dihydroxymandelic acid including its stereo isomers or their mixtures in the cosmetic or dermatological preparations is 0.001% by weight to 1% by weight, preferably 0.001% by weight to 0.5% by weight, based on the total weight of the preparations.
  • the cosmetic or dermatological preparations can be used as “water in oil”, “oil in water”, “water in oil in water” or “oil in water in PP” emulsions, as microemulsions, as gels, as Soaps, as solutions, for example in oils, alcohols or silicone oils, as sticks, as aerosols, sprays or even foams
  • Further conventional cosmetic auxiliaries and additives can be present in amounts of 0.001-99.999% by weight, preferably 1-99% by weight %, based on the total weight of the formulation, and the formulations may also contain water in an amount of up to 99.999% by weight, preferably 1 to 99% by weight, based on the total weight of the
  • the amount of further antioxidants, one or more compounds being able to be used, in the cosmetic or dermatological preparations is preferably 0.001 to 10% by weight, preferably 0.001 to 5% by weight, particularly preferably 0.001 to 1% by weight, based on the total weight of the preparations.
  • the 3,4-dihydroxymandelic acid including its stereoisomers and their mixtures can also be previously prepared in liposomes, e.g. starting from
  • Phosphatidylcholine in microspheres, in nanospheres or in capsules from a suitable matrix, for example from natural waxes such as e.g. Beeswax, candellila wax, carnauba wax or synthetic waxes such as Silicone waxes, paraffin waxes or from proteins such as e.g. Gelatin or from polysaccharides such as e.g. Agar, hyaluronic acid, starch, cellulose or chitin can be incorporated.
  • natural waxes such as e.g. Beeswax, candellila wax, carnauba wax or synthetic waxes such as Silicone waxes, paraffin waxes or from proteins such as e.g. Gelatin or from polysaccharides such as e.g. Agar, hyaluronic acid, starch, cellulose or chitin can be incorporated.
  • the cosmetic and dermatological preparations contain cosmetic auxiliaries and additives as are usually used in such preparations, e.g. Sun protection agents (eg organic or inorganic UV sun protection filters, preferably micropigments), preservatives, bactericides, fungicides, virucides, cooling agents, plant extracts, anti-inflammatory agents, substances that accelerate wound healing (e.g. chitin or chitosan and its derivatives), film-forming substances (e.g. polyvinylpyrrolidones or chitosan or its derivatives), vitamins (e.g. vitamin C and derivatives, tocopherols and derivatives,
  • Vitamin A and derivatives include 2-hydroxycarboxylic acids (e.g. citric acid, malic acid, L-, D- or dl-lactic acid), perfumes, substances to prevent foaming, dyes, pigments that have a coloring effect, thickeners, surface-active substances, Emulsifiers, softening, moisturizing and / or moisturizing substances (e.g. glycerin or urea), fats, oils, unsaturated
  • 2-hydroxycarboxylic acids e.g. citric acid, malic acid, L-, D- or dl-lactic acid
  • perfumes substances to prevent foaming, dyes, pigments that have a coloring effect, thickeners, surface-active substances, Emulsifiers, softening, moisturizing and / or moisturizing substances (e.g. glycerin or urea), fats, oils, unsaturated
  • Fatty acids or their derivatives e.g. linoleic acid, ⁇ -linolenic acid, ⁇ -linolenic acid or Arachidonic acid and its respective natural or synthetic esters
  • waxes or other usual components of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents, silicone derivatives or chelating agents (eg ethylenediamine tetraacetic acid and its derivatives).
  • the cosmetic and dermatological preparations are applied to the skin and / or the hair in a sufficient amount in the manner customary for cosmetics.
  • the cosmetic and dermatological preparations can also contain UVA and / or UVB filter substances, the total amount of filter substances being 0.1 to 30% by weight, preferably 0.5 to 10% by weight, based on the total weight of the preparations , can be obtained, for example, sunscreens for skin and hair.
  • UV filter substances which can be used are 3-benzylidene camphor derivatives (for example 3- (4-methylbenzylidene) dl-camphor), aminobenzoic acid derivatives (for example 2- (N, N-dimethylamino) benzoic acid 2-ethylhexyl ester or menthyl anthranilate), 4-methoxycinnamates (e.g.
  • Triazine ⁇ e.g. 2,4-bis- [4- (2-ethylhexyloxy) -2-hydroxyphenyl] -6- (4-methoxyphenyl) -l, 3,5-triazine, 4,4 '- ([6 - ([(l, l-dimethylethyl) aminocarbonyl] phenylamino) -l, 3,5-triazine-2,4-diyl] diimino) bisbenzo- acid bis (2-ethylhexyl) ester) ⁇ , 2-cyanopropenoic acid derivatives (e.g.
  • 2-ethylhexyl-2-cyano-3,3-diphenyl-2-propenoate dibenzoyl derivatives (e.g. 4-tert-butyl-4'-methoxy- dibenzoylmethane), polymer-bound UV filters (e.g. polymer of N- [2- (or 4) - (2-oxo-3-bornylidene) methyl] benzylacrylamide) or pigments (e.g. titanium dioxide, zirconium dioxide, iron oxide, silicon dioxide, manganese oxide, aluminum oxide .
  • dibenzoyl derivatives e.g. 4-tert-butyl-4'-methoxy- dibenzoylmethane
  • polymer-bound UV filters e.g. polymer of N- [2- (or 4) - (2-oxo-3-bornylidene) methyl] benzylacrylamide
  • pigments e.g. titanium dioxide, zirconium dioxide, iron oxide, silicon dioxide, manganese oxide,
  • Cerium oxides or zinc oxides can be used.
  • the lipid phase in the cosmetic or dermatological preparations can advantageously be selected from the following groups of substances: mineral oils (advantageously paraffin oil), mineral waxes, hydrocarbons (advantageously squalane or squalene), synthetic or semisynthetic triglyceride oils (e.g. triglycerides of capric or caprylic acid), natural oils (e.g. Castor oil, olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oil, borage seed oil and the like), natural ester oils (e.g.
