WO2006102777A1 - Procedes, compositions et produits pour eclaircir la peau - Google Patents

Procedes, compositions et produits pour eclaircir la peau Download PDF

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Publication number
WO2006102777A1
WO2006102777A1 PCT/CH2006/000161 CH2006000161W WO2006102777A1 WO 2006102777 A1 WO2006102777 A1 WO 2006102777A1 CH 2006000161 W CH2006000161 W CH 2006000161W WO 2006102777 A1 WO2006102777 A1 WO 2006102777A1
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Prior art keywords
skin lightening
skin
methyl
personal care
lightening
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PCT/CH2006/000161
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English (en)
Inventor
Andreas Natsch
Michael Wasescha
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Givaudan Sa
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Priority to JP2008503342A priority Critical patent/JP2008534524A/ja
Publication of WO2006102777A1 publication Critical patent/WO2006102777A1/fr

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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
    • 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
    • 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
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • 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
    • A61K8/41—Amines
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume 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
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin

Definitions

  • the present invention is directed to methods of providing a skin lightening effect by employing certain compounds, perfume compositions comprising said compounds to provide said effect, and personal care products formed by admixing said compounds or compositions.
  • Products that have a skin lightening, also called skin whitening, effect are available on the market for consumers who wish to prevent or reverse skin tanning, age spots and/or hyperpigmentation for aesthetic reasons.
  • Skin tanning is caused by the accumulation of melanin in the skin. If melanin accumulates in isolated spots, age spots and hyperpigmentations result.
  • Melanin is formed from tyrosine, which reaction is catalysed by the enzyme Tyrosinase.
  • Known skin lightening compounds are tyrosinase inhibitors that directly inhibit the enzyme, for example, Arbutin, and Kojic acid.
  • Arbutin is a plant-derived hydroquinone derivative from the leaves of the bearberry, cranberry and blueberry shrubs, and most types of pears.
  • antioxidants such as ascorbic acid and its derivatives, such as palmitoyl - ascorbic acid, glucosides of ascorbic acid and particularly ascorbic acid 2 - phosphate, and the natural polyphenol ⁇ compounds Emblicanin A and Emblicanin B.
  • Another potential mechanism of action for achieving reduction of melanin formation and therefore a skin lightening effect is the suppression of tyrosinase formation at the transcription or translation level. Such an effect may be achieved with octadecendioic acid.
  • perfume ingredients to reduce melanin formation in melanocyte cultures is known, for example, the use of eugenol, the use of certain trimethylcyclohexane derivatives, and the use of sandalwood oil as a skin lightening agent.
  • perfume ingredients are known as inhibitors of melanine formation, for example, beta-ionone, tetrahydro- ionone, and both forms of di-hydro-beta-ionone, the fragrant macrocyclic ketones described in EP 1264594 A2, and the fragrance terpene alcohols and their esters described in US 5466718.
  • the skin lightening agents should have a sufficient skin lightening activity, in particular when used at a concentration of maximally 0.2 to 2%, in the personal care product.
  • a compound may have a strong unpleasant odor, a high volatility so that it does not stay on the skin for long, it may be too hydrophilic so that it cannot penetrate the skin sufficiently to have an effect, or it may lack stability either in the composition or on the skin when exposed to oxygen and UV.
  • skin lightening agents While several skin lightening agents are known, there remains a need for additional or alternative skin lightening compounds, in particular ones that have one or more of the following desirable characteristics: a high skin lightening activity at a low concentration, the ability to penetrate the skin at least partially, a low volatility in order to stay on the skin for a sufficient time to have an effect, good stability in a perfume composition, in a formulation for a personal care product as well as on the skin.
  • perfumes that may comprise, among others, iso E super and Galaxolide (WO 96/12467).
  • Products according to WO 96/12467 include such perfumes and optionally, for skin bleaching, bleaching agents (hydrochinone, ascorbic acid, kojic acid, sodium bisulfite).
