WO2005012222A1 - Ester alicyclique sentant le musc - Google Patents

Ester alicyclique sentant le musc Download PDF

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Publication number
WO2005012222A1
WO2005012222A1 PCT/EP2004/051361 EP2004051361W WO2005012222A1 WO 2005012222 A1 WO2005012222 A1 WO 2005012222A1 EP 2004051361 W EP2004051361 W EP 2004051361W WO 2005012222 A1 WO2005012222 A1 WO 2005012222A1
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Prior art keywords
methyl
mixture
formula
compound
propenyl
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PCT/EP2004/051361
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German (de)
English (en)
Inventor
Marcus Eh
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Symrise Gmbh & Co. Kg
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Publication of WO2005012222A1 publication Critical patent/WO2005012222A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/003—Esters of saturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Definitions

  • the present invention relates to (a) new alicyclic esters, (b) mixtures which comprise an alicyclic ester according to the invention, (c) the use of the alicyclic esters according to the invention or the mixtures according to the invention as fragrance, (d) processes for producing, amplifying or modifying them a musk smell in a mixture, (e) fragrance mixtures with a musk smell, (f) perfumed products and (g) a process for producing an alicyclic ester according to the invention.
  • Compounds with a musky smell are sought-after components in the fragrance industry. They are characterized both by their property of giving radiance to perfume compositions and by their ability to ability to act as a fixator. This means that musk fragrances are used in many perfume compositions today.
  • R 1 is for example an ethyl group and R 2 is a methyl group.
  • the compounds disclosed all comprise a 3,3-dimethyl-1-cyclohexyl radical. It is stated in the US document that the disclosed compounds have a musky smell which is paired with amber and fruity aspects.
  • WO 00/14051 A1 discloses esters of type IV, where R 1 can in particular be an alkyl group.
  • the compounds disclosed in EP 1 262 474 A1 always include a 3,3-dimethyl-1-cyclohexyl radical.
  • the disclosed compounds are said to have a musky note, which can compete with the smell of known macrocyclic musk fragrances.
  • the musky note is at best pronounced of natural muscon.
  • the object of the present invention to provide musk fragrances whose odor profile differs from that of the compounds from the said documents and is preferably closely based on the olfactory properties of Muscon.
  • the musk fragrances to be specified should have original olfactory aspects in order to expand the range of raw materials available for the composition of perfumes.
  • R 1 is an optionally substituted (a) branched or unbranched Ci to C 5 alkyl group or (b) branched or unbranched C 2 to C 5 alkylene group or (c) C 3 to C 5 cycloalkyl group
  • the bond shown in dashed lines means a single or double bond.
  • the following can be used as the branched or unbranched C 1 to C 5 alkyl group: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, iso-pentyl and 3-methylbutyl.
  • the alkyl radicals methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl and isobutyl are preferred, and particularly preferably the alkyl radicals methyl, ethyl and n-propyl.
  • branched or unbranched C 2 to C 5 alkylene groups ethenyl, methylethenyl, 1-propenyl, 2-propenyl, 2-methyl-1-propenyl, 1-methyl-1-propenyl, 1-butenyl, 3-butenyl , 1-methyl-1-butenyl, 1-methyl-3-butenyl, 3-methyl-3-butenyl, 1-pentenyl, 2-pentenyl and 4-pentenyl.
  • substituted or unsubstituted C 3 to C 5 cycloalkyl groups can be used: cyclopropyl, 2-methylcyclopropyl, 1,2-dimethylcyclopropyl, cyclobutyl and cyclopentyl.
  • the cycloalkyl groups cyclopropyl, cyclobutyl and cyclopentyl are preferred.
  • the compounds of the formula I or II according to the invention can be in the form of a pure optically active enantiomer, an optically active mixture of different entantiomers or any other mixture of the stereoisomers encompassed by the formula I or II.
  • the compounds according to the invention (alicyclic esters) Formulas I and II have perfume-like musky scent notes and are also characterized by the desired interesting leg notes.
  • the compounds of the formula I have very beautiful floral and jasmine aspects in addition to the musk note.
