Compound having a muguet odor

Patent metadata

Field	Value
Publication number	US-11091722-B2
Application number	US-201615744100-A
Country	US
Kind code	B2
Filing date	Jul 7, 2016
Priority date	Jul 14, 2015
Publication date	Aug 17, 2021
Grant date	Aug 17, 2021

Abstract

The present invention relates to phenylpropanal derivatives of formula (I)

in the form of any one of its stereoisomers or a mixture thereof, and wherein the dotted line represents a carbon-carbon single or double bond; X represents a CN or CHO group; each R 1 , R 2 and R 3 independently from each other, represents a hydrogen atom or a C 1-2 alkyl group; and R represents a group of formula —[CH 2 ] n C(Me) 2 OH, wherein n is 1 or 2; said R being a meta or para substituent of the aromatic ring, relative position 1;

and their uses as perfuming ingredients as well as the composition and consumer product including such derivatives.

First claim

The invention claimed is:

1. A compound of formula

in the form of any one of its stereoisomers or a mixture thereof, and wherein
the dotted line represents a carbon-carbon single or double bond;
X represents a CN or CHO group;
R 1 represents a hydrogen atom and each R 2 and R 3 independently from each other represents a hydrogen atom or a C 1-2 alkyl group; and
R represents a group of formula [CH 2 ] n C(Me) 2 OH, wherein n is 1 or 2; said R being a meta or para substituent of the aromatic ring, relative position 1;
wherein the compound of formula (I) imparts odor notes of the lily of the valley.

2. A compound according to claim 1 , wherein the compound comprises formula

in the form of any one of its stereoisomers or a mixture thereof, and wherein
the dotted line represents a carbon-carbon single or double bond;
n is 1 or 2;
X represents a CN or CHO group; and
le represents a hydrogen atom and each R 2 and R 3 independently from each other represents a hydrogen atom or a C 1-2 alkyl group.

3. A compound according to claim 1 , wherein the compound comprises formula

wherein n, R 2 and R 3 are as defined in claim 1 .

4. A compound according to claim 1 , characterized in that n is 1.

5. A compound according to claim 1 , characterized in that one of R 2 and R 3 is a hydrogen atom, and the other a methyl group.

6. A compound according to claim 1 , wherein the compound is 3-[4-(2-hydroxy-2-methylpropyl)phenyl]propanal.

7. A perfuming composition comprising
i) at least one compound of formula (I) of 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.

8. A perfuming consumer product comprising at least one compound of formula (I) of claim 1 .

9. A perfuming consumer product according to claim 8 , 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.

10. A perfuming consumer product according to claim 8 , characterized in that the perfumery consumer product is a fine perfume, a splash or eau de perfume, a cologne, an 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 cleaners, curtain-care products 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, hair remover, tanning or sun product, nail products, skin cleansing, a makeup, a perfumed soap, shower or bath mousse, oil or gel, or a foot/hand care products, a hygiene product, an air freshener, a “ready to use” powdered air freshener, a mold remover, furnisher care, wipe, a dish detergent or hard-surface detergent, a leather care product, a car care product.

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 at least one compound of formula (I) of claim 1 .

12. A compound of formula

in the form of any one of its stereoisomers or a mixture thereof, and wherein the dotted line represents a carbon-carbon single or double bond;
X represents a CN or CHO group;
each R 1 , R 2 and R 3 independently from each other, represents a hydrogen atom or a C 1-2 alkyl group; and
R represents a group of formula [CH 2 ] n C(Me) 2 OH, wherein n is 1 or 2; said R being a para substituent of the aromatic ring, relative to position 1,
wherein the compound is a perfuming ingredient; and
wherein the compound of formula (I) imparts odor notes of the lily of the valley.

13. A compound according to claim 12 , wherein the compound comprises formula

wherein n, R 1 , R 2 and R 3 are as defined in claim 12 .

14. A compound according to claim 12 , characterized in that n is 1.

Assignees

• Firmenich & Cie

Inventors

• Coulomb Julien

Classifications

• C11B9/0061 Primary

  compounds containing a six-membered aromatic ring not condensed with another ring · CPC title

• A61Q13/00

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

• C07C47/27 Primary

  containing six-membered aromatic rings · CPC title

• A61K8/34

  Alcohols · CPC title

• A61K2800/10

  General cosmetic use · CPC title