WO2006074979A1 - Utilisation de 2,2-dimethyl-3-cyclohexyl-1-propanol en tant que parfum - Google Patents

Utilisation de 2,2-dimethyl-3-cyclohexyl-1-propanol en tant que parfum Download PDF

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Publication number
WO2006074979A1
WO2006074979A1 PCT/EP2006/050055 EP2006050055W WO2006074979A1 WO 2006074979 A1 WO2006074979 A1 WO 2006074979A1 EP 2006050055 W EP2006050055 W EP 2006050055W WO 2006074979 A1 WO2006074979 A1 WO 2006074979A1
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Prior art keywords
dimethyl
propanol
cyclohexyl
oil
methyl
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PCT/EP2006/050055
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German (de)
English (en)
Inventor
Berthold Weber
Johannes Panten
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Symrise Gmbh & Co. Kg
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Publication of WO2006074979A1 publication Critical patent/WO2006074979A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • 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
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • 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
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes

Definitions

  • the present invention relates to 2,2-dimethyl-3-cyclohexyl-1-propanol, certain products with a proportion of this substance (in particular fragrance compositions and perfumed articles) and certain uses of the substance, in particular as a fragrance.
  • fragrances in the perfume industry continues to have a general need for new fragrances, especially those that have additional positive secondary properties beyond their odor properties, such.
  • B. a higher stability under certain conditions of use, a higher yielding, a better adhesion or better dermatological and toxicological results over comparable fragrances.
  • fragrances are z.
  • B 4- (1,1-dimethylethyl) - ⁇ -methylbenzylpropanal (lilial ®) and 4- (4-hydroxy-4-methylpentyl) cyclohex-3-enecarbaldehyde (Lyral ®), which, as their name suggests, characterized by a pronounced Muguet smell ("Lily of the valley", also called lily of the valley smell).
  • fragrances which are capable of producing a muguet-like odor note in fragrance, in particular perfume compositions.
  • this object is achieved by 2,2-dimethyl-3-cyclohexyl-1-propanol and its use as a fragrance.
  • the invention also relates to fragrance compositions and perfumed articles which comprise a sensorially effective amount of 2,2-dimethyl-3-cyclohexyl-1-propanol and to production processes for a fragrance composition according to the invention and for 2,2-dimethyl-3-cyclohexyl-1-propanol even.
  • the invention is u. a. based on the surprising finding that the compound 2,2-dimethyl-3-cyclohexyl-1-propanol is suitable as a fragrance.
  • the substance according to the invention has a cycloaliphatic ring and a hydroxy functionality.
  • the cycloaliphatic compounds in turn, it differs by the presence of only one side chain, which also has a different structure.
  • fragrance compositions according to the invention or perfumed articles containing an amount of 2,2-dimethyl-3-cyclohexyl-1-propanol which is sufficient to impart, modify and / or enhance a muguet-like odor note.
  • An odoriferous substance composition according to the invention is preferably prepared by a process according to the invention in which 2,2-dimethyl-3-cyclohexyl-1-propanol is mixed with customary further constituents of a fragrance composition. is mixed, wherein the 2,2-dimethyl-3-cyclohexyl-1-propanol is used in a sensory effective amount, that is, in an amount sufficient to provide in the fragrance kom position a Muguet odor note (a) or (b) to modify and / or enhance it (compared to a mixture of the other ingredients).
  • Muguet-like odor notes are used in a variety of perfume compositions, eg. B. in flower scent themes.
  • Example 1, below, of a "white flower” fragrance topic demonstrates in an illustrative manner the olfactory effect of 2,2-dimethyl-3-cyclohexyl-1-propanol.
  • 2,2-dimethyl-3-cyclohexyl-1-propanol is preferably carried out starting from (i) 2,2-dimethyl-3-phenyl-1-propanol or (ii) 2,2-dimethyl-3-phenyl 1-propanal (see Example 2, below) by catalytic hydrogenation with hydrogen gas in an autoclave according to the following reaction equations:
  • the pressures used are between 30 to 250 bar, preferably between 60 and 150 bar, the temperatures in the range of 50 to 250 ° C, preferably in the range of 100 to 200 0 C, and depend essentially on the catalyst system used. Numerous homogeneous or heterogeneous catalyst systems are known from the literature (PN Rylander Catalytic Hydrogenation in Organic Synthesis, Academic Press, New York, 1979; Robert L.
  • a nuclear hydrogenation in FaIIe of 2,2-dimethyl-3-phenyl-1-propanol or (ii) a ring hydrogenation and carbonyl hydrogenation in the case of 2,2-dimethyl-3-phenyl-1-propanals can be performed.
  • the heterogeneous catalyst systems consist for example of Raney nickel or of ruthenium, platinum or palladium on certain carrier materials. Activated charcoal, coal, aluminum oxides, metal oxides, silica gels, zeolites, clays, clay granules or amorphous aluminum silicates may be mentioned as advantageous support materials.
  • Preferred catalysts are rhodium and ruthenium, preferred carrier material is activated carbon.
  • the hydrogenation can be carried out with or without solvent.
  • 2,2-Dimethyl-3-cyclohexyl-1-propanol can be obtained, for example, from 2,2-dimethyl-3-phenyl-1-propanol by nuclear hydrogenation with Ru / activated carbon (ruthenium on activated carbon; Ru content 5% by weight) to the dry catalyst; water content: about 50% by weight) in isopropanol at up to 170 ° C. and 70 bar pressure on hydrogen gas.
  • Ru / activated carbon ruthenium on activated carbon; Ru content 5% by weight
  • water content about 50% by weight
  • 2,2-dimethyl-3-cyclohexyl-1-propanol can be prepared by reduction according to methods known from the literature (Jerry March Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 4th Ed., John Wiley and Sons, 1992 and Richard C. Larock Comprehensive Organic Transformations: A Guide to functional Group Preparations, VCH Verlag, 1989) of 3-cyclohex-3-enyl-2,2-dimethyl-1-propanal, which in turn z. B. by bisalkylation by conventional methods (Jerry March and Richard L. Larock, see above) can be formed from 3-cyclohex-3-enyl-1-propanal, can be prepared.
  • the synthesis of 2,2-dimethyl-3-cyclohexyl-1-propanol can be carried out in two steps, starting with an alkylation reaction of isobutyraldehyde with cyclohexylmethyl chloride, cyclohexylmethylbromide, cyclohexylmethyliodide or cyclohexylmethyltosylate and finally with a reduction of the carbonyl function according to the above-mentioned methods (Jerry March and Richard L. Larock, supra), see the reaction scheme below.
  • Fragrance mixtures and perfume oils containing 2,2-dimethyl-3-cyclohexyl-1-propanol can be used in liquid form, undiluted or diluted with a solvent, for perfuming.
  • Suitable solvents are, for. Ethanol, isopropanol, diethylene glycol monoethyl ether, glycerin, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, etc.
  • a carrier which is suitable both for a fine distribution of the fragrances in Product as well as providing controlled release during use.
  • Such carriers may be porous inorganic materials such as light sulfate, silica gels, zeolites, gypsum, clays, clay granules, aerated concrete, etc., or organic materials such as woods, cellulosic based materials, sugars or plastics such as PVC, polyvinyl acetates or polyurethanes.
  • perfume oils perfume mixtures
  • microencapsulated containing 2,2-dimethyl-3-cyclohexyl-1-propanol, microencapsulated, spray-dried, as an inclusion complex or as an extrusion product and in this form to be perfumed (pre-). Add product.
  • perfume oils modified in this way are in some cases further optimized by so-called “coating” with suitable materials with a view to a more targeted release of fragrance, to which end preferably waxy plastics such as polyvinyl alcohol are used.
  • the microencapsulation of the perfume oils can be carried out, for example, by the so-called coacervation method with the aid of capsule materials, e.g. made of polyurethane-like substances or soft gelatin.
  • the spray-dried perfume oils can be prepared, for example, by spray-drying a perfume oil-containing emulsion or dispersion, it being possible to use as starches modified starches, proteins, dextrin and vegetable gums.
  • Inclusion complexes can e.g. by incorporating dispersions of the perfume oil and cyclodextrins or urea derivatives into a suitable solvent, e.g. Water, to be produced.
  • Extrusion products can be made by fusing the perfume oils with a suitable waxy substance and by extrusion followed by solidification, optionally in a suitable solvent, e.g. Isopropanol, done.
