WO2008040451A1 - Préparations cosmétiques ou dermatologiques comprenant de l'ester éthylique de la 2-isopropyl-5- méthyl-cyclohexanecarbonyl-d-alanine et un ou plusieurs antioxydants - Google Patents

Préparations cosmétiques ou dermatologiques comprenant de l'ester éthylique de la 2-isopropyl-5- méthyl-cyclohexanecarbonyl-d-alanine et un ou plusieurs antioxydants Download PDF

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Publication number
WO2008040451A1
WO2008040451A1 PCT/EP2007/008185 EP2007008185W WO2008040451A1 WO 2008040451 A1 WO2008040451 A1 WO 2008040451A1 EP 2007008185 W EP2007008185 W EP 2007008185W WO 2008040451 A1 WO2008040451 A1 WO 2008040451A1
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WO
WIPO (PCT)
Prior art keywords
cosmetic
preparations
isopropyl
antioxidants
ethyl ester
Prior art date
Application number
PCT/EP2007/008185
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German (de)
English (en)
Inventor
Julia Eckert
Ludger Kolbe
Gitta Neufang
Original Assignee
Beiersdorf Ag
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
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Publication of WO2008040451A1 publication Critical patent/WO2008040451A1/fr

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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
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/223—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of alpha-aminoacids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/002—Aftershave preparations
    • 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
    • A61Q19/10—Washing or bathing preparations
    • 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
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24—Thermal properties
    • A61K2800/244—Endothermic; Cooling; Cooling sensation