  • these perfumes do not contain the identified skin lighteners in a high concentration and in combination of at least two skin lightening compounds according to the invention.
  • perfume composition that is both active as skin lightener in a product and has a fragrance acceptable for the consumer.
  • Some compounds may be known not only as perfume but also as actives that are used in specialist personal care products, for example deodorants, antiperspirants, antibacterials, anti-acne products, and shampoos. This is the case for Sandela which has an antibacterial and thereby anti-malodorant effect (EP 1181866).
  • Such specialised formulations are not normally used on parts of the body where skin lightening is of interest and may be unsuitable for achieving a skin lightening effect.
  • products against acne and antibacterials are usually not evenly applied, and deodorants, anti-perspirants or shampoos are applied to the human skin in regions that are not exposed to sun (axilla, hair) and where the skin will not need lightening.
  • the identified skin lightening compounds can be admixed to personal care products to lighten the human skin. Because of their pleasant fragrance characteristics and their high skin lightening activity even at low concentrations, they are easily integrated into perfume compositions for skin lightening personal care products. Because of their lipophilic nature, they are able to penetrate the skin, and they have a low volatility so they will stay on the skin for a longer time.
  • Skin lightening compounds for use in compositions and methods according to the invention as defined hereinabove have a high degree of lipophilic nature, preferably a clogP of higher than 3.6. ClogP is calculated using the ACD program ACD/LogP, version 4.0, Advanced Chemistry Development, Inc., Toronto ON, Canada. Further, skin lightening compounds have a low volatility, in particular a vapour pressure of below 250 ⁇ (micro)g/L, as measured by the saturated concentration in air at 25°C.
  • Skin lightening compounds for use in compositions and methods according to the invention can be used to form stable skin lightening perfume compositions and skin lightening personal care products.
  • skin lightening compounds for use in compositions and methods according to the invention can be combined with other known skin lightening compounds, in particular one or more compounds selected from the group consisting of arbutin, and octadecendioic acid (CAS 70445-23-7, commercially available as Arlatone dioic DCATM from Seppic, Netherlands), and have an enhancing effect. Therefore, they can be used to reduce the concentration of the skin lightener used in combination while keeping the effectiveness, or enhance the effect at a given concentration.
  • a similar advantageous combination of skin lightening compounds as defined hereinabove with deoxyarbutin (4-[(tetrahydro-2H-pyran-2-yl)oxy]phenol) also has said enhancing effect and can be used accordingly.
  • the invention is directed to the use of skin lightening compounds as defined hereinbelow for the cosmetic lightening of the skin, and in particular, to a cosmetic method employing one or more such skin lightening compounds for the lightening of the human skin.
  • This method involves applying at least one skin lightening compound, preferably at least two skin lightening compounds, to the skin in regular intervals to achieve a lightening of the skin.
  • the application may be in form of a skin lightening personal care product.
  • Skin lightening compounds for use in compositions and methods according to the invention are selected from the group consisting of 2-[2-(4-methyl-3-cyclohexen-1-yl)-propyl]-cyclopentanone, 1-(2,6,6-trimethyl-2-cyclohexen-1- yl)-2-buten-1-one, 1-(2,6,6-trimethylcyclohex-1-en-1-yl)-but-2-ene-1-one, 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-but- 2-ene-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-but-2-ene-1-one, alpha ionone, 1-(2,6,6-trimethyl-2- cyclohexen-1-yl)-1-penten-3-one, 6-isopropyl-octahydro-naphthalen-2-one, 4,7,7-trimethyl-2-(3-methyl-but-2-en
  • the invention is directed to skin lightening perfume compositions.
  • Said skin lightening perfume composition comprises
  • the invention is directed to a method of preparing a skin lightening personal care product wherein at least one skin lightening compound or composition, as hereinabove defined, is admixed to a personal care product formulation.
