Benzodioxole derivatives as watery odorants

• US 8,987,188 B2
• Filed: 09/29/2011
• Issued: 03/24/2015
• Est. Priority Date: 10/04/2010
• Status: Active Grant

• Current Assignee: Firmenich SA
• Original Assignee: Firmenich SA
• Inventors: Huboux, Alexandre, Gaudin, Jean-Marc, Millet, Pascal, Robvieux, Fabrice
• Primary Examiner(s): Choi, Ling
• Assistant Examiner(s): REUTHER, ARRIE L
• Application Number:
  US13/876,404
• Publication Number:
  US 20130288947A1
• Time in Patent Office: 1,272 Days
• Field of Search: 512/12
• US Class Current: 512/12
• CPC Class Codes: A61K 8/4973 with oxygen as the only hetero atom
• CPC Class Codes: A61K 8/498 having 6-membered rings or their condensed derivatives, e.g. coumarin
• CPC Class Codes: A61Q 13/00 Formulations or additives for perfume preparations essential oils or perfumes per se C11B9/00
• CPC Class Codes: C07D 317/06 condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 317/46 condensed with one six-membered ring
• CPC Class Codes: C11B 9/0076 the hetero rings containing less than six atoms

Abstract

The present invention relates to compounds of formula (I) in the form of any one of its stereoisomers or a mixture thereof, and wherein R¹ represents a substituent of the benzene ring and is a bromine atom or a linear, branched or cyclic C_1-8 alkyl, alkenyl, alkoxy or alkenyloxy group; R² represents a C_1-3 alkyl group; and R³ represents a hydrogen atom or a methyl or ethyl group; and their use as perfuming ingredients, for instance to impart odor notes of the watery/ozone type.

Claims

1. 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 a compound of formula

2. A method according to claim 1 wherein said compound (I) is of formula

3. A method according to claim 2 wherein said R¹ independently represents a substituent of the benzene ring and is a linear or branched C_1-6alkyl, alkenyl, alkynyl or alkoxy group or represents a C_5-6 cyclic alkyl, alkenyl or methylcyloalkyl group.

4. A method according to claim 3 wherein R¹ independently represents a substituent of the benzene ring and is a bromine atom or a linear, branched or cyclic C_1-6 alkyl, alkenyl, alkynyl, alkoxy or alkenyloxy group.

5. A method according to claim 4 wherein said R¹ independently represents a substituent of the benzene ring and is a linear or branched C_1-6 alkyl or alkenyl group.

6. A method according to claim 2 wherein said R³ represents a hydrogen atom or a methyl group.

7. A method according to claim 1 wherein said R¹ independently represents a substituent of the benzene ring and is a linear or branched C_1-6 alkyl, alkenyl, alkynyl or alkoxy group or represents a C_5-6 cyclic alkyl, alkenyl or methylcyloalkyl group.

8. A method according to claim 7 wherein R¹ independently represents a substituent of the benzene ring and is a bromine atom or a linear, branched or cyclic C_1-6 alkyl, alkenyl, alkynyl, alkoxy or alkenyloxy group.

9. A method according to claim 8 wherein said R¹ independently represents a substituent of the benzene ring and is a linear or branched C_1-6 alkyl or alkenyl group.

10. A method according to claim 1 wherein said R² represents a methyl or ethyl group.

13. A method according to claim 1 or 11 wherein the compound is added to a perfumed article comprising a perfuming consumer product that includes a perfumery consumer base.

14. A method according to claim 13 wherein the perfumery consumer base is a perfume, a fabric care product, a body-care product, an air care product or a home care product.

15. A method according to claim 14 wherein the perfumery consumer is a fine perfume, a cologne, an after-shave lotion, a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, a paper, a bleach, a shampoo, a coloring preparation, a hair spray, a vanishing cream, a deodorant or antiperspirant, a perfumed soap, shower or bath mousse, oil or gel, a hygiene product, an air freshener, a “

ready to use”

powdered air freshener, a wipe, a dish detergent or hard-surface detergent.

16. A method according to claim 1 or 11 wherein the compound is added to a perfuming composition comprising at least one ingredient selected from the group consisting of a perfumery carrier and a perfumery base;

and optionally at least one perfumery adjuvant.

17. A method according to claim 16 wherein the perfumery base is a perfume, a fabric care product, a body-care product, an air care product or a home care product.

18. A method according to claim 17 wherein the perfumery base is a fine perfume, a cologne, an after-shave lotion, a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, a paper, a bleach, a shampoo, a coloring preparation, a hair spray, a vanishing cream, a deodorant or antiperspirant, a perfumed soap, shower or bath mousse, oil or gel, a hygiene product, an air freshener, a “

ready to use”

powdered air freshener, a wipe, a dish detergent or hard-surface detergent.

19. A method according to claim 1 or 11 wherein the compound to be added is of formula (I)

11. 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 a compound of Formula (I) selected from the group consisting of 1-(5-isopropylbenzo[d][1,3]dioxol-2-yl)ethanone, 1-(5-propyl-1,3-benzodioxol-2-yl)-1-ethanone, 1-(5-pentylbenzo[d][1,3]-dioxol-2-yl)ethanone, 1-(2-methyl-5-propylbenzo[d][1,3]-dioxol-2-yl)ethanone, 1-(5-butylbenzo[d][1,3]dioxol-2-yl)ethanone, 1-(5-hexylbenzo[d][1,3]dioxol-2-yl)ethanone, 1-(5-tert-pentylbenzo[d][1,3]dioxol-2-yl)ethanone, 1-(5-tert-butyl-1,3-benzodioxol-2-yl)-ethanone, 1-(5-cyclopentylbenzo[d][1,3]dioxol-2-yl)ethanone, 1-(5-(3-methylbut-2-enyl)benzo[d][1,3]dioxol-2-yl)ethanone, 1-(5-(cyclopentylmethyl)benzo[d][1,3]-dioxol-2-yl)ethanone, (E)-1-(5-(prop-1-enyl)benzo[d][1,3]dioxol-2-yl)ethanone, (E/Z)-1-(5-(hex-2-enyl)benzo[d][1,3]dioxol-2-yl)ethanone and 1-(4-methyl-1,3-benzodioxol-2-yl)-1-ethanone.

12. A method according to claim 11, wherein said compound is selected from the group consisting of 1-(5-isopropylbenzo[d][1,3]dioxol-2-yl)ethanone, 1-(5-propyl-1,3-benzodioxol-2-yl)-1-ethanone, 1-(5-pentylbenzo[d][1,3]dioxo-2-yl)ethanone, 1-(2-methyl-5-propylbenzo[d][1,3]dioxol-2-yl)ethanone, (E)-1-(5-(prop-1-enyl)benzo[d][1,3]dioxol-2-yl)ethanone, (E/Z)-1-(5-(hex-2-enyl)benzo[d][1,3]dioxol-2-yl)ethanone and 1-(5-butylbenzo[d][1,3]-dioxol-2-yl)ethanone.