Definitions

  • Cosmetic or dermatological preparations containing 2-isopropyl-5-methyl-cyclohexanecarbonyl-D-alanine ethyl ester and one or more antioxidants containing 2-isopropyl-5-methyl-cyclohexanecarbonyl-D-alanine ethyl ester and one or more antioxidants
  • the present invention relates to cosmetic or dermatological preparations containing 2-isopropyl-5-methylcyclohexanecarbonyl-D-alanine ethyl ester and one or more antioxidants.
  • the present invention relates, in a particular embodiment, to cosmetic or pharmaceutical preparations with a reduced tack feeling, processes for their preparation and the use of active ingredients for reducing the stickiness of cosmetic preparations.
  • the present invention relates to cosmetic and dermatological preparations with a long-lasting cooling effect, in particular skin-care cosmetic and dermatological preparations.
  • the present invention relates to cosmetic and dermatological preparations with reduced skin irritation.
  • cooling agents which interact with the heat receptors of the skin and thus trigger a sensation of cold without generating a measurable physical cooling
  • menthol and various menthol derivatives Rescolate, Physcool, Questice L, etc.
  • high ethanol contents as well as menthol and its derivatives are not suitable for numerous applications under olfactory aspects in addition to the irritative potential, in particular because of their distinct inherent odor Frequently enough, such substances also simultaneously increase the circulation, which on the contrary causes a feeling of warmth.
  • cooling agents in particular ammonium salts
  • cooling preparations are also widely used isopropanolic gels with camphor and menthol additive.
  • a further object of the present invention was to provide preparations which markedly improve the condition of the skin, in particular reduce skin roughness.
  • an object of the present invention to provide products with the widest possible variety of applications available.
  • principles should be created for preparation forms such as cleansing emulsions, face and body care preparations, but also pronounced medical-pharmaceutical dosage forms, for example preparations for acne and other skin conditions.
  • 2-Isopropyl-5-methylcyclohexanecarbonyl-D-alanine ethyl ester is characterized by the following structure:
  • the antioxidants are selected from the group consisting of amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (eg urocaninic acid) and derivatives thereof, peptides such as D, L-carnosine, D-carnosine, L-carnosine.
  • amino acids eg glycine, histidine, tyrosine, tryptophan
  • imidazoles eg urocaninic acid
  • peptides such as D, L-carnosine, D-carnosine, L-carnosine.
  • Carnosine and its derivatives eg anserine
  • carotenoids eg ⁇ -carotene, ⁇ -carotene, lycopene
  • their derivatives derivatives eg dihydroliproic acid
  • unsaturated fatty acids and their derivatives eg .gamma.-linolenic acid, linoleic acid, oleic acid
  • ubiquinone and ubiquinol and their derivatives eg ascorbyl palmitate , Mg ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (eg vitamin E acetate), vitamin A and derivatives (vitamin A palmitate) and flavonoids such as rutinic acid and its derivatives, ⁇ -glycosylrutin, catechins (epicatechin), isoflavonoids, ferulic acid , furfuryl furylidenglucitol, butylhydroxytoluene, man
  • the preparations are characterized in that they contain 0.001% by weight to 10% by weight, preferably 0.05% by weight to 5% by weight, in particular 0.1-2, 0 wt .-%, based on the total weight of the preparations, of one or more antioxidants.
  • the antioxidants used in the invention are selected from the group of flavonoids and isoflavones.
  • the active substance (s) selected from the group of flavones, flavanones and flavonoids in the narrower sense are also subsumed in the context of the present invention under the generic term "flavonoids”.
  • Flavone and its derivatives are characterized by the following basic structure (substitution positions given):
  • flavones usually occur in glycosidated form.
  • Flavonoids in the narrower sense are glycosides of flavones, flavanones whose backbone is characterized by the following structure:
  • the flavonoids are preferably selected from the group of substances of the generic structural formula
  • Z 1 - Z 7 are independently selected from the group H, OH, alkoxy and hydroxyalkoxy, wherein the alkoxy or hydroxyalkoxy groups can be branched and unbranched and 1-18 have C atoms, and wherein GIy is selected from the group of mono- and oligoglycoside radicals.
  • the flavonoids can also be chosen advantageously from the group of substances of the generic structural formula
  • Z 1 - Z 6 are independently selected from the group H, OH, alkoxy and hydroxyalkoxy, where the alkoxy or hydroxyalkoxy groups can be branched and unbranched and 1-18 have C atoms, and wherein GIy is selected from the group of mono- and oligoglycoside radicals.
  • such structures can be selected from the group of substances of the generic structural formula
  • GIy 1 , GIy 2 and GIy 3 are independently monoglycoside or. GIy 2 or GIy 3 can also individually or together represent hydrogen atom saturation.