  • the invention is directed to skin lightening personal care products comprising skin lightening compounds or compositions as herein defined.
  • the invention is directed to the cosmetic use of at least one skin lightening compounds as defined hereinabove as skin lightening actives in skin lightening personal care products.
  • the invention is directed to a method of preparing a skin lightening personal care product comprising the steps of a) providing a personal care product prepared by admixing at least one skin lightening compound, as hereinabove defined, to a personal care product formulation and forming a personal care product b) packaging the personal care product c) providing instructions for the use for cosmetic lightening of the skin to the packaged personal care product.
  • the invention is directed to a method of cosmetic lightening of the skin by applying at least one skin lightening compound, as hereinabove defined, to pigmented or hyperpigmented human skin regularly and in a sufficient amount.
  • the skin lightening personal care product is formed by admixing at least one skin lightening compound, preferably at least 2, 3, 4 or 5 skin lightening compounds, as hereinabove defined, to a personal care product formulation in a sufficient concentration to provide a skin lightening effect.
  • a skin lightening personal care product may by formulated by first preparing a skin lightening perfume composition and then combining this perfume composition with the rest of the formulation.
  • Such a perfume composition is made up of skin lightening ingredients as hereinabove described and other optional ingredients, such as perfume ingredients and excipients.
  • concentration of a skin lightening compound suitable in a personal care product applied to the skin depends on the particular compound. Because of skin penetration and dilution in the underlying tissue, the concentration needed in a personal care product generally is considerably higher than the active concentration in a cell culture system (compare example 1 and 2).
  • a useful concentration in a personal care product usually is about 100 - 1000 times that of the concentration active in a cell culture assay system as described herein and may be easily tested.
  • a preferred sufficient concentration is 0.1% to 2%, preferably to 0.2% to 1.5%, most preferably 0.6% to 1.2%.
  • the concentration also depends on the type of personal care product, and in particular how the product is applied to the skin and how long it stays on the skin, as will be apparent to the skilled person. For rinse-off products, i.e. products applied to the skin only for a short time, e.g. a few seconds up to a few minutes (soap, shower gel etc.), a higher concentration should be used, for example 0.6% to 2%, preferably 0.8 to 2%, more preferably 1 to 2%. For personal care products that stay on the skin for a longer period, e.g. of several hours (creams, lotions and similar), a concentration of 0.1% to 1.5%, preferably 0.4% to 1.2%, more preferably 0.5% to 1 % is preferred.
  • Skin lightening personal care products are formed by admixing skin lightening compounds or perfume compositions with ingredients for personal care products, as is well-known in the art. Such products may be formed, for example, as described in Kosmetik, ed. W. Umbach, 1988, Georg Thieme Verlag, Stuttgard, New York.
  • the products include personal care products for application to the human skin, such as creams, lotions, gels, talcum powders, sprays, sunscreen and after-sun preparations in any suitable form, such as creams, lotions, gels and sprays, wash formulations for the human skin including hand wash formulations, soap bars, aqueous soap formulations, syndet solutions (synthetic detergents), and shower gels.
  • excipients including, for example, surfactants, emulsifiers, soap acids, solvents, colorants, preservatives, antioxidants, antifoaming agents, antimicrobial agents, antiredeposition agents, enzymes, vegetal or mineral oils, fats, fluorescent materials, fungicides, hydrotropes, moisturizers, perfume carriers, perfume, preservatives, proteins, silicones, solubilizers, sugar derivatives, sun screens, vitamins, plant extracts and waxes.
  • Excipients generally used in such products may be found in the "International cosmetic ingredient dictionary",6th ed., The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1995.
  • Perfume compositions according to the present invention comprise at least one skin lightening compound as defined hereinabove, preferably at least 2, 3, 4 or 5, in a concentration (v/v) of at least 30%, preferably at least 50%, more preferably at least 70% based on volume per total volume of perfume ingredients.
