WO2005030156A1 - Verwendung von 3-cyclohexenyl-1-propanol als riechstoff - Google Patents
Verwendung von 3-cyclohexenyl-1-propanol als riechstoff Download PDFInfo
- Publication number
- WO2005030156A1 WO2005030156A1 PCT/EP2004/052261 EP2004052261W WO2005030156A1 WO 2005030156 A1 WO2005030156 A1 WO 2005030156A1 EP 2004052261 W EP2004052261 W EP 2004052261W WO 2005030156 A1 WO2005030156 A1 WO 2005030156A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- propanol
- cyclohexenyl
- oil
- methyl
- fragrance
- Prior art date
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Classifications
-
- 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
Definitions
- the present invention relates to a novel use of 3-cyclohexenyl-1-propanol, the compound containing
- Fragrance compositions and perfumed articles and a method for producing a fragrance composition with the compound are disclosed.
- fragrances that have additional positive secondary properties in addition to their primary, namely odor properties, such as greater stability under certain application conditions, higher yield, better adhesion or but also better dermatological and toxicological results compared to comparable fragrances.
- odor properties such as greater stability under certain application conditions, higher yield, better adhesion or but also better dermatological and toxicological results compared to comparable fragrances.
- concerns about some of the commonly used fragrances have been raised regarding the latter properties. It is to be expected that their use will be limited in the future or that it will have to be dispensed with entirely.
- Such a fragrance is, for example, cinnamon aldehyde, which, as its name suggests, is characterized by a distinctive cinnamon smell.
- fragrances which are suitable for producing fragrance compositions or perfumed articles.
- fragrance substances with a cinnamon character that are able to produce a cinnamon-like odor note in fragrance substance compositions, in particular perfume compositions.
- the fragrances should not have any negative toxicological properties.
- this object is achieved by the use according to the invention according to claim 1, the fragrance composition or the perfumed article according to claim 4 and the manufacturing method for a fragrance composition according to claim 8.
- the invention lies inter alia. based on the surprising finding that the compound 3-cyclohexenyl-1-propanol is suitable as a fragrance.
- the fragrance can be present as an R-configured enantiomer, S-configured enantiomer or any mixture of the two enantiomers, in particular as a racemate.
- 3-cyclohexenyl-1-propanol is excellent for imparting, modifying and / or enhancing an odor with one or more of the notes hydrocinnamic alcohol-like, mushroom-like, hay, cinnamon, balsamic, flowery and / or an aftertaste one or more of the notes rosy, fruity, damascenon-like.
- 3-Cyclohexenyl-1-propanol is particularly suitable for imparting, modifying and / or enhancing a cinnamon-like odor note.
- This compound has an expressive cinnamon-like smell is particularly surprising since it is not an aromatic aldehyde, but an alicyclic alcohol, as is the case with the common fragrances with a cinnamon-like smell.
- a change in the functionalities usually leads to significantly different olfactory properties even with otherwise structurally similar connections.
- Table 1 shows Exemplarily selected fragrance descriptions of structurally similar alicyclic alcohols and known aldehydes (Source: S. Arctander, Perfume and Flavor Chemicals, Vol. I and II, Montclair, NJ, 1969, diverlag or K. Bauer, D. Garbe and H.
- a fragrance composition or a perfumed article further contains 3-cyclohexenyl-1-propanol.
- Fragrance compositions or perfumed articles which contain an amount of 3-cyclohexenyl-1-propanol which is sufficient to impart, modify and / or amplify a cinnamon-like odor note are particularly preferred.
- fragrance compositions or perfumed articles which is sufficient to remove one or more of the odor notes hydrocinnamic-alcoholic, mushroom-like, hay, cinnamon, balsamic, flowery and / or one or to convey, modify and / or reinforce several of the aftertaste notes rosy, fruity, damascenon-like.
- a fragrance composition is produced according to the invention by mixing 3-cyclohexenyl-1-propanol with customary further constituents of a fragrance composition, the 3-cyclohexenyl-1-propanol being used in an amount which is sufficient to impart an odor note to the fragrance composition modify and / or reinforce.
