Lily of the valley odorant

Patent metadata

Field	Value
Publication number	US-2023159426-A1
Application number	US-202117908525-A
Country	US
Kind code	A1
Filing date	Apr 12, 2021
Priority date	Apr 14, 2020
Publication date	May 25, 2023
Grant date	—

Abstract

The present invention relates to the field of perfumery. More particularly, it relates to a compound of formula (I) as defined herein below, and its uses as perfuming ingredient, to control arthropods or as antimicrobial ingredient. Therefore, following what is mentioned herein, the present invention comprises the invention compound as part of a perfuming composition or of a perfumed consumer product. Moreover, the present invention relates to a properfume compound suitable to release the compound of formula (I).

First claim

1 . A compound of formula (I):

in the form of any one of its stereoisomers or as a mixture thereof, wherein one dotted line represents a carbon-carbon double bond and the other dotted lines represent a carbon-carbon single bond; R 1 represents a hydrogen atom or a C 1-2 alkyl group; R 2 represents a C 1-4 alkyl group or a C 2-4 alkenyl group; R 3 represents a hydrogen atom or a C 1-3 alkyl group or a C 2-3 alkenyl group; R 4 represents a hydrogen atom or R 4 represents a hydrogen atom or a methyl group when R 2 and R 3 represent a methyl group; or R 3 and R 4 , when taken together, represent a methylidene group; or R 2 and R 3 , when taken together, represent a C 4-9 alkanediyl or a C 4-9 alkenediyl group; or R 2 , R 3 and R 4 , when taken together, represent a phenyl group optionally substituted by a C 1-3 alkyl group.

2 . The compound according to claim 1 , wherein the compound is of formula (II):

in the form of any one of its stereoisomers or as a mixture thereof, wherein one dotted line represents a carbon-carbon double bond and the other dotted line represents a carbon-carbon single bond; R 1 , R 2 , R 3 and R 4 have the same meaning as defined in claim 1 .

3 . The compound according to claim 1 , wherein R 1 and R 4 are a hydrogen atom.

4 . The compound according to claim 1 , wherein R 3 is a hydrogen atom or a methyl group.

5 . The compound according to claim 1 , wherein R 2 is a methyl, ethyl or propyl group.

6 . The compound according to claim 1 , wherein the compound of formula (I) is selected from the group consisting of 3-(3/4-ethylcyclopent-1-en-1-yl)-2-methylpropanal, 3-(3/4-propylcyclopent-1-en-1-yl)-2-methylpropanal, 3-(3/4-butylcyclopent-1-en-1-yl)-2-methylpropanal, 3-(3/4-isopropylcyclopent-1-en-1-yl)-2-methylpropanal, 3-(3/4-(sec-butyl)cyclopent-1-en-1-yl)-2-methylpropanal and 3-(3/4-(tert-butyl)cyclopent-1-en-1-yl)-2-methylpropanal.

7 . (canceled)

8 . A method to confer, enhance, improve or modify the odor properties of a perfuming composition or of a perfumed article, which method comprises adding to said composition or article an effective amount of at least one compound of formula (I) as defined in claim 1 .

9 . A properfume compound suitable to release the compound of formula (I):

in the form of any one of its stereoisomers or as a mixture thereof, wherein one dotted line represents a carbon-carbon double bond and the other dotted lines represent a carbon-carbon single bond; le represents a hydrogen atom or a C 1-2 alkyl group; R 2 represents a C 1-4 alkyl group or a C 2-4 alkenyl group; R 3 represents a hydrogen atom or a C 1-3 alkyl group or a C 2-3 alkenyl group; R 4 represents a hydrogen atom or R 4 represents a hydrogen atom or a methyl group when R 2 and R 3 represent a methyl group; or R 3 and R 4 , when taken together, represent a methylidene group; or R 2 and R 3 , when taken together, represent a C 4-9 alkanediyl or a C 4-9 alkenediyl group; or R 2 , R 3 and R 4 , when taken together, represent a phenyl group optionally substituted by a C 1-3 alkyl group.