  • such floral and jasmine aspects completely take a back seat and the compounds are distinguished by a natural musk note which is pronounced of Muscon.
  • a compound of the formula VII according to the invention is particularly valuable from a sensor standpoint, where R 1 has the meaning given above, but is preferably ethyl or cyclopropyl.
  • the compound of formula VII has a 2-methyl-1-cylohexyl group and thus no double bond in the 6-ring; the compound of Formula VII has an odor pronounced of Muscon.
  • the present invention also relates to mixtures which comprise a compound of the formula VII (according to the invention) and a compound of the formula VI (per se not according to the invention),
  • R 1 is an optionally substituted (a) branched or unbranched Ci to C 5 alkyl group or (b) branched or unbranched C 2 to C 5 alkylene group or (c) C 3 to C 5 cycloalkyl group.
  • R 1 is ethyl or cyclopropyl.
  • the Muscon-like scent of the formula VII esters is paired with the floral, jasmine musk scent of the formula VI esters in a unique way to create a distinctive, complex musk scent.
  • the mixtures of the compounds of the formulas VI and VII can be synthesized in a particularly economical manner.
  • Another aspect of the invention relates to a mixture comprising (a) a compound of the formula I and (b) a compound of the formula II,
  • R 1 is an optionally substituted (a) branched or unbranched Ci to C 5 alkyl group or (b) branched or unbranched C 2 to C 5 alkylene group or (c) C 3 to C 5 cycloalkyl group
  • the bond shown in dashed lines means a single or double bond.
  • R 1 is preferably selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl; Ethenyl, methylethenyl, 1-propenyl, 2-propenyl, 2-methyl-1-propenyl, 1-methyl-1-propenyl, cyclopropyl, 2-methylcyclopropyl, 1,2-dimethylcyclopropyl, cyclobutyl and cyclopentyl.
  • the invention also relates to the use of a compound or a mixture according to the invention as a fragrance.
  • the invention relates to a method for producing, amplifying or modifying a musk odor in a mixture, with the following steps
  • composition of other constituents Providing a composition of other constituents and mixing the composition of other constituents with an amount of the compound according to the invention or the mixture according to the invention which is sufficient (a) to produce a musk odor in the resulting overall mixture, (b) to present an existing musk odor in the composition of other constituents reinforce or (c) an existing model Modify shot odor in the composition of other components.
  • the present invention also relates to fragrance mixtures with a musk odor, comprising - a sensorially effective amount of a compound according to the invention or a mixture according to the invention and optionally further conventional constituents such as solvents, other fragrances or the like.
  • the invention also relates to perfumed products comprising a fragrance mixture according to the invention and a carrier or a substrate which is in direct contact with the fragrance mixture.
  • the scented product can advantageously be selected from the group consisting of alcoholic perfumes, personal care products and household cleaning or care products.
  • the compounds of the formula I and II according to the invention can be used as individual substances or in the form of mixtures (see also above) in a large number of fragrance mixtures and perfumed products.
  • the compounds according to the invention of the formulas given above can be combined particularly advantageously with other fragrances to form novel perfume compositions.
  • fragrances with which the alicyclic esters of the formula (I) according to the invention can advantageously be combined can be found, for example, in K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Materials, 3 rd . Ed., WileyNCH, Weinheim 1997.
  • Extracts from natural raw materials such as essential oils, concretes, absolues, resins, resinoids, balms, tinctures such as B. ambratincture; Amyrisöl; Angelica seed oil; Angelica root oil; anise oil; Valerian oil; Basil oil; Baummoos -Absolue; Bay oil; Mugwort oil; Benzoeresin; Bergamot oil; Beeswax absolute; birch tar; Bitter almond oil; Savory oil; Buccoblatterol; Cabreuvaol; cade oil; calamus; Campherol; Cananga oil; cardamom; Cascarillaöl; cassia; Cassie absolute; Castoreum- absolue; Cedern diligentöl; cedarwood; cistus; citronella; lemon; copaiba balsam; Copaivabalsamöl; Coriander oil; costus root; Cumin oil; Cypress oil; Davanaöl; Dill herb oil; Dill seed oil; Eau de brouts
  • fragrances from the group of hydrocarbons such as 3- caren; ⁇ -pinene; beta-pinene; ⁇ -terpinene; ⁇ -terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; Myrcene; ocimene; valencene; (E, Z) -1, 3,5-undecatriene;
  • B hexanol; octanol; 3-octanol; 2,6-dimethylheptanol; 2-methylhectanol, 2-methyloctanol; (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-meth-oxyoctan-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol; the aliphatic aldehydes and their 1,4-dioxacycloalken-2-ones such as B.
