Pro-fragrance compounds

Patent metadata

Field	Value
Publication number	US-9718753-B2
Application number	US-201414889858-A
Country	US
Kind code	B2
Filing date	May 5, 2014
Priority date	May 8, 2013
Publication date	Aug 1, 2017
Grant date	Aug 1, 2017

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=0 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 -0(C=0)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

The invention claimed is:

1. A compound selected from the group consisting of (E)-(3-(2,6-dimethyloct-7-en-2-yloxy)prop-1-enyl)benzene; (E)-(3-(2,6-dimethyloct-7-en-2-yloxy)prop-1-enyl)benzene; (E)-(3-((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-1-yl)benzene; (E)-(3-(cinnamyloxy)butyl)benzene; 1-(3-(2,6-dimethyloct-7-en-2-yloxy)prop-1-enyl)-4-methoxybenzene; 1-(3-(2,6-dimethyloctan-2-yloxy)prop-1-enyl)-4-methoxybenzene; 1-(3-(3,7-dimethylocta-1,6-dien-3-yloxy)prop-1-enyl)-4-methoxybenzene; 1-(3-(3,7-dimethyloct-1-en-3-yloxy)prop-1-enyl)-4-methoxybenzene; 1-methoxy-4-((E)-3-((1RS,2SR)-2-pentylcyclopentyloxy)prop-1-enyl)benzene; 1-(3-((2,6-dimethyloct-7-en-2-yl)oxy)prop-1-en-1-yl)-4-ethylbenzene; 4-(3-((2,6-dimethyloct-7-en-2-yl)oxy)prop-1-en-1-yl)-1,2-dimethoxybenzene; (E)-1-methoxy-4-(3-(4-phenylbutan-2-yloxy)prop-1-enyl)benzene; 1-methoxy-4-((E)-3-((E)-4-(2,6,6-trimethylcyclohex-2-enyl)but-3-en-2-yloxy)prop-1-enyl)benzene; and 1-(3-(3,7-dimethyloct-1-en-3-yloxy)prop-1-enyl)-4-methoxybenzene.

2. A 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 which contains therein a precursor compound according to claim 1 , wherein the precursor compound release a fragrant compound upon exposure to an environment which oxidizes the precursor compound to release the fragrant compound and provide a perfuming effect to the product.

3. The product of claim 2 wherein the fragrant compound is an alcohol, aryl aldehyde or formate ester which is derived from the precursor compound and which is released during use of the product.

4. A method of releasing a fragrant compound from a precursor compound by exposing a precursor compound according to claim 1 to an environment wherein the compound is oxidized to release an alcohol, aryl aldehyde or formate ester that prolongs or intensifies the perfuming effect of the precursor compound.

5. The method as recited in claim 4 wherein the compound is exposed to the 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.

6. The method as recited in claim 5 wherein the all-purpose cleaner is an all-purpose household cleaner, a window cleaner, a furniture polish, a fabric conditioner, softener or wash in form of a powder, a liquid or a tablet, a shampoo, a hair conditioner, a leave-in hair conditioner, or a hairspray.

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

8. The method of claim 7 , which further comprises providing the odor by release releasing a fragrant compound from the precursor compound upon exposure of the perfuming composition or perfumed article to an environment which oxidizes the precursor compound.

9. The method of claim 8 wherein the fragrant compound is an alcohol, aryl aldehyde or formate ester which is derived from the precursor compound and which is released during use of the perfuming composition or perfumed article.

10. The method of claim 8 wherein the perfuming composition or perfumed article is an all-purpose household cleaner, a window cleaner, a furniture polish, a fabric conditioner, a softener or wash product in powder, liquid or tablet form, a shampoo, a hair conditioner, a leave-in hair conditioner, or a hairspray.

11. A perfumed article comprising a compound according to claim 1 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.

12. The perfumed article according to claim 11 wherein the all-purpose cleaner is an all-purpose household cleaner, a window cleaner, a furniture polish, a fabric conditioner, softener or wash in form of a powder, a liquid or a tablet, a shampoo, a hair conditioner, a leave-in hair conditioner, or a hairspray.

Assignees

• Firmenich & Cie

Inventors

• Indradas Brinda
• Virtucio Gilbert
• Womack Gary

Classifications

• C07C45/36

  in compounds containing six-membered aromatic rings · CPC title

• C11D3/001

  Softening compositions · CPC title

• C07C43/215

  having unsaturation outside the six-membered aromatic rings · 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