EP1718270A1 - Utilisation d'alcools 2-hydroxyphenyle et formulations cosmetiques ou therapeutiques contenant ces composes - Google Patents

Utilisation d'alcools 2-hydroxyphenyle et formulations cosmetiques ou therapeutiques contenant ces composes

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Publication number
EP1718270A1
EP1718270A1 EP05707811A EP05707811A EP1718270A1 EP 1718270 A1 EP1718270 A1 EP 1718270A1 EP 05707811 A EP05707811 A EP 05707811A EP 05707811 A EP05707811 A EP 05707811A EP 1718270 A1 EP1718270 A1 EP 1718270A1
Authority
EP
European Patent Office
Prior art keywords
substituted
branched
unbranched
group
acid
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.)
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Application number
EP05707811A
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German (de)
English (en)
Inventor
Gabriele Vielhaber
Karin Jacobs
Heinz-Jürgen BERTRAM
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
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Symrise AG
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Publication date
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Publication of EP1718270A1 publication Critical patent/EP1718270A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • 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
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/08—Preparations for bleaching the hair

Definitions

  • the invention relates to the use of compounds from the group of (2-hydnoxyphenyl) alcohols and their derivatives for lightening skin and / or hair, and to cosmetic or therapeutic formulations which contain the compounds.
  • the usually brown to black colored melanin pigments are formed in the melanocytes of the skin, transferred to the keratinocytes and cause the coloring of the skin or hair.
  • the brown-black eumelanins are mainly formed from hydroxy-substituted aromatic amino acids such as L-tyrosine and L-DOPA, the yellow to red phaeomelanins are additionally formed from sulfur-containing molecules (Cosm ⁇ tics & Toiletries 1996, 111 (5),
  • L-tyrosine the copper-containing key enzyme tyrosinase L-3,4-dihydroxyphenylalanine (L-DOPA) is formed, which in turn is converted to dopachrome by tyrosinase.
  • L-DOPA tyrosinase L-3,4-dihydroxyphenylalanine
  • the latter is oxidized to melanin through several steps catalyzed by different enzymes.
  • Skin-lightening agents are used for various reasons: If the melanin-forming melanocytes in the human skin are not evenly distributed for any reason, pigment spots appear that are either lighter or darker than the surrounding skin areas. To remedy this problem, skin and hair lightening agents are available on the market that help to at least partially compensate for such pigment spots. There is also a need for many people to lighten their naturally dark skin tone or to prevent skin pigmentation.
  • UV-absorbing substances are also used to protect against the increase in skin pigmentation induced by UV light.
  • this is a purely physical effect and must be distinguished from the biological effect of skin-lightening agents on the cellular melanin formation, which can also be demonstrated in the absence of UV light.
  • UV absorbers also do not really lighten the skin, but only prevent the increase in skin pigmentation induced by UV light.
  • hydroquinone In commercial cosmetic or therapeutic skin and hair lightening formulations, hydroquinone, hydroquinone derivatives such as e.g. Arbutin, vitamin C, derivatives of ascorbic acid such as e.g. Ascorbyl palmitate, kpjic acid and derivatives of kojic acid such as Kojic acid dipalmitate used.
  • Hydroquinone has a cytotoxic effect on melanocytes and is irritating to the skin. Therefore, such preparations are not, for example, in Europe, Japan and South Africa for cosmetic applications more permissible. In addition, hydroquinone is very sensitive to oxidation and is difficult to stabilize in cosmetic formulations.
  • Arbutin is a hydroquinone glucoside that hydrolyzes to hydroquinone in situ and is therefore toxicologically as harmful as hydroquinone.
  • Vitamin C and ascorbic acid derivatives have an insufficient effect on the skin. They also do not act directly as tyrosinase inhibitors, but reduce the colored intermediate stages of melanin biosynthesis.
  • Kojic acid (5-hydroxy-2-hydroxymethyl-4-pyranone) is a tyrosinase inhibitor which inhibits its catalytic action by chelating the copper atoms of the enzyme; it is used in commercial skin and
  • Hair lighteners used but has a high sensitizing potential and causes contact allergies.
  • Salicin is widely used in cosmetics as an active ingredient against wrinkles, old, dry and rough skin, as well as protection against inflammation and to promote wound healing.
  • JP 2002275060 A2 describes salicylic acid and salicyl alcohol derivatives as active ingredients which stimulate skin tanning.
  • R 1 is selected from the group consisting of: H, branched or unbranched Ci-Cu alkyl, branched or unbranched C 2 -C 4 alkenyl, branched or unbranched C ⁇ Cw alkynyl, substituted or unsubstituted arylalkyl, cyclohexyl, cyclopentyl, substituted or unsubstituted phenyl, substituted or unsubstituted monosaccharide, SO 3 H, SO 3 Na,
  • R 2 is an enzymatically cleavable substituent or selected from the group consisting of: H, branched or unbranched C 1 -C 4 alkyl, branched or unbranched C ⁇ C ⁇ alkenyl, branched or unbranched C 2 -C 14 -
  • the compounds of formula (I) include their stereoisomers and tautomers as well as any mixtures of these isomers. Furthermore, the compounds of the formula (I) include all associated salts, in particular alkali and alkaline earth salts.
  • Active ingredients are used in cosmetic (including dermatological) and therapeutic skin and hair lightening agents.