  • Perfume oils containing 2,2-dimethyl-3-cyclohexyl-1-propanol can be used in concentrated form, in solutions or in another modified form for the preparation of, for example, perfume extracts, perfume oils, toilet waters, shaving waters , Eau de C perfumes, Pre-shave products, splash colognes and perfumed refreshing wipes, as well as the perfuming of acidic, alkaline and neutral detergents, such as floor cleaners, window glass cleaners, dishwashing detergents, bathroom and sanitary cleaners, scouring cream, solid and liquid toilet cleaners, powder and foam carpet cleaners , liquid detergents, powdered detergents, laundry pretreatment agents such as bleaches, soaking and stain removers, fabric softeners, laundry soaps, washing tablets, disinfectants, surface disinfectants and air fresheners in liquid, gel or solid support, aerosol sprays, waxes and polishes such as furniture polishes , Floor waxes, shoe creams and personal care products such as solid and
  • the amount of 2,2-dimethyl-3-cyclohexyl-1-propanol used is usually in the range of 0.001 to 70 wt .-%, preferably 0.05 to 50 wt .-% and especially preferably 0.5 to 25 wt .-%, based on the total perfume oil composition.
  • Preservatives Preservatives, abrasives, anti-acne agents, anti-aging agents, anti-bacterial agents, anticellulitic agents, antidandruff agents, anti-inflammatory agents anti-irritants, anti-irritants, anti-irritants, anti-microbial agents, antioxidants, astringents, antiperspirants, antiseptics, antistatic agents, binders, buffers, excipients, chelating agents, cell stimulants, cleansing agents, skin care agents, depilatories, surface-active substances, deodorants Agents, antiperspirants, emollients, emulsifiers, enzymes, essential oils, fibers, film formers, fixatives, foaming agents, foam stabilizers, foaming inhibitors, foam boosters, fungicides, gelling agents, gelling agents, hair care products, hair styling agents, hair relaxers, moisturizing agents, moisturizers Substances, moisturizing substances, bleaching agents, restorers, stain removers, optical
  • the compound can be used as a single substance or combined with a variety of other fragrances in a variety of products. Particularly advantageously, the compound can be combined with other fragrances in different, different proportions to novel perfume compositions (as a special fragrance mixtures). Examples of fragrances with which the compound of the invention can be advantageously combined, are found, for. In S. Arctander, Perfume and Flavor Chemicals, Vol. I and II, Montclair, NJ, 1969, diverlag or K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Materials, 4rd. Ed., Wiley-VCH, Weinheim 2001. The following may be mentioned:
  • Extracts from natural raw materials such as essential oils, concretes, absolues, resines, resinoids, balsams, tinctures such.
  • ambergris tincture Amyrisöl; Angelica seed oil; Angelica root oil; anise oil; Valerian oil;
  • Coriander oil costus root; Cuminöl; Cypress oil; Davanaöl; Dill herb oil; Dill seed oil; Eau de Brouts absolute; Oak moss absolute; elemi; Tarragon oil;
  • Eucalyptus citriodora oil eucalyptus oil; Fennel oil; Pine needle oil; galbanum;
  • Galbanumresin geranium; Grapefruit oil; guaiac wood; gurjun balsam; Gurjung balsam oil; Helichrysum absolute; Helichrysumöl; Ginger oil; Iris root absolute;
  • Orris root oil Jasmine absolute; calamus; Chamomile oil blue; Camomile oil Roman; Carrot seed oil; Kaskarillaöl; Pine needle oil; spearmint; Seed oil; Labdanum oil; Labdanum absolute; Labdanumresin; Lavandin absolute; Lavandin oil;
  • Lavender absolute Lavender oil; Lemongrass oil; Lovage oil; Distilled lime oil;
  • myrtle Clove leaf oil; Clove flower oil; neroli; Olibanum absolute; Olibanum oil; Opopanaxöl; Orange blossom absolute; Orange oil; oregano; Palmarosa oil;
  • patchouli oil perilla oil; Peruvian balsam oil; Parsley leaf oil; Parsley seed oil; Petrolatum oil; Peppermint oil; Pepper oil; chilli; pine oil; Poleyöl; Rose absolute; Rosewood oil; Rose oil; Rosemary oil; Sage oil Dalmatian; Sage oil spanish; sandalwood; Celery seed oil; spike lavender oil; star anise; Styraxöl; tagetes; Pine needle oil; Tea-tree-oil; turpentine; Thyme oil; Tolu; Tonka absolute; Tuberose absolute; Vanilla extract; Violet leaf absolute; verbena; vetiver; Juniper berry oil; Wine yeast oil; Wormwood oil; Wintergreen oil; ylang oil; Y-sopoil; Civet absolute; cinnamon leaf; Cinnamon bark oil and fractions thereof, or ingredients isolated therefrom;