  • aliphatic ketones and their oximes such as 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; the aliphatic sulfur-containing compounds such as 3-methylthiohexanol; 3-methylthiohexyl acetate; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1-menthene-8-thiol;
  • aliphatic nitriles such as e.g. 2-nonenoic acid nitrile; 2-tridecenonitrile; 2,12-Tridecen Acid Taritrile; 3,7-dimethyl-2,6-octadienonitrile; 3,7-dimethyl-6-octen Aciditril;
  • Methyl-2-noninat Allyl-2-isoamyloxyacetat; Methyl 3,7-dimethyl-2,6-octadienoate;
  • acyclic terpene alcohols such as citronellol; geraniol; nerol;
  • cyclic terpene aldehydes and ketones such as e.g. menthone; Isomerhon; 8-mercaptomenthan-3-one; carvone; camphor; fenchon; alpha- lonon; beta-ionone; alpha-n-methylionone; beta-n-methylionone; alpha-
  • nootkatone Di hydronootkaton; alpha-sinensal; beta-sinensal; Acetylated cedemwood oil (methyl cedryl ketone);
  • cyclic alcohols such as e.g. 4-tert-butylcyclohexanol; 3,3,5-trimethylcyclohexanol; 3-lsocamphylcyclohexanol; 2,6,9-trimethyl-Z2, Z5, E9-cyclododecatrien-1-ol; 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol;
  • cycloaliphatic alcohols such as alpha, 3,3-trimethylcyclohexylmethanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) butanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 2-ethyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) pentan-2-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 3,3-dimethyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 1- (2,2,6-trimethylcyclohexyl) pentan-3-ol; 1- (2,2,6-trimethylcyclohexyl) hex
  • cyclic ketones such as e.g. 4-tert.-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 2-heptylcyclopentanone; 2-pentylcyclopentanone; 2-hydroxy-3-methyl-2-cyclopenten-1-one; 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one; 3-methyl-2-pentyl-2-cyclopenten-1-one; 3-methyl-4-cyclopentadecenone; 3-methyl-5-cyclopentadecenone; 3-methylcyclopentadecanone; 4- (1-ethoxyvinyl) -3,3,5,5-tetra-methylcyclohexanone; 4-tert.-pentylcyclohexanone; 5-cyclohexadecen-1 - one; 6,7-Dihydro-1,1,2,3,3-pentamethyl-4 (5H) -indanon; 5
  • cycloaliphatic aldehydes such as e.g. 2,4-dimethyl-3-cyclohexenecarbaldehyde; 2-methyl-4- (2,2,6-trimethyl-cyclohexen-1-yl) -2-butenal; 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene carbaldehyde; 4- (4-methyl-3-penten-1-yl) -3-cyclohexenecarbaldehyde;
  • cycloaliphatic ketones such as. B. 1 - (3,3-Dimethylcyclohexyl) -4-penten-1-one; 1- (5,5-dimethyl-1-cyclohexen-1-yl) ⁇ 4-penten-1-one; 2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthalenyl methyl ketone; Methyl 2,6, 10-trimethyl-2,5,9-cyclododecatrienyl ketone; tert-butyl- (2,4-dimethyl-3-cyclohexen-1-yl) ketone;
  • ester of cyclic alcohols such as 2-tert-butylcyclohexyl acetate; 4-tert butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-pentylcyclohexyl acetate; Decahydro-2-naphthyl acetate; 3-pentyltetrahydro-2H-pyran-4-ylacetate; Decahydro-2,5,5,8a-tetramethyl-2 naphthyl acetate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, or 6-indenyl acetate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, or
  • 6-indenylpropionat 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5 J or 6-indenyl isobutyrate; 4,7-methanooctahydro-5 or 6-indenyl acetate;
  • ester of cycloaliphatic carboxylic acids such as.