- cinnamon-like scents are used in a variety of perfume compositions, e.g. also in flower fragrance topics.
- the example below of a "white flower” fragrance theme clearly demonstrates the olfactory effect of 3-cyclohexenyl-1-propanol.
- 3-cyclohexenyl-1-propanol is particularly suitable for use in perfume compositions.
- the compound can be used as a single substance or a large number of other fragrances combined in a large number of products.
- the connection with others can be particularly advantageous Combine fragrances in different, different proportions to create new types of perfume compositions.
- fragrances with which the alcohol according to the invention can advantageously be combined can be found e.g. in S. Arctander, Perfume and Flavor Chemicals, Vol. 1 and II, Montclair, N.J., 1969, Adverlag or K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Materials, 4rd. Ed., Wiley-VCH, Weinheim 2001. The following may be mentioned in detail:
- Extracts from natural raw materials such as essential oils, concretes, absolute, resins, resinoids, balms, tinctures such as B.
- ambergris tincture Amyrisol; Angel icasamenol; Angelicawurzelol; anise oil;
- Copaivabalsamöl Coriander oil; costus root; Cuminöl; Cypress oil;
- Davanaöl Dill herb oil; Dill seed oil; Eau de brouts absolute; Oakmoss absolute; elemi; Tarragon oil; Eucalyptus citriodora oil; eucalyptus oil;
- Fennel oil Pine needle oil; galbanum; Galbanumresin; geranium;
- Grapefruit oil Grapefruit oil; guaiac wood; gurjun balsam; Gurju ⁇ balsamöl;
- Orris root oil Jasmine absolute; calamus; Chamomile oil blue; Roman calla oil; Carrot seed oil; Kaskarillaöl; Kiefemadelöl; spearmint;
- Lovage oil Distilled lime oil; Lime oil pressed; linaloe; Litsea cubeba oil; Bay leaf oil; Macisöl; Marjoram oil; Mandarin oil; Massoirindenöl; Mimosa absolute; Musk seed oil; musk tincture; Clary sage oil; nutmeg; Myrrh absolute; Myrrh oil;
- Palmarosa oil oregano; Palmarosa oil; patchouli oil; perilla oil; Peruvian balsam oil; Parsley leaf oil; Parsley seed oil; Petitgrain oil; Peppermint oil;
- sandalwood Celery seed oil; spike lavender oil; star anise; Styraxöl;
- cinnamon leaf Cinnamon bark oil and fractions thereof, or ingredients isolated therefrom;
- 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; styrene; diphenylmethane;
- 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-methoxyoctan-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol;
- aliphatic aldehydes and their acetals such as hexanal; heptanal; octanal; nonanal; decanal; undecanal; dodecanal; tridecanal; 2-methyloctanal; 2-methyl nonanal; (E) -2-hexenal; (Z) -4-heptenal; 2,6-dimethyl-5-heptenal; 10-undecenal; (E) -4-decenal; 2-dodecenal; 2,6,10-trimethyl-9-undecenal; 2 J 6,10-trimethyl-5,9- undecadienal; Heptanaldiethylacetal; 1, 1-dimethoxy-2,2,5-trimethyl-4-hexene; citronellyloxyacetaldehyde; 1 - (1-methoxy-propoxy) - (E / Z) -3-hexene;
- the aliphatic ketones and their oximes such as 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;
- aliphatic sulfur-containing compounds such as e.g. 3-methylthiohexanol; 3-Methylthiohexylacetat; 3-mercaptohexanol; 3
- aliphatic nitriles such as e.g. 2-nonenoic acid nitrile; 2-undecenonitrile; 2-Tridecen Textrenitril; 3,12-Tridecadienklarenitril; 3,7-dimethyl-2,6-octadiene-acid nitrile; 3,7-dimethyl-6-octen Aciditril;
- ester of aliphatic carboxylic acids such as e.g. (E) - and (Z) -3- hexenyl formate; ethylacetoacetate; isoamyl; hexyl acetate; 3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (E) -2-hexenyl acetate; (E) - and (Z) -3-hexenyl acetate; octyl acetate; 3-octyl acetate; 1-octen-3-ylacetate; ethyl butyrate; Butyl butyrate,; isoamyl; hexyl butyrate; (E) - and (Z) -3-hexenyl isobutyrate; hexyl crotonate; Ethylisovalerianat; Ethyl 2-methylpentanoate; ethylhexanoate;