  • fragrances from the group of hydrocarbons such as e.g. 3-carene; ⁇ -pinene; beta-pinene; ⁇ -terpinene; ⁇ -terpinene; p-cymene; bisabolene; camphene; Caryophyllene; cedrene; Famesen; limonene; longifolene; myrcene; ocimene; valencene; (E, Z) -1, 3,5-undecatriene; styrene; diphenylmethane;
  • the aliphatic alcohols such as e.g. hexanol; octanol; 3-octanol; 2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E) -2-hexenol; (E) - and (Z) -3-hexenol; 1-octene-3-ol; Mixture of 3,4,5,6,6-pentamethyl-3/4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol; (E, Z) -2,6-nonadienol; 3,7-dimethyl-7-methoxyoctane-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol;
  • the aliphatic ketones and their oximes e.g. 2-heptanone; 2-octanone; 3- Octanone; 2-nonanone; 5-methyl-3-heptanone; 5-methyl-3-heptanone oxime; 2,4,4,7-tetramethyl-6-octen-3-one; 6-methyl-5-hepten-2-one;
  • the aliphatic sulfur-containing compounds such as 3-methylthio-hexanol; 3-Methylthiohexylacetat; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1-menthene-8-thiol; the aliphatic nitriles such as 2-nonenitrile; 2-Undecen Textrenitril; 2-tridecenoic acid nitrile; 3,12-Tridecadienklarenitril; 3,7-dimethyl-2,6-octadienitrile; 3,7-dimethyl-6-octen Aciditril;
  • ester of aliphatic carboxylic acids e.g. (E) - and (Z) -3-hexenylformate; ethylacetoacetate; isoamyl; hexyl acetate; 3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (E) -2-hexenyl acetate; (E) - and (Z) -3-hexenylacetate; Octyl acetate; 3-octyl acetate; 1-octen-3-yl acetate; ethyl butyrate; Butyl butyrate, Isoamylbutyrate; hexyl butyrate; (E) - and (Z) -3-hexenyl isobutyrate; hexyl crotonate; Ethyl isovalerate; Ethyl 2-methylpentanoate; ethylhexanoate; allyl
  • Citronellol Citronellol; geraniol; nerol; linalool; Lavadulol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2,6-dimethyl-7-octene-2-ol; 2,6-dimethyl octane-2-ol; 2-methyl-6-methylene-7-octen-2-ol; 2,6-dimethyl-5,7-octadiene-2-ol; 2,6-dimethyl-3,5-octadiene-2-ol; 3,7-dimethyl-4,6-octadien-3-ol; 3,7-dimethyl-1, 5,7-octatrien-3-ol 2,6-dimethyl-2,5,7-octatrien-1-ol; as well as their formates, acetates, propionates, isobutyrates, butyrate
  • the cyclic terpene alcohols such. Menthol; isopulegol; alpha-terpineol; Terpinenol-4; Menthane-8-ol; Menthane-1-ol; Menthane-7-ol; borneol; Isobomeol; linalool; monopoly; cedrol; ambrinol; Vetyverol; guaiol; as well as their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates; the cyclic terpene aldehydes and ketones such.
  • cyclic alcohols such as 4-tert-butylcyclohexanol; 3,3,5-trimethylcyclohexanol; S-isocamphylcyclohexanol; 2.6 J 9-trimethyl-Z2 J Z5, E9-cyclododecatrien-1-ol; 2-isobutyl-4-methyl tetrahydro-2H-pyran-4-ol;
  • cycloaliphatic alcohols e.g. alpha, 3,3-
  • cyclic and cycloaliphatic ethers such as e.g. cineol; cedryl methyl ether; cyclododecyl; 1,1-dimethoxycyclododecane; (Ethoxymethoxy) cyclododecane; alpha-Cedrenepoxid; 3a, 6,6,9a-
  • cyclic and macrocyclic ketones such as 4-tert-butylcyclohexanone; 2 J 2,5-trimethyl-5-pentylcyclopentanone; 2-heptylcyclopentanone; 2 pentylcyclopentanone; 2-hydroxy-3-methyl-2-cyclopentene-1-one; 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one; 3-methyl-2-pentyl-2-cyclopentene-1-one; 3-methyl-4-cyclopentadecenone; S-methyl- ⁇ -cyclopentadecenone; 3
  • methylcyclopentadecanone 4- (1-ethoxyvinyl) -3,3,5,5-tetrannethylcyclohexanone; 4-tert-pentylcyclohexanone; 5-cyclohexadecen-i-one; 6,7-dihydro-1,1,3,3,3-pentamethyl-4 (5H) -indanone; 8-cyclohexadecen-1-one; 9-cycloheptadecene-i -one; cyclopentadecanone; cyclohexadecanone;
  • cycloaliphatic aldehydes such as 2,4-dimethyl-3-cyclohexene carbaldehyde; 2-methyl-4- (2,2 J 6-trimethyl-cyclohexen-1-yl) -2-butenal; 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene carbaldehyde; 4- (4-methyl-3-penten-1-yl) -3-cyclohexene carbaldehyde;
  • ester of cyclic alcohols e.g. 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-
  • ester of cycloaliphatic alcohols such as I-cyclohexylethyl crotonate
  • esters of cycloaliphatic carboxylic acids such as.
  • allyl-3-cyclohexylpropionate Allylcyclohexyloxyacetat; cis and trans methyldihydrojasmonate; egg and trans methyl jasmonate;
  • Methyl-2-hexyl-3-oxocyclopentanecarboxylate Ethyl 2-ethyl-6,6- dimethyl-2-cyclohexenecarboxylate; Ethyl 2,3,6,6-tetrannethyl 2-cyclohexene carboxylate; Ethyl 2-methyl-1,3-dioxolane-2-acetate;