  • aromatic hydrocarbons such.
  • araliphatic alcohols such as e.g. benzyl alcohol; 1-phenylethyl alcohol; 2-PhenylethylaIkohol; 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-propen-1-ol; 4-methoxybenzyl; 1- (4-isopropylphenyl) ethanol;
  • the ester of araliphatic alcohols and aliphatic carboxylic acids such as; benzyl acetate; benzylpropionate; benzyl isobutyrate; Benzyl isovalerate; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-phenylethyl isobutyrate; 2-Phenylethylisovalerianat; 1 -phenylethyl acetate; alpha-Trichlormethylbenzylacetat; alpha, alpha-dimethylphenylethyl acetate; alpha.alpha-Dimethylphenylethylbutyrat; Cinamate acetate; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate; the araliphatic ether such as 2-phenylethyl methyl ether; 2-phenylethyl isoamyl ether; 2-phenylethyl-1-ethoxyethy
  • aromatic and araliphatic aldehydes such as.
  • aromatic and araliphatic ketones such as e.g. acetophenone; 4-methyl acetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6-dimethylacetophenone; 4-phenyl-2-butanone; 4- (4-hydroxyphenyl) -2-butanone; 1- (2-naphthalenyl) ethanone; benzophenone; 1,1,2,3,3,6-hexamethyl-5-indanyl methyl ketone; 6-tert-butyl-1,1-dimethyl-4-indanyl methyl ketone; 1 - [2,3-dihydro-1,1,2,6-tetramethyl-3- (1-methylethyl) -1 H-5-indenyl] ethanone; 5 ⁇ 6 ', 7', 8'-tetrahydro-3 ', 5', 5 ', 6', 8 ', 8'-hexamethyl-2-acetonaphthone;
  • aromatic and araliphatic carboxylic acids and their esters such as benzoic acid; phenylacetic acid; Methyl benzoate; ethyl benzoate; hexyl benzoate; Benzyl benzoate; Methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; Phenylethyl phenylacetate; Methylcinnmat; Ethyl cinnamate; Benzyl; Phenylethylcinnamat; cinnamyl cinnamate; allyl phenoxyacetate; methyl salicylate; isoamyl; hexyl salicylate; Cyclohexyl salicylate; Cis-3-hexenyl salicylate; benzyl; phenyl ethyl salicylate; Methyl-2,4-dihydroxy-3,6-dimethylbenzoate; Ethyl 3-phen
  • the nitrogenous aromatic compounds such as e.g. 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert-butylacetophenone; cinnamic acid; 5-phenyl-3-methyl-2-pentenoic acid nitrile; 5-phenyl-3-methylpentanklaitril; methyl anthranilate; Methyl-N-methylanthranilate; SchifFsche bases of methylanthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3- (4-tert-butylphenyl) propanal or 2,4-dimethyl-3-cyclohexenecarbaldehyde; 6-lsopropylchinolin; 6-isobutylquinoline; 6-sec-butylquinoline; indole; skatol; 2-methoxy-3-isopropylpyrazine; 2-isobut
  • phenols, phenyl ethers and phenyl esters such as e.g. estragole; anethole; eugenol; Eugenylmethyiether; isoeugenol; Isoeugenylmethylether; Thymol; carvacrol; diphenyl ether; beta-naphthyl methyl ether; beta-naphthyl ethyl ether; beta-Naphthylisobutylether; 1,4-dimethoxybenzene; Eugenylacetat; 2-methoxy-4-methyl phenol; 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-fura ⁇ -3-one; 3-hydroxy-2-methyl-4H-pyran-4-one; 2-ethyl-3-hydroxy-4H-pyran-4-one;
  • the lactones such as 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; 1.15 PentadecanoIid; cis- and trans-11-pentadecen-1,15-olide; ice and trans-12-pentadecen-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; Ethylene 1, 13-tridecanedioate;
  • Perfume oils which contain the compounds of the above formulas according to the invention can be used in liquid form, undiluted or diluted with a solvent for perfuming.