  • R 2 is an enzymatically cleavable substituent from the group SO 3 H, SO 3 Na,
  • R is independently selected from the group consisting of: H, -C-C 14 alkyl, C 2 -C 14- alkenyl, C 2 -Ci4-alkynyl, cyclohexyl, cyclopentyl, substituted or unsubstituted phenyl and heterocyclic ring.
  • R 2 is an enzymatically cleavable, substituted or unsubstituted monosaccharide from the group consisting of glucose, mannose or galactose.
  • the latter monosaccharides are preferably in a pyranose form.
  • Substituted monosaccharides include in particular 6'-O-
  • R 1 is selected from the group consisting of: H, branched or unbranched C 1 -C 4 alkyl, branched or unbranched C 2 -C 14 alkenyl, branched or unbranched C 2 -Ci4 alkynyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted monosaccharide, (CH 2 ) ⁇ - ⁇ 0 OH, COR, SR,
  • R, R ' are independently selected from the group consisting of: H and -CC 4 alkyl.
  • R 1 is selected from the group consisting of: H, branched or unbranched C 1 -C 4 alkyl, branched and unbranched C ⁇ -C ⁇ alkenyl, branched or unbranched C 2 -C 4 4 alkynyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted monosaccharide, (CH 2 ) ⁇ - ⁇ oOH, COR, SR,
  • R 2 is selected from the group consisting of: H, branched or unbranched CrCu-alkyl, branched or unbranched C ⁇ Cu alkenyl, branched or unbranched C 2 -C 14 alkynyl and substituted or unsubstituted phenyl.
  • the task is solved in particular by using
  • Saligenin (2-hydroxybenzyl alcohol), fragilin ( ⁇ '-O-acetylsalicin), populin (6-O-benzoylsalicin), tremuloidin (2'-benzoylsalicin), salicortin, 2-O-acetylsalicortin or tremulacin (2-O-benzoylsalicin) for lightening skin and / or hair.
  • Salicin ((hydroxymethyl) phenyl- ⁇ -D-glucopyranoside) is very particularly preferred in the sense of the invention.
  • a second aspect of the invention relates to cosmetic or therapeutic formulations, in particular topical cosmetic formulations which contain an amount of one or more compounds of the formula (I) which lightens skin and / or hair.
  • topical cosmetic formulations which contain an amount of one or more compounds of the formula (I) which lightens skin and / or hair.
  • the cosmetic or therapeutic formulations according to the invention are prepared using conventional methods known per se, in such a way that one or more of the (2-hydroxyphenyl) alcohols used according to the invention are incorporated into cosmetic or dermatological formulations which are composed as usual and in addition to the skin and hair lightening effect can also be used for the treatment, care and cleaning of the skin or hair and as make-up products in decorative cosmetics.
  • the present invention also relates (in particular) to topical cosmetic or therapeutic formulations, in particular cosmetic (including the dermatological) skin and hair lightening compositions which comprise the (2-hydroxyphenyl) alcohols to be used according to the invention in an effective amount, in addition to other, otherwise customary composition components.
  • cosmetic including the dermatological
  • hair lightening compositions which comprise the (2-hydroxyphenyl) alcohols to be used according to the invention in an effective amount, in addition to other, otherwise customary composition components.
  • Formulations according to the invention preferably contain from 0.01% by weight to
  • Emulsions with a low oil content as microemulsions, as gels, as solutions e.g. in oils, alcohols or silicone oils, as pens, as soaps, as aerosols, sprays or foams or as impregnation solutions for cosmetic wipes. It is also advantageous to present the (2-hydroxyphenyl) alcohols in encapsulated form, e.g. in gelatin,
  • Wax materials, liposomes or cellulose capsules Wax materials, liposomes or cellulose capsules. Further customary cosmetic auxiliaries and additives can be present in amounts of 5-99% by weight, preferably 10-80% by weight, based on the total weight of the formulation. Furthermore, the formulations can contain water in an amount of up to 99.99% by weight, preferably 5 to 80% by weight, based on the total weight of the formulation.
  • the (2-hydroxyphenyl) alcohols of formula (I) according to the invention can e.g. extracted from willow bark (Salix purpurea or Salix daphinoides) and purified chromatographically or by two-phase extraction or enzymatically using hydrolases such as e.g. Glycosidases or lipases can be produced from 2-hydroxybenzyl alcohol.
  • the (in particular topical) cosmetic or therapeutic formulations according to the invention can contain cosmetic auxiliaries and additives as are usually used in such preparations, for example Sunscreens, preservatives, bactericides, fungicides, virucides, cooling agents, insect repellents (e.g. DEET, IR 3225, Dragorepel), 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 chitos whose
  • Derivatives include common antioxidants, vitamins (e.g. vitamin C and derivatives, tocopherols and derivatives, vitamin A and derivatives), 2-hydroxycarboxylic acids (e.g. citric acid, malic acid, L-, D- or dl-lactic acid), skin colorants (e.g. walnut extracts or dihydroxyacetone ), skin care agents (e.g. cholesterol, ceramides, pseudoceramides), softening, moisturizing and / or moisturizing substances (e.g. glycerin or urea), fats, oils, saturated fatty acids, mono- or polyunsaturated fatty acids, ⁇ -hydroxy acids, polyhydroxy fatty acids or their derivatives (e.g.
