WO2009087242A2 - Compositions comprising trans-tert-butyl cyclohexanol as skin irritation-reducing agent - Google Patents
Compositions comprising trans-tert-butyl cyclohexanol as skin irritation-reducing agent Download PDFInfo
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- WO2009087242A2 WO2009087242A2 PCT/EP2009/054336 EP2009054336W WO2009087242A2 WO 2009087242 A2 WO2009087242 A2 WO 2009087242A2 EP 2009054336 W EP2009054336 W EP 2009054336W WO 2009087242 A2 WO2009087242 A2 WO 2009087242A2
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- 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
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C11/00—Milk substitutes, e.g. coffee whitener compositions
- A23C11/02—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins
- A23C11/10—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins containing or not lactose but no other milk components as source of fats, carbohydrates or proteins
- A23C11/103—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins containing or not lactose but no other milk components as source of fats, carbohydrates or proteins containing only proteins from pulses, oilseeds or nuts, e.g. nut milk
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C9/00—Milk preparations; Milk powder or milk powder preparations
- A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
- A23C9/13—Fermented milk preparations; Treatment using microorganisms or enzymes using additives
- A23C9/1307—Milk products or derivatives; Fruit or vegetable juices; Sugars, sugar alcohols, sweeteners; Oligosaccharides; Organic acids or salts thereof or acidifying agents; Flavours, dyes or pigments; Inert or aerosol gases; Carbonation methods
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L11/00—Pulses, i.e. fruits of leguminous plants, for production of food; Products from legumes; Preparation or treatment thereof
- A23L11/60—Drinks from legumes, e.g. lupine drinks
- A23L11/65—Soy drinks
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/02—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation containing fruit or vegetable juices
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/385—Concentrates of non-alcoholic beverages
- A23L2/39—Dry compositions
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0216—Solid or semisolid forms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0216—Solid or semisolid forms
- A61K8/0229—Sticks
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/005—Preparations for sensitive skin
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- 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
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/75—Anti-irritant
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- 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
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/87—Application Devices; Containers; Packaging
- A61K2800/874—Roll-on
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- 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
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/92—Oral administration
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61Q15/00—Anti-perspirants or body deodorants
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- 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
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
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- A—HUMAN NECESSITIES
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- A61Q19/04—Preparations for care of the skin for chemically tanning the skin
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- A—HUMAN NECESSITIES
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- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
Definitions
- Capsaicin is a natural agonist of the Transient Receptor Potential V1 (TRPV1 , vanilloid receptor, VR1 ).
- TRPV1 Transient Receptor Potential V1
- VR1 Transient Receptor Potential V1
- TRPV1 is expressed on central and peripheral neurons.
- Different types of stimuli activate the receptor such as low pH ( ⁇ 5.9), noxious heat (> 42°C), the cannabinoid/endovanilloid anandamide, leukotriene B4 and exogenous capsaicin.
- TRPV1 is stimulated to either transmit burning pain or a burning pruritus.
- trans-4-tert-butyl cyclohexanol as skin irritation-reducing agent, in particular for
- US 2,927,127 discloses that hydrogenation of p-tert-butyl phenol with a Ni catalyst yields p-tert-butyl cyclohexanol having proportions of approximately 30% cis-isomer and approximately 70% trans-isomer. US 2,927,127 further describes the hydrogenation of p- tert-butyl phenol using Rh/C as catalyst in ethanol to yield p-tert-butyl cyclohexanol containing 87.5% of the cis-isomer, which was subsequently converted to the corresponding acetates by reaction with acetic anhydride.
- EP 0 755 910 relates to a process for preparing 4-tert-butyl cyclohexanol predominantly containing the cis-isomer by hydrogenation of p-tert-butyl phenol.
- the hydrogenations according to EP 0 755 910 can be carried out in various solvents, e.g. alkanes, cyclic alkanes, acyclic ethers or alcohols like ethanol, iso-propanol or 4-methyl-2-pentanol are mentioned.
- Steffen Arctander describes 4-tert-butyl cyclohexanol in "Perfume and Flavor Chemicals", private publication, Montclair, N.J., 1969, entry 433, as having an extremely dry, woody- camphoraceous odour with leather-like undertones which can used in artificial patchouli oils and to lend power, diffusiveness and radiance to soap fragrances. No information is given regarding the cis- and/or trans-isomer ratio.
- GB 1 ,580,184 discloses a fragrance mixture in form of a patchouli base comprising about 4.9 wt. % of p-tert-butyl cyclohexanol. No information is given regarding the cis- and/or trans-isomer content of the p-tert-butylcyclohexanol used therein.
- WO 2008/117254 decribes a perfuming composition of the patchouli type comprising p- tert-butyl cyclohexanol in an amount of 12.94 wt.%.
- Said perfuming composition contains dipropylene glycol at a level of 7.09 wt.%, based on the total weight of said perfuming composition.
- No information is given regarding the cis- and/or trans-isomer content of the p-tert-butylcyclohexanol used therein.
- US 5,858,958 relates to the use of 4-tert-butyl cyclohexanol as antioxidant, in particular as stabilizing agent against oxidation in cleaning or cosmetic products.
- a perfume oil comprising 10 wt.% of p-tert-butyl cyclohexanol which was incorporated into a soap base resulting in amounts of 0.15 to 0.2 wt.% of 4-tert-butyl cyclohexanol in the final soap.
- US 5,858,958 is overall silent regarding the cis- and/or trans-isomer content of the 4-tert-butylcyclohexanol used therein.
- a (topical) formulation according to the present invention comprising trans-4- tert-butyl cyclohexanol or a cosmetically or pharmaceutically acceptable salt thereof is suitable for topical application on human skin, preferably used for application in the region of the head.