  • ester oils preferably esters of saturated and / or unsaturated, linear and / or branched alkane carboxylic acids of 3 to 30 carbon atoms with saturated and / or unsaturated, linear and / or branched alcohols with 3 to 30 carbon atoms and esters of aromatic carboxylic acids with saturated and / or unsaturated, linear and / or branched alcohols with 3 up to 30 carbon atoms, especially selected from d he group isopropyl myristate, isopropyl stearate, isopropyl palmitate,
  • Fatty alcohols with low C number alcohols e.g. with isopropanol, propylene glycol or glycerin
  • esters of fatty alcohols with low C number alkanoic acids or with fatty acids alkyl benzoates (e.g. mixtures of n-dodecyl, n-tri-decyl, n Tetradecyl and n-pentadecyl benzoate) and cyclic or linear silicone oils (such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof).
  • the aqueous phase in the cosmetic or dermatological preparations optionally advantageously contains alcohols, diols or polyols of low C number, and also their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl ether, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous products, furthermore low C number alcohols, for example ethanol, isopropanol, 1,2-propanediol, glycerol, furthermore ⁇ - or ⁇ -hydroxy acids, preferably lactic acid, Citric acid or sahcylic acid, in addition emulsifiers, which can advantageously be selected from the group of ionic, nonionic, polymeric, phosphate-containing and zwitterionic emulsifiers, and in particular one or more thicken
  • the present invention also includes a method for protecting cosmetic or pharmaceutical, preferably dermatological, preparations and foods against oxidation or photooxidation, the components of which bring stability problems due to oxidation or photooxidation during storage, characterized in that the preparations have an effective content have 3,4-dihydroxymandelic acids.
  • the use according to the invention can also be used analogously in other areas of application, e.g. for the protection of paints or technical polymers.
  • the amount of 3,4-dihydroxymandelic acids in the cosmetic or pharmaceutical, preferably dermatological, preparations and in foods is 0.001% by weight to 1% by weight, preferably 0.001% by weight to 0.5% by weight, based on the total weight of the preparations.
  • Example 1 Activity as a radical scavenger
  • Active, as radical scavenger (%) 100 - (absorption of test compounds) / (absorption of control) x 100.
  • Vitamin C 50-81-7 0.270 ⁇ -tocopherol 59-02-9 0.250
  • the antioxidative index (AOI) was obtained according to the following equation:
  • Vitamin C 0.7 ⁇ -tocopherol 39
  • the experiments were carried out as described in Example 2.
  • the measured AOI values for the combinations were compared with the AOI values calculated according to the following formula:
  • Test compound c (% by weight) AOI, soybean oil, c (% by weight) AOI, squalene, 100 ° C 80 ° C
  • Example 4 Determination of the protective action against ultraviolet light-induced sebum oxidation
  • solution A 200 mg of 3,4-dihydroxymandelic acid were dissolved in 200 ml of 1,3-butylene glycol (solution A).
  • solution B a 0.2% ethanolic solution of tocopherol was prepared (solution B). 12 subjects were each on the back skin for 2 days Apply a dose of 2 mg / cm of solution A twice a day. Before the following irradiation, solution B was applied to a control area (2 mg / cm 2 ). The 2 treated and one untreated area were irradiated with ultraviolet light (320 to 400 nm, 10 joules / cm 2 ). The respective test areas were treated with 4 ml of ethanol for 2 min, the solutions were dried under nitrogen at room temperature and the residue was taken up in 1 ml of ethanol.
  • Example 6 Oil in water emulsion with 3,4-dihydroxymandelic acid
  • Part A was mixed and heated to 80 ° C.
  • Part B was mixed and heated to 90 ° C and added to Part A with stirring.
  • Carbopol was carefully dispersed in water and neutralized with sodium hydroxide solution (pH 5.3). Part C was then added to the mixture of parts A and B at 60 ° C.
  • Example 7 "Oil in water” emulsion with 3,4-dihydroxymandelic acid and ⁇ -tocopherol
  • a Arlatone 983 S ® (ICI) 1,2 with glyceryl monostearate 3,6,9,12,15,18,21,24,27,30,33,
  • Cutina MD ® (Henkel) glyceryl monostearate 3.5
  • Baysilone oil MIO ® (GE Bayer) polydimethylsiloxane 0.8
  • Phenopip ® (Nipa laboratories) ethyl ester and 4-hydroxy-0.5-benzoic acid propyl ester and 4-hydroxybenzoic acid butyl ester
  • Part A was mixed and heated to 80 ° C.
  • Part B was mixed and heated to 90 ° C and added to Part A with stirring.
  • Carbopol was carefully dispersed in water and neutralized with sodium hydroxide solution (pH 5.3). Part C was then added to the mixture of parts A and B at 60 ° C.
  • Example 8 "Oil in water” emulsion with UVA B broadband protection, 3,4-dihydroxymandelic acid and ⁇ -tocopherol
  • Part A was heated to 85 ° C.
  • Part B Carbopol and Keltrol were cold-dispersed in the remaining constituents, the mixture was heated to 85 ° C. and added to Part A.
  • Part C was immediately added to the mixture of parts A and B at 80 ° C. and homogenized for 5 minutes using a dispersing tool.
  • Part D was finally added at room temperature and the mixture was homogenized (pH 6.6) using a dispersing tool.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Wood Science & Technology (AREA)
  • Toxicology (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Zoology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biochemistry (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