  • Suitable solvents for this are, for example, ethanol, isopropanol, diethylene glycol monoethyl ether, glycerin, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, etc.
  • Perfume oils which contain the compounds according to the invention can be absorbed on a carrier which ensures both a fine distribution of the fragrances in the product and a controlled release during use.
  • a carrier which ensures both a fine distribution of the fragrances in the product and a controlled release during use.
  • Such carriers can be porous inorganic materials such as light sulfate, silica gels, zeolites, gypsum, clays, clay granules, gas concrete etc. or organic materials such as woods and cellulose-based substances.
  • Perfume oils which contain the compounds according to the invention can also be microencapsulated, spray-dried, present as inclusion complexes or as extrusion products and can be added in this form to the product to be perfumed.
  • the properties of the perfume oils modified in this way can be further optimized by so-called “coating” with suitable materials with a view to a more targeted fragrance release, for which purpose wax-like plastics such as polyvinyl alcohol are preferably used.
  • the microencapsulation of the perfume oils can take place, for example, by means of the so-called coacervation process with the aid of capsule materials, for example made of polyurethane-like substances or soft gelatin.
  • the spray-dried perfume oils can be produced, for example, by spray drying an emulsion or dispersion containing the perfume oil, it being possible to use modified starches, proteins, dextrin and vegetable gums as carriers.
  • Inclusion- Complexes can be prepared, for example, by adding dispersions of the perfume oil and cyclodextrins or urea derivatives in a suitable solvent, for example water.
  • Extrusion products can be made by fusing the perfume oils with a suitable wax-like substance and by extrusion with subsequent solidification, if necessary in a suitable solvent, eg isopropanol.
  • the amount of the compounds according to the invention used is preferably 0.05 to 50% by weight, preferably 0.5 to 20% by weight, based on the total perfume oil.
  • Perfume oils containing the compounds according to the invention can be used in concentrated form, in solutions or in the modified form described above for the production of, for example, perfume extracts, eau de parfms, eau de toilettes, aftershaves, eau de logos, pre -shave products, splash colognes and scented refreshing wipes as well as the scenting of acidic, alkaline and neutral cleaning agents, such as floor cleaners, window glass cleaners, dishwashing detergents, bathroom and sanitary cleaners, scouring milk, solid and liquid toilet cleaners, powder and foam-shaped tep- Pichrillian, liquid detergents, powder detergents, laundry pretreatment agents such as bleach, soak and stain removers, fabric softeners, washing soaps, washing tablets, disinfectants, surface disinfectants and air fresheners in liquid, gel-like or applied to a solid carrier, aerosol spray ys, waxes and polishes such as furniture polishes, floor waxes, shoe creams as well as personal care products such as solid and liquid
  • the invention also relates to a method for producing a compound according to the invention, comprising the following steps:
  • Processes for producing mixtures according to the invention comprise corresponding steps and are preferably based on alcohol mixtures; see. in particular the following synthetic routes according to Scheme 2.
  • R 1 has the meaning given above and the dashed line is a single bond
  • the esterification can be carried out by heating the alcohol (XI) and the corresponding carboxylic acid on a water separator in the presence of an entrainer (for example toluene or cyclohexane) with the addition of 0.01 mol% to 10 mol%, preferably 0.1 mol% to 5 mol% of an acid, preferably p-toluenesulfonic acid or sulfuric acid or by reacting the alcohol (XI) with the corresponding carboxylic anhydride in the presence of triethylamine and 0.5 mol% to 50 mol%, preferably 1.0 mol% to 30 mol%, 4-dimethylaminopyridine.
  • an entrainer for example toluene or cyclohexane
  • Scheme 2 In the first step of the synthetic route shown in Scheme 2, a Diels-Alder reaction of 1,3-pentadiene and methyl vinyl ketone, in the presence of catalytic amounts of a Lewis acid, is carried out by methods familiar to the person skilled in the art.