- Such a medicament can be employed in the field of human medicine against a large number of pains and diseases, such as, for example, urticaria, contact dermatitis, atopy and generally all inflammation processes, included tooth and gum inflammations, such as parodontosis.
- pains and diseases such as, for example, urticaria, contact dermatitis, atopy and generally all inflammation processes, included tooth and gum inflammations, such as parodontosis.
- the pure cis-isomer and the pure trans-isomer of racemic 4-tert-butyl cyclohexanol were tested separately for TRPV1 antagonism at parallel application with capsaicin as agonist. It was found that the pure trans-isomer was significantly more active than a 50/50 mixture of cis- and trans-isomer, whereas the pure cis-isomer was inactive.
- trans-4-tert-butyl cyclohexanol is a very effective, highly specific TRPV1 antagonist in vitro as well as in vivo.
- trans-isomer of 4-tert- butyl cyclohexanol was shown to be the bioactive, TRPV1 antagonizing isomer.
- the cis-isomer has a marked, unpleasant earthy odour which was clearly stronger than that of the trans-isomer and which was clearly perceivable at a dosage of 1 wt. % in a non-perfumed cosmetic composition.
- This odour makes the cis-isomer far less suitable for (topical) cosmetic formulations at higher dosages, in particular at use level above 0.3 wt.%, based on the total weight of the cosmetic composition. It was also found that the trans-isomer exhibits only a weak odour which is not or only slightly perceivable at a dosage of 1 wt.% in a non-perfumed cosmetic composition.
- trans-4-tert-butyl cyclohexanol is a solid at
- trans-4-tert-butyl cyclohexanol rather difficult to handle and to store, in particular in (topical) cosmetic compositions and products, in particular those comprising water in an amount of 10 wt.% or more, based on the total weight of the formulation or product, or comprising a water and an oil phase (e.g. O/W- or W/O- emulsions).
- water in an amount of 10 wt.% or more, based on the total weight of the formulation or product, or comprising a water and an oil phase (e.g. O/W- or W/O- emulsions).
- Preferred formulations and products according to the invention comprising (preferred) cosmetically acceptable carriers and fragrance materials mentioned (in particular those with higher Clog P values) were found to have improved stability (regarding the sublimation and/or (re-)crystallization properties of trans-4-tert-butyl cyclohexanol), in particular in (topical) cosmetic composition and products, in particular those comprising water (preferably in an amount of 10 to 95 wt.%, more preferably 25 to 90 wt.%, even more preferably 40 to 90 wt.%, in each case based on the total weight of the composition or product), and in (topical) cosmetic composition and products comprising water and an oil phase (e.g. O/W or W/O-emulsions).
- the present invention thus also relates to a concentrated composition comprising or consisting of
- compositions are easy to handle and stable over a prolonged period of time (even at lower temperatures of about +1O 0 C), typically more than 3 months, preferably more than 6 months (at + 5 0 C), without trans-4-tert-butyl cyclohexanol crystallizing out of these compositions.
- compositions comprising one or more (alkane) diols having 3 to 10 carbon atoms prepared according to the invention are readily further processable, in particular for (topical) cosmetic purposes.
- the present invention als relates to the use of such a concentrated composition for the preparation of a cosmetic formulation or product or for the preparation of a medicament.
- the one or more cosmetically acceptable carriers b) are selected from the group consisting of
- a cosmetically acceptable carrier having a Clog P value of at least 4, preferably of at least 5, more preferably of at least 6, and preferably selected from groups (ii-1 ) and/or (ii- 2) and/or (ii— 3) or mixtures thereof, said groups consisting of
- esters having 6 to 36 carbon atoms preferably monoesters, diesters or triesters, preferably selected from the group consisting of diethyl phthalate, diethylhexyl 2,6- naphthalate, isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate, isononyl isononanoate, 3,5,5-trimethylhexyl 3,5,5-trimethylhexanoate, 2-ethylhexyl isononanoate, 2-ethylhexyl 3,5,5-trimethylhexanoate, 2-ethylhexyl 2-ethylhexanoate, 2- ethylhexanoate
- the weight ratio as described above of trans-4-tert- butyl cyclohexanol to cis-4-tert-butyl cyclohexanol, if present, is 75 : 25 or greater, preferably greater than 80 : 20, more preferably greater than 90 : 10, most preferably greater than 95 : 5..
- the Clog P value (also known as log Pow) is the decimal logarithm of the distribution coefficient of a substance or material between 1-octanol to water.
- Clog P values are well known in the chemical arts as a calculated value that represents the relative affinity that a substance or material has for partitioning between octanol and water. Clog P values can be obtained or calculated as described and referenced in WO 2008/114189.
- compositions or products comprising one or more cosmetically acceptable carriers b) according to the invention are easy to handle and stable over a long period of time, typically more than 3 months, preferably more than 6 months, without trans-4-tert- butyl cyclohexanol crystallizing out of these compositions, which is particularly of importance in (cosmetic) compositions or (cosmetic) products comprising water in an amount of 10 wt.% or more, based on the total weight of the formulation or product, or comprising a water and an oil phase, in particular emulsions, e.g. of the O/W- or W/O- type.
- compositions are readily further processable, in particular for (topical) cosmetic purposes.
- compositions and products according to the present invention advantageously comprise a total amount of 5 to 70 wt.%, preferably 7.5 to 60 wt.%, more preferably 10 to 50 wt.%, even more preferably 10 - 40 wt.%, of the one or more (preferred) cosmetically acceptable carriers b), in each case based on the total weight of the composition or product.