  • inventive perfume compositions may contain further perfume ingredients (single compounds or complex mixtures such as natural oils) of up to 30%, up to 50%, or up to 70%, respectively.
  • inventive perfume compositions contain skin lightening compounds as defined hereinabove selected from more than one of the fragrance note classes, preferably 2, 3, 4, or 5 of these classes detailed hereinunder.
  • the variety of skin lightening perfume compounds of the present invention allows the perfumer to compose perfume compositions that are skin lightening as well as pleasing to the senses, which has not been possible to the same extent before.
  • Skin lightening perfume compounds of the present invention are classified into 5 classes according to their chemical structure and their fragrance notes. These classes and the skin lightening compounds of said classes are detailed below.
  • Class 1 fruity-woody ketones
  • Class 2 polycyclic woody-musky compounds
  • Class 3 Floral Schiff bases of anthranilate and aldehydes
  • Class 4 Sandalwood alcohols
  • Class 5 macrocyclic musky lactones and ketones.
  • Class 1 skin lightening compounds are selected from the group consisting of 2-[2-(4-methyl-3-cycIohexen-1 -yl)- propyfj-cyclopentanone, 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one, 1-(2,6,6-trimethylcyclohex-1-en-1-yl)- but-2-ene-1-one, 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-but-2-ene-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)- but-2-ene-1-one, alpha ionone, 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-penten-3-one, 6-isopropyl-octahydro- naphthalen-2-one, 4,7,7-trimethyl-2-(3-methyl-but-2-enyl)-bicy
  • Class 2 skin lightening compounds are selected from the group consisting of 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8- hexamethyl-2-naphthal-enyl)-ethanone , 1,1,2,3,3,8-hexamethyl-1,2,3,5,7,8-hexahydro-6-oxa- cyclopenta[b]naphthalene, 6,7-epoxy-1,1,2,4,4,7-hexamethyl-octahydro-naphthalene, 1,1,2,3,3-pentamethyl- 1,2,3,5,6,7-hexahydro-inden-4-one, 1-(2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-naphthalen-2-yl)-ethanone, and 2,2,3',7',7'-pentamethylspiro-(1,3-dioxan-5,2'-norcarane).
  • Class 3 skin lightening compounds are selected from the group consisting of methyl-n-3,7-dimethyl-7- hydroxyoctylidene anthranilate, 2-[3-(4-tert-butyl-phenyl)-2-methyl-propenylamino]-benzoic acid methyl ester, 2- [(2,4-dimethyl-cyclohex-3-enylmethylene)-amino]-benzoic acid methyl ester, 2-methyl-4-(2,6,6-trimethyl-cyclohex- 2-enyl)-butyraldehyde, 3-(3-isopropyl-phenyl)-butyraldehyde, 3-(4-isobutyl-phenyl)-2-methyl-propionaldehyde.
  • Class 4 skin lightening compounds are selected from the group consisting of [1-methyl-2-(1 ,2,2-trimethyl- bicyclo[3.1.0]hex-3-ylmethyl)-cyclopropyl]-methanol, 2-ethyl-4-(2,2,3-trimethyl-cyclopent-3-en-1-yl)-but-2-en-1-ol, 3-(5,5,6-trimethylbicyclo[2.2.1]hept-2-yl)-cyclohexanol, the product of the sandela-process comprising 3-(5,5,6- trimethylbicyclo[2.2.1]hept-2-yl) cyclohexanol (commercially available as "sandelaTM), 3-methyI-5-(2,2 J 3-trirriethyl- cyclopent-3-enyl)-pentan-2-ol, 3-methy!-5-(2,2 l 3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol l
  • Class 5 skin lightening compounds are selected from the group consisting of (e)-oxacycloheptadec-10-en-2-one, S-methylcyclotetradec- ⁇ -en-i-on, ⁇ methylcyclotetradec- ⁇ -en-i-on, and oxacyclohexadec- ⁇ -en ⁇ -one.
