Organic compounds

Patent metadata

Field	Value
Publication number	US-2025382252-A1
Application number	US-202318878347-A
Country	US
Kind code	A1
Filing date	Jun 28, 2023
Priority date	Jun 29, 2022
Publication date	Dec 18, 2025
Grant date	—

Abstract

Disclosed are cyclopent-2-enone derivatives possessing woody odor profile with some peppery notes.

First claim

1 . A method of using a compound of formula (I) or a mixture thereof as a fragrance or flavor

wherein
indicates a carbon-carbon single or double bond,
R is hydrogen and R 1 is hydrogen or methyl, or
R and R 1 form together with the C-atom to which they are attached a vinyl group,
R 2 is selected from methyl and ethyl,
R 3 and R 4 are hydrogen, or
R 3 and R 4 together with the C—C bond represent a double bond, or
R 2 and R 3 form together a methylene group,
R 5 is selected from C 5 -C 7 alkyl and C 5 -C 7 alkenyl, and
R 6 is selected from hydrogen and methyl.

2 . The method according to claim 1 wherein the compound of formula (I) is selected from the group consisting of 3-methyl-2-(oct-5-en-2-yl)cyclopent-2-en-1-one;
3-methyl-2-(6-methylhept-5-en-2-yl)cyclopent-2-en-1-one;
3-methyl-2-(6-methylocta-2,5-dien-2-yl)cyclopent-2-en-1-one;
3-methyl-2-(6-methylocta-1,5-dien-2-yl)cyclopent-2-en-1-one;
3-methyl-2-(6-methyloct-5-en-2-yl)cyclopent-2-en-1-one;
3-methyl-2-(octa-2,5-dien-2-yl)cyclopent-2-en-1-one;
3-methyl-2-(octa-1,5-dien-2-yl)cyclopent-2-en-1-one;
3-methyl-2-(nonan-2-yl)cyclopent-2-en-1-one;
3-methyl-2-(non-5-en-2-yl)cyclopent-2-en-1-one;
3,4-dimethyl-2-(6-methylhept-5-en-2-yl)cyclopent-2-en-1-one;
3-methyl-2-(5-methylhept-4-en-2-yl)cyclopent-2-en-1-one;
3-methyl-2-(5-methylheptan-2-yl)cyclopent-2-en-1-one;
2-(4,7-dimethyloct-6-en-2-yl)-3-methylcyclopent-2-en-1-one;
2-(6-methylhept-5-en-2-yl)-3-vinylcyclopent-2-en-1-one;
3-ethyl-2-(6-methylhept-5-en-2-yl)cyclopent-2-en-1-one;
3-methyl-2-(6-methylheptan-2-yl)cyclopent-2-en-1-one;
3-ethyl-2-(6-methylheptan-2-yl)cyclopent-2-en-1-one;
3-methyl-2-(octan-2-yl)cyclopent-2-en-1-one;
3-ethyl-2-(oct-5-en-2-yl)cyclopent-2-en-1-one;
2-(oct-5-en-2-yl)-3-vinylcyclopent-2-en-1-one and mixtures thereof.

3 . The method according to claim 1 wherein the indicates a carbon-carbon double bond, and a compound of formula (II)

wherein
R 1 is hydrogen or methyl,
R 2 is selected from methyl and ethyl,
R 3 and R 4 are hydrogen, or
R 3 and R 4 together with the C—C bond represent a double bond, or
R 2 and R 3 form together a methylene group,
R 5 is selected from C 5 -C 7 alkyl and C 5 -C 7 alkenyl, and
R 6 is selected from hydrogen and methyl.

4 . A fragrance composition comprising a compound of formula (I) or a mixture thereof

wherein
indicates a carbon-carbon single or double bond,
R is hydrogen and R 1 is hydrogen or methyl, or
R and R 1 form together with the C-atom to which they are attached a vinyl group,
R 2 is selected from methyl and ethyl,
R 3 and R 4 are hydrogen, or
R 3 and R 4 together with the C—C bond represent a double bond, or
R 2 and R 3 form together a methylene group,
R 5 is selected from C 5 -C 7 alkyl, and C 5 -C 7 alkenyl, and
R 6 is selected from hydrogen and methyl;
and
at least one other odorant.