  • linoleic acid ⁇ -linolenic acid, ⁇ -linolenic acid or arachidonic acid and their 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 ethylenediaminetetraacetic acid and deriva te), anti-dandruff agents (e.g. Climbazole, ketoconazole, piroctonoleamine, zinc pyrithione), hair care products,
  • Perfumes anti-foaming substances, dyes, pigments that have a coloring effect, thickeners, surface-active substances, emulators, parts of plants and plant extracts (e.g. arnica, aloe, beard lichen, ivy, nettle, ginseng, henna, chamomile, calendula , Rosemary, sage, horsetail or thyme), animal extracts such as B.
  • the amount of the aforementioned exemplary active ingredients for skin and hair lightening can be in the Cosmetic and dermatological preparations according to the invention are 0.01 to 30% by weight, preferably 0.01 to 20% by weight, particularly preferably 0.01 to 5% by weight, based on the total weight of the preparation.
  • the formulations according to the invention can preferably also contain further active ingredients which stimulate the skin and hair tinting or lightening in a chemical or natural manner. This achieves a faster effect based on synergistic effects.
  • Particularly preferred are substrates or substrate analogs of tyrosinase such as L-tyrosine, L-DOPA or L-dihydroxyphenylalanine, stimulators of tyrosinase activity or expression such as theophylline, caffeine, Proopiornelanocortin-
  • Peptides such as ACTH, alpha-MSH, their peptide analogs and other substances that bind to the melanocortin receptor, purines, pyrimidines, folic acid, phenylalanine derivatives such as e.g. Undecylenoylphenylalanine, diacylglyerols, aliphatic or cyclic diols, psoralens, prostaglandins and their analogues, activators of adenylate cyclase and compounds which the
  • keratinocytes such as serine proteases or agonists of the PAR-2 receptor
  • extracts from plants and parts of plants of the Chrysanthemum species such as serine proteases or agonists of the PAR-2 receptor
  • walnut extracts such as walnut extracts, erytrulose and dihydroxyacetone.
  • the formulations according to the invention can also additionally UV-A and / or UV-B filter substances such as Contain Neo Heliopane®, the total amount of filter substances being 0.1 to 30% by weight, particularly preferably 0.2 to 10% by weight, in particular 0.5 to 5% by weight, based on the total weight of the preparations, where, for example, sunscreens for skin and hair are obtained.
  • UV-A and / or UV-B filter substances such as Contain Neo Heliopane®
  • the total amount of filter substances being 0.1 to 30% by weight, particularly preferably 0.2 to 10% by weight, in particular 0.5 to 5% by weight, based on the total weight of the preparations, where, for example, sunscreens for skin and hair are obtained.
  • Suitable light-treatment agents are, for example, organic UV absorbers from the class of 4-aminobenzoic acid and derivatives, salicylic acid derivatives, benzophenone derivatives, dibenzoylmethane derivatives, diphenylacrylates, 3-imidazol-4-yl-acrylic acid and their esters, benzofuran derivatives, benzylidene malonate Derivatives, polymeric UV absorbers, containing one or more organosilicon residues, cinnamic acid derivatives, camphor derivatives, trianilino-s-triazine derivatives, 2-hydroxyphenylbenzotriazole derivatives, Phenylbenzimidazole sulfonic acid derivatives and their salts, anthranile acid methyl esters, benzotriazole derivatives, indole derivatives.
  • organic UV absorbers from the class of 4-aminobenzoic acid and derivatives, salicylic acid derivatives, benzophenone derivatives, dibenzoylmethan
  • UV absorbers mentioned below, which can be used for the purposes of the present invention, should of course not be limiting.
  • Trimethylammonium -benzylidene-bornan-2-one-methyl sulfate, terephthalylidene-dibornanesulfonic acid and salts, 4-t-butyl-4'-methoxy-dibenzoylmethane, ß-imidazole-4 (5) -acrylic acid (urocanic acid), 2-hydroxy- 4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid, dihydroxy-4-methoxybenzophenone, 2,4-dihydroxybenzophenone,
  • particulate UV filters or inorganic pigments can be used, which can optionally be hydrophobized, such as the oxides of titanium 0 " iO), zinc (ZnO), iron (Fe 2 O 3 ), zirconium (ZrO 2 ), silicon (SiO), manganese (e.g. MnO), aluminum (Al 2 O 3 ), cerium (e.g. Ce 2 O 3 ) and / or mixtures.
  • the formulations according to the invention can also contain (additional) antioxidants or preservatives.
  • antioxidants or preservatives all antioxidants suitable or customary for cosmetic and / or dermatological applications can be used.
  • Antioxidants in the sense of the invention are all substances which reduce the amount of free radicals in cells and tissues. Antioxidants are advantageously selected from the group consisting of amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (eg urocanic acid) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L-
  • Carnosine and its derivatives e.g. anserine
  • carotenoids e.g. anserine
  • carotenes e.g. ⁇ -carotene, ß-carotene, lycopene
  • lipoic acid and their derivatives e.g. dihydroliponic acid
  • aurothioglucose propylthiouracil and other thiols
  • thioredoxin glutathione, cysteine , Cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl
  • Heptathioninsulfoximine in very low tolerable doses (e.g. pmol to ⁇ mol / kg), further (metal) chelators (e.g. ⁇ -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin, ⁇ -hydroxy acids (e.g. citric acid, lactic acid, malic acid), humic acid , Bile acid, bile extracts, tannins, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (e.g.