  • the araliphatic alcohols e.g. benzyl alcohol; 1-phenylethyl; 2-phenylethyl alcohol; 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2,2-dimethyl-3-phenylpropanol; 2,2-dimethyl-3- (3-methylphenyl) propanol; 1,1-dimethyl-2-phenylethyl alcohol; 1, 1-dimethyl-3-phenylpropanol; 1-ethyl-1-methyl-3-phenylpropanol; 2-methyl-5-phenylpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propene-1-ol; 4-methoxybenzyl; 1 - (4-isopropylphenyl) ethanol;
  • ester of araliphatic alcohols and aliphatic carboxylic acids e.g. benzyl acetate; benzylpropionate; benzyl isobutyrate; Benzylisovalerianat; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-Phenylethylisobutyrat; 2-phenylethyl isovalerate; 1-phenylethyl acetate; alpha-Trichlormethylbenzylacetat; alpha, alpha-dimethylphenylethyl acetate; alpha, alpha-dimethylphenylethyl butyrate; cinnamyl; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate;
  • the araliphatic ethers such as 2-phenylethyl methyl ether; 2-phenylethyl isoamyl ether; 2-phenylethyl-1-ethoxyethyl ether; Phenylacetaldehyde dimethylacetal; phenylacetaldehyde; Hydratropaldehyde dimethylacetal; Phenylacetaldehydglycerinacetal; 2,4,6-trimethyl-4-phenyl-1,3-dioxane; 4 J 4a J 5 J 9b-tetrahydroindeno [1,2-d] -m-dioxin; 4,4a, 5 J 9b-tetrahydro-2 J 4-dimethylindo [1, 2-d] -m-dioxin;
  • aromatic and araliphatic ketones such as e.g. acetophenone; 4-methylacetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6-dimethylacetophenone; 4-phenyl-2-butanone; 4- (4-hydroxyphenyl) -2-butanone; 1- (2-naphthalenyl) ethanone; 2-benzofuranylethanone; (3-methyl-2-benzofuranyl) ethanone; benzophenone; 1, 1 ⁇ S.S.-hexamethyl-S-indanyl methyl ketone; 6-tert-butyl-1, 1-dimethyl-4-indanyl methyl ketone; 1 - [2,3-dihydro-i, 1, 2,6-tetramethyl-3- (1-methylethyl) -1H-5-indenyl] ethanone; 5 ', 6', 7 ', 8'-tetrahydro-3', 5 ', 5',
  • aromatic and araliphatic carboxylic acids and their esters e.g. benzoic acid; phenylacetic acid; Methyl benzoate; ethyl benzoate; hexyl benzoate; Benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; Phenylethyl phenylacetate; Methylcinnmat; ethylcinnamate; Benzyl; Phenylethyl cinnamate; cinnamyl cinnamate; allyl phenoxyacetate; methyl salicylate; Isoamylsalicylate; hexyl salicylate; cyclohexyl; Cis-3-hexenyl salicylate; Benzyl salicylate; phenylethyl; Methyl-2,4-dihydroxy-3,6-dimethylbenzoate; Ethy
  • nitrogen-containing aromatic compounds such as e.g. 2,4,6-trinitro-i, 3-dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert.-butylacetophenone;
  • the phenols, phenyl ethers and phenyl esters such as estragole; anethole; eugenol; Eugenylmethylether; isoeugenol; Isoeugenylmethylether; thymol; carvacrol; diphenyl ether; beta-naphthyl methyl ether; beta-Naphthylethylether; beta-naphthyl isobutyl ether; 1,4-dimethoxybenzene; Eugenylacetat; 2-methoxy-4-methylphenol; 2-ethoxy-5- (1-propenyl) phenol; p-Kresylphenylacetat;
  • heterocyclic compounds such as e.g. 2,5-dimethyl-4-hydroxy-2H-furan-3-one; 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one; 3-hydroxy-2-methyl-4H-pyran-4-one; 2-ethyl-3-hydroxy-4H-pyran-4-one;
  • the lactones e.g. 1,4-octanolide; 3-methyl-1,4-octanolide; 1,4-nonanolide; 1,4-decanolide; 8-decen-1,4-olide; 1,4-undecanolide; 1,4-dodecanolide; 1,5-decanolide; 1, 5-dodecanolide; 4-methyl-1,4-decanolide; 1,15-pentadecanolide; cis and trans-11-pentadecene-1, 15-olide; cis- and trans-12-pentadecene-1, 15-olide; 1, 16-hexadecanolide; 9-hexadecene-1, 16-olide; 10-oxa-1, 16-hexadecanolide; 11-oxa-1, 16-hexadecanolide; 12-oxa-1,16-hexadecanolide; Ethylene-1,12-dodecanedioate
  • the amount of the 2,2-dimethyl-3-cyclohexyl-1-propanol according to the invention is preferably 0.01 to 99.9% by weight, preferably 0.1 to 90% by weight and particularly preferably 0.5 to 70 % By weight, based on the total perfume composition.
  • the compound of the invention was therefore found to be superior.
  • the wet strands of hair thus obtained were dried for 1 minute with an electric mid-stage hairdryer.
  • the odor evaluation of the moist and dry strands of hair showed that the substance according to the invention 2,2-dimethyl-3-cyclohexyl-1-propanol is perceived more intensively on both wet and dry hair.
  • perfumed products according to the invention are therefore detergents, hygiene or care products, in particular in the field of personal care, cosmetics and the household.