- compositions and products in particular emulsions having a water content of more than 40 wt.%, based on the total weight of the emulsion
- had improved storage stability more than 3 months, generally more than 5 months
- a total amount of 15 wt.% or more (preferably up to 30 wt.%) of the one or more (preferred) cosmetically acceptable carriers b) were present in case the amount of trans- 4-tert-butyl cyclohexanol was higher than 0.5 wt.% to about 1.0 wt.%,
- a total amount of 20 wt.% or more (preferably up to 35 wt.%) of the one or more (preferred) cosmetically acceptable carriers b) were present in case the amount of trans- 4-tert-butyl cyclohexanol was higher than 1.0 wt.% to about 2.0 wt.%,
- compositions and products according to the present invention comprise water in an amount of up to 98 wt.%, preferably 10 to 95 wt.%, more preferably 25 to 90 wt.%, in each case based on the total weight of the composition or product.
- a composition or product according to the present invention additionally comprises one or more fragrance materials, preferably having a Clog P value of at least 3, preferably of at least 4, more preferably of at least 5.
- suitable fragrance materials are mentioned in S. Arctander, Perfume and Flavor Chemicals, Vol. I and II, Montclair, N. J., 1969, self-published or H. Surburg and J. Panten, Common Fragrance and Flavor Materials, 5th. Ed., Wiley-VCH, Weinheim 2006, particularly those explicitly mentioned in US 2008/0070825.
- compositions and products according to the present invention advantageously comprise a total amount of 0.1 to 5 wt.%, preferably 0.2 to 4 wt.%, more preferably 0.25 to 3 wt.%, even more preferably 0.3 - 2.5 wt.%, of the one or more (preferred) fragrance materials, in each case based on the total weight of the composition or product.
- a composition or product according to the present invention additionally comprises one or more of fragrance materials having a boiling point of 25O 0 C or greater (at 1013 mbar).
- the total amount of fragrance materials selected from the above group preferably having a boiling point of 25O 0 C or greater at 1013 mbar, preferably is at least 10 wt.%, more preferably at least 20 wt.%, based on the total amount of fragrance materials present in a composition or product according to the present invention.
- a composition or product according to the present invention is - in contrast to WO 2008/117254 - free of 2,6,10,10-Tetramethyl-1- oxaspiro[4.5]decan-6-ol (CAS number 65620-50-0 ).
- compositions according to the present invention advantageously additionally comprise one or more actives providing a benefit for the skin, in particular other skin irritation- reducing or skin-soothing agents, preferably selected from the group consisting of antiinflammatory agents, physiological cooling agents, compounds that alleviate itching and/or compounds that alleviate reddening which are suitable for cosmetic and/or dermatological applications.
- actives providing a benefit for the skin, in particular other skin irritation- reducing or skin-soothing agents, preferably selected from the group consisting of antiinflammatory agents, physiological cooling agents, compounds that alleviate itching and/or compounds that alleviate reddening which are suitable for cosmetic and/or dermatological applications.
- composition according to the present invention comprise the one or more actives selected from the groups consisting of:
- steroidal anti-inflammatory substances of the corticosteroid type in particular hydrocortisone, hydrocortisone derivatives such as hydrocortisone 17-butyrate, dexamethasone, dexamethasone phosphate, methylprednisolone or cortisone; and/or
- pure substances preferably alpha-bisabolol, apigenin, apigenin-7-glucoside, gingerols, shogaols, gingerdiols, dehydrogingerdiones, paradols, natural avenanthramides, non-natural avenanthramides, preferably dihydroavenanthramide D, boswellic acid, phytosterols, glycyrrhizin, glabridin and licochalcone A; and/or (v) skin care agents, preferably skin moisture retention regulators or skin repair agents, preferably selected from the group consisting of sodium lactate, urea and derivatives, glycerol, propylene glycol, 1 ,2-pentanediol, 1 ,2-hexanediol and 1 ,2-octanediol, collagen, elastin or hyaluronic acid, diacyl adipates, petrolatum,
- menthyl 3-hydroxybutyrate monomenthyl succinate, monomenthyl glutarate, 2-mercaptocyclodecanone, menthyl 2- pyrrolidin-5-onecarboxylate, 2,3-dihydroxy-p-menthane, 3,3,5-trimethylcyclohexanone glycerol ketal, 3-menthyl 3,6-di- and -trioxaalkanoates, 3-menthyl methoxyacetate and icilin.
- compositions comprise one or more actives selected from the groups consisting of:
- urea hyaluronic acid, allantoin, panthenol, lanolin, alpha-hydroxy acids (preferably citric acid, lactic acid), vitamin E and derivatives (preferably tocopherol, tocopheryl acetate).
- bisabolol when used in the context of the present invention it can be of natural or synthetic origin, and is preferably "alpha-bisabolol".
- the bisabolol used is synthetically prepared or natural (-)-alpha-bisabolol and/or synthetic mixed-isomer alpha- bisabolol. If natural (-)-alpha-bisabolol is used, this can also be employed as a constituent of an essential oil or of a plant extract or of a fraction thereof, for example as a constituent of (fractions of) oil or extracts of camomile or of Vanillosmopsis (in particular Vanillosmopsis erythropappa or Vanillosmopsis arborea).
- Synthetic alpha-bisabolol is obtainable, for example, under the name "Dragosantol" from Symrise.
- extracts of the fresh or dried ginger root are used which are prepared by extraction with methanol, ethanol, iso-propanol, acetone, ethyl acetate, carbon dioxide (CO 2 ), hexane, methylene chloride, chloroform or other solvents or solvent mixtures of comparable polarity.
- the extracts are characterized by the presence of active skin irritation-reducing amounts of constituents such as e.g. gingerols, shogaols, gingerdiols, dehydrogingerdiones and/or paradols.