  • metal chelators e.g. ⁇ -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin, ⁇ -hydroxy acids (e.g. citric acid, lactic acid, malic acid), humic acid , Bile acid, bile extracts, tannins, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated
  • ⁇ -linolenic acid linoleic acid, oleic acid
  • folic acid and their derivatives ubiquinone and ubiquinol and their derivatives
  • vitamin C and derivatives e.g. ascorbyl palmitate, Mg - ascorbyl phosphate, ascorbyl acetate
  • tocopherols and derivatives e.g.
  • vitamin E acetate
  • vitamin A and derivatives vitamin A palmitate
  • coniferyl benzoate of benzoin rutinic acid and its derivatives
  • ferulic acid and its derivatives caffeic acid and its Derivatives
  • sinapic acid and its derivatives curcuminoids and their derivatives
  • retinoids ursolic acid
  • levulinic acid butylated hydroxytoluene
  • butylated hydroxya nisole nordihydroguajakh resin acid
  • nordihydroguajaretic acid trihydroxybutyrophenone
  • uric acid and its derivatives mannose and its derivatives
  • Zinc and its derivatives e.g. ZnO, ZnS04
  • stilbenes e.g. selenium methionine
  • stilbenes and their derivatives e.g. stilbene oxide, trans-
  • Stilbene oxide and the derivatives suitable according to the invention (salts, esters,
  • Ethers sugars, nucleotides, nucleosides, peptides and lipids
  • Natural extracts e.g. from green tea, algae, grape seeds, Wheat germ, Phyllantus emblica, rosemary; Flavonoids, their glycosylated precursors, quercetin, phenolic benzylamines.
  • Coenzymes such as e.g. Coenzyme Q10, plastoquinone, menaquinone, ubiquinols 1-10, ubiquinones 1-10 or derivatives of these substances.
  • the amount of the antioxidants (one or more compounds) in the formulations according to the invention is preferably 0.01 to 20% by weight, particularly preferably 0.05-10% by weight, in particular 0.2-5% by weight, based on the total weight the preparation.
  • vitamin E and / or its derivatives represent the antioxidant (s)
  • vitamin A or vitamin A derivatives or carotenes or their derivatives represent the antioxidant (s)
  • Anti-irritation can here be all active substances which are suitable or customary for cosmetic and / or dermatological applications and which relieve inflammation or relieve redness and itching. All substances which reduce the amount of cytokines, interleukins, prostaglandins and / or leukotrienes in cells and tissues are preferred.
  • Steroidal anti-inflammatory substances of the corticosteroid type are advantageous as anti-inflammatory or anti-redness and anti-itching agents.
  • such as hydrocortisone, dexamethasone, dexamethasone phosphate, methylprednisolone or cortisone the list being expandable by adding further steroidal anti-inflammatories.
  • Nonsteroidal anti-inflammatories can also be used.
  • Oxicams such as Piroxicam or tenoxicam
  • Salicylates such as aspirin, disalcid, solprin or fendosal
  • Acetic acid derivatives such as Didofenac, Fenclofenac, Indomethacin, Sulindac, Tolmetin, or Clindanac
  • Fenamates such as mefenamic, medofenamic, flufenamic or niflumic
  • Propionic acid derivatives such as ibuprofen, naproxen, benoxaprofen or pyrazoles such as phenylbutazone, oxyphenylbutazone, febrazone or
  • Extracts, fractions and active substances from chamomile, aloe vera, Commiphora species, Rubia species, Echinacea species, willows, willow herb, oats, black and green tea, gingko, coffee, pepper, currant, tomato, vanilla, almonds are particularly preferred , as well as pure substances such as Bisabolol, apigenin-7-glucoside, boswellic acid, phytosterols, glycyrrhizic acid, glabridine or licochalkon A.
  • the amount of anti-irritants (one or more compounds) in formulations according to the invention is preferably 0.01 to 20% by weight, particularly preferably 0.03-10% by weight, in particular 0.05-5% by weight, based on the total weight of the Preparation.
  • the formulations according to the invention can contain other humectant regulators.
  • the following substances are used, for example, as moisture regulators: sodium lactate, urea, alcohols, sorbitol, glycerol, propylene glycol, collagen, elastin or hyaluronic acid, diacyl adipates, petrolatum, ectoin, urocanic acid, lecithin, pantheol, phytantriol, lycopene
  • alpha-hydroxy acids e.g. citric acid, lactic acid, malic acid
  • sugars e.g. inosrtol
  • alpha-hydroxy Fatty acids e.g. phytosterols
  • tritic acids such as betulinic acid or ursolic acid
  • the lipid phase in the formulations according to the invention can advantageously be selected from following substance groups: mineral oils (paraffin oil advantageous), mineral waxes, hydrocarbons (squalane or squalene advantageous), synthetic or semi-synthetic triglyceride oils (e.g. triglycerides of capric or caprylic acid), natural oils (e.g. apricot kernel oil, avocado oil, cottonseed oil, borage seed oil, safflower oil, petroleum oil, petroleum oil, petroleum gamma-oryzanol
  • Ethylhexylethylhexanoat Cetearyl-2-ethylhexanoat, 2-Hexyldecylstearat, 2-Octyldecylpalmitat, Oleyloleat, Oleylerucat, Erucyloleat, Erucylerucat as well as synthetic or natural mixtures of such esters), fats, waxes and other natural and synthetic fat bodies, preferably alcohols of lower alcohols -Number (e.g. with isopropanol, propylene glycol or glycerol) or esters of fatty alcohols with alkanoic acids with a low C number or with fatty acids, alkyl benzoates (e.g.
