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EP1797026A1 - (z)-8-cycloheptadecene-1-one utilisee comme parfum - Google Patents

(z)-8-cycloheptadecene-1-one utilisee comme parfum

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Publication number
EP1797026A1
EP1797026A1 EP05786850A EP05786850A EP1797026A1 EP 1797026 A1 EP1797026 A1 EP 1797026A1 EP 05786850 A EP05786850 A EP 05786850A EP 05786850 A EP05786850 A EP 05786850A EP 1797026 A1 EP1797026 A1 EP 1797026A1
Authority
EP
European Patent Office
Prior art keywords
cycloheptadecen
mixture
fragrance
oil
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP05786850A
Other languages
German (de)
English (en)
Inventor
Aurelia Reckziegel
Marcus Eh
Horst Surburg
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Symrise AG
Original Assignee
Symrise AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Symrise AG filed Critical Symrise AG
Publication of EP1797026A1 publication Critical patent/EP1797026A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/42—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/203—Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • 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
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2072—Aldehydes-ketones
    • 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
    • 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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/264—Aldehydes; Ketones; Acetals or ketals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered

Definitions

  • the present invention relates primarily to the novel compound (Z) -8-cycloheptadecen-1-one, fragrance and flavoring mixtures comprising (E 1 Z) - 8-cycloheptadecen-1-one, their respective use as fragrance or flavoring (mixture) , corresponding perfumed products and processes for the preparation of ⁇ -cycloheptadecen-i-on.
  • musk fragrances In the perfume industry, there is a general need for musk fragrances as consumers are constantly provided with new and modern fragrances with musk fragrance. Scents with musk odor are used in large quantities and innumerable variations in perfumes, fragrance mixtures (perfume compositions) and perfumes for a variety of applications. With consumer demand for new, modern fragrances, the fragrance industry has a constant need for fragrances that create new effects in perfumes, creating new fashion trends. Compounds with musk odor have always been important and sought-after components in the fragrance industry. Thus musk fragrances are used in many perfume compositions today.
  • Typical macrocyclic musk fragrances are characterized by a ring with 13 to 17 carbon atoms, which carries a ketone or an ester as a functional group.
  • Classic musk fragrances include Zibeton, Muscon, Cyclopentadecanolid, Ethylenbrassilat and Cylopentadecanone.
  • Perfumers generally refer to these musk bodies of a "macromusic odor", the individual compounds differ in some notes and aspects in part very clearly from each other.
  • musk fragrances with special odor properties which are suitable to serve as a basis for the composition of novel modern perfumes with a complex musk character.
  • the odoriferous mixtures C - F were composed as follows (values according to GC analysis):
  • Mixture D d. H. the mixture of (E, Z) -8- and (E.ZJ- ⁇ -cycloheptadecen-i-on according to GC analysis contained 34.5% (EJ- ⁇ -cyclohexadecen-i-one, 17.5% (Z ) -Cycloheptadecen-1-one of the formula (I), 30.8% (EJ- ⁇ -cycloheptadecen-1-one and 16.3% (Z) -9-cycloheptadecen-1-one (see Example 2 below).
  • Mixture F d. H. the mixture of (E, Z) -8- and (E, Z) -9-cycloheptadecen-1-one with high (Z) content according to GC analysis contained 2.3% (E) - ⁇ -cyclohexadecen-i 49.5% of (Z) -8-cycloheptadecen-1-one of the formula (I), 1.8% of (E) -9-cycloheptadecen-1-one and 42.8% of (Z) -9- Cycloheptadecen-1-one (see Example 2 below).
  • (Z) -8-Cycloheptadecen-1-one shows of the compounds and mixtures investigated here the strongest and most elegant musk odor, especially a powdery Nitromoschusnote.
  • the combination of (ZJ- ⁇ -cycloheptadecen-i-one (I) and (E) -8-cycloheptadecen-1-one to (E.ZJ- ⁇ -cycloheptadecen-i-one (II) already has a more complex musk odor
  • Preferred is the weight ratio of (E) -8-cycloheptadecen-1-one to (Z) -8-cycloheptadecen-1-one in the range of 6: 1 as the individual isomers, namely the wished nitro musk odor, to which a woody aspect is added to 1:30, more preferably in the range 4: 1 to 1:25.