- the amount of other antiirritants (one or more compounds, other than trans-4-tert-butyl cyclohexanol) in the formulation of the present invention is preferably 0.0001 to 20 wt.%, particularly preferably 0.0001 - 10 wt.%, in particular 0.001 - 5 wt.%, based on the total weight of the formulation.
- the cosmetic, dermatological or therapeutic products according to the invention can be produced by conventional processes known per se, such that trans-4-tert-butyl cyclohexanol is incorporated into (topical) cosmetic, dermatological or therapeutic products which can have a conventional composition and which in addition to the aforementioned effects can also be used for the treatment, care and cleansing of the skin or hair.
- compositions according to the invention are (preferably topical) cosmetic, dermatological or therapeutic products which serve for cosmetic or dermatological light protection, for treatment, care and cleansing of the skin and/or hair or as a make-up product in decorative cosmetics.
- Such products can accordingly be present e.g. as a cleansing composition, such as e.g. soap, syndet, liquid washing, shower and bath preparation, skin care composition, such as e.g.
- emulsion (as a solution, dispersion, suspension; cream, lotion or milk of the W/O, O/W or multiple emulsion, PIT emulsion, emulsion foam, micro- or nanoemulsion, Pickering emulsion type, depending on the preparation process and constituents), ointment, paste, gel (including hydro-, hydrodispersion-, oleogel), alcoholic or aqueous/alcoholic solution, oil, toner, balsam, serum, powder (e.g.
- shampoo including shampoo for normal hair, for greasy hair, for dry, stressed (damaged) hair, 2-in-1 shampoo, anti-dandruff shampoo, baby shampoo, shampoo for a dry scalp, shampoo concentrate
- conditioner hair treatment cure, hair tonic, hair lotion, hair rinse, styling cream, pomade, permanent wave and fixing compositions, hair smoothing composition (straightening composition, relaxer), hair setting composition, styling aid (e.g. gel or wax); blonding composition, hair colouring composition, such as e.g. temporary, directly absorbed, semi-permanent hair colouring composition, permanent hair colouring composition), skin care composition as a decorative body care composition, such as e.g. nail care composition (nail varnish and nail varnish remover), decorative cosmetic (e.g. powder, eye shadow, kajal pencil, lipstick, mascara), make-up, make-up remover, skin care composition as a deodorant and/or antiperspirant.
- nail care composition nail varnish and nail varnish remover
- decorative cosmetic e.g. powder, eye shadow,
- Preferred products according to the present inventions are selected from the group of cosmetic products for treatment, protecting, care and cleansing of the skin and/or hair or as a make-up product, preferably as a leave-on product (meaning that trans-4-tert-butyl cyclohexanol stays on the skin for a longer period of time, e.g.
- the present invention also relates to a cosmetic or therapeutic method for prophylaxis of and/or treatment of human skin irritation, comprising the step of
- trans-4-tert-butyl cyclohexanol of the composition or of the medicament to non-irritated (prophylaxis) or irritated (treatment) skin in an effective amount, - said application preferably remaining for at least 5 minutes, more preferably for at least 10 minutes, on said skin ("leave-on product").
- antimicrobial agents such as e.g. antibacterial agents or agents to treat yeast and mold, in particular those described in WO 2005/123101 , antiacne and sebum reducing agents, in particular those described in WO 2008/046791 , compounds against ageing of the skin, in particular those described in WO 2005/123101 , antidandruff agents, in particular those described in WO 2008/046795, antiirritants (antiinflammatory agents, irritation-preventing agents, irritation- inhibiting agents), in particular those described in WO 2007/042472 and US 2006/0089413, antioxidants, in particular those described in WO 2005/123101 , carrier materials, in particular those described in WO 2005/123101 , chelating agents, in particular those described in WO 2005/123101 , deodorizing agents and antiperspirants, in particular those described in WO 2005/123101 , moisture regulators (moisture-donating agents, moisturizing substance, moisture-retaining substances), in particular those
- the (in particular topical) cosmetic or pharmaceutical products according to the invention can comprise cosmetic auxiliary substances and additives such as are conventionally used in such formulations, e.g. sunscreen agents, preservatives, bactericides, fungicides, virucides, cooling active compounds, insect repellents (e.g. DEET, IR 3225), plant extracts, plant parts, antiinflammatory active compounds, substances which accelerate wound healing (e.g. chitin or chitosan and derivatives thereof), film-forming substances (e.g. polyvinylpyrrolidones or chitosan or derivatives thereof), antioxidants, vitamins, 2- hydroxycarboxylic acids (e.g.
- citric acid, malic acid, L-, D- or dl-lactic acid), skin-colouring agents e.g. walnut extracts or dihydroxyacetone
- active compounds for promoting hair growth or inhibiting hair growth e.g. skin care compositions (e.g. cholesterol, ceramides, pseuodceramides), softening, moisturizing and/or humectant substances, fats, oils, saturated fatty acids, mono- or polyunsaturated fatty acids, ⁇ -hydroxy acids, polyhydroxy- fatty acids or derivatives thereof, waxes or other conventional constituents of a cosmetic or dermatological formulation, such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents, silicone derivatives of chelating agents (e.g.
- ethylenediaminetetraacetic acid and derivatives ethylenediaminetetraacetic acid and derivatives
- antidandruff active compounds e.g. climbazole, ketoconazole, piroctonoleamine, zinc pyrithione
- hair care agents perfumes, substances for preventing foaming, dyestuffs, pigments which have a colouring action, thickening agents (advantageously silicon dioxide, aluminium silicates, such as e.g. bentonites, polysaccharides or derivatives thereof, e.g. hyaluronic acid, guar bean flour, xanthan gum, hydroxypropylmethylcellulose or allulose derivatives, particularly advantageously polyacrylates, such as e.g. Carbopols or polyurethanes), surface-active substances and emulsifiers.
