Benzodioxole derivatives as watery odorants

• US 9,382,500 B2
• Filed: 02/09/2015
• Issued: 07/05/2016
• Est. Priority Date: 10/04/2010
• Status: Active Grant

• Current Assignee: Firmenich SA
• Original Assignee: Firmenich SA
• Inventors: Gaudin, Jean-Marc, Huboux, Alexandre, Millet, Pascal, Robvieux, Fabrice
• Primary Examiner(s): Choi, Ling
• Assistant Examiner(s): Reuther, Lanee
• Application Number:
  US14/617,279
• Publication Number:
  US 20150152352A1
• Time in Patent Office: 512 Days
• Field of Search: 512/2
• US Class Current: 1/1
• 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

A compound of formula (I) or (A)

in the form of any one of its stereoisomers or a mixture thereof, and wherein and wherein

• R¹ independently represents a substituent of the benzene ring and is a halogen atom or a linear, branched or cyclic C_1-8 alkyl, alkenyl, alkynyl, alkoxy or alkenyloxy group;
• R² represents a C_1-3 alkyl group or —OH; and
• R³ represents a hydrogen atom or a methyl or ethyl group and its use in a perfuming composition or perfuming consumer product.

Claims

1. A compound of formula (I)

2. A compound 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.

3. A compound according to claim 1 wherein said 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.

4. A compound according to claim 1 wherein said R² represents a methyl or ethyl group.

5. A compound according to claim 1 wherein said R³ represents a hydrogen atom or a methyl group.

6. A compound according to claim 1 wherein the compound of Formula I 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, 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)-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.

7. A compound according to claim 1 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.

8. 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 the perfumery base; and

iii) optionally at least one perfumery adjuvant.

9. A perfuming consumer product comprising:

i) at least one compound of formula (I), as defined in claim 1; and

ii) a perfumery consumer base.

10. A perfuming consumer product according to claim 9, 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.

11. A perfuming consumer product according to claim 9, 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.