Pro-fragrance compounds

Patent metadata

Field	Value
Publication number	US-10752862-B2
Application number	US-201715631647-A
Country	US
Kind code	B2
Filing date	Jun 23, 2017
Priority date	May 8, 2013
Publication date	Aug 25, 2020
Grant date	Aug 25, 2020

Abstract

A compound is provided of Formula (I)

wherein R 1 represents a C 3 to C 20 hydrocarbon group derived from an alcohol of formula R 1 OH, from a formate of formula R 1 OCH═O, or a cinnamyl aldehyde of Formula (II)

wherein a compound of Formula I is capable of releasing a compound, when oxidized, selected from the group consisting of a fragrant alcohol of formula R 1 OH, a fragrant formate ester of formula R 1 OCH═O and aryl aldehyde of Formula (III)

wherein R 2 is, independently, hydrogen atom, hydroxyl group, optionally substituted C 1 -C 6 alkyl group, C 1 -C 6 alkoxy group, or —O(C═O)CH(CH3) 2 wherein any two of R 2 may form an optionally substituted 5 or 6 membered ring. The compounds are useful for example as a precursor for the prolonged delivery or release of fragrant compounds such as fragrant alcohols, fragrant aldehydes or fragrant formates.

First claim

What is claimed is:

1. A compound of Formula (I)

wherein n is 1 or 2; R 1 is a radical group of an alcohol of formula R 1 OH selected from the group consisting of anisic alcohol, fenchylic alcohol, 9-decen-1-ol, phenethylol, citronellol, 3-methyl-5-phenyl-1-pentanol, (4-isopropylcyclohexyl)methanol, 4-phenylbutan-2-ol, 2,6-dimethyl-7-octen-2-ol, 3,7-dimethyl-2,6-octadien-1-ol, (Z)-3-hexen-1-ol, 5-ethyl-2-nonanol, 2,6-nonadien-1-ol, borneol, 1-octen-3-ol, 4-cyclohexyl-2-methyl-2-butanol, 2-methyl-4-phenyl-2-butanol, 2-methyl-1-phenyl-2-propanol, cyclomethylenecitronellol, dihydroeugenol, 8-p-menthanol, 3,7-dimethyl-1-octanol, 2,6-dimethyl-2-heptanol, dodecanol, eugenol, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, isoeugenol, linalool, 2-methoxy-4-propyl-1-cylohexanol, α-terpineol, tetrahydromuguol, 3,7-dimethyl-3-octanol, 4-(4-hydroxy-4-methylpentyl)-cyclohex-3-ene-1-carbaldehyde, 5,6-dimethyl-1-methylethenylbicyclo[2.2.1]hept-5-ene-2-methanol, 2-phenylethanol, 1-phenylpropanol, 2-phenylpropanol, (2,5-dimethyl-2,3-dihydro-1H-inden-2-yl)methanol, 2,2-dimethyl-3-(3-methylphenyl)-propan-1-ol, 2-pentylcyclopentanol, 7-hydroxy-3,7-dimethyloctanal, 1,1-dimethyl-2-phenylethanol, 4-cyclohexyl-2-methylbutan-2-ol, menthol, 2,6-dimethylheptan-2-ol, 2-tert-butylcyclohexanol, 4-tert-butylcyclohexanol, 2,6-dimethyl-3,5-octadien-2-ol, 2-methyl-6-methylene-7-octen-2-ol, 3,7,9-trimethyl-1,6-decadien-3-ol, methyl salicylate, cis-3-hexenyl salicylate, 3,6-dimethyloctan-3-ol, 1,2-dimethyl-3-prop-1-en-2-ylcyclopentan-1-ol, 2-methyl-4-phenylpentanol, 3-methyl-5-phenylpentanol, 3-methyl-5-(2,2,3-trimethyl-1-cyclopent-3-enyl)pentan-2-ol, (E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol, (E)-4-methyldec-3-en-5-ol, and 4-(4-hydroxyphenyl)butan-2-one; and R 2 is, independently, a hydrogen atom, a hydroxyl group, an optionally substituted C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, or O(C═O)CH(CH 3 ) 2 wherein any two of R 2 may form an optionally substituted 5 or 6 membered ring;
wherein the compound of Formula I releases a compound, when oxidized, selected from the group consisting of a fragrant alcohol of formula R 1 OH as defined above, and a fragrant aryl aldehyde selected from the group consisting of benzaldehyde, anisaldehyde, 4-methylbenzaldehyde, 4-ethylbenzaldehyde, 4-isopropylbenzaldehyde, 4-(tert-butyl) benzaldehyde, 2-methoxybenzaldehyde, 3,4-dimethoxybenzaldehyde, heliotropin, 4-hydroxybenzaldehyde, vanillin, 3-ethoxy-4-hydroxybenzaldehyde, 4-formyl-2-methylphenyl acetate, 4-formyl-2-methoxyphenyl isobutyrate and 3,5,5,6,7,8,8-heptanmethyl-5-6-7-8-tetrahydronaphthalene-2-carbaldehyde.