- thickening agents advantageously silicon dioxide, aluminium silicates, such as e.g. bentonites, polysaccharides or derivatives thereof, e.g
- the products according to the present invention preferably contain water in a quantity of up to 98 wt.%, preferably 10 to 95 wt.%, more preferably 25 to 90 wt.%, even more preferably 40 to 90 wt.%, in each case based on the total weight of the product.
- the formulations according to the invention can also comprise antioxidants, it being possible for all the antioxidants which are suitable or usual for cosmetic and/or dermatological uses to be used.
- the antioxidants are advantageously chosen from the group consisting of amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and derivatives thereof, imidazoles (e.g. urocanic acid) and derivatives thereof, peptides, such as D,L-carnosine, D-carnosine, L-carnosine and derivatives thereof (e.g. anserine), carotenoids, carotenes (e.g.
- ⁇ -carotene, ⁇ -carotene, lycopene) and derivatives thereof chlorogenic acid and derivatives thereof, liponic acid and derivatives thereof (e.g. dihydroliponic acid), aurothioglucose, propylthiouracil and other thiols (e.g.
- thioredoxin glutathione, cysteine, cystine, cystamine and glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, ⁇ -linoleyl, cholesteryl and glyceryl esters thereof) and salts thereof, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and derivatives thereof (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts), (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, bilirubin, biliverdin, EDTA, EGTA and derivatives thereof, unsaturated fatty acids and derivatives thereof (e.g. ⁇ -linolenic acid, linoleic acid, oleic acid), folic acid and derivatives thereof, ubiquinone and ubiquinol and derivatives thereof, vitamin C and derivatives (e.g.
- ascorbyl palmitate Mg ascorbyl phosphate, ascorbyl acetate, ascorbyl glycosides, such as e.g. 6-O-acyl-2-O- ⁇ -D-glucopyranosyl-L-ascorbic acid, 6-O-acyl-2-O- ⁇ -D-glucopyranosyl-L-ascorbic acid, 2-O- ⁇ -D-glucopyranosyl-L-ascorbic acid or 2-O- ⁇ -D- glucopyranosyl-L-ascorbic acid), tocopherols and derivatives thereof (e.g.
- vitamin E acetate
- vitamin A and derivatives thereof vitamin A palmitate
- coniferylbenzoate of benzoin resin rutic acid and derivatives thereof, ⁇ -glucosylrutin, quercetin and derivatives thereof, rosemary acid, carnosol, carnosol acid, resveratrol, caffeic acid and derivatives thereof, sinapic acid and derivatives thereof, ferulic acid and derivatives thereof, furfurylideneglucitol, curcuminoids, butylhydroxytoluene, butylhydroxyanisole, nordihydroguaiac resin acid, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and derivatives thereof, mannose and derivatives thereof, superoxide dismutase, zinc and derivatives thereof (e.g.
- ZnO, ZnSO 4 selenium and derivatives thereof (e.g. selenium methionine), stilbenes and derivatives thereof (e.g. stilbene oxide, trans-stilbene oxide) and derivatives (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these active compounds mentioned or antioxidatively active extracts or fractions from plants, such as e.g.
- the amount of antioxidants (one or more compounds) in the formulations according to the invention is preferably 0.01 to 20 wt.%, particularly preferably 0.05 to 10 wt.%, in particular 0.2 - 5 wt.%, based on the total weight of the formulation.
- the formulations and products according to the present invention can also comprise physiological warming (heating) agents, which in some cases are TRPV1 agonists and thus are substances which may cause skin irritations.
- the formulations can be in various forms such as are conventionally employed e.g. for sunscreen formulations for protecting the skin and hair against ultraviolet radiation. They can thus form e.g. a solution, an emulsion of the water-in-oil (W/O) type or of the oil-in-water (O/W) type or a multiple emulsion, for example of the water-in-oil-in-water (W/O/W) type, a gel, a hydrodispersion, a solid stick or also an aerosol.
- W/O water-in-oil
- O/W oil-in-water
- the total amount of UV-filter substances is from 0.01 wt.% to 40 wt.%, preferably 0.1 to 10 wt.%, in particular 1.0 to 5.0 wt.%, based on the total weight of the formulations.
- UV filters are e.g.: p-aminobenzoic acid, p-aminobenzoic acid ethyl ester (25 mol) ethoxylated, p-dimethylaminobenzoic acid 2-ethylhexyl ester, p-aminobenzoic acid ethyl ester (2 mol) N-propoxylated, p-aminobenzoic acid glycerol ester, salicylic acid homomenthyl ester (homosalate) (Neo Heliopan ® HMS), salicylic acid 2-ethylhexyl ester (Neo Heliopan ® OS), triethanolamine salicylate, 4-isopropylbenzyl salicylate, anthranilic acid menthyl ester (Neo Heliopan ® MA), diisopropylcinnamic acid ethyl ester, p- methoxycinnamic acid 2-e
- UV absorbers which are particularly suitable for combination are p- aminobenzoic acid, 3-(4'-trimethylammonium)-benzylidene-bornan-2-one methyl-sulfate, salicylic acid homomenthyl ester (Neo Heliopan ® HMS), 2-hydroxy-4-methoxy- benzophenone (Neo Heliopan ® BB), 2-phenylbenzimidazolesulfonic acid (Neo Heliopan ® Hydro), terephthalylidene-dibornanesulfonic acid and salts (Mexoryl ® SX), 4- tert-butyl-4'-methoxydibenzoylnnethane (Neo Heliopan ® 357), 3-(4'-sulfo)benzylidene- bornan-2-one and salts, 2-ethylhexyl 2-cyano-3,3-diphenylacrylate (Neo Heliopan ® 303), N-[(Neo
- formulations according to the invention in combination with substances which are chiefly employed for inhibition of the growth of undesirable microorganisms.