  • GIy 1 , GIy 2 and GIy 3 are independently selected from the group of hexosyl radicals, in particular the rhamnosyl radicals and glucosyl radicals.
  • hexosyl radicals for example allosyl, altrosyl, galactosyl, gulosyl, idosyl, mannosyl and talosyl, may also be advantageous to use. It may also be advantageous according to the invention to use pentosyl radicals.
  • Z 1 - Z 5 are independently selected from the group H, OH, methoxy, ethoxy and 2-hydroxyethoxy, and the flavone glycosides have the structure
  • Glyi, Gly 2 and Gly 3 independently represent monoglycoside radicals or.
  • GIy 2 or GIy 3 can also individually or together represent hydrogen atom saturation.
  • GIy 1 , GIy 2 and GIy 3 are independently selected from the group of hexosyl radicals, in particular the rhamnosyl radicals and glucosyl radicals.
  • hexosyl radicals for example allosyl, altrosyl, galactosyl, gulosyl, idosyl, mannosyl and talosyl, may also be advantageous to use. It may also be advantageous according to the invention to use pentosyl radicals.
  • flavone glycoside (s) from the group ⁇ -glucosylrutin, ⁇ -glucosylmyricetin, ⁇ -glucosylisoquercitrin, ⁇ -glucosylisoquercetin and ⁇ -glucosylquercitrin.
  • a particularly advantageous flavonoid according to the invention is ⁇ -glucosylrutin. It is characterized by the following structure:
  • naringin aurantiine, naringenin-7-rhamnoglucoside
  • hesperidin (3 ', 5,7-trihydroxy-4'-methoxyflavanone-7-rutinoside, hesperidoside, hesperetin-7-O-rutinoside). It is characterized by the following structure:
  • rutin (3, 3 ', 4', 5, 7-pentahydroxyfly of 3-rutinoside, quercetin-3-rutinoside, sophorin, birutane, rutabion, taurutin, phytomelin, melin). It is characterized by the following structure:
  • roxerutin (3,5-dihydroxy-3 ', 4', 7-tris (2-hydroxyethoxy) flavone-3- (6-O- (6-deoxy- ⁇ -L -mannopyranosyl) - ⁇ -D-glucopyranoside)). It is characterized by the following structure:
  • Another particularly advantageous flavonoid according to the invention is monoxerutin (3,3 ', 4', 5-tetrahydroxy-7- (2-hydroxyethoxy) flavone-3- (6-O- (6-deoxy- ⁇ -L-mannopyranosyl) - ⁇ -D-glucopyranoside)). It is characterized by the following structure:
  • dihydrorobinetine (3,3 ', 4', 5 ', 7-pentahydroxyflavanone). It is characterized by the following structure:
  • taxifolin (3, 3 ', 4', 5,7-pentahydroxyflavanone). It is characterized by the following structure:
  • eriodictyol-7-glucoside (3 ', 4', 5,7-tetrahydroxyflavanone-7-glucoside). It is characterized by the following structure:
  • flavanomare ⁇ n (3 ', 4', 7, ⁇ -Tetrahydroxyf ⁇ avanon-7-glucoside). It is characterized by the following structure:
  • isoquercetin (3, 3 ', 4', 5, 7-pentahydroxyflavanone-3- ( ⁇ -D-glucopyranoside), which has the following structure:
  • the flavonoid or flavonoids are advantageously according to the invention in cosmetic or dermatological preparations preferably to 0.001 wt .-% to 10 wt .-%, preferably to 0.05 wt .-% to 5 wt .-%, particularly preferably to 0.1 - , 0 wt .-%, based on the total weight of the preparations.
  • Isoflavones are flavonoids, sometimes referred to as isoflavonoids, a group of mostly yellowish plant dyes derived from isoflavone.
  • the unsubstituted body, the actual isoflavone (3-phenylchromone, 3-phenyl-4H-1-benzopyran-4-one) occurs in clover species.
  • isoflavones are daidzeen (4 ', 7-dihydroxy-isoflavone), as 7-O-glucoside daidzin in soybean meal; Genistein (4 ', 5,7-trihydroxy-isoflavone) from soybeans and red clover; Prunetin (4 ', 5-dihydroxy-7-methoxy-isoflavone) from the bark of plum trees; Biocharin A (5,7-dihydroxy-4'-methoxy-isoflavone) from chick peas, red clover and other clover species; Orobol (3 ', 4', 5,7-tetrahydroxy isoflavone); Santal (3 ', 4', 5-trihydroxy-7-methoxy-isoflavone) from sandalwood, redwood and other woods; Pratense ⁇ n (3 ', 5,7-trihydroxy-4'-methoxyiso- flavone) from fresh red or meadow clover.
  • Suitable isoflavones to be used according to the invention are preferably the isoflavones listed in the table above.
  • Genistein 5,7-dihydroxy-3- (4-hydroxyphenyl) -4H-1-benzopyran-4-one, 4 ', 5,7-trihydroxyisoflate, also called differenol A, prunetol and sophoricol, has the following structure :
  • Genistein is a secondary metabolite of plants (legumes, papilionoids, rosaceae), but has also been found in cultures of microorganisms (Actinomycetes, Aspergillus, Mycobacteria). Low estrogens and antibacterial effects have been described.
  • Cosmetic or dermatological preparations according to the invention preferably contain 0.001-10% by weight, particularly preferably 0.01-1% by weight, of one or more isoflavonoids, based on the total composition of the preparations.
  • the cosmetic or dermatological preparations may be composed as usual and used for the treatment, care and cleansing of the skin and / or the hair and as a make-up product in decorative cosmetics.
  • They preferably contain from 0.001% by weight to 10% by weight, preferably from 0.05% by weight to 5% by weight, in particular from 0.1% to 2.0% by weight, based on the total weight of the preparations, 2-isopropyl-5-methylcyclohexanecarbonyl-D-alanine ethyl ester.
  • Cosmetic and dermatological preparations according to the invention can be present in various forms.
