Powdery, Musky Odorant Macrocycles

Patent metadata

Field	Value
Publication number	US-2023031807-A1
Application number	US-202017757728-A
Country	US
Kind code	A1
Filing date	Dec 17, 2020
Priority date	Dec 20, 2019
Publication date	Feb 2, 2023
Grant date	—

Abstract

Described herein is a composition of matter including
a) 0.5 to 85% w/w of (Z)-oxacyclohexadec-12-en-2-one; b) 0.5 to 30% w/w of (E)-oxacyclohexadec-12-en-2-one; c) 0 to 30% w/w of (E)-oxacyclohexadec-13-en-2-one; and d) 0.5 to 85% w/w of (Z)-oxacyclohexadec-13-en-2-one, the percentage being relative to the total weight of the composition of matter; wherein the weight ratio of the E-diastereoisomers to the Z-diastereoisomers is in the range between 40:60 and 15:85.

First claim

1 . A composition of matter comprising:
a) 0.5 to 85% w/w of (Z)-oxacyclohexadec-12-en-2-one; b) 0.5 to 30% w/w of (E)-oxacyclohexadec-12-en-2-one; c) 0 to 30% w/w of (E)-oxacyclohexadec-13-en-2-one; and d) 0.5 to 85% w/w of (Z)-oxacyclohexadec-13-en-2-one, the percentage being relative to the total weight of the composition of matter; wherein the weight ratio of the E-diastereoisomers to the Z-diastereoisomers is comprised in the range between 40:60 and 15:85.

2 . The composition of matter according to claim 1 , wherein said composition comprises:
a) 7 to 85% w/w of (Z)-oxacyclohexadec-12-en-2-one; b) 0.5 to 25% w/w of (E)-oxacyclohexadec-12-en-2-one; c) 0 to 30% w/w of (E)-oxacyclohexadec-13-en-2-one; and d) 0.5 to 85% w/w of (Z)-oxacyclohexadec-13-en-2-one.

3 . The composition of matter according to claim 1 , wherein said composition comprises:
a) 40 to 85% w/w of (Z)-oxacyclohexadec-12-en-2-one; b) 2 to 25% w/w of (E)-oxacyclohexadec-12-en-2-one; c) 0 to 20% w/w of (E)-oxacyclohexadec-13-en-2-one; and d) 0.5 to 35% w/w of (Z)-oxacyclohexadec-13-en-2-one.

4 . The composition of matter according to claim 1 , wherein said composition comprises:
a) 50 to 85% w/w of (Z)-oxacyclohexadec-12-en-2-one; b) 5 to 20% w/w of (E)-oxacyclohexadec-12-en-2-one; c) 0 to 20% w/w of (E)-oxacyclohexadec-13-en-2-one; and d) 0.5 to 25% w/w of (Z)-oxacyclohexadec-13-en-2-one.

5 . The composition of matter according to claim 1 , wherein the weight ratio of the E-diastereoisomers to the Z-diastereoisomers is comprised in the range between 30:70 and 17:83.

6 . 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 consumer product an effective amount of the composition of matter according to claim 1 .

7 . (canceled)

8 . A perfuming composition comprising
i) at least a composition of matter according to 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.

9 . A perfumed consumer product comprising the perfuming composition according to claim 8 .

10 . The perfumed consumer product according to claim 9 , wherein 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.

11 . The perfumed consumer product according to claim 10 , wherein 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, oil or gel, a foot/hand care product, a hygiene product, an air freshener, a “ready to use” powdered air freshener, a mold remover, a furnisher care product, a wipe, a dish detergent or hard-surface detergent, a leather care product, or a car care product.

12 . A process to prepare the composition of matter according to claim 1 , wherein the process comprises a thermal elimination of a mixture comprising
i) 0.5 to 85% w/w of compound of formula

in the form of any one of its stereoisomers or a mixture thereof, wherein R 1 represents a OR 2 or a NR 2 2 group, and wherein R 2 represents a C 1-3 alkyl group;
ii) 0.5 to 85% w/w of compound of formula

in the form of any one of its stereoisomers or a mixture thereof, wherein R 1 has the same meaning as defined above;
iii) 0.5 to 30% w/w of compound of formula

in the form of any one of its stereoisomers or a mixture thereof, wherein R 1 has the same meaning as defined above; and
iv) 0 to 30% w/w of compound of formula

in the form of any one of its stereoisomers or a mixture thereof, wherein R 1 has the same meaning as defined above.

13 . The process according to claim 12 , wherein the preparation of the mixture comprising from 0.5 to 85% of compound of formula (I), from 0.5 to 85% of compound of formula (II), from 0.5 to 30% of compound of formula (III) and from 0 to 30% of compound of formula (IV) comprises:
a) an epoxidation of a composition comprising at least 70% of oxacyclohexadec-12-en-2-one and oxacyclohexadec-13-en-2-one with the double bond with E configuration and at most 30% of oxacyclohexadec-12-en-2-one and oxacyclohexadec-13-en-2-one with the double bond with Z configuration; b) a hydrolysis of the mixture obtained in step a) to form a mixture of diols comprising
i) 0.5 to 85% w/w of diol (12RS,13SR)-12,13-dihydroxyoxacyclohexadecan-2-one;
ii) 0.5 to 85% w/w of diol (13RS,14SR)-13,14-dihydroxyoxacyclohexadecan-2-one;
iii) 0.5 to 30% w/w of diol (12RS,13RS)-12,13-dihydroxyoxacyclohexadecan-2-one; and
iv) 0 to 30% w/w of diol (13SR,14SR)-13,14-dihydroxyoxacyclohexadecan-2-one; and
c) treating the diols obtained in step b) with a tri C 1-3 alkyl orthoformate or DMF acetal.

14 . A compound of formula

in a form of any one of its stereoisomers or a mixture thereof; wherein when m is 1, then n is 1 or when m is 0, then n is 2; wherein the R groups each represent a hydrogen or both R groups, taken together, represent a C 1-6 alkyl, a CHOR 2 or a CHNR 22 group; and wherein R 2 represents a C 1-3 alkyl group.

15 . 13-(1,3-dihydroxypropyl)oxacyclotridecan-2-one in a form of any one of its stereoisomers or a mixture thereof.

16 . The composition of matter according to claim 1 , wherein the weight ratio of the E-diastereoisomers to the Z-diastereoisomers is comprised in the range between 25:75 and 18:82.

17 . A perfumed consumer product comprising at least a composition of matter according to claim 1 .

18 . The perfumed consumer product according to claim 17 , wherein 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.

19 . The perfumed consumer product according to claim 18 , wherein 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 b

Assignees

• Firmenich & Cie

Inventors

• Birkbeck Anthony Alexander
• Maddalena Umberto

Classifications

• C07D313/00

  Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom · CPC title

• C11B9/0084 Primary

  the hetero rings containing more than six atoms · CPC title