- further active compounds which are worth mentioning, alongside the large group of conventional antibiotics, are, in particular, the products relevant for cosmetics, such as triclosan, climbazole, zinc pyrithione, ichthyol, Octopirox (1-hydroxy-4-methyl-6- (2,4,4-trimethylpentyl)-2(1 H)-pyridone, 2-aminoethanol), chitosan, farnesol, octoxyglycerol, glycerol monolaurate, arylalkyl alcohols, such as e.g.
- the pharmaceutical composition referred to herein are administered at least once in order to treat or ameliorate or prevent a disease or condition recited in this specification.
- the said pharmaceutical compositions may be administered more than one time, for example from one to four times daily up to a non-limited number of days.
- the required amounts of the substances or additives can be determined by those skilled in the art without further ado, e.g. by trial and error, dependent on the envisaged formulation and its application provided that the formulation provides a therapeutically effective dosage of trans-4-tert-butyl cyclohexanol as discussed above.
- trans-4-tert-butyl cyclohexanol can be administered in combination with other substances, such as drugs or cosmetic agents, either in a common pharmaceutical composition or as separated pharmaceutical compositions wherein said separated pharmaceutical compositions may be provided in form of a kit of parts.
- the present invention also contemplates trans-4-tert-butyl cyclohexanol to be used for treating or preventing a pain condition or the use of trans-4-tert-butyl cyclohexanol for the manufacture of a pharmaceutical composition for treating or preventing a pain condition.
- the present invention thus also relates to trans-4-tert-butyl cyclohexanol for treating or preventing a pain condition.
- Pain condition refers to an unpleasant sensory and emotional experience associated with actual or potential tissue damage or described in terms of such damage.
- the said experience is caused by stimulation of specific nerve sensors also called nociceptors. Pain is a defense reaction of the body which also triggers or encompasses biological counteractions, i.e. a pain condition is characterized by efferent as well as afferent nervous actions.
- the vanilloid receptor TRPV1 plays a central role as multiple pain stimuli integrator.
- the receptor is a nonselective cation channel found in polymodal sensory neurons.
- a pain condition according to the present invention preferably, refers to a disease or disorder involving sensory nerve action mediated by TRPV1.
- trans-4-tert-butyl cyclohexanol is applied in a method for treating or preventing a pain condition in a subject suffering therefrom comprising administering a therapeutically effective amount of trans-4-tert-butyl cyclohexanol to the said subject.
- trans-4-tert-butyl cyclohexanol can be successfully applied for treating pain conditions and symptoms accompanied therewith, in particular, the pain conditions mediated by receptor TRPV1.
- antagonistic activity for TRPV1 was demonstrated in cell culture for trans-4-tert-butyl cyclohexanol.
- the present invention also relates to the use of trans-4-tert-butyl cyclohexanol for the manufacture of a pharmaceutical composition for treating or preventing a pain condition as well as to a method for treating or preventing a pain condition in a human being suffering therefrom comprising administering a therapeutically effective amount of trans- 4-tert-butyl cyclohexanol to said human being, wherein said pain condition preferably is selected from the group consisting of: somatic pain, inflammatory pain, visceral pain, neuropathic pain, dental pain, general headache, migraine, cluster headache, mixed- vascular and non- vascular syndromes, tension headache, general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, depression, anxiety, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, inflammatory pain and associated hyperalgesia and allodynia, neuropathic pain and associated hyperalgesia and allodyn
- sweeteners such as e.g. saccharin, flavour correctants for unpleasant taste impressions, flavour correctants for further, as a rule not unpleasant taste impressions, flavour-modulating substances (e.g. inositol phosphate, nucleotides, such as guanosine monophosphate, adenosine monophosphate or other substances, such as sodium glutamate or 2-phenoxypropionic acid), cooling agents, such as e.g. menthol derivatives (e.g.
- sodium fluoride sodium monofluorophosphate, tin difluoride, quaternary ammonium fluorides, zinc citrate, zinc sulfate, tin pyrophosphate, tin dichloride, mixtures of various pyrophosphates, triclosan, cetylpyridinium chloride, aluminium lactate, potassium citrate, potassium nitrate, potassium chloride, strontium chloride, hydrogen peroxide, aromas, sodium bicarbonate and/or odour correctants.
- the formulations according to the invention comprise at least one aroma substance, preferably 2, 3, 4, 5, 6, 7, 8, 9, 10 or more aroma substances, chosen from the following group: menthol (preferably l-menthol and/or racemic menthol), anethole, anisole, anisaldehyde, anisyl alcohol, (racemic) neomenthol, eucalyptol (1 ,8-cineol), menthone (preferably L-menthone), isomenthone (preferably D- isomenthone), isopulegol, menthyl acetate (preferably L-menthyl acetate), menthyl propionate, carvone (preferably (-)-carvone, optionally as a constituent of a spearmint oil), methyl salicylate (optionally as a constituent of a wintergreen oil), eugenol acetate, isoeugenol methyl ether, beta-homocyclocitral, eugenol,
- menthol
- cooling agents for oral care compositions comprise one or more cooling agents selected from the group consisting of: menthone glycerol acetal (trade name: Frescolat ® MGA), menthyl lactate (preferably I- menthyl lactate, in particular l-menthyl l-lactate, trade name: Frescolat ® ML), substituted menthyl-3-carboxylic acid amides (e.g., menthone glycerol acetal (trade name: Frescolat ® MGA), menthyl lactate (preferably I- menthyl lactate, in particular l-menthyl l-lactate, trade name: Frescolat ® ML), substituted menthyl-3-carboxylic acid amides (e.g.