  • mixture E.ZJ- ⁇ . ⁇ -cycloheptadecen-i-on with a high (Z) proportion, ie, mixture F according to Table 1 has in comparison to a mixture of trans-isomer (E) -8,9-cycloheptadecene 1-on enriched mixture E according to Table 1 has a much greater intensity, complexity and elegance and is therefore particularly suitable for use in new and modern perfume compositions.
  • the mixture D according to Table 1 shows the highest complexity of the mixtures examined here, and is characterized by naturalness and radiation.
  • the slightly woody accent harmonizes perfectly with the elegant, natural musk smell.
  • the (Z) -8-cycloheptadecen-1-one according to the invention is able to intensify the intensity of a fragrance mixture even at low dosages and to round off the overall appearance of the fragrance mixture in an odor, and to give the mixture more charisma and naturalness. In higher dosages comes the clean, strong Musky scent to wear, accompanied by the beautiful nitro musk note.
  • Cycloheptadecen-1-one preferably in the range from 10: 1 to 1:10, is preferably in the range from 5: 1 to 1: 5, particularly preferably in the range from 2: 1 to 1
  • a closely related aspect of the invention discussed above relates to the use of (Z) -8-cycloheptadecen-1-one or a (Z) -8-cycloheptadecen-1-one odoriferous or flavoring mixture (as characterized above) as musketry - or -aromastoff or musketry or - flavoring mixture.
  • a sensory effective amount of (Z) -8-cycloheptadecen-1-one or a (Z) - ⁇ -cyclohepta-decen-1-one comprising fragrance or flavoring mixture ( as characterized above) are contacted or mixed with a product.
  • the preparation of the mixture (E, Z) -8,9-cycloheptadecen-1-one can advantageously be prepared from the known (E / Z) -8-cyclohexadecen-1-one by means of ring expansion in four synthesis routes A, B explained in detail below , C or D preferably on synthesis route A or B and particularly preferably on synthesis route A, take place.
  • Synthetic route A relates to a process according to the invention for the preparation of (i) (Z) -8-cycloheptadecen-1-one or (ii) a mixture containing (Z) -8-cycloheptadecen-1-one, comprising the following steps:
  • thermal fragmentation which preferably proceeds by saponification plus decarboxylation, preferably as a one-pot reaction.
  • synthesis route A preferably (E / ZJ- ⁇ -cyclohexadecen-1-one is reacted, for example according to the instructions of J. Org. Chem. 1983, 48, 2590-2598 with a diazoacetic acid ester (eg.
  • a further subject of the invention concerns the 1-aminomethylcyclohexadec-8-enol, hitherto not described in the literature, preferably as a mixture of isomers of the formula (III)
  • Another closely related aspect of the present invention relates to a process for preparing a mixture comprising (Z) -8-cycloheptadecen-1-one and (Z) -9-cycloheptadecen-1-one, comprising the following step:
  • the preparation of the (E, Z) -8-cycloheptadecen-1-one (II) according to the invention is finally carried out starting from the ⁇ , ⁇ -unsaturated diene 1,18-nonadecadien-9-one in a ring-closing olefin metathesis.
  • 1, 18-nonadecadien-9-one for example, as 0.01 to 0.001 molar solution in the presence of 0.5 to 10 mol% of a metathesis catalyst based on Mo, W or Ru implemented.
  • the reaction is advantageous in the presence of benzylidene bis (cyclohexylphosphine) -J-dichlororuthenium (Grubbs catalyst) [cf. Synthesis 1997, 792; Synlett 1997, 1010], cf. Example 1.3.
  • the invention also relates to perfumed products comprising a solid or semi-solid carrier and a carrier-contacting, sensory effective amount of (ZJ- ⁇ -cycloheptadecen-i-one or olfactory or (Z) -8-cycloheptadecen-1-one Flavoring mixture (as characterized above).
  • Extracts from natural raw materials such as essential oils, concretes, absolues, resines, resinoids, balsams, tinctures such.
  • calamus camphor oil
  • Cananga oil cardamom; Cascarillaöl; cassia; Cassie absolute; Beaver-absolue; Cedemenseöl; Cedemholzöl; cistus;
  • citronella lemon; copaiba balsam; Copaivabalsamöl; Coriander oil;
  • Orris root oil Jasmine absolute; calamus; Chamomile oil blue; Camomile oil Roman; Carrot seed oil; Kaskarillaöl; Pine needle oil; spearmint; Seed oil;
  • Parsley leaf oil Parsley seed oil; Petitgrain oil; Peppermint oil; Pepper oil;
  • vanilla extract Violet leaf absolute; verbena; vetiver; Juniper berry oil;
  • cinnamon leaf cinnamon bark oil; and fractions thereof, or ingredients isolated therefrom;
  • fragrances from the group of hydrocarbons such as 3-carene; ⁇ -pinene; beta-pinene; ⁇ -terpinene; ⁇ -terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E 1 Z) -1, 3,5-undecatriene;