- acyclic terpene alcohols such as B. 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-octadien-2-ol; 3,7-dimethyl-4,6-octadiene-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, buty
- acyclic terpene aldehydes and ketones such as B. Geranial; neral; citronellal; 7-hydroxy-3,7-dimethyloctanal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; geranyl acetone; as well as the dimethyl and diethyl acetals of geranial, neral, 7-hydroxy-3,7-dimethyloctanal;
- cyclic terpene alcohols such as B. 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, isovalerianates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoate;
- cyclic alcohols such as 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 e.g. alpha, 3,3-trimethylcyclohexylmethanol; 1- (4-isopropylcyclohexyl) ethanol; 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) pen
- cyclic and cycloaliphatic ethers such as e.g. cineol; cedryl methyl ether; cyclododecyl; 1,1-
- cyclic and macrocyclic ketones such as 4-part-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-tetramethylcyclohexanone; 4-tert-
- cycloaliphatic ketones such as.
- B. 1- S-dimethylcyclohexylH-penten-1-one; 2,2-DimethyM - (2,4-dimethyl-3-cyclohexen-1-yl) -1 - propanone; 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-cyclododecatrienylketon; tert-butyl- (2,4-dimethyl-3-cyclohexen-1-yl) ketone;
- esters of cyclic alcohols such as e.g. 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-pentylcyclohexyl acetate; 3,3,5-Trimethylcyclohexylacetat; Decahydro-2-naphthyl acetate; 2-cyclopentylcyclopentyl crotonate; 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-indenyl acetate; 4,
- esters of araliphatic alcohols and aliphatic carboxylic acids such as e.g. benzyl acetate; benzylpropionate; benzyl isobutyrate; Benzylisovalerianat; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-phenylethyl isobutyrate; 2-Phenylethylisovalerianat; 1 -phenylethyl acetate; alpha-Trichlormethylbenzylacetat; alpha.alpha-
- the araliphatic ether such as e.g. 2-phenylethyl; 2-phenylethyl isoamyl ether; 2-phenylethyl-1-ethoxyethyl ether;
- 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; 2-benzofuranylethanone; (3 ⁇ methyl-2-benzofuranyl) ethanone; benzophenone; 1,1, 2,3,3, 6-hexamethyl-5-indanyl methyl ketone; 6-tert-butyl-1,1-dimethyl-4-inda ⁇ ylmethylketone; 1 - [2,3-dihydro-1,1,2,6-tetramethyl-3- (1-methylethyl) -1 H-5-indenyl] ethanone; ⁇ '.e'y. ⁇ '-tetrahydro-S ' ⁇ '. ⁇ ⁇ ⁇ '
- aromatic and araliphatic carboxylic acids and their esters such as e.g. benzoic acid; phenylacetic acid; methylbenzoate; ethyl benzoate;
- hexyl benzoate Benzyl benzoate; Methyl phenylacetate; ethyl phenylacetate;
- cinnamyl cinnamate allyl phenoxyacetate; methyl salicylate; isoamyl;
- nitrogen-containing aromatic compounds such as 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert-butylacetophenone; cinnamic acid; 3-methyl-5-phenyl-2-penten Aciditril; 3-methyl-5-phenylpentanklaritril; methyl anthranilate; Methyl-N-methylanthranilate; SchifF's 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; 2- (3-phenylpropyl) pyridine; indole; skatol; 2-methoxy-3-isopropyl
- 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 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; 4-methyl-1,4-decanolide; 1.15 pentadecanolide; ice and trans-11-pentadecen-1,15-olide; ice and trans-12-pentadecen-1,15-olide; 1,16-hexadecanolide; 9-hexadecen-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 amount of alcohol used according to the invention is 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 oil composition.