  • the isomer mixture of the two unsaturated ketones (XII) / (XIII) which is formed is subsequently reduced on the one hand to the unsaturated alcohols (XIV) / (XV) and on the other hand converted into the saturated alcohols (XVIII) / (XIX) by hydrogenation.
  • the reduction with sodium borohydride, as well as the hydrogenation can be carried out according to methods well known to the person skilled in the art.
  • the further reaction of the alcohols (XIV) / (XV) and (XVIII) / (XIX) is carried out analogously to the reaction shown in Scheme 1 with isobutylene oxide and subsequent esterification.
  • Example 2 The following compound from Example 2 was prepared analogously to the instructions described in Example 1, with the change that the esterification was carried out with cyclopropanecarboxylic acid. Only the spectroscopic data are listed here:
  • the spectroscopic data correspond to the literature data (Hersh,
  • Example 4 The following compounds of Example 4 were prepared analogously to the instructions described in Example 3, with the change tion that the esterification was carried out with cyclopropanecarboxylic acid.
  • the spectroscopic data of the regioisomer mixtures correspond to that of the pure individual compounds and are therefore not listed:
  • composition The present perfume oil can be used to perfume various cosmetic products.
  • BA benzyl alcohol
  • IPM isopropyl myristate
  • DEP diethyl phthalate
  • composition an incomparable musk note that cannot be achieved with existing musk fragrances. Furthermore, the entire composition gains in abundance and appears more valuable.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un composé correspondant à la formule (I) ou (II). Dans les formules (I) et (II), R1 représente : (a) un groupe alkyle C1-C5 ramifié ou non ramifié, ou (b) un groupe alkyle C2-C5 ramifié ou non ramifié, ou bien (c) un groupe cycloalkyle C3-C5, tous ces groupes pouvant être éventuellement substitués. Dans la formule (II) la liaison représentée en pointillé est une liaison simple ou double.
PCT/EP2004/051361 2003-07-31 2004-07-05 Ester alicyclique sentant le musc WO2005012222A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10335053A DE10335053A1 (de) 2003-07-31 2003-07-31 Alicyclische Ester mit Moschusgeruch
DE10335053.5 2003-07-31

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WO2005012222A1 true WO2005012222A1 (fr) 2005-02-10

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DE (1) DE10335053A1 (fr)
WO (1) WO2005012222A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102060700A (zh) * 2010-12-27 2011-05-18 营口市风光化工有限公司 一种从生产抗氧剂1010母液的醇解液中回收3,5-甲酯的方法
WO2024003271A1 (fr) * 2022-06-30 2024-01-04 Firmenich Sa Procédé de préparation de dérivés d'éther, de thioéther ou d'amine secondaire en présence d'un catalyseur acide hétérogène

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110227487B (zh) * 2019-06-24 2022-08-16 西安凯立新材料股份有限公司 一种羰基加氢催化剂的制备方法及应用

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0472966A1 (fr) * 1990-08-28 1992-03-04 Firmenich Sa Esters nouveaux et leur utilisation en parfumerie
EP1262474A1 (fr) * 2001-06-01 2002-12-04 Givaudan SA Dérivés d'acides cycloalcane carboxyliques ayant une notes odorante de type musqué

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0472966A1 (fr) * 1990-08-28 1992-03-04 Firmenich Sa Esters nouveaux et leur utilisation en parfumerie
EP1262474A1 (fr) * 2001-06-01 2002-12-04 Givaudan SA Dérivés d'acides cycloalcane carboxyliques ayant une notes odorante de type musqué

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102060700A (zh) * 2010-12-27 2011-05-18 营口市风光化工有限公司 一种从生产抗氧剂1010母液的醇解液中回收3,5-甲酯的方法
WO2024003271A1 (fr) * 2022-06-30 2024-01-04 Firmenich Sa Procédé de préparation de dérivés d'éther, de thioéther ou d'amine secondaire en présence d'un catalyseur acide hétérogène

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