  • the aliphatic alcohols such. Hexanol; octanol; 3-octanol; 2,6-dimethylheptanol; 2-methylheptanol, 2-methyl-octanol; (E) -2-hexenol; (E) - and (Z) -3-hexenol; 1-octene-3-ol; Mixture of SA ⁇ , ⁇ , ⁇ -pentamethyl-SM-heptene-1-ol and SS ⁇ , ⁇ -tetramethyl, -ethyleneheptane, -ol; (E, Z) -2,6-Nonadienol; 3,7-dimethyl-7-methoxyoctan-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol; the aliphatic aldehydes and their 1,4-dioxacycloalkene-2-ones such.
  • the 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 J 4 J 7-tetramethyl-6-octen-3-one; the aliphatic sulfur-containing compounds such as, for example, 3-methylthiohexanol; 3-Methylthiohexylacetat; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3
  • aliphatic nitriles e.g. 2-nonenoic acid nitrile; 2-Tridecen Textrenitril; 2,12-Tridecen Acid Citril; 3,7-dimethyl-2,6-octadienklarenitril; 3,7-dimethyl-6-octenoic acid nitrile;
  • acyclic terpene alcohols e.g. 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-octene-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-i, 5,7-octatrien-3-ol 2,6-dimethyl-2,5,7-octatrien-1-ol; as well as their formates, acetates, propionates, isobut
  • geranial e.g. geranial; neral; citronellal; 7-hydroxy-3,7-dimethyloctanal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; geranyl acetone; and the dimethyl and diethyl acetals of geranial, neral, 7-hydroxy-3,7-dimethyloctanal;
  • the cyclic terpene alcohols e.g. 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, 3-methyl-2-butenoates;
  • Menthol isopulegol
  • alpha-terpineol Terpinenol-4
  • Menthane-8-ol Menthane-1-ol
  • Menthane-7-ol borneol
  • Isobomeol linalool
  • monopoly cedrol
  • the cyclic terpene aldehydes and ketones such as menthone; menthone; 8-mercaptomenthan-3-one; carvone; camphor; fenchon; alpha-ionone; beta-ionone; alpha-n-methylionone; beta-n-methylionone; alpha-isomethylionone; beta-isomethyl-ionone; alpha-lron; alpha-damascone; beta-damascone; beta Damascenon; delta-damascone; gamma-damascone; 1- (2,4,4-trimethyl-2-cyclohexene-1-yl) -2-butene-1-one; 1, 3,4,6,7,8a-hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methanonaphthalene-8 (5H) -one; nootkatone; Dihydronootkaton; alpha-Sinensal; beta
  • cycloaliphatic alcohols such as alpha ⁇ S-trimethylcyclohexylmethanol; 2-methyl-4- (2,2- J- 3-trimethyl-3-cyclopent-1-yl) butanol; 2-methyl-4- (2 J 2,3-trimethyl-cyclopent-3-1-yl) -2-buten-1-ol; 2-ethyl-4- (2,2- J- 3-trimethyl-3-cyclopent-1-yl) -2-butene-1-ol; 3-methyl-5- (2,2- J- 3-trimethyl-3-cyclopent-1-yl) -pentan-2-ol; 3-methyl-5- (2,2- J- 3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 3 J 3-dimethyl-5- ( 2J 2 J 3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 1 - (2,2 J 6-trimethylcyclohexyl) pentan-3-ol; 1 - (2,2,6-
  • cyclic and cycloaliphatic ethers such as e.g. cineol; cedryl methyl ether; cyclododecyl; (Ethoxymethoxy) cyclododecane; alpha-Cedrenepoxid; Sa.e.beta.-tetramethyldodecahydronaphthop, 1-b] furan; 3a-ethyl-6,6,9a-trimethyldodecahydronaphtho [2,1-b] furan; 1.S. ⁇ -trimethyl-IS-oxabicyclo [10.1.0] trideca-4,8-diene; rose oxide; 2- (2,4-dimethyl-3-cyclohexene-1-yl) -5-methyl-5- (1-methylpropyl) -1,3-dioxane;
  • cyclic ketones such as e.g. 4-tert.-butylcyclohexanone; 2,2,5- ⁇ 016 ⁇ - 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-cyclopenten-1-one; 3-methyl-4-cyclopentadecenone; 3-methyl-5-cyclopentadecenone; S-methylcyclopentadecanone; 4- (1-ethoxyvinyl) -3,3,5,5-tetramethylcyclohexanone; 4-tert.-pentylcyclohexanone; 5-cyclohexadecen-1-one; 6,7-dihydro-1,1,3,3,3-pentamethyl-4 (5H) -indanone; 9-cyclohept
  • cycloaliphatic aldehydes such as 2,4-dimethyl-3-cyclohexene carbaldehyde; 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-cyclohexene carbaldehyde; the cycloaliphatic ketones such.
  • ester of cyclic alcohols e.g. 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-yl acetate;
  • esters of cycloaliphatic carboxylic acids such as.
  • allyl-3-cyclohexylpropionate Allylcyclohexyloxyacetat; methyldihydrojasmonate; methyl jasmonate; Methyl 2-hexyl-3-oxocyclopentanecarboxylate; Ethyl--ethyl-.,--Dimethylcyclohexenecarboxylate; .
  • Ethyl ⁇ ⁇ . ⁇ -tetramethyl ⁇ -cyclohexencarboxylat Ethyl 2-methyl-1,3-dioxolane-2-acetate;
  • aromatic hydrocarbons such as Styrene and diphenylmethane
  • the araliphatic alcohols e.g. benzyl alcohol; 1-phenylethyl; 2-phenylethyl; 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;
  • ester of araliphatic alcohols and aliphatic carboxylic acids such as; benzyl acetate; benzylpropionate; benzyl isobutyrate; Benzylisovalerianat; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-Phenylethylisobutyrat;