  • they may contain a solution, an anhydrous preparation, an emulsion or microemulsion of the water-in-oil (W / O) type or of the oil-in-water (O / W) type, a multiple emulsion, for example water-type. in-oil-in-water (W / O / W), a gel, a solid stick, an ointment or even an aerosol.
  • folic acid and / or its derivatives in encapsulated form, for example in collagen matrices and other customary encapsulating materials, for example as encapsulated encapsulations, in gelatin, wax matrices or liposomally encapsulated.
  • wax matrices as described in DE-OS 43 08 282 have been found to be favorable.
  • the cosmetic and dermatological preparations according to the invention may comprise cosmetic adjuvants conventionally used in such preparations, for example preservatives, bactericides, perfumes, foaming inhibitors, colorants, pigments having a coloring effect, thickeners, surface-active substances, emulsifiers, softening, moisturizing and / or moisturizing substances, fats, oils, waxes or other customary constituents of a cosmetic or dermatological formulation, such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • cosmetic adjuvants conventionally used in such preparations, for example preservatives, bactericides, perfumes, foaming inhibitors, colorants, pigments having a coloring effect, thickeners, surface-active substances, emulsifiers, softening, moisturizing and / or moisturizing substances, fats, oils, waxes or other customary constituents of a cosmetic or dermatological formulation, such as alcohols, polyols, poly
  • the lipid phase can advantageously be selected from the following substance group: mineral oils, mineral waxes
  • Oils such as triglycerides of capric or caprylic acid, further natural oils such as e.g. Castor oil;
  • Fats, waxes and other natural and synthetic fats preferably esters of fatty acids with lower C-number alcohols, e.g. with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low C number or with fatty acids; benzoates;
  • Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof.
  • the oil phase of the emulsions, oleogels or hydrodispersions or lipodispersions in the context of the present invention is advantageously selected from the group of esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of 3 to 30 carbon atoms and saturated and / or or unsaturated, branched and / or unbranched alcohols having a chain length of 3 to 30 carbon atoms, from the group of esters of aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols having a chain length of 3 to 30 carbon atoms.
  • ester oils can then advantageously be selected from the group isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate, isononyl isononanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexyldecyl stearate, 2 Octyldodecyl palmitate, oleyl oleate, oleyl erucate, erucyl oleate, erucyl erucate and also synthetic, semisynthetic and natural mixtures of such esters, eg jojoba oil.
  • the aqueous phase of the preparations according to the invention optionally advantageously contains alcohols, diols or polyols of low C number, and their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or -mob nobutyl ether, propylene glycol monomethyl, -monoethyl- or monobutyl ether , Diethylene glycol monomethyl or monoethyl ether and analogous products, furthermore low-C alcohols, for example ethanol, isopropanol, 1,2-propanediol, glycerol and, in particular, one or more thickeners, which may advantageously be selected from the group silicon dioxide, Aluminum silicates, polysaccharides or their derivatives, for example hyaluronic acid, xanthan gum, hydroxypropylmethylcellulose, particularly advantageously from the group of the polyacrylates, preferably a polyacryl
  • mixtures of the abovementioned solvents are used.
  • alcoholic solvents water can be another ingredient.
  • Emulsions of the invention are advantageous and contain e.g. the said fats, oils, waxes and other fatty substances, as well as water and an emulsifier, as commonly used for such a type of formulation.
  • Gels according to the invention usually contain low C number alcohols, e.g. Ethanol, isopropanol, 1, 2-propanediol, glycerol and water or an above-mentioned oil in the presence of a thickener which is preferably silica or an aluminosilicate in oily-alcoholic gels, in aqueous-alcoholic or alcoholic gels, preferably a polyacrylate.
  • a thickener which is preferably silica or an aluminosilicate in oily-alcoholic gels, in aqueous-alcoholic or alcoholic gels, preferably a polyacrylate.
  • Suitable propellants for preparations which can be sprayed from aerosol containers according to the invention are the customary known highly volatile, liquefied propellants, for example hydrocarbons (propane, butane, isobutane), which can be used alone or mixed with one another. Also, compressed air is advantageous to use.
  • preparations according to the invention may also contain substances which absorb UV radiation in the UVB range, the total amount of the filter substances For example, 0.1 wt .-% to 30 wt .-%, preferably 0.5 to 10 wt .-%, in particular 1, 0 to 6.0 wt .-%, based on the total weight of the preparations to cosmetic preparations to provide the hair or the skin against the entire range of ultraviolet radiation. They can also serve as a sunscreen for hair or skin.