  • the compounds or mixtures of compounds are available commercially under the tradenames as indicated in the table above, except for 3-methylcyclotetradec-5-en-1-on and 4-methylcyclotetradec-6-en-1-on.
  • the latter compounds may be prepared by various known methods, for example as described in US6,326,349.
  • 4-carboxy-3-methylbutyl)triphenylphosphonium bromide is subjected to a Wittig reaction, for example by treatment with potassium t-butoxide in tetrahydrofuran and subsequent addition of methyl 9- oxononanoate.
  • the resulting product, dimethyl 3-methyltetradec-5-enedioate is subjected to an acyloin condensation and then treated with acetic anhydride/pyridine.
  • the resulting mixture of mainly Z-4-methyl-2- oxocyclotetradec-6-enyl acetate and Z-S-methyl-M-oxocyclotetradec- ⁇ -enyl acetate is treated with calcium in ammonia at a low temperature (e.g., between about -30° C to about -70° C). The excess calcium is destroyed using bromobenzene.
  • This method produces a mixture of the following compounds: E-3-methyl-cyclotetradec-5- enone, Z-3-methyl-cyclotetradec-5-enone, and Z-4-methyl-cyclotetradec-6-enone; the ratio of compounds may vary. A possible ratio is for example about 11%, 35%, and 49% of the above compounds.
  • the compounds may be used as a mixture or may be separated by a suitable separation method as is well known in the art.
  • 3-methylcyclotetradec-5-en-1-one (E- and Z-S-methylcyclotetradec- ⁇ -en-i-one isomers) may be obtained by pyrolysis of the silyl ether of cis/trans propenylcyclododec-3-en-1-ol, in analogy to the method described in WO02068372, as will be apparent to the skilled person.
  • SandelaTM is the reaction product which is formed from Camphene and Guaiacol with an acidic catalyst followed by hydrogenation (US 3'499'937). It is a mixture of isomers with 3-(5,5,6-Trimethylbicyclo[2.2.1]hept-2-yl)- cyclohexan-1-ol as the main constituent, but further comprising 2-(5,5,6-Trimethylbicyclo[2.2.1]hept-2-yl)- cyclohexan-1-ol and 4-(5,5,6-Trimethylbicyclo[2.2.1]hept-2-yl)-cyclohexan-1-ol.
  • perfume mixtures of skin lightening compounds as defined hereinabove are particularly preferred for their pleasant fragrance as well as good skin lightening activity:
  • the skin lightening compounds as defined hereinabove should together total to at least 30%, preferably at least 50%, most preferably at least 70% of the perfume composition, which may contain optional ingredients including other perfume ingredients.
  • A) Perfume mixture comprising
  • Particularly preferred skin-lightening compounds are selected from the group consisting of (E)-oxacycloheptadec- 10-en-2-one, 3-methylcyclotetradec-5-en-1-on, and 4-methylcyclotetradec-6-en-1-one and Oxacyclohexadec- 12-en-2-one. These compounds are particularly beneficial when combined with other skin lightening compounds.
  • these compounds in addition to their own intrinsic skin lightening potential, have a chemical structure that allows them to interact with other skin lightening compounds of a more hydrophilic nature, and therefore enhance the skin lightening effect by increasing the penetration into the skin.
  • the known skin lightening compounds arbutin, deoxyarbutin, octadecendioic acid, kojic acid, emblicanin A, emblicanin B, ascorbic acid, and ascorbic acid derivatives may be enhanced in their skin lightening activity by the combination with at least one skin lightening compound selected from the group consisting of (E)- oxacycloheptadec-10-en-2-one, 3-methylcyclotetradec-5-en-1-one, 4-methylcyclotetradec-6-en-1-one, and oxacyclohexadec-12-en-2-one (HabanolideTM).