- menthone glycerol acetal trade name: Frescolat ® MGA
- menthyl lactate preferably I- menthyl lactate, in particular l-menthyl l
- menthyl-3-carboxylic acid N-ethylamide 2- isopropyl-N-2,3-trimethylbutanamide, 3-menthoxypropane-1 ,2-diol, 2-hydroxyethyl menthyl carbonate, 2-hydroxypropyl menthyl carbonate, isopulegol, monomenthyl succinate and monomenthyl glutarate.
- Formulations according to the invention which comprise l-menthol and at least one, particularly preferably at least two cooling substances are preferred according to the invention.
- the invention likewise provides a cosmetic or therapeutic method for prophylaxis of skin irritation, with the following steps:
- the invention furthermore provides a cosmetic or therapeutic method for treatment of skin irritation, with the following steps:
- the invention furthermore provides a method for prophylaxis of the skin-irritating action or for reducing, eliminating or suppressing the skin-irritating action of a substance or substance mixture, with the following steps:
- the present invention also relates to the use of a formulation, a product or a medicament according to the present invention
- One advantage of the method according to the invention mentioned last is that the skin- irritating action of substances or substance mixtures can be moderated in this way to the extent that they are accessible for uses for which they were hitherto not available.
- higher concentrations of skin-irritating substances and substance mixtures can also be employed in uses where there is the possibility of skin contact.
- the skin-irritating action of the skin-irritating compound is eliminated completely (i.e. it no longer exists) or is suppressed completely (i.e. it no longer has an effect).
- the method according to the invention mentioned last can be employed, for example, against the skin-irritating action of detergents and allergy-inducing substances.
- racemic trans-4-tert-butyl cyclohexanol (purity >96 wt.%, amount of racemic cis-isomer ⁇ 4 wt.%) was used in the following examples, obtainable as described in Organic Syntheses Collective Volume 5, 175-178, Wiley, New York, 1973 or J. Am. Chem. Soc. 1955, 77, 5562-5578.
- Example 1 In vitro assays and in vivo testing
- HEK293 cells stably overexpressing recombinant human TRPV1 were plated onto black-walled assay plates, at a density of 45,000 cells per well.
- the change of the cellular calcium concentration (calcium influx) induced by TRPV1 activation was monitored using the calcium sensitive fluorescent dye fluo-4 (494 nm / 516 nm (exitation / emission)).
- the pharmacological TRPV1 antagonist Ruthenium Red (1 ⁇ M) was used as positive control [J. Biol. Chem. 2004, 279 (34): 35741-8].
- the dye-loaded stable cells in plates were placed into the fluorescence microtiter plate reader to monitor fluorescence (excitation 488 nm, emission 520 nm) change after the addition of 50 ⁇ l assay buffer (118 mM NaCI; 4,7 mM KCI; 1 ,2 mM MgSO 4 ; 1 ,2 mM KH 2 PO 4 ; 4,2 mM NaHCO 3 ; 1 ,3 mM CaCI 2 ; 10 mM HEPES (N-(2- hydroxyethyl)-piperazine-N'-2-ethanesulfonic acid) (pH: 7.4)) supplemented with an antagonist.
- 50 ⁇ l assay buffer 118 mM NaCI; 4,7 mM KCI; 1 ,2 mM MgSO 4 ; 1 ,2 mM KH 2 PO 4 ; 4,2 mM NaHCO 3 ; 1 ,3 mM CaCI 2 ; 10 mM HEPES (N-
- TRPV1 antagonists were tested at an effective range of 0.5 - 50 ⁇ M. The test compounds were either applied in parallel to 30 nM capsaicin or 10 min prior to the agonist. TRPV1 antagonists were tested for their antagonistic activity in the presence of 30 nM capsaicin, which is the EC 8O effective capsaicin concentration leading to 80 % of the maximum capsaicin dependent TRPV1 activation.
- Example 1.1 A Antagonistic efficacy of the isomers of 4-tert-butyl cyclohexanol on transient receptor potential ion channel 1 in cell based fluorescent analysis.
- Example 1.1 B TRPV1 antagonist in vitro at incubation prior to capsaicin: cis-4-tert-butyl cyclohexanol and trans-4-tert-butyl cyclohexanol were applied to HEK293 cells 10 min before capsaicin treatment.
- Example 1.2 In vivo testing
- the stinging effect was evaluted 5 minutes later on the following scale: 0 (no effect), 1 (stinging slightly reduced), 2 (stinging moderately reduced), 3 (stinging strongly reduced by still some stinging perceptible), and 4 (stinging completely suppressed).
- the TRPV1 antagonist (trans-4-tert-butyl cyclohexanol) was rated an average of 3.10 on said scale (for placebo: 0.25) and inhibited the stinging sensation with very high significance (p ⁇ 0.000013).
- the TRPV1 antagonist (trans-4-tert-butyl cyclohexanol) was rated an average of 2.95 on said scale (for placebo: 0.35) and inhibited / reduced both stinging and burning sensation with high significance (p ⁇ 0.001 ).
- the rating for trans-4-tert-butyl cyclohexanol regarding inhibition / reduction for the sum of all sensations stinging, burning, tingling, tickling and skin tightness were confirmed with very high significance (p ⁇ 0.0001 ).
