BENZODIOXOLE DERIVATIVES AS WATERY ODORANTS

• US 20130288947A1
• Filed: 09/29/2011
• Published: 10/31/2013
• Est. Priority Date: 10/04/2010
• Status: Active Grant

• Current Assignee: Firmenich SA (DSM-Firmenich AG)
• Original Assignee: Firmenich SA (DSM-Firmenich AG)
• Inventors: Gaudin, Jean-Marc, Huboux, Alexandre, Millet, Pascal, Robvieux, Fabrice
• Granted Patent: US 8,987,188 B2
• Time in Patent Office: Days
• 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

1-15. -15. (canceled)

16. 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

17. A method according to any one of claim 16-31 wherein said compound (I) is of formula

18. A method according to claim 16 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.

19. A method according to claim 17 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.

20. A method according to claim 18 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.

21. A method according to claim 19 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.

22. A method according to claim 20 wherein said R¹ independently represents a substituent of the benzene ring and is a linear or branched C_1-6 alkyl or alkenyl group.

23. A method according to claim 21 wherein said R¹ independently represents a substituent of the benzene ring and is a linear or branched C_1-6 alkyl or alkenyl group.

24. A method according to claim 16 wherein said R² represents a methyl or ethyl group.

25. A method according to claim 17 wherein said R³ represents a hydrogen atom or a methyl group.

28. A perfuming consumer product comprising:

i) at least one compound of formula (I), as defined in claim 16; and

ii) a perfumery consumer base.

29. A perfuming composition according to claim 28 comprising:

(i) at least one ingredient selected from the group consisting of a perfumery carrier and the perfumery base; and

(ii) optionally at least one perfumery adjuvant.

30. A perfuming consumer product according to claim 28, 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.

31. A perfuming consumer product according to claim 29, 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.

32. A perfuming consumer product according to claim 30, wherein the perfumery consumer 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.

33. A perfuming consumer product according to claim 31, wherein the perfumery consumer 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.

35. A compound according to claim 34 having the formula:

24-1. A method according to claim 16 wherein said R² represents a methyl or ethyl group.

24-2. A method according to claim 16 wherein said R³ represents a hydrogen atom or a methyl group.

26. 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 Forumla (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-benzo dioxol-2-yl)-1-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 or 1-(4-methyl-1,3-benzodioxol-2-yl)-1-ethanone.

27. A method according to claim 26, 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]dioxol-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 or 1-(5-butylbenzo[d][1,3]dioxol-2-yl)ethanone.

34. A compound of formula