Ethers and esters of 1-substituted cycloalkanols for use as aroma chemicals

Patent metadata

Field	Value
Publication number	US-11920104-B2
Application number	US-201917286301-A
Country	US
Kind code	B2
Filing date	Oct 15, 2019
Priority date	Oct 16, 2018
Publication date	Mar 5, 2024
Grant date	Mar 5, 2024

Abstract

The present invention relates to the use of an ether or an ester of a 1-substituted cycloalkanol or of mixtures of two or more ethers or esters of 1-substituted cycloalkanols or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof as aroma chemicals; to the use thereof for modifying the scent character of a fragranced composition; to an aroma chemical composition containing an ether or an ester of a 1-substituted cycloalkanol or of mixtures of two or more ethers or esters of 1-substituted cycloalkanols or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof; and to a method of preparing a fragranced composition or for modifying the scent character of a fragranced composition. The invention further relates to specific ethers or esters of 1-substituted cycloalkanols.

First claim

The invention claimed is:

1. An aroma chemical composition comprising
a compound of formula (I) or a mixture of two or more compounds of the general formula (I) or a stereoisomer thereof or a mixture of two or more stereoisomers thereof,

wherein
X is linear C 1 -C 4 -alkylene, which is unsubstituted or substituted by 1, 2, 3 or 4 radicals independently of each other selected from C 1 -C 4 -alkyl,
R 1 is ethyl or ethenyl, and
R 2 is C 1 -C 4 -alkyl or C 1 -C 5 -alkanoyl,
and
at least one further aroma chemical and/or a non-aroma chemical carrier, where the non-aroma chemical carrier is selected from the group consisting of surfactants, oil components and solvents; where the solvents are selected from the group consisting of ethanol, isopropanol, dipropylene glycol, propylene glycol, 1,2-butylene glycol, glycerol, diethylene glycol monoethyl ether, isopropyl myristate, triethyl citrate, benzyl benzoate, and mixtures thereof.

2. The composition according to claim 1 , selected from the group consisting of perfume compositions, body care compositions, products for oral and dental hygiene, hygiene articles, cleaning compositions, textile detergent compositions, compositions for scent dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.

3. A method of preparing a fragranced composition, comprising incorporating a compound of formula (I) or a mixture of two or more compounds of the general formula (I) or a stereoisomer thereof or a mixture of two or more stereoisomers thereof, according to claim 1 , into said composition.

4. The composition according to claim 1 , where X is selected from linear C 1 -C 3 -alkylene, which is unsubstituted or substituted by 1, 2 or 3 radicals independently of each other selected from C 1 -C 3 -alkyl, where X is chosen such that the total number of carbon atoms in the compound of the general formula (I) is 16 or less.

5. The composition according to claim 1 , where X is selected from linear C 1 -C 3 -alkylene, which is unsubstituted or substituted by 1, 2 or 3 radicals selected from methyl.

6. The composition according to claim 1 , where X is selected from the group consisting of unsubstituted 1,2-ethanediyl, unsubstituted 1,3-propanediyl and 1,3-propanediyl substituted by 1, 2 or 3 methyl radicals.

7. The composition according to claim 1 , where R 1 is ethyl.

8. The composition according to claim 1 , where R 2 is C 1 -C 4 -alkyl.

9. The composition according to claim 8 , where X is unsubstituted 1,2-ethanediyl.

10. The composition according to claim 8 , where R 2 is methyl or ethyl.

11. The aroma chemical according to claim 1 , where R 2 is C 1 -C 5 -alkanoyl.

12. The composition according to claim 1 , where R 2 is methyl, acetyl, or propanoyl.

13. The composition according to claim 1 , which comprises a mixture of two or more compounds of formula (I).

14. The composition according to claim 13 , where the compounds of formula (I) in the mixture differ in the definition of the radical R 1 .

15. The composition according to claim 1 , which comprises the compound of formula (I) or a mixture of two or more compounds of formula (I) or a stereoisomer thereof or a mixture of two or more stereoisomers thereof for modifying the scent character of a fragranced composition.

16. The composition according to claim 1 , in a composition selected from the group consisting of perfume compositions, body care compositions, products for oral and dental hygiene, hygiene articles, cleaning compositions, textile detergent compositions, compositions for scent dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.