2. The compound as recited in claim 1 wherein R 2 is a methoxy, ethoxy, propoxy, isopropoxy or butoxy group.

3. The compound as recited in claim 1 wherein R 2 is a methoxy group.

4. The compound as recited in claim 2 wherein the R 2 group is in the ortho or para position in the ring.

5. The compound as recited in claim 2 wherein the R 2 group is in the para position in the ring.

6. The compound as recited in claim 3 wherein the R 2 group is in the ortho or para position in the ring.

7. The compound as recited in claim 3 wherein the R 2 group is in the para position in the ring.

8. A method of releasing a fragrant compound from a precursor compound, comprising exposing a compound of Formula I according to claim 1 to an environment where the compound is oxidized, wherein the fragrant compound is selected from the group consisting of R 1 OH selected from the group consisting of anisic alcohol, cinnamic alcohol, fenchylic alcohol, 9-decen-1-ol, phenethylol, citronellol, 3-methyl-5-phenyl-1-pentanol, (4-isopropylcyclohexyl)methanol, 4-phenylbutan-2-ol, 2,6-dimethyl-7-octen-2-ol, 3,7-dimethyl-2,6-octadien-1-ol, (Z)-3-hexen-1-ol, 2-hexanol, 5-ethyl-2-nonanol, 2,6-nonadien-1-ol, borneol, 1-octen-3-ol, 4-cyclohexyl-2-methyl-2-butanol, 2-methyl-4-phenyl-2-butanol, 2-methyl-1-phenyl-2-propanol, cyclomethylenecitronellol, dihydroeugenol, 8-p-menthanol, 3,7-dimethyl-1-octanol, 2,6-dimethyl-2-heptanol, dodecanol, eugenol, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, isoeugenol, linalool, 2-methoxy-4-propyl-1-cylohexanol, α-terpineol, tetrahydromuguol, 3,7-dimethyl-3-octanol, 4-(4-hydroxy-4-methylpentyl)-cyclohex-3-ene-1-carbaldehyde, 5,6-dimethyl-1-methylethenylbicyclo[2.2.1]hept-5-ene-2-methanol, 2-phenylethanol, 1-phenylpropanol, 2-phenylpropanol, (2,5-dimethyl-2,3-dihydro-1H-inden-2-yl)methanol, 2,2-dimethyl-3-(3-methylphenyl)-propan-1-ol, 2-pentylcyclopentanol, 7-hydroxy-3,7-dimethyloctanal, 1,1-dimethyl-2-phenylethanol, 4-cyclohexyl-2-methylbutan-2-ol, menthol, 2,6-dimethylheptan-2-ol, 2-tert-butylcyclohexanol, 4-tert-butylcyclohexanol, 2,6-dimethyl-3,5-octadien-2-ol, 2-methyl-6-methylene-7-octen-2-ol, 3,7,9-trimethyl-1,6-decadien-3-ol, methyl salicylate, cis-3-hexenyl salicylate, 3,6-dimethyloctan-3-ol, 1,2-dimethyl-3-prop-1-en-2-ylcyclopentan-1-ol, 2-methyl-4-phenylpentanol, 3-methyl-5-phenylpentanol, 3-methyl-5-(2,2,3-trimethyl-1-cyclopent-3-enyl)pentan-2-ol, (E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol, (E)-4-methyldec-3-en-5-ol, and 4-(4-hydroxyphenyl)butan-2-one and an aryl aldehyde selected from the group consisting of benzaldehyde, anisaldehyde, 4-methylbenzaldehyde, 4-ethylbenzaldehyde, 4-isopropylbenzaldehyde, 4-(tert-butyl) benzaldehyde, 2-methoxybenzaldehyde, 3,4-dimethoxybenzaldehyde, heliotropin, 4-hydroxybenzaldehyde, vanillin, 3-ethoxy-4-hydroxybenzaldehyde, 4-formyl-2-methylphenyl acetate, 4-formyl-2-methoxyphenyl isobutyrate and 3,5,5,6,7,8,8-heptanmethyl-5-6-7-8-tetrahydronaphthalene-2-carbaldehyde.

9. A method to improve, enhance or modify odoriferous properties of a perfuming composition or a perfumed article, comprising adding to said composition or article an effective amount of a compound according to claim 1 to improve, enhance or modify the odor of the perfuming composition or perfumed article.

10. The method according to claim 9 wherein the compound is exposed to an environment through a perfumed article comprising the compound wherein the perfumed article is provided in a perfumed product selected from the group consisting of perfume, cologne, bath gel, shower gel, hair-care product, cosmetic preparation, body deodorant, solid or liquid air freshener, detergent, fabric softener, and all-purpose cleaner.

11. A method to improve, enhance or modify odoriferous properties of a perfuming composition or a perfumed article, comprising adding to said composition or article an effective amount of a compound according to claim 2 to improve, enhance or modify the odor of the perfuming composition or perfumed article.

12. The method according to claim 11 wherein the compound is exposed to an environment through a perfumed article comprising the compound wherein the perfumed article is provided in a perfumed product selected from the group consisting of perfume, cologne, bath gel, shower gel, hair-care product, cosmetic preparation, body deodorant, solid or liquid air freshener, detergent, fabric softener, and all-purpose cleaner.

13. A method to improve, enhance or modify odoriferous properties of a perfuming composition or a perfumed article, comprising adding to said composition or article an effective amount of a compound according to claim 3 to improve, enhance or modify the odor of the perfuming composition or perfumed article.

14. The method according to claim 13 wherein the compound is exposed to an environmen

Assignees

• Firmenich & Cie

Inventors

• Indradas Brinda
• Virtucio Gilbert
• Womack Gary

Classifications

• C11D3/507

  Compounds releasing perfumes by thermal or chemical activation · CPC title

• C11B9/0003

  Compounds of unspecified constitution defined by the chemical reaction for their preparation · CPC title

• C07C45/37

  of >C—O—functional groups to >C=O groups · CPC title

• C07C43/23

  containing hydroxy or O-metal groups · CPC title

• C07C29/50

  with molecular oxygen only · CPC title