  • n-dodecyl n-tridecyl, n-tetradecyl and n-pentadecyl benzoate
  • cyclic or linear silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof.
  • the aqueous phase of formulations according to the invention 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 analog products, furthermore low C number alcohols, for example ethanol, isopropanol, 1,2-propanediol, glycerol, furthermore ⁇ - or ß-hydroxy acids, preferably lactic acid, citric acid or salicylic acid, in addition emulsifiers, which can advantageously be selected from the group of ionic, nonionic, polymeric, phosphate-containing and zwitterionic emulsifiers, and in particular
  • Polysaccharides or their derivatives e.g. Hyaluronic acid, guar gum, xanthan gum, hydroxypropylmethyl cellulose or allulose derivatives, particularly advantageously from the group of polyacrylates, preferably a polyacrylate from the group of so-called carbopols, in each case individually or in combination or from the group of polyurethanes.
  • the formulations according to the invention advantageously contain coolants.
  • coolants are: I-menthol, menthone glycerol acetal, menthyl lactate, substituted menthyl 3-carboxamides (e.g. menthyl 3-carboxylic acid N-ethylamide), 2-isopropyl-N, 2,3-trimethylbutanamide
  • Acetylglycine methyl ester menthyl hydroxycarboxylic acid ester (e.g. menthyl 3-hydroxybutyrate), monomenthyl succinate 2-mercaptocyclodecanone, menthyl 2-pyrrolidin-5-oncarboxylate.
  • menthyl hydroxycarboxylic acid ester e.g. menthyl 3-hydroxybutyrate
  • monomenthyl succinate 2-mercaptocyclodecanone menthyl 2-pyrrolidin-5-oncarboxylate.
  • compositions according to the invention e.g. topical cosmetic formulations
  • antimicrobial active ingredients examples include:
  • Double or triple bonds including mixed en-in compounds) fatty alcohols, aldehydes and acids of chain lengths C_ to C 40 - Aryl- or aryloxy-substituted unbranched or mono- and polyalkyl-branched saturated or one to five times unsaturated (up to five double or triple bonds, also mixed en-in compounds) alkanediols, dialdehydes and dicarboxylic acids with chain lengths C? to C40, chain lengths C 4 to C 12 are particularly preferred.
  • Mono- and oligoglycerides up to 4 glycerol units
  • fatty alcohols mono- and oligoglycerol monoalkyl ether
  • fatty acids mono- and
  • Oligoglycerol monoalkyl esters are Oligoglycerol monoalkyl esters), alkanediols (mono- and
  • Oligoglycerinmonoalkylether Bis (mono- / oligoglyceryl) alkyl diether) and
  • Dicarboxylic acids (mono- and oligoglycerol monoalkyl esters; bis (mono- / oligoglyceryl) alkyl diesters) of chain lengths C 2 to C 40 .
  • fatty alcohols eg coconut fatty acids, palm kernel fatty acids, wool wax acids.
  • aldehydes eg coconut fatty acids, palm kernel fatty acids, wool wax acids.
  • Mono- and oligoglycerides of lanolin, of lanolin alcohols and lanolin acids e.g. glyceryl lanolate, neocerite
  • glycyrrhezitic acid and derivatives e.g. glycyrrhetinyl stearate
  • Cardenolides e.g. digitoxin, dogoxin, digoxygenin, gitoxygenin, strophanthin and strophanthidine
  • natural and synthetic bufadienolides e.g. scillaren A, scillarenin and bufotalin
  • sapogenins and steroid sapogenins e.g. amyrins, oleanolic acid, digitonin, gitogenin, tigogenin and diosgenin
  • steroid alkaloids of plant and animal origin e.g. tomatidine, solanine, solanidine, conessin, batrachotoxin and homobatrachotoxin).
  • Mono- and oligohydroxy fatty acids of chain lengths C to C 24 eg lactic acid, 2-hydroxypalmitic acid
  • their oligo- and / or polymers as well as vegetable and animal raw materials containing the same.
  • Acydic terpenes hydrocarbons (e.g. ocimen, myrcene), terpene alcohols (e.g. geraniol, linalool, citronellol), terpene aldehydes and ketones (e.g. citral, pseudoionone, ß-ionone); Monocydic particles:
  • Terpene hydrocarbons e.g. Te ⁇ inen, Te ⁇ inolen Limonen
  • Terpene alcohols e.g. terpineol, thymol, menthol
  • Te ⁇ enketone e.g.
  • Pulegon, Carvon Bicydic tephene: terpene hydrocarbons (e.g. caran, pinan, bornan), tephene alcohols (e.g. borneol, isobomeol),
  • Terpene ketones e.g. camphor
  • Sesquiterpenes Acydic sesquiterpenes (e.g. camphor)
  • Bicydic sesquiterpenes e.g. cadins, tendons vetivazulene, guajazulene
  • Tricydic sesquiterpenes e.g. Santalen
  • Dite ⁇ ene e.g. Phytol
  • Tricydic Dite ⁇ ene e.g. Abietic Acid
  • Trite ⁇ ene Squalenoids; e.g.