Abstract

La présente invention concerne des préparations cosmétiques ou dermatologiques comprenant de l'ester éthylique de la 2-isopropyl-5-méthyl-cyclohexanecarbonyl-D-alanine et un ou plusieurs antioxydants.
PCT/EP2007/008185 2006-09-29 2007-09-20 Préparations cosmétiques ou dermatologiques comprenant de l'ester éthylique de la 2-isopropyl-5- méthyl-cyclohexanecarbonyl-d-alanine et un ou plusieurs antioxydants WO2008040451A1 (fr)

Applications Claiming Priority (2)

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DE102006047155.5 2006-09-29
DE200610047155 DE102006047155A1 (de) 2006-09-29 2006-09-29 Kosmetische oder dermatologische Zubereitungen mit einem Gehalt an 2-Isopropyl-5-Methyl-Cyclohexancarbonyl-D-Alaninethylester und einem oder mehreren Antioxidantien

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WO2008040451A1 true WO2008040451A1 (fr) 2008-04-10

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DE102013112065A1 (de) * 2013-11-01 2015-05-07 Minasolve Germany Gmbh Stabile Lösungen mit physiologischem Kühlreagenz und deren Verwendung

Citations (4)

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Publication number Priority date Publication date Assignee Title
DE2205255A1 (fr) * 1971-02-04 1972-11-30
WO2002030367A2 (fr) * 2000-10-10 2002-04-18 The Procter & Gamble Company Systeme de conditionnement pour objet presentant une forme determinee
WO2002032381A2 (fr) * 2000-10-10 2002-04-25 The Procter & Gamble Company Compositions cosmetiques emballees destinees au cuir chevelu
EP1639993A1 (fr) * 2003-06-17 2006-03-29 Takasago International Corporation Composition de shampooing ou de nettoyage corporel

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Publication number Priority date Publication date Assignee Title
DE4342560A1 (de) * 1993-12-14 1995-06-22 Marbert Gmbh Ectoin und Ectoinderivate als Feuchtigkeitsspender in Kosmetikprodukten
DK0900211T3 (da) * 1996-04-23 2003-10-27 Upjohn Co Thiadiazolyl(thio)urinstoffer, der er nyttige som matrixmetalloproteaseinhibitorer
TW544310B (en) * 1998-04-02 2003-08-01 Ajinomoto Kk Amino acid derivatives and anti-inflammatory agents

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2205255A1 (fr) * 1971-02-04 1972-11-30
WO2002030367A2 (fr) * 2000-10-10 2002-04-18 The Procter & Gamble Company Systeme de conditionnement pour objet presentant une forme determinee
WO2002032381A2 (fr) * 2000-10-10 2002-04-25 The Procter & Gamble Company Compositions cosmetiques emballees destinees au cuir chevelu
EP1639993A1 (fr) * 2003-06-17 2006-03-29 Takasago International Corporation Composition de shampooing ou de nettoyage corporel

Non-Patent Citations (1)

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Title
WATSON H R ET AL: "NEW COMPOUNDS WITH THE MENTHOL COOLING EFFECT", JOURNAL OF THE SOCIETY COSMETIC CHEMISTS, SOCIETY OF COSMETIC CHEMISTS,, US, vol. 29, no. 4, 1978, pages 185 - 200, XP009045124, ISSN: 0037-9832 *

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