  • a particularly preferred skin lightening perfume composition comprises one or more compounds selected from the group consisting of (E)-oxacycloheptadec-10-en-2-one or 3-methylcyclotetradec-5-en-1-on, 4-methylcyclotetradec-6-en-1-on and oxacyclohexadec-12-en-2-one (HabanolideTM); in combination with one or more other skin lightening compounds as defined hereinabove selected from the group consisting of arbutin, octadecendioic acid, deoxyarbutin, kojic acid, emblicanin A, emblicanin B, ascorbic acid, and ascorbic acid derivatives.
  • HabanolideTM oxacyclohexadec-12-en-2-one
  • Skin lightening perfume compositions according to the invention are obtained by admixing one or more of skin lightening compounds as defined hereinabove in a concentration of at least 30%, at least 50%, or at least 70%, and one or more optional ingredients in a concentration of up to 70%, up to 50% or up to 30%.
  • the optional ingredients in skin lightening perfume compositions comprise solvents, non-skin lightening perfume ingredients for aesthetic reasons, known skin lightening actives for an additive effect, and other known additives and excipients. Additional perfume ingredients may be added to provide or change a particular desired perfume note.
  • Such additives or excipients are, for example, described in "Perfume and Flavor Materials of Natural Origin", S. Arctander, Ed., Elizabeth, N.J., 1960; in “Perfume and Flavor Chemicals", S. Arctander, Ed., Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 1994; and "International cosmetic ingredient dictionary",,6th ed., The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1995.
  • a skin lightening activity of a skin lightening compound as defined hereinabove is determined by employing the classical test using the mouse melanoma cell line B16V, which has a high intrinsic ability to form melanin in vitro.
  • skin lightening compounds as defined hereinabove are compared with known skin lightening compounds such as arbutin, deoxyarbutin, octadecendioic acid, or kojic acid. It has been found that skin lightening compounds as defined hereinabove inhibit melanin formation in the mouse melanoma cell line B16V at concentrations where they do not affect cell viability or cell growth and are thus identified to have a specific suppressive effect on melanin formation.
  • Skin lightening compounds as defined hereinabove have therefore a comparable or improved skin lightening effect when compared to the known skin lighteners arbutin and kojic acid, as shown in example 2.
  • the effect of skin lightening compounds as defined hereinabove is, for example, an inhibition of melanine formation in the B16V test of at least 25% at a test concentration of 6.3 parts per million (ppm) or by an inhibition of at least 30% at a concentration of 12.5 ppm.
  • Preferred skin lightening compounds have an inhibition of at least 30% at a test concentration of 6.3 parts per million (ppm) or by an inhibition of at least 35% at a concentration of 12.5 ppm.
  • Perfume compositions according to the invention inhibit the melanine formation in the B16V cell line test by at least 30% at 12.5 ppm, or by at least 20% at 6.25 ppm, or at least 20% at 3.125 ppm.
  • Preferred perfume compositions according to the invention inhibit the melanine formation in the B16V cell line test by at least 50% at 12.5 ppm, or by at least 30% at 6.25 ppm or by at least 30% at 3.125 ppm without affecting cell viability at any of these test concentrations.
  • Skin lightening compounds or perfume compositions as defined herein- above may be admixed to personal care products in addition to known skin lightening compounds to form a perfumed skin lightening personal care product.
  • a personal care product may, for example, comprise as a known skin lightening ingredient, for example arbutin, deoxyarbutin, or octadecendioic acid, or a combination thereof, in a concentration from 0.05 to 1 %.
  • Skin lightening compounds as defined hereinabove are compatible with a wide variety of compounds and instead of arbutin, deoxyarbutin, or octadecendioic acid, other compatible ingredients with skin lightening activity may be added.
  • ascorbic acid derivatives of ascorbic acid such as ascorbic acid 2 -phosphate, kojic acid, eugenol, beta-ionone, tetrahydro-ionone, both forms of di-hydro-beta-ionone, macrocyclic ketones described in EP 1264594 A2, especially Cyclohexadec-5-ene-1-one and 4-(4-hydroxyphenyl)-butan-2-one.