  • Antimicrobial peptides and proteins with an amino acid number of 4 to 200 e.g. skin antimicrobial peptides (SAPs), lingual antimicrobial peptides (LAPs), human ß-defensins (especially h-BD1 and h-BD2), lactoferrins and their hydrolysates and those derived therefrom Peptides, Bactericidal / Permeability Increasing Proteins [BPIs], Cationic Microbial Proteins [CAPs], Lysozyme.
  • Well-suited carbohydrates or "carbohydrate derivatives" which should also come under the term “carbohydrates” in short, are sugars and substituted sugars or compounds containing sugar residues.
  • the sugars in particular also include the deoxy and dideoxy forms, N-acetyl-galactosamine, N-acetyl glucosamine and sialic acid-substituted derivatives as well as sugar esters and ethers.
  • monosaccharides including in
  • Amylose amylopectin, xanthan, ⁇ -, ⁇ - and ⁇ -dextrin are particularly suitable.
  • the polysaccharides can e.g. from 4 to 1,000,000, especially 10 to
  • Chain lengths are preferably selected in each case which ensure that the active ingredient is soluble in the particular preparation or is to be incorporated into it.
  • Sphingolipids such as sphingosine; N-monoalkylated sphingosines; N, N-dialkylated sphingosines; Sphingosine-1 phosphate; Sphingosine-1 sulfate; psychosine
  • Lysosulfatide sphingosylgalactosyl sulfate; lysocerebroside sulfate); lecithin; sphingomyelin; Sphinganine.
  • So-called "natural" antibacterial agents can also be used, most of which are essential oils.
  • Typical antibacterial oils are, for example, oils from anise, lemon, orange, rosemary, wintergreen, clove, thyme, lavender, hops, citronella, wheat, lemongrass, cedarwood, cinnamon, geranium, sandalwood, violet, eucalyptus,
  • Important antimicrobial substances that can be found in essential oils are, for example, anethole, catechol, camphene,
  • Carvacrol Eugenol, Eucalyptol, Ferulaklare, Famesol, Hinok ' rtiol, Tropolon, Limonen, Menthol, Methylsalicylat, Thymol, Terpineol, Verbenon, Berberin, Curcumin, Caryophyllenoxid, Nerolodol, Geraniol.
  • the amount of active substances in the preparations is preferably 0.01 to 20% by weight, based on the total weight of the preparations, particularly preferably 0.05-10% by weight.
  • the (especially cosmetic, including dermatological) formulations according to the invention may contain deodorants, i.e.
  • Active ingredients with deodorant and antiperspirant properties include, for example, odor maskers, such as the common perfume ingredients, antiperspirants based on aluminum, zirconium or zinc salts, odor absorbers, for example the layered silicates described in patent publication DE-P 40 09 347, of which in particular montmorillonite, kaolinite, nontronite, saponite, hectorite , Smectite, furthermore, for example, zinc salts of ricinoleic acid.
  • odor maskers such as the common perfume ingredients, antiperspirants based on aluminum, zirconium or zinc salts
  • odor absorbers for example the layered silicates described in patent publication DE-P 40 09 347, of which in particular montmorillonite, kaolinite, nontronite, saponite, hectorite , Smectite, furthermore, for example, zinc salts of ricinoleic acid.
  • deodorants bactericidal or
  • the amount of deodorant and / or antiperspirant active ingredients in the formulations is preferably 0.01 to 20% by weight, based on the total weight of the preparations, particularly preferably 0.05-10% by weight.
  • Formulations according to the invention can also contain preservatives. All the antioxidants suitable or customary for cosmetic and / or dermatological applications can be used as preservatives.
  • Classic preservatives e.g. formaldehyde, glutardialdehyde, parabens (e.g. methyl, ethyl, propyl and butyl paraben),
  • Flavonoids e.g. lantadine A, caryophyllene, hesperidin, diosmin, phellandrene, pigenin, quercetin, hypericin, aucubin, diosgenin, plumbagin, corlilagin etc.
  • glycosylated derivatives e.g. glycosyl rutin
  • Formulations according to the invention in particular dermatological formulations, can furthermore advantageously contain dyes and / or color pigments, in particular if they are to be used in the field of decorative cosmetics.
  • the dyes and pigments can be selected from the corresponding positive list in the Cosmetics Ordinance or the EC list of cosmetic colorants. In most cases, they are identical to the colorants approved for food.
  • Advantageous color pigments are, for example
  • Titanium dioxide mica, iron oxides (e.g. Fe 2 O 3 Fe 3 O, FeO (OH)) and / or Tin oxide.
  • Advantageous dyes are, for example, carmine, Berlin blue, chrome oxide green, ultramarine blue and / or manganese violet.
  • dermatological formulations according to the invention are intended for use in the facial area, it is advantageous to choose one or more substances from the following group as the dye:
  • Oil-soluble natural dyes such as e.g. Pepper extracts, ß-carotene or cochineal.
  • dermatological formulations containing pearlescent pigments are also advantageous.
  • Particularly preferred are the types of pearlescent pigments listed below:
  • Natural pearlescent pigments such as
  • Monocrystalline pearlescent pigments such as bismuth oxychloride (BiOCI)
  • Layer-substrate pigments e.g. Mica / metal oxide
  • pearlescent pigments for example, powdered pigments or castor oil dispersions of bismuth oxychloride and / or titanium dioxide and bismuth oxychloride and / or titanium dioxide on mica.