- the compound 3-cyclohexenyl-1-propanol can be prepared in a manner known per se from the commercially available hydroformylation product of vinylcyclohexene. Depending on the hydroformylation conditions, the hydroformylation product can also contain the isomeric branched aldehyde (usually about 3-5% by weight). The alcohol of the formula formed from the isomeric branched aldehyde by reduction
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/573,451 US20070037733A1 (en) | 2003-09-26 | 2004-09-21 | Use of 3-cyclohexenyl-1-propanol as a fragrance |
EP04787184A EP1670420A1 (de) | 2003-09-26 | 2004-09-21 | Verwendung von 3-cyclohexenyl-1-propanol als riechstoff |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10344899.3 | 2003-09-26 | ||
DE10344899A DE10344899A1 (de) | 2003-09-26 | 2003-09-26 | Verwendung von 3-Cyclohexenyl-1-propanol als Riechstoff |
Publications (1)
Publication Number | Publication Date |
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WO2005030156A1 true WO2005030156A1 (de) | 2005-04-07 |
Family
ID=34353119
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2004/052261 WO2005030156A1 (de) | 2003-09-26 | 2004-09-21 | Verwendung von 3-cyclohexenyl-1-propanol als riechstoff |
Country Status (4)
Country | Link |
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US (1) | US20070037733A1 (de) |
EP (1) | EP1670420A1 (de) |
DE (1) | DE10344899A1 (de) |
WO (1) | WO2005030156A1 (de) |
Families Citing this family (1)
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BRPI0910268B8 (pt) | 2008-03-19 | 2021-05-25 | Tyratech Inc | composição para controlar uma praga alvo, formulação antiparasitária, uso da dita composição, e método para produzir um agente aperfeiçoado para o controle de uma praga alvo |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3408381A (en) * | 1965-10-23 | 1968-10-29 | Parke Davis & Co | S-2-[(cycloalkyl-alkyl and cycloalkenyl-alkyl)amino]ethyl thiosulfates and salts thereof |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2892858A (en) * | 1959-06-30 | Certificate of correction | ||
US3536687A (en) * | 1968-07-16 | 1970-10-27 | Ashland Oil Inc | Polymers and copolymers from cyclohexenyl-alkyl alcohol ester of alpha,beta-unsaturated acids |
DE60014639T2 (de) * | 1999-06-28 | 2005-05-25 | Quest International B.V. | Riechstoffe |
DE10222850B4 (de) * | 2001-05-30 | 2013-07-18 | Daicel Chemical Industries, Ltd. | Verfahren zur Herstellung eines alicyclischen ungesättigten Alkohols |
-
2003
- 2003-09-26 DE DE10344899A patent/DE10344899A1/de not_active Withdrawn
-
2004
- 2004-09-21 US US10/573,451 patent/US20070037733A1/en not_active Abandoned
- 2004-09-21 EP EP04787184A patent/EP1670420A1/de not_active Withdrawn
- 2004-09-21 WO PCT/EP2004/052261 patent/WO2005030156A1/de not_active Application Discontinuation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3408381A (en) * | 1965-10-23 | 1968-10-29 | Parke Davis & Co | S-2-[(cycloalkyl-alkyl and cycloalkenyl-alkyl)amino]ethyl thiosulfates and salts thereof |
Non-Patent Citations (1)
Title |
---|
E. N. MARVELL, D. STURMER, R. S. KNUTSON: "Products of Acetolysis of 3-(3-Cyclohexenyl)propyl and 4-(3-Cyclohexenyl)butyl p-Toluenesulfonates", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 33, no. 7, 1968, pages 2991 - 2993, XP002313027 * |
Also Published As
Publication number | Publication date |
---|---|
EP1670420A1 (de) | 2006-06-21 |
US20070037733A1 (en) | 2007-02-15 |
DE10344899A1 (de) | 2005-04-21 |
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