  • 2-Phenylethylisovalerianat 1-phenylethyl acetate; alpha- Trichlormethylbenzylacetat; alpha.alpha-Dimethylphenylethylacetat; alpha.alpha dimethylphenyl ethyl butyrate; cinnamyl; 2-phenoxyethyl isobutyrate; 4-methoxybenzylacetate; the araliphatic ethers such as 2-phenylethyl methyl ether; 2-Phenylethylisoamylether; 2-phenylethyl-1-ethoxyethyl ether; phenylacetaldehyde; Phenylacetaldehyde diethyl acetal; Hydratropaaldehyddimethylacetal; Phenylacetaldehyde glycerin acetal; 2,4,6-trimethyl-4-phenyl-1,3-dioxane; 4,4a, 5,9b-tetrahydr
  • 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;
  • 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) -1H-5-indenyl] ethanone; S'.e'y'. ⁇ '-tetrahydro-S'.S'.S'.e'. ⁇ '. ⁇ '-hexamethyl-acetonaphthone;
  • aromatic and araliphatic carboxylic acids and their esters such as benzoic acid; phenylacetic acid; methylbenzoate; ethyl benzoate; hexyl benzoate; Benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; Phenylethyl phenylacetate; Methylcinnmat; ethylcinnamate; Benzyl; Phenylethylcinnamat; cinnamyl cinnamate; AIIyI phenoxyacetate; methyl salicylate; isoamyl; hexyl salicylate; cyclohexyl; Cis-3-hexenyl salicylate; benzyl; phenylethyl; Methyl-2,4-dihydroxy-3,6-dinnethylbenzoat; Ethyl 3-phenylglycidate; E
  • nitrogen-containing aromatic compounds such as e.g. 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dinnethyl-4-tert.-butylacetophenone;
  • the phenols, phenyl ethers and phenyl esters e.g. 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; 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; Ethylene-1,13-tride
  • the (E, Z) -8,9-cycloheptadecen-1-one, (E, Z) -8-cycloheptadecen-1-one or (Z) -8-cycloheptadecen-1-one-containing perfume oils 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, glycerol, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, etc.
  • Such supports may include porous inorganic materials such as light sulfate, silica gels, zeolites, gypsum, clays, clay granules, aerated concrete, etc., or organic materials such as woods; Cellulose-based substances, sugars or plastics such as PVC, polyvinyl acetates or polyurethanes.
  • porous inorganic materials such as light sulfate, silica gels, zeolites, gypsum, clays, clay granules, aerated concrete, etc.
  • organic materials such as woods
  • Cellulose-based substances, sugars or plastics such as PVC, polyvinyl acetates or polyurethanes.
  • 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, for example of polyurethane-type substances or soft gelatin.
  • the spray-dried perfume oils can be prepared, for example, by spray-drying a perfume oil-containing emulsion or dispersion, with starches modified as carriers, proteins, dextrin and vegetable gums can be used.
  • Inclusion complexes can be prepared, for example, by introducing dispersions of the perfume oil and cyclodextrins or urea derivatives into a suitable solvent, for example water.
  • Extrusion products can be made by fusing the perfume oils with a suitable waxy substance and by extrusion with subsequent solidification, optionally in a suitable solvent, for example isopropanol.
  • inventive substances (E, Z) -8,9-cycloheptadecen-1-one, (E, Z) -8-Cyloheptadecen-1-one or (Z) -8-cycloheptadecen-1-one containing perfume oils can in concentrated Form, used in solutions or in any other modified form for the production of eg Perfume extracts, eau de perfumees, eau de toilettes, shaving waters, eau de colognes, pre-shave products, splash colognes and perfumed tea towels, and the perfuming of acidic, alkaline and neutral detergents, e.g.
  • the amount of (Z) -8-cycloheptadecen-1-one used is usually in the range of 0.001 to 70 wt .-%, preferably 0.05 to 50 wt .-% and particularly preferably 0 , 5 to 25 wt .-%, based on the total perfume oil composition.
  • the amount of (E, Z) -8-cycloheptadecen-1-one or (E, Z) -8,9-cycloheptadecen-1-one used is usually in the range of 0.01 to 90% by weight. %, preferably 0.1 to 70 wt .-% and particularly preferably 1 to 40 wt .-%, based on the total perfume oil composition.
  • Preservatives abrasives, anti-acne agents, anti-aging agents, anti-bacterial agents, anti-cellulite agents, antidandruff agents, antiinflammatory agents, anti-irritants, anti-irritants, antimicrobials, antioxidants, astringents, antiperspirants, antiseptics, antistatics, binders , Buffers, Carrier Materials, Chelating Agents, Cell Stimulants, Cleansing Agents, Nursing Agents, Depilatories, Surfactants, Deodorants, Antiperspirants, Plasticizers, 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 straightening agents, moisturizing agents, moisturizing substances, moisturizing substances, bleaching agents, restorative agents, stain removing agents, optically bright
