Synthesis and use of 2-ethyl-5,5-dimethyl-cyclohexanol as fragrance and flavor material

Patent metadata

Field	Value
Publication number	US-11946019-B2
Application number	US-201917292807-A
Country	US
Kind code	B2
Filing date	Nov 12, 2019
Priority date	Nov 12, 2018
Publication date	Apr 2, 2024
Grant date	Apr 2, 2024

Abstract

The present invention relates to the compound 2-ethyl-5,5-dimethyl-cyclohexanol, which can impart, modify and/or enhance one or more odours selected from the group consisting of minty, fresh tobacco leaf, cresol, horse and animalistic, mixtures comprising 2-ethyl-5,5-dimethyl-cyclohexanol, and a new method for producing the same, a fragrance composition comprising 2-ethyl-5,5-dimethyl-cyclohexanol, the use of 2-ethyl-5,5-dimethyl-cyclohexanol as a fragrance, particularly for imparting, modifying and/or enhancing one or more odours selected from the group consisting of minty, fresh tobacco leaf, cresol, horse and animalistic, a perfumed product comprising 2-ethyl-5,5-dimethyl-cyclohexanol, a method for perfuming such a product and a method for modifying an olfactory impression.

First claim

The invention claimed is:

1. A compound according to formula (I) (2-ethyl-5,5-dimethyl-cyclohexanol)

2. The compound according to claim 1 , wherein the compound is obtainable by a method comprising:
i) providing methyl-N—[(Z)-1-(2-hydroxy-4,4-dimethyl-cyclohexyl)-ethylidene amino] carbamate (formula II),

ii) converting the methyl-N—[(Z)-1-(2-hydroxy-4,4-dimethyl-cyclohexyl)-ethylidene amino] carbamate (formula II) to 2-ethyl-5,5-dimethyl-cyclohexanol (formula I) with a base.

3. The compound according to claim 2 , wherein step i) of the method is performed by providing 1-(2-hydroxy-4,4-dimethylcyclohexyl)ethan-1-one (formula III)

and converting the 1-(2-hydroxy-4,4-dimethylcyclohexyl)ethan-1-one (formula III) to the methyl-N—[(Z)-1-(2-hydroxy-4,4-dimethyl-cyclohexyl)-ethylidene amino] carbamate (formula II).

4. The compound according to claim 2 , wherein the base in step ii) is provided in a solvent.

5. The compound according to claim 2 , wherein the base is heated to at least 80° C. before or during addition to the methyl-N—[(Z)-1-(2-hydroxy-4,4-dimethyl-cyclohexyl)-ethylidene amino] carbamate (formula II) and/or wherein step ii) of the method is performed at a temperature of least 80° C.

6. A mixture comprising the compound according to claim 2 .

7. A method for perfuming a product comprising adding the 2-ethyl-5,5-dimethyl-cyclohexanol (formula I) according to claim 2 to the product in a sensorially effective amount.

8. The method according to claim 7 , wherein the 2-ethyl-5,5-dimethyl-cyclohexanol (formula I) is added to the product in an amount sufficient to impart, modify, and/or enhance an odour selected from minty, fresh tobacco leaf, cresol, horse and animalistic.

9. A method for modifying one or more olfactory impression(s) of one or more fragrance(s) comprising combining a sensorially effective amount of the 2-ethyl-5,5-dimethyl-cyclohexanol (formula I) according to claim 2 with the one or more fragrance(s).

10. A perfumed product comprising the 2-ethyl-5,5-dimethyl-cyclohexanol (formula I) according to claim 1 .

11. The perfumed product according to claim 10 , wherein the product is selected from washing and cleaning agents, hygiene or care products, perfumed refreshing tissues, acid, alkaline or neutral cleaning agents, textile refreshing agents, ironing aids, liquid washing agents, washing agents in powder form, laundry pre-treatment agents, fabric softeners, laundry soap, laundry tablets, disinfectants, surface disinfectants, air refreshers, aerosols, waxes and polishes, body care agents, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, tanning creams and lotions, hair-care products, deodorants, anti-perspirants, products of decorative cosmetics, candles, lamp oils, joss sticks, insecticides, repellents, and propellants.

12. The perfumed product according to claim 10 , wherein the 2-ethyl-5,5-dimethyl-cyclohexanol (formula I) in the product is in an amount of 0.00001 to 10 wt.-%, based on the total weight of the product.

13. A method for producing 2-ethyl-5,5-dimethyl-cyclohexanol (formula I)

comprising:
i) providing methyl-N—[(Z)-1-(2-hydroxy-4,4-dimethyl-cyclohexyl)-ethylidene amino] carbamate (formula II),

ii) converting the methyl-N—[(Z)-1-(2-hydroxy-4,4-dimethyl-cyclohexyl)-ethylidene amino] carbamate (formula II) to 2-ethyl-5,5-dimethyl-cyclohexanol (formula I) with a base.

14. The method according to claim 13 , wherein step i) is performed by providing 1-(2-hydroxy-4,4-dimethylcyclohexyl)ethan-1-one (formula III)

and converting the 1-(2-hydroxy-4,4-dimethylcyclohexyl)ethan-1-one (formula III) to methyl-N—[(Z)-1-(2-hydroxy-4,4-dimethyl-cyclohexyl)-ethylidene amino] carbamate (formula II).

15. The method according to claim 13 , wherein the base in step ii) is provided in a solvent.

16. The method according to claim 13 , wherein the base is heated to at least 80° C. before or during addition to the methyl-N—[(Z)-1-(2-hydroxy-4,4-dimethyl-cyclohexyl)-ethylidene amino] carbamate (formula II) and/or wherein step ii) is performed at a temperature of at least 80° C.

17. A fragrance composition comprising the 2-ethyl-5,5-dimethyl-cyclohexanol (formula I) according to claim 1 in an amount sufficient to enhance an odour selected from minty, fresh tobacco leaf, cresol, horse, and animalistic.

18. The fragrance composition according to claim 17 , wherein the total amount of the 2-ethyl-5,5-dimethyl-cyclohexanol (formula I) in the fragrance composition is 0.0001 to 99.9 wt.-%, based on the total weight of the fragrance composition.

19. A method for imparting, modifying, and/or enhancing one or more odours selected from minty, fresh tobacco leaf, cresol, horse, and animalistic comprising incorporating the 2-ethyl-5,5-dimethyl-cyclohexanol (formula I) according to claim 1 into a composition in an amount sufficient to impart, modify, and/or enhance the one or more odours selected from minty, fresh tobacco leaf, cresol, horse, and animalistic.

Assignees

• Symrise Ag

Inventors

• Chandrasekaran Vijayanand
• Hölscher Bernd

Classifications

• C07C269/00

  Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups [IMAGE cpc-sch-C07C-0964.gif], the nitrogen atom not being part of nitro or nitroso groups · CPC title

• C07C35/08

  containing a six-membered rings · CPC title

• C07C29/147

  of carboxylic acids or derivatives thereof · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C11B9/0034 Primary

  the ring containing six carbon atoms · CPC title