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  • Emergency Medicine (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne le 2,2-diméthyl-3-cyclohexyl-1-propanol, son utilisation en tant que parfum et des procédés de fabrication de ce composé et de mélanges de parfum correspondants.
PCT/EP2006/050055 2005-01-15 2006-01-05 Utilisation de 2,2-dimethyl-3-cyclohexyl-1-propanol en tant que parfum WO2006074979A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005002010A DE102005002010A1 (de) 2005-01-15 2005-01-15 Verwendung von 2,2-Dimethyl-3-cyclohexyl-1-propanol als Riechstoff
DE102005002010.0 2005-01-15

Publications (1)

Publication Number Publication Date
WO2006074979A1 true WO2006074979A1 (fr) 2006-07-20

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/050055 WO2006074979A1 (fr) 2005-01-15 2006-01-05 Utilisation de 2,2-dimethyl-3-cyclohexyl-1-propanol en tant que parfum

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Country Link
DE (1) DE102005002010A1 (fr)
WO (1) WO2006074979A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4091090A (en) * 1974-07-08 1978-05-23 Johnson & Johnson Potentiated anesthetics
CH604716A5 (en) * 1975-11-28 1978-09-15 Firmenich & Cie 3-Methyl 4-cyclohexyl butanol-2 used in perfume compsns.
US4701278A (en) * 1984-11-06 1987-10-20 Firmenich Sa Utilization of a cycloaliphatic carbinol as perfuming ingredient
WO2001004253A1 (fr) * 1999-07-12 2001-01-18 Bush Boake Allen Inc. Materiaux parfumes
EP1108703A1 (fr) * 1999-12-17 2001-06-20 Takasago International Corporation Composition parfumante

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4091090A (en) * 1974-07-08 1978-05-23 Johnson & Johnson Potentiated anesthetics
CH604716A5 (en) * 1975-11-28 1978-09-15 Firmenich & Cie 3-Methyl 4-cyclohexyl butanol-2 used in perfume compsns.
US4701278A (en) * 1984-11-06 1987-10-20 Firmenich Sa Utilization of a cycloaliphatic carbinol as perfuming ingredient
WO2001004253A1 (fr) * 1999-07-12 2001-01-18 Bush Boake Allen Inc. Materiaux parfumes
EP1108703A1 (fr) * 1999-12-17 2001-06-20 Takasago International Corporation Composition parfumante

Also Published As

Publication number Publication date
DE102005002010A1 (de) 2006-07-20

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