  • Skin lightening personal care products are products intended for the cosmetic lightening of the skin.
  • the directed use for skin lightening may be determined from the statements made on or in a product's label or labelling, insert or flyer provided with the product.
  • Such use involves the regular application of a sufficient amount to the skin , in particular at least once daily, preferably twice daily , more peferably three times daily.
  • the skin lightening personal care product especially when left on the skin without rinsing off, should be applied evenly to the skin to ensure that the skin is lightened evenly.
  • a skin lightening perfume composition is one intended for the cosmetic lightening of the skin.
  • the directed use to perfume skin lightening personal care products in particular by admixture of skin lightening compounds as defined hereinabove to personal care product formulations to form skin lightening personal care products, may be determined from the statements made on or in the perfume compositions label or labelling, insert or flyer provided with the skin lightening perfume composition.
  • mouse melanoma cell line B-16V which may be obtained from the German collection of microorganisms and cell cultures (DSMZ, Braunschweig, Germany). It is maintained in medium RPM1 1640
  • a confluent culture is diluted to a final cell density of 2 x 10 4 cells/ml and 2 ml of the cell suspension are added to each well of 6 well plate.
  • Cells are cultivated for a period of 24 h at a humidity of 98% in a 5% carbon dioxide atmosphere.
  • Test compounds are then added in dimethylsulfoxide (DMSO), with the maximal concentration in the culture medium not exceeding 0.5% DMSO.
  • DMSO dimethylsulfoxide
  • the cultures are further incubated for 72 h under the same conditions in presence of the test compounds.
  • the supernatant is then removed, the cells are washed in phosphate buffered saline (PBS) and lysed by the addition of 0.5 ml per well of a solution containing 500 mM NaOH and incubation at
  • PBS phosphate buffered saline
  • optical density of control cultures receiving DMSO only and no test compound is set as 100%, and the relative viability of treated cultures is assessed.
  • Results of these parallel assays show (a) the reduction in melanin formation at a given concentration of the test compound and (b) the relative viability of cultures at the same test concentration .
  • Example 2 Compounds with a skin lightening effect
  • mouse melanoma cell line B16V is used as described in example 1.
  • a large number of commercially available materials including a collection of a large number of perfumery ingredients is tested.
  • perfume compounds are found to have a skin lightening effect at least comparable or better than known skin lightening compounds that were also tested (For chemical names of perfume compounds, see table in the description hereinabove. )
  • These known skin lightening compounds are: Arbutin, Kojic acid, Emblicanin A / Emblicanin B extracted from Phyllanthus emblica fruit, sold under the trade name EMBLICA by Merck, Darmstadt, Germany and 4-(4- hydroxyphenyl)-butan-2-one..
  • 3-Methylcyclotetradec-5-en-1-on may be replaced partly orcompeltely with 4-Methylcyclotetradec-6-en-1-on to give similar results.
  • Example 3 perfume compositions with skin lightening effect
  • Skin lightening perfume composition C Skin lightening compounds: Parts per 100
  • perfume composition D containing a high concentration of monoterpenic alcohols is used.
  • Monoterpenic alcohols are perfume compounds that have been reported to have skin lightening activity.
  • perfume compositions A-C are compared to perfume composition D employing the test method as described in example 1:
  • the skin lightening effect of skin lightening perfume compositions of the present invention is much higher than the one of the comparative perfume composition.
  • perfume composition A and C have no or only a minor effect on cell growth at concentrations where they block the formation of melanine.
  • Perfume composition B stops the cell growth at 12.5ppm but has no effect at lower concentrations.
  • Inventive perfume composition E as described below is tested at various concentrations in combination with various concentrations of Arbutin.
  • the effect of a low concentration of Arbutin is enhanced by the addition of a low concentration of perfume compositions E.