17. The composition according to claim 1 , wherein X is 1,3-propanediyl and R1 is ethyl and R2 is C 1 -C 5 -alkanoyl.

18. The composition according to claim 1 , wherein the at least one further aroma chemical and/or a non-aroma chemical carrier is selected from the group consisting of geranyl acetate (3,7-Dimethyl-2,6 octadien-lyl acetate), alpha-hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate, dihydromyrcenol (2,6-dimethyl-7-octen-2-ol), methyl dihydrojasmonate, 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]benzopyran, tetrahydrolinalool (3,7-dimethyloctan-3-ol), ethyllinalool, benzyl salicylate, 2-methyl-3-(4-tert-butylphenyl)propanal, cinnamyl alcohol, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5-indenyl acetate and/or 4,7-methano-3a,4,5,6,7,7a-hexahydro-6-indenyl acetate, citronellol, citronellyl acetate, tetrahydrogeraniol, vanillin, linalyl acetate, styrolyl acetate (1-phenylethyl acetate), octahydro-2,3,8,8-tetramethyl-2-acetonaphthone and/or 2-acetyl-1,2,3,4,6,7,8-octahydro-2,3,8,8-tetramethylnaphthalene, hexyl salicylate, 4-tert-butylcyclohexyl acetate, 2-tert-butylcyclohexyl acetate, alpha-ionone (4-(2,2,6-trimethyl-2-cyclohexen-l-yl)-3-buten-2-one), n-alpha-methylionone, alpha-isomethylionone, coumarin, terpinyl acetate, 2-phenylethyl alcohol, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarboxaldehyde, alpha-amylcinnamaldehyde, ethylene brassylate, (E)- and/or (Z)-3-methylcyclopentadec-5-enone, 15-pentadec-11-enolide and/or 15-pentadec-12-enolide, 15-cyclopentadecanolide, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenyl)ethanone, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, 2-ethyl-4-(2,2,3-trim ethyl-3 -cy cl op enten-l-yl)-2-buten-l-ol, cis-3 -hexenyl acetate, trans-3 -hexenyl acetate, trans-2/ci s-6-nonadienol, 2,4-dimethyl-3 -cyclohexenecarboxaldehyde, 2,4,4,7-tetramethyl oct-6-en-3 -one, 2,6-dimethyl-5-hepten-l-al, borneol, 3 -(3 - isopropylphenyl)butanal, 2-methyl-3 -(3,4-methylenedioxyphenyl)propanal, 3 -(4-ethylphenyl)-2,2-dimethylpropanal, 7-methyl-2H-1,5-b enzodi oxepin-3 (4H)-one, 3,3,5-trimethylcyclohexyl acetate, 2,5,5-trim ethyl-1,2,3,4,4a,5, 6,7-octahy dronaphthal en-2-ol, 3-(4-tert-butylphenyl)-propanal, ethyl 2-methylpentanoate, ethoxymethoxycyclododecane, 2,4-dimethyl-4,4a,5,9b -tetrahydroindeno [1,2-d][1,3]dioxine, (2-tert-butylcyclohexyl) acetate), and 3-[5,5,6-trimethylbicyclo[2.2.1]hept-2-yl]cyclohexan-1-ol .

19. The composition according to claim 1 , wherein the at least one further aroma chemical and/or a non-aroma chemical carrier is an antioxidant selected from the group consisting of pentaerythrityl, tetra-di-t-butyl hydroxyhydrocinnamate, nordihydroguaiaretic acid, ferulic acid, resveratrol, propyl gallate, butylhydroxytoluene (BHT), butylhydroxyanisole (BHA), ascorbyl palmitate and tocopherol.

20. A body care composition comprising the composition according to claim 1 wherein the at least one further aroma chemical and/or a non-aroma chemical carrier is selected from the group consisting of anionic or zwitterionic surfactants.

Assignees

• Basf Se

Inventors

• Stock Christoph
• Bru Roig Miriam
• Pelzer Ralf
• Garlichs Florian
• Danz Manuel

Classifications

• C11B9/0019 Primary

  carbocylic acids; Salts or esters thereof · CPC title

• C07C43/184 Primary

  to a carbon atom of a non-condensed ring · CPC title

• C07C43/188

  Unsaturated ethers · CPC title

• C07C69/013

  Esters of alcohols having the esterified hydroxy group bound to a carbon atom of a ring other than a six-membered aromatic ring · CPC title

• C07C69/14

  of monohydroxylic compounds · CPC title