NOVEL ORGANOLEPTIC COMPOUNDS

• US 20200131451A1
• Filed: 10/22/2019
• Published: 04/30/2020
• Est. Priority Date: 10/24/2018
• Status: Active Grant

• Current Assignee: International Flavors & Fragrances Incorporated
• Original Assignee: International Flavors & Fragrances Incorporated
• Inventors: Narula, Anubhav P.S., WEISS, Richard A., DENUTTE, Hugo Robert Germain, SMETS, Johan, PORTER, Philip John, VRIELYNCK, Freek Annie Camiel, VAN AKEN, Koen, RUTTENS, Bart Antoon Judith
• Granted Patent: US 10,982,172 B2
• Time in Patent Office: Days
• CPC Class Codes: C07C 2601/16 the ring being unsaturated
• CPC Class Codes: C07C 33/14 containing six-membered rings
• CPC Class Codes: C07C 49/21 containing rings other than six-membered aromatic rings
• CPC Class Codes: C11B 9/0034 the ring containing six carbon atoms

Abstract

The present invention relates to novel compounds and their use as fragrance materials.

Claims

1. A compound of formula:

2. The compound of claim 1 selected from the group consisting of:

(E)-1-((1R,6R)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one;

(E)-1-((1S,6S)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one;

(E)-1-((1R,6S)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one;

(E)-1-((1S,6R)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one;

(E)-1-((1R,6R)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-ol;

(E)-1-((1S,6S)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-ol;

(E)-1-((1R,6S)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-ol;

(E)-1-((1S,6R)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-ol; and

a mixture thereof.

3. The compound of claim 2, wherein the compound is the mixture of (E)-1-((1R,6R)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one, (E)-1-((1S,6S)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one, (E)-1-((1R,6S)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one and (E)-1-((1S,6R)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one.

4. A fragrance formulation comprising an olfactory acceptable amount of a compound of formula:

5. The fragrance formulation of claim 4, wherein the compound is selected from the group consisting of:

(E)-1-((1R,6R)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one;

(E)-1-((1S,6S)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one;

(E)-1-((1R,6S)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one;

(E)-1-((1S,6R)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one;

(E)-1-((1R,6R)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-ol;

(E)-1-((1S,6S)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-ol;

(E)-1-((1R,6S)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-ol;

(E)-1-((1S,6R)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-ol; and

a mixture thereof.

6. The fragrance formulation of claim 5, wherein the compound is the mixture of (E)-1-((1R,6R)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one, (E)-1-((1S,6S)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one, (E)-1-((1R,6S)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one and (E)-1-((1S,6R)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one.

7. The fragrance formulation of claim 4, wherein the olfactory acceptable amount is from about 0.005 to about 50 weight percent of the fragrance formulation.

8. The fragrance formulation of claim 4, wherein the olfactory acceptable amount is from about 0.5 to about 25 weight percent of the fragrance formulation.

9. The fragrance formulation of claim 4, wherein the olfactory acceptable amount is from about 1 to about 10 weight percent of the fragrance formulation.

10. A method of improving, enhancing or modifying a fragrance formulation through the addition of an olfactory acceptable amount of a compound of formula:

11. The method of claim 10, wherein the compound is selected from the group consisting of:

(E)-1-((1R,6R)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one;

(E)-1-((1S,6S)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one;

(E)-1-((1R,6S)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one;

(E)-1-((1S,6R)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one;

(E)-1-((1R,6R)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-ol;

(E)-1-((1S,6S)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-ol;

(E)-1-((1R,6S)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-ol;

(E)-1-((1 S,6R)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-ol; and

a mixture thereof.

12. The method of claim 11, wherein the compound is the mixture of (E)-1-((1R,6R)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one, (E)-1-((1S,6S)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one, (E)-1-((1R,6S)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one and (E)-1-((1S,6R)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one.

13. The method of claim 10, wherein the olfactory acceptable amount is from about 0.005 to about 50 weight percent of the fragrance formulation.

14. The method of