  • powdered pigments or castor oil dispersions of bismuth oxychloride and / or titanium dioxide and bismuth oxychloride and / or titanium dioxide on mica for example, it is particularly advantageous the gloss pigment listed under CIN 77163.
  • pearlescent pigments which are advantageous in the sense of the present invention are obtainable in numerous ways known per se.
  • other substrates besides mica can also be coated with other metal oxides, e.g. Silica and the like.
  • Advantages are e.g. SiO2 particles (“Ronaspheren”) coated with TiO2 and Fe2O3, which are sold by Merck and are particularly suitable for the optical reduction of fine wrinkles.
  • Iron pearlescent pigments which are produced without the use of mica are particularly preferred. Such pigments are e.g. Available under the trade name Sicopearl Kupfer 1000 from BASF.
  • the dyes and pigments can be present either individually or in a mixture and can be coated with one another, different color effects generally being produced by different coating thicknesses.
  • the total amount of dyes and coloring pigments is advantageously in the range of, for example, 0.1% by weight. up to 30% by weight, preferably from 0.5 to 15% by weight, in particular from 1.0 to 10% by weight, in each case based on the total weight of the cosmetic formulations.
  • the amount of active ingredients in the formulations according to the invention is preferably 0.01 to 20% by weight, based on the total weight of the formulation, particularly preferably 0.05-10% by weight.
  • topical formulations according to the invention in particular formulations for lightening the skin and hair, are applied to the skin and / or the hair in a sufficient amount in the manner customary for cosmetics.
  • Example 1 "Oil in water” emulsion
  • 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 6.9).
  • Part C was then added to the mixture of parts A and B at 60 ° C.
  • Part D was added to the mixture of parts A, B, and C at room temperature.
  • Example 2 Water in oil emulsion with UVA / B broadband protection
  • part A all substances except the zinc oxide were heated to 85 ° C. and the zinc oxide was carefully dispersed in the mixture.
  • the components of Part B were mixed, heated to 85 ° C and added to Part A with stirring.
  • Part C was added to the mixture of parts A and B and the mixture was then homogenized using a dispersing tool.
  • Example 3 "Oil in water” emulsion with UVA / B broadband protection
  • Part C added and then the mixture homogenized with a dispersing tool.
  • Example 4 "Oil in water” emulsion with UVA / B broadband protection
  • Part A was heated to 85 ° C. Carbopol and Keltrol were cold dispersed into 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 using a dispersing tool.
  • Example 5 "Oil in water" emulsion with UVA / B broadband protection
  • Part A was heated to 80 ° C. After all components had been dissolved, the mixture was warmed to 85 ° C., Keltrol was added and the mixture was stirred for 5 min. Homogenization was then carried out for 10 minutes using a dispersing tool. The mixture was heated to 85 ° C., part B was added, the mixture was stirred at 80 ° C. for 10 minutes and then homogenized at 60 ° C. Part C. was finally added at room temperature and the mixture was homogenized using a dispersing tool.
  • Example 6 Oil-free sun spray with UVA / B broadband protection
  • the pH of the end product should be between 7.2 to 7.5.
  • Neo Heliopan® Hydro Dissolve two thirds of the sodium hydroxide in water, then add Neo Heliopan® Hydro while stirring. Add the remaining sodium hydroxide until the solution becomes clear.
  • the pH of the finished Neo Heliopan® Hydro solution should be 7.5 -
  • Example 8 Skin-lifting aerosol foam with UVB / UVA protection
  • For Part B disperse Carbopol evenly in water, then add all other raw materials from Part B and heat to 85 ° C. Add part B to part A while stirring. Add part C directly to part AB and let cool. Add part D to part A / B / C and fill in aerosol container.
  • the pH of the end product should be around 7.5.
  • Example 11 Skin lightening hair conditioner with UVB / UVA protection
  • Example 12 Skin Lightening Moisturizer O / W
  • Soak Cabopol in water Heat phases A and B separately to 80 ° C. Add phase B to phase A, then emulsify. Stir under a blade stirrer. Reduce the stirring speed with decreasing temperature. Add the raw materials of phase C at 40 ° C.
  • Example 13 Skin lightening face cream O / W
  • B16V mouse melanoma cells are sown in a 96well microtiter plate in a concentration of 5 x 10 3 cells / well. After 24 h of cultivation at 37 ° C. and 5% CO 2 in RPMI medium, enriched with 10% fetal calf serum, various concentrations of the test substances as well as 0.3 mM tyrosine and 10 nM ⁇ -MSH ( ⁇ -melanocyte stimulating hormones) are added and incubated for another 96 h. The maximum use concentration of the test substances corresponds to 0.1 times the value of the respective IC2o value of the cytotoxicity assay.
  • incubation is carried out with kojisaure as standard in concentrations of 0.01 mM, 0.1 mM and 1 mM. After the incubation, the culture medium with SDS and NaOH (Final concentrations: 1 mM or 1 M) added and the absorption (A) measured after 3 h at 400 nm.
  • the IC » is calculated for each test compound from the inhibition of pigmentation (%) in a series of dilutions of test compounds. This is the concentration of a test compound at which pigmentation is inhibited by 50%.