L'invention concerne l'utilisation d'acide 3,4-dihydroxymandélique comme antioxydant ou comme phagocyte de radicaux libres pour la protection de la peau, notamment chez l'homme, contre des dommages oxydatifs dus à la lumière ultraviolette ainsi que pour la protection de préparations cosmétiques ou pharmaceutiques, d'autres objets et d'aliments contre l'oxydation ou la photo-oxydation.
EP01923646A 2000-03-18 2001-03-07 Utilisation d'acide 3,4-dihydroxymandelique pour la protection contre des dommages oxydatifs dus a la lumiere ultraviolette Withdrawn EP1267822A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10013578 2000-03-18
DE10013578A DE10013578A1 (de) 2000-03-18 2000-03-18 Verwendung von 3,4-Dihydroxymandelsäure zum Schutz vor Ultraviolettlicht-induzierten oxidativen Schädigungen
PCT/EP2001/002546 WO2001070176A2 (fr) 2000-03-18 2001-03-07 Utilisation d'acide 3,4-dihydroxymandelique pour la protection contre des dommages oxydatifs dus a la lumiere ultraviolette

Publications (1)

Publication Number Publication Date
EP1267822A2 true EP1267822A2 (fr) 2003-01-02

Family

ID=7635491

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01923646A Withdrawn EP1267822A2 (fr) 2000-03-18 2001-03-07 Utilisation d'acide 3,4-dihydroxymandelique pour la protection contre des dommages oxydatifs dus a la lumiere ultraviolette

Country Status (7)

Country Link
US (1) US20030053967A1 (fr)
EP (1) EP1267822A2 (fr)
JP (1) JP2003528831A (fr)
CN (1) CN1418087A (fr)
AU (1) AU2001250368A1 (fr)
DE (1) DE10013578A1 (fr)
WO (1) WO2001070176A2 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1864963A1 (fr) * 2006-06-02 2007-12-12 DSMIP Assets B.V. Composés hydroxyaromatiques, procedé pour leur préparation et leur utilisation comme anti-oxidants
CN105078775A (zh) * 2014-05-15 2015-11-25 谢铭峻 杏仁酸在抗氧化中的用途

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6053004B2 (ja) * 1977-06-18 1985-11-22 サンスタ−株式会社 染毛剤
JPS54132243A (en) * 1978-04-04 1979-10-15 Sunstar Inc Skin coloring composition
AU541247B2 (en) * 1979-12-20 1985-01-03 R.P. Scherer Corporation Adjuvants for rectal delivery of drug substances
AU618517B2 (en) * 1986-12-23 1992-01-02 Eugene J. Van Scott Additives enhancing topical actions of therapeutic agents
US5389677B1 (en) * 1986-12-23 1997-07-15 Tristrata Inc Method of treating wrinkles using glycalic acid
ATE177629T1 (de) * 1991-04-10 1999-04-15 Yu Ruey J Verwendung von 2-hydroxycarbonsäure oder deren derivaten enthaltende zusammensetzung zur linderung von wechseln nagelveränderungen
US5961999A (en) * 1995-06-08 1999-10-05 Wella Aktiengesellschaft Method of skin care using a skin care preparation containing a betaine ester and an α-hydroxy acid
IL126076A (en) * 1998-09-04 2005-05-17 Ibr Ltd Transparent composition comprising phytoene and phytofluene
EP1029849A1 (fr) * 1999-02-19 2000-08-23 Haarmann & Reimer Gmbh Hydroxymandelamides d'amines phénoliques

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0170176A2 *

Also Published As

Publication number Publication date
US20030053967A1 (en) 2003-03-20
AU2001250368A1 (en) 2001-10-03
WO2001070176A3 (fr) 2002-03-07
CN1418087A (zh) 2003-05-14
DE10013578A1 (de) 2001-09-20
JP2003528831A (ja) 2003-09-30
WO2001070176A2 (fr) 2001-09-27

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