5 . The fragrance composition according to claim 4 , wherein the compound is selected from the group consisting of 3-methyl-2-(oct-5-en-2-yl)cyclopent-2-en-1-one; 3-methyl-2-(6-methylocta-2,5-dien-2-yl)cyclopent-2-en-1-one; 3-methyl-2-(6-methylocta-1,5-dien-2-yl)cyclopent-2-en-1-one; 3-methyl-2-(6-methyloct-5-en-2-yl)cyclopent-2-en-1-one; 3-methyl-2-(octa-2,5-dien-2-yl)cyclopent-2-en-1-one; 3-methyl-2-(octa-1,5-dien-2-yl)cyclopent-2-en-1-one; 3-methyl-2-(nonan-2-yl)cyclopent-2-en-1-one; 3-methyl-2-(non-5-en-2-yl)cyclopent-2-en-1-one; 3,4-dimethyl-2-(6-methylhept-5-en-2-yl)cyclopent-2-en-1-one; 3-methyl-2-(5-methylhept-4-en-2-yl)cyclopent-2-en-1-one; 3-methyl-2-(5-methylheptan-2-yl)cyclopent-2-en-1-one; 2-(4,7-dimethyloct-6-en-2-yl)-3-methylcyclopent-2-en-1-one; 2-(6-methylhept-5-en-2-yl)-3-vinylcyclopent-2-en-1-one; 3-ethyl-2-(6-methylhept-5-en-2-yl)cyclopent-2-en-1-one; 3-ethyl-2-(6-methylheptan-2-yl)cyclopent-2-en-1-one; 3-methyl-2-(octan-2-yl)cyclopent-2-en-1-one; 3-ethyl-2-(oct-5-en-2-yl)cyclopent-2-en-1-one; 2-(oct-5-en-2-yl)-3-vinylcyclopent-2-en-1-one and mixtures thereof.

6 . A fragranced article comprising
a) as odorant a compound of formula (I)

wherein
indicates a carbon-carbon single or double bond,
R is hydrogen and R 1 is hydrogen or methyl, or
R and R 1 form together with the C-atom to which they are attached a vinyl group,
R 2 is selected from methyl and ethyl,
R 3 and R 4 are hydrogen, or
R 3 and R 4 together with the C—C bond represent a double bond, or
R 2 and R 3 form together a methylene group,
R 5 is selected from C 5 -C 7 alkyl and C 5 -C 7 alkenyl, and
R 6 is selected from hydrogen and methyl;
and
b) a consumer product base.

7 . The fragranced article according to claim 6 wherein the odorant compound is a compound of formula (I) where indicates a carbon-carbon double bond.

8 . The fragranced article according to claim 7 further comprising as odorant a compound of formula (II)

wherein
R 1 is hydrogen or methyl,
R 2 is selected from methyl and ethyl,
R 3 and R 4 are hydrogen, or
R 3 and R 4 together with the C—C bond represent a double bond, or
R 2 and R 3 form together a methylene group,
R 5 is selected from C 5 -C 7 alkyl and C 5 -C 7 alkenyl, and
R 6 is selected from hydrogen and methyl.

9 . The fragranced article according to claim 6 wherein the consumer product base is selected from fine perfumery, personal care products and fabric care products.

10 . A method of improving, enhancing or modifying a consumer product base by means of addition thereto of an olfactory acceptable amount of a compound of formula (I) or a mixture thereof

wherein
indicates a carbon-carbon single or double bond,
R is hydrogen and R 1 is hydrogen or methyl, or
R and R 1 form together with the C-atom to which they are attached a vinyl group,
R 2 is selected from methyl and ethyl,
R 3 and R 4 are hydrogen, or
R 3 and R 4 together with the C—C bond represent a double bond, or
R 2 and R 3 form together a methylene group,
R 5 is selected from Cs-C 7 alkyl and C 5 -C 7 alkenyl, and
R 6 is selected from hydrogen and methyl.

11 . The method according to claim 10 comprising a mixture comprising a compound of formula (I) and a compound of formula (II)

wherein
R is hydrogen,
R 1 is hydrogen or methyl,
R 2 is selected from methyl and ethyl,
R 3 and R 4 are hydrogen, or
R 3 and R 4 together with the C—C bond represent a double bond, or
R 2 and R 3 form together a methylene group,

Assignees

• Givaudan Sa

Inventors

• Zhou Lijun
• Chai An
• Chen Chun
• Ding Changming
• Goeke Andreas
• Huang Feng
• Liniger Marc
• Yu Zhiyu

Classifications

• C11B9/003

  the ring containing less than six carbon atoms · CPC title

• C07C49/597 Primary

  of a five-membered ring · CPC title

• C07C49/395

  of a five-membered ring · CPC title

• C07C2601/10

  the ring being unsaturated · CPC title

• C07C2601/08

  the ring being saturated · CPC title