  • Cycloheptadecen-1-one or the compounds of the invention or mixtures (E, Z) -8,9-cycloheptadecen-1-one, (E, Z) -8-Cyloheptadecen-1-one and (ZJ- ⁇ -Cycloheptadecen -i-on containing fragrance or
  • Flavor blends are characterized by high build up (adhesion to a substrate) and high substantivity (ability to grow out of a mostly aqueous phase onto a substrate or after a wash or rinse on a substrate remain). This effect is particularly evident Substrates such as skin, hair and textile fibers (eg wool, cotton, linen, synthetic fibers).
  • perfumed products according to the invention are therefore detergents, hygiene or care products, in particular in the field of personal care, cosmetics and household.
  • fragrances that improve the adhesive strength of the composition (ie act as fixatives) or increase the strength of the smell perception (so act as a booster).
  • (Z) -8-cycloheptadecen-1-one and the mixtures according to the invention are distinguished by their fixing properties.
  • Such a fixative increases the adhesion of other fragrances, whether by lowering their vapor pressure or adding odor (e.g., lowering the threshold).
  • the invention therefore also relates to the use of (ZJ- ⁇ -cycloheptadecen-1-one or a (Z) -8-cycloheptadecen-1-one comprising fragrance or flavoring mixture (as characterized above) as a fixative.
  • (Z) -8-cycloheptadecen-1-one and the mixtures of the invention act not only as fixatives but also as so-called boosters or enhancers, i. they increase the odor or odor perception of fragrances, perfume mixtures and perfume compositions.
  • the invention therefore also relates to the use of (Z) - 8-cycloheptadecen-1-one or a (Z) -8-cycloheptadecen-1-one comprising fragrance mixture (as characterized above) as a means of increasing the odor perception of fragrances or fragrance compositions ,
  • HPLC conditions column Grom sapphire 110 Si, 5 ⁇ m, 125 ⁇ 20 mm, eluent: heptane / t-butyl methyl ether (v / v) 97: 3, flow: 15 ml / min, pressure: 30 bar, temperature: 40 ° C., detection: rl.
  • Odor Elegant musk smell; powdery and natural, with a nice nitro musk note.
  • Odor strong musk odor, dry, woody aspect
  • Nose strong, noble, clean and elegant musk scent, warm and erogenous note, nice nitro musk note, with a pudgy aspect, very natural.
  • Odor strong musk scent, woody aspect, warm, erogenous.
  • a mixture of 15 g (0.05 mol) of i-nitromethyl-cyclohexadec- ⁇ -enol, 40 ml of 95% ethanol, 10 ml of water, 30 g of iron filings and 0.5 ml of hydrochloric acid was prepared and allowed to stir for 1 h Reflux heated. It was then filtered off from the iron and washed three times with 10 ml of warm ethanol. The combined filtrates were washed with 50 ml of sodium chloride solution and concentrated. The crude mixture obtained was separated by column chromatography to obtain 10 g of 1-amino-methyl-cyclohexadec-8-enol.
  • BA benzyl alcohol
  • IPM isopropyl myristate
  • DEP diethyl phthalate
  • composition according to Example 2.2 55 parts by weight of (E, Z) -8,9-cycloheptadecenone (composition according to Example 2.2, sum of base perfume oil: 700 parts by weight) gave the overall composition a slightly erogenous, crystalline note of Norromuschus, which is not achieved with existing macrocyclic musk fragrances. Furthermore, the entire composition gained in naturalness and radiation, it seemed more rounded and elegant.
  • the pH of the fabric softener concentrate is typically in the range 2 - 3. Then three cotton towels and three towels were mixed fabric at 40 0 C in washing machines (manufacturer: Miele) first with 80 g of a non-perfumed standard washing powder and subsequently separately with the washed fabric softener washed.
  • the wet laundry thus obtained was dried on a leash for 24 hours.
  • the odor evaluation of the dry towels showed that the mixture according to the invention (E, Z) -8,9-cycloheptadecenone had a significantly higher intensity of fragrance. Moreover, this musk note lasted longer and more intensively over several days on the towels, which shows the better Aufzieh GmbH.
  • the wet strands of hair thus obtained were dried for 1 minute with an intermediate level electric hair dryer.
  • the olfactory evaluation of the hair strands showed that the mixture (E, Z) -8,9-cycloheptadecenone according to the invention was more intensively perceived and preferred to be odor on both wet and dry hair.