- Formulation Examples 1 - 10 Formulations comprising trans-4-tert-butyl cyclohexanol according to the present invention having a skin irritation-reducing action
- Formulation Example 4 Body spray Formulation Example 5: Sunscreen lotion (O/W), broad-band protection
- Formulation Example 15 Sugar-free chewing gum Formulation Example 16: Gelatine capsules for direct consumption
- Aroma B here had the following composition (data in each case in wt.%):
- neotame powder 0.05 % aspartame, 29.3 % peppermint oil arvensis, 29.3 % peppermint piperita oil Willamette, 2.97 % sucralose, 2.28 % triacetin, 5.4 % diethyl tartrate, 12.1 % peppermint oil yakima, 0.7 % ethanol, 3.36 % 2-hydroxyethyl menthyl carbonate, 3.0 % 2-hydroxypropyl menthyl carbonate, 0.27 % vanillin, 5.5% D-limonene, 5.67% L-menthyl acetate.
- the gelatine capsule which is suitable for direct consumption, had a diameter of 5 mm, and the weight ratio of core material to shell material was 90 : 10.
- the capsules opened in the mouth within less than 10 seconds and dissolved completely within less than 50 seconds.
- Formulation Example 18 Instant beverage mix Formulation Example 19: Sugar-free instant beverage mix Formulation Example 20: Soja-fruit drink Formulation Example 21 : Low-fat yoghurt
- Formulation Examples 22 - 31 Formulations comprising trans-4-tert-butyl cyclohexanol according to the present invention having a skin irritation-reducing action
- Formulation Example 22 "Oil-in-water” emulsion with UV-A/B-broadband protection
- Formulation Example 23 “Oil-in-water” emulsion with UV-A/B-broadband protection
- Formulation Example 25 Skin-lightening balm with UV-A/UV-B protection Formulation
- Example 26 Skin-lightening aerosol foam with UV-B/UV-A protection Formulation
- Example 27 Skin-lightening non-aerosol foam
- Formulation Example 28 Shampoo with skin-lightening properties
- Formulation Example 29 Skin-lightening hair conditioner with UV-B/UV-A protection
- Formulation Example 30 Skin-lightening moisturizing cream O/W
- Example 31 Skin-lightening face cream O/W
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Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
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EP09701247.0A EP2416766B1 (en) | 2009-04-09 | 2009-04-09 | Compositions comprising trans-tert-butyl cyclohexanol as skin irritation-reducing agent |
JP2012503873A JP5763048B2 (en) | 2009-04-09 | 2009-04-09 | Composition comprising trans-tert-butylcyclohexanol as a skin irritation reducing agent |
CN2009801596160A CN102448450B (en) | 2009-04-09 | 2009-04-09 | Compositions comprising trans-tert-butyl cyclohexanol as skin irritation-reducing agent |
KR1020117026761A KR101676375B1 (en) | 2009-04-09 | 2009-04-09 | Compositions comprising trans-tert-butyl cyclohexanol as skin irritation-reducing agent |
BRPI0925036A BRPI0925036B8 (en) | 2009-04-09 | 2009-04-09 | use of trans-t-butyl cyclohexanol, cosmetic composition, medicine, its uses and processes to treat skin irritation |
US13/263,016 US9060943B2 (en) | 2009-04-09 | 2009-04-09 | Compositions comprising trans-tert-butyl cyclohexanol as skin irritation-reducing agent |
PCT/EP2009/054336 WO2009087242A2 (en) | 2009-04-09 | 2009-04-09 | Compositions comprising trans-tert-butyl cyclohexanol as skin irritation-reducing agent |
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PCT/EP2009/054336 WO2009087242A2 (en) | 2009-04-09 | 2009-04-09 | Compositions comprising trans-tert-butyl cyclohexanol as skin irritation-reducing agent |
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DE102010027947A1 (en) | 2010-04-20 | 2011-10-20 | Henkel Ag & Co. Kgaa | Skin-friendly deodorants and antiperspirants |
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JP2013053104A (en) * | 2011-09-05 | 2013-03-21 | Takara Belmont Co Ltd | Skin irritation relieving agent for cosmetic and cosmetic composition |
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US20130202543A1 (en) * | 2010-06-14 | 2013-08-08 | Symrise Ag | Use of polyols for enhancing the cooling effect of a cooling substance and cooling mixtures having an enhanced cooling effect |
DE102012008892A1 (en) | 2012-05-08 | 2013-11-14 | Merck Patent Gmbh | Use of substituted cyclohexanol ether derivatives e.g. as antimicrobial active substance, preferably antibacterial active substance and as anti-acne-, antidandruff-, deodorant- or antiperspirant active substance, and in cosmetic formulation |
WO2013167220A1 (en) | 2012-05-08 | 2013-11-14 | Merck Patent Gmbh | Use of cyclohexanol ethers having antimicrobial properties |
WO2013176897A2 (en) | 2012-05-25 | 2013-11-28 | The Procter & Gamble Company | Composition for reduction of trpa1 and trpv1 sensations |
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BRPI0925036B1 (en) | 2020-01-07 |
BRPI0925036B8 (en) | 2021-05-25 |
KR20120043167A (en) | 2012-05-03 |
CN102448450A (en) | 2012-05-09 |
WO2009087242A3 (en) | 2010-02-25 |
JP5763048B2 (en) | 2015-08-12 |
KR101676375B1 (en) | 2016-11-15 |
EP2416766A2 (en) | 2012-02-15 |
BRPI0925036A2 (en) | 2017-06-06 |
JP2012523381A (en) | 2012-10-04 |
US20120121737A1 (en) | 2012-05-17 |
EP2416766B1 (en) | 2014-04-09 |
CN102448450B (en) | 2013-11-20 |
US9060943B2 (en) | 2015-06-23 |
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