Lily of the valley odorant

Patent metadata

Field	Value
Publication number	US-10980722-B2
Application number	US-201916757955-A
Country	US
Kind code	B2
Filing date	Jan 17, 2019
Priority date	Jan 19, 2018
Publication date	Apr 20, 2021
Grant date	Apr 20, 2021

Abstract

The present disclosure concerns a perfuming ingredient of a compound of formula (I)

in the form of any one of its stereoisomers or a mixture thereof, and wherein X represents a CHO group when R1 represents a C1-2 alkyl group or X represents a CH(R6)CHO group when R1 represents a hydrogen atom or a C1-2 alkyl group. Each of R2, R3, R4, R5 and R6 represents, independently from each other, a hydrogen atom or a C1-2 alkyl group; or R3 and R4 represent, when taken together, a ethanediyl group; and —C(R3)(R4)—CH(R5)—OH group is, relative to position 1, an ortho, a meta, a para substituent of the aromatic ring or a mixture thereof. Also disclosed is the compound of formula (I) as part of a perfuming composition or of a perfumed consumer product.

First claim

The invention claimed is:

1. A method to confer, enhance, improve or modify odor properties of a perfuming composition or of a perfumed article, the method comprising adding to said composition or article an effective amount of a compound of formula (I) use as a perfuming ingredient, wherein formula (I) is:

in the form of any one of its stereoisomers or a mixture thereof, and wherein
X represents a CHO group when R 1 represents a C 1-2 alkyl group or X represents a CH(R 6 )CHO group when R 1 represents a hydrogen atom or a C 1-2 alkyl group;
each R 2 , R 3 , R 4 , R 5 and R 6 represents, independently from each other, a hydrogen atom or a C 1-2 alkyl group; or R 3 and R 4 represent, when taken together, an ethanediyl group; and —C(R 3 )(R 4 )—CH(R 5 )—OH group is, relative to position 1, an ortho, a meta, a para substituent of the aromatic ring or a mixture thereof.

2. The method according to claim 1 , characterized in that the —C(R 3 )(R 4 )—CH(R 5 )—OH group is a meta or para substituent of the aromatic ring, relative to position 1.

3. The method according to claim 1 , characterized in that the compound (I) is a compound of formula II

in the form of any one of its stereoisomers or a mixture thereof, and wherein X, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 have the same meaning as defined in claim 1 .

4. The method according to claim 1 , characterized in that R 1 is a methyl group when X represents a CHO group or R 1 is a hydrogen atom or a methyl group when X represents a CH(R 6 )CHO group, R 6 having the same meaning as defined in claim 1 .

5. The method according to claim 1 , characterized in that the compound (I) is a compound of formula (III)

in the form of any one of its stereoisomers or a mixture thereof, and wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 have the same meaning as defined in claim 1 .

6. The method according to claim 1 , characterized in that R 2 , R 5 , and R 6 is a hydrogen atom or a methyl group.

7. The method according to claim 1 , characterized in that R 3 is a methyl group and R 4 may be a hydrogen atom or a methyl group or R 3 and R 4 represent, when taken together, an ethanediyl group.

8. The method according to claim 1 , characterized in that the compound (I) is a compound of formula IV

in the form of any one of its stereoisomers or a mixture thereof, and wherein R 1 , R 2 , R 5 , and R 6 have the same meaning as defined in claim 1 .

9. The method according to claim 8 , characterized in that R 1 , R 2 , R 5 , and R 6 represent, independently from each other, a hydrogen atom.

10. A compound of formula (I) as defined in claim 1 provided that 3-(4-(1-hydroxy-2-methylpropan-2-yl)phenyl)propanal, 3-(4-(2-hydroxyethyl)phenyl)propanal, 3-(4-(1-(hydroxymethyl)cyclopropyl)phenyl)propanal, 3-(4-(1-hydroxy-2-methylpropan-2-yl)phenyl)butanal, 3-(4-(2-hydroxypropyl)phenyl)propanal, 3-(4-(1-(hydroxymethyl)cyclopropyl)phenyl)butanal, 3-(3-(1-(hydroxymethyl)cyclopropyl)phenyl)butanal, 3-(3-(1-(hydroxymethyl)cyclopropyl)phenyl)propanal, 3-(2-(1-(hydroxymethyl)cyclopropyl)phenyl)propanal, 3-(2-(1-(hydroxymethyl)cyclopropyl)phenyl)butanal, 3-(3-(2-hydroxypropyl)phenyl)butanal, 3-(3-(2-hydroxypropyl)phenyl)propanal, 3-(3-(2-hydroxyethyl)phenyl)propanal, 3-(3-(2-hydroxyethyl)phenyl)butanal, 3-(3-(1-hydroxy-2-methylpropan-2-yl)phenyl)butanal, 3-(3-(1-hydroxy-2-methylpropan-2-yl)phenyl)propanal, 3-(2-(1-hydroxy-2-methylpropan-2-yl)phenyl)propanal, 3-(2-(1-hydroxy-2-methylpropan-2-yl)phenyl)butanal, 3-(2-(2-hydroxypropyl)phenyl)butanal, 3-(2-(2-hydroxypropyl)phenyl)propanal, 3-(4-(2-hydroxyethyl)phenyl)butanal and 3-(4-(2-hydroxypropyl)phenyl)butanal are excluded.

11. 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
optionally at least one perfumery adjuvant.

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

13. The perfumed consumer product according to claim 12 , characterized in that the perfumed 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.

14. The perfumed consumer product according to claim 13 , characterized in that the perfumed 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, an oil or gel, a foot/hand care product, a hygiene product, an air freshener, a “ready to use” powdered, an air freshener, a mold remover, a furnisher care, a wipe, a dish detergent or a hard-surface detergent, a leather care product, a car care product.

15. A perfumed consumer product comprising at least the composition as defined in claim 11 .

16. The perfumed consumer product according to claim 15 , characterized in that the perfumed 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.

17. The perfumed consumer product according to claim 16 , characterized in that the perfumed 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, an oil or gel, a foot/hand care product, a hygiene product, an air freshener, a “ready to use” powdered, an air freshener, a mold remover, a furnisher care, a wipe, a dish detergent or a hard-surface detergent, a leather care product, a car care product.

Assignees

• Firmenich & Cie

Inventors

• Coulomb Julien
• Oddon Gilles

Classifications

• C07C47/27

  containing six-membered aromatic rings · CPC title

• C11B9/0061 Primary

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

• C07C47/267

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

• A61Q19/00

  Preparations for care of the skin · CPC title

• A61K8/34 Primary

  Alcohols · CPC title