  • the % inhibition of melanin formation in the cell line B16V after 3 days incubation with perfume composition and arbutin in various concentrations from O -3.2 ppm perfume composition and 0-3.2 ppm arbutin is shown.
  • Example 5 Evaluation of the effect of inventive perfume compositions on the skin tone of a reconstituted epidermis Cocultures of normal human keratinocytes and melanocytes as a model of a pigmented human epidermis are purchased from MatTek (200 Homer Avenue, Ashland, MA 01721, USA). Skin lightening perfume compositions according to the invention are homogenized at a concentration of 0.02 to 0.1% in water by ultrasonification. The resulting solutions are applied every second day to the surface of the epidermal model for a period of 14 days. The epithelium is subsequently dissolved in 50OmM NaOH and the melanin content is determined by measuring absorbance at 405 nm. Epithelium samples show a reduced melanine content after treatment with skin lightening perfume compositions.
  • a skin lightening cream is formed from the ingredients indicated in the table above as follows.
  • the ingredients of phases A are admixed, for phase B the same applies.
  • Phases A and B are each heated to 75-80 0 C 1 then B is added into A with slow stirring.
  • the mixture is slowly cooled and as the cream thickens, stirring is increased.
  • phase C is added and the mixture is homogenized.
  • one of the skin lightening perfume compositions A-C (compare examples hereinabove ) is added.
  • room temperature about 20-25 0 C), stirring is stopped.

Abstract

L'invention concerne des procédés cosmétiques pour éclaircir la peau, des composés et des compositions de parfum ayant un effet éclaircissant sur la peau et des produits de soin personnel à appliquer sur la peau, contenant ces composés et compositions de parfum éclaircissant la peau. Un certain nombre de composés dont l'effet éclaircissant sur la peau était inconnu ont été identifiés. Ces composés éclaircissant la peau confèrent au parfum une plus grande palette de notes parfumées et offrent davantage de possibilités de créer des accords parfumés souhaités dans des compositions de parfum et des produits de soin personnel éclaircissant la peau. Des compositions de parfum et des produits de soin personnel éclaircissant la peau selon l'invention contiennent au moins un des composés éclaircissants parfumés identifiés.
PCT/CH2006/000161 2005-03-29 2006-03-17 Procedes, compositions et produits pour eclaircir la peau WO2006102777A1 (fr)

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GB0506263.3 2005-03-29
GBGB0506263.3A GB0506263D0 (en) 2005-03-29 2005-03-29 Skin lightening methods, composition and products

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WO2008113495A2 (fr) * 2007-03-16 2008-09-25 Givaudan Nederland Services B.V. Compositions de parfum
US8030524B2 (en) 2006-11-03 2011-10-04 Gibaudan SA Organic compounds

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DE102013204088A1 (de) * 2013-03-11 2014-09-11 Beiersdorf Ag Wirkstoffkombinationen aus Alkylamidothiazolen und einen oder mehreren kosmetisch oder dermatologisch relevanten Duftstoffen
JP6272463B2 (ja) * 2014-04-16 2018-01-31 株式会社コーセー 新規な化合物、これを含有する化粧料及び皮膚外用剤
KR101648739B1 (ko) * 2014-07-08 2016-08-17 인하대학교 산학협력단 (4aS,5S,6R,8aS)-5-((R)-3-((((E)-3-(3,4-디하이드록시페닐)아크릴로일)옥실)메틸)-5-하이드록시펜틸)-5,6,8a-트리메틸-3,4,4a,5,6,7,8,8a-옥타하이드로나프탈렌-1-카복실릭엑시드 화합물을 유효성분으로 함유하는 피부 미백용 조성물 및 이의 용도
JP7206219B2 (ja) * 2017-05-05 2023-01-17 フイルメニツヒ ソシエテ アノニム 香水原料および食品原料における有機ヒドロペルオキシドの低減

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