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Abstract

L'invention concerne l'utilisation de composés du groupe des alcools 2-hydroxyphényle et de leurs dérivés pour éclaircir la peau et/ou les cheveux, ainsi que des formulations cosmétiques ou thérapeutiques contenant les composés du groupe des alcools 2-hydroxyphényle. Dans un premier mode de réalisation, on utilise pour éclaircir la peau et/ou les cheveux, entre autres un composé de formule (I), dans laquelle n = 1 - 10, R<1> signifie un substituant du groupe H, alkyle C1-C14 ramifié ou non ou alcényle ramifié ou non, arylalkyle substitué ou non, cyclohexyl substitué ou non, cyclopentyle substitué ou non, phényle substitué ou non, monosaccharide substitué ou non, SO3, (CH2)1-10OH, COR, SiRR'R", SR, PO3RR' ou un composé de formule (Ia), où R, R', R" représentent indépendamment H, alkyle C1-C14, alcényle C1-C14 ou alkynyle C1-C14, cyclohexyl, cyclopentyle, phényle substitué ou non, ou un noyau hétérocyclique, R<2> désignant un substituant fissible par enzyme ou un substituant sélectionné indépendamment de R<1 >dans le groupe H, alkyle C1-C14 ramifié ou non ou alcényle ramifié ou non, cyclohexyl, cyclopentyle, phényle substitué ou non.
EP05707811A 2004-02-19 2005-01-20 Utilisation d'alcools 2-hydroxyphenyle et formulations cosmetiques ou therapeutiques contenant ces composes Withdrawn EP1718270A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004008035A DE102004008035A1 (de) 2004-02-19 2004-02-19 Verwendung von (2-Hydroxyphenyl)-alkoholen sowie diese Verbindungen enthaltende kosmetische oder therapeutische Formulierungen
PCT/EP2005/050244 WO2005079743A1 (fr) 2004-02-19 2005-01-20 Utilisation d'alcools 2-hydroxyphenyle et formulations cosmetiques ou therapeutiques contenant ces composes

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EP1718270A1 true EP1718270A1 (fr) 2006-11-08

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EP (1) EP1718270A1 (fr)
JP (1) JP2007523127A (fr)
KR (1) KR20070002010A (fr)
CN (1) CN1933801A (fr)
DE (1) DE102004008035A1 (fr)
WO (1) WO2005079743A1 (fr)

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DE102005026006A1 (de) * 2005-06-03 2006-12-07 Beiersdorf Ag Kosmetische Zubereitungen mit einem Gehalt an einem besonderen Anisfruchtextrakt und Triazin-Lichtfiltern
DE102005026007A1 (de) * 2005-06-03 2006-12-07 Beiersdorf Ag Kosmetische Zubereitungen mit einem Gehalt an einem besonderen Anisfruchtextrakt und sulfonierten Lichtfiltern
DE102006055043A1 (de) * 2006-11-17 2008-05-21 Beiersdorf Ag Kosmetische Formulierung mit Glucosylglyceriden und Hautaufhellern
JP5204399B2 (ja) * 2006-12-28 2013-06-05 株式会社ナチュラルネットワーク 食品害虫忌避剤
DE102007013857A1 (de) 2007-03-20 2008-09-25 Maria Clementine Martin Klosterfrau Vertriebsgesellschaft Mbh Neue Zusammensetzungen, insbesondere für die topische Behandlung von Hauterkrankungen
CN102958498B (zh) * 2010-06-24 2015-09-09 赫尔克里士公司 施加在角蛋白基体上以提供长期益处的个人护理组合物添加剂
CA2860624A1 (fr) * 2012-01-05 2013-07-11 Merz North America, Inc. Compositions d'eclaircissement de la peau
CN102626374A (zh) * 2012-04-28 2012-08-08 佛山拜澳生物科技有限公司 一种医用皮肤护理剂及其制备方法
WO2020157494A1 (fr) * 2019-01-30 2020-08-06 Rothamsted Research Ltd Cylodimère de déshydrosalicortine et ses dérivés isolés à partir d'une plante du genre salix pour utilisation dans le traitement du cancer
CN109674743B (zh) * 2019-03-07 2020-06-26 牡丹江医学院 一种伤口护理凝胶及其制备方法

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DE19615577A1 (de) * 1996-04-19 1997-10-23 Beiersdorf Ag Verwendung von Salicin als antiirritativer Wirkstoff in kosmetischen und topischen dermatologischen Zubereitungen
DE19924688A1 (de) * 1999-05-05 2000-11-09 Henkel Kgaa Neue Salicylalkohol-Derivate
EP1366757A1 (fr) * 2002-05-28 2003-12-03 Ciba SC Holding AG Utilisation de composés d'éther hydroxydiphénylique pour le traitement de la peau
CA2499817A1 (fr) * 2002-09-25 2004-04-08 Forbes Medi-Tech Inc. Derives comprenant des sterols et/ou des stanols et des classes specifiques d'agents anti-inflammatoires, et utilisation desdits derives pour le traitement ou la prevention de maladies cardiovasculaires

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KR20070002010A (ko) 2007-01-04
JP2007523127A (ja) 2007-08-16
DE102004008035A1 (de) 2005-09-08
WO2005079743A1 (fr) 2005-09-01
CN1933801A (zh) 2007-03-21

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