10 . A perfuming composition comprising
i) at least one compound of formula (I), as defined in claim 1 ; ii) at least one ingredient selected from the group consisting of a perfumery carrier and a perfumery base; and iii) optionally at least one perfumery adjuvant.

11 . A perfumed consumer product comprising at least one compound of formula (I), as defined in claim 1 .

12 . The perfumed consumer product according to claim 11 , characterized in that the perfumery consumer product is a perfume, a fabric care product, a body-care product, a cosmetic preparation, a skin-care product, an air care product or a home care product.

13 . The perfumed consumer product according to claim 12 , characterized in that the perfumery consumer product is a fine perfume, a splash or eau de parfum, a cologne, a shave or after-shave lotion, a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, a paper, a bleach, a carpet cleaner, a curtain-care product, a shampoo, a coloring preparation, a color care product, a hair shaping product, a dental care product, a disinfectant, an intimate care product, a hair spray, a vanishing cream, a deodorant or antiperspirant, a hair remover, a tanning or sun product, a nail product, a skin cleansing, a makeup, a perfumed soap, a shower or bath mousse, oil or gel, or a foot/hand care product, a hygiene product, an air freshener, a “ready to use” powdered air freshener, a mold remover, a furnisher care, a wipe, a dish detergent or hard-surface detergent, a leather care product, a car care product, a pest control article, an insect repellent product.

14 . A method to confer, enhance, improve or modify the arthropod control properties of an arthropod control composition or of an arthropod control article, which method comprises adding to said composition or article an effective amount of at least a compound of formula (I) as defined in claim 1 .

15 . A non-therapeutic method of reducing, arresting or inhibiting the growth rate of bacterial cells or inactivating or killing bacterial cells, the method comprising treating a substrate comprising microbes with an effective amount of at least a compound of formula (I) as defined in claim 1 .

16 . The compound according to claim 2 , wherein:
R 1 and R 4 are a hydrogen atom; R 3 is a hydrogen atom or a methyl group; and R 2 is a methyl, ethyl or propyl group.

17 . A perfuming composition comprising
i) at least one properfume compound as defined in claim 9 ; ii) at least one ingredient selected from the group consisting of a perfumery carrier and a perfumery base; and iv) optionally at least one perfumery adjuvant.

18 . A perfumed consumer product comprising at least one properfume compound as defined in claim 9 .

19 . The perfumed consumer product according to claim 18 , characterized in that the perfumery consumer product is a perfume, a fabric care product, a body-care product, a cosmetic preparation, a skin-care product, an air care product or a home care product.

20 . The perfumed consumer product according to claim 19 , characterized in that the perfumery consumer product is a fine perfume, a splash or eau de parfum, a cologne, a shave or after-shave lotion, a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, a paper, a bleach, a carpet cleaner, a curtain-care product, a shampoo, a coloring preparation, a color care product, a hair shaping product, a dental care product, a disinfectant, an intimate care product, a hair spray, a vanishing cream, a deodorant or antiperspirant, a hair remover, a tanning or sun product, a nail product, a skin cleansing, a makeup, a perfumed soap, a shower or bath mousse, oil or gel, or a foot/hand care product, a hygiene product, an air freshener, a “ready to use” powdered air freshener, a mold remover, a furnisher care, a wipe, a dish detergent or hard-surface detergent, a leather care product, a car care product, a pest control article, an insect repellent product.

Assignees

• Firmenich & Cie

Inventors

• Lem George
• Harraca Vincent

Classifications

• C07C47/225 Primary

  containing rings other than six-membered aromatic rings · CPC title

• A61K2800/874

  Roll-on · CPC title

• A61Q13/00

  Formulations or additives for perfume preparations (essential oils or perfumes per se C11B9/00) · CPC title

• A61K8/33

  containing oxygen · CPC title

• C11B9/003

  the ring containing less than six carbon atoms · CPC title