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

Abstract

La présente invention concerne une (Z)-8-cycloheptadécène-1-one utilisée comme parfum, ainsi qu'un mélange de substances de parfum ou d'arôme comprenant de la (Z)-8-cycloheptadécène-1-one et une ou plusieurs autres substances de parfum ou d'arôme.
EP05786850A 2004-09-23 2005-09-20 (z)-8-cycloheptadecene-1-one utilisee comme parfum Withdrawn EP1797026A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004046282A DE102004046282A1 (de) 2004-09-23 2004-09-23 (Z)-8-Cycloheptadecen-1-on als Riechstoff
PCT/EP2005/054704 WO2006032665A1 (fr) 2004-09-23 2005-09-20 (z)-8-cycloheptadecene-1-one utilisee comme parfum

Publications (1)

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EP1797026A1 true EP1797026A1 (fr) 2007-06-20

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EP (1) EP1797026A1 (fr)
DE (1) DE102004046282A1 (fr)
WO (1) WO2006032665A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MY162962A (en) 2010-12-03 2017-07-31 Unilever Plc Fabric conditioners
WO2012072369A1 (fr) * 2010-12-03 2012-06-07 Unilever Plc Conditionneurs de tissu

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006032665A1 *

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DE102004046282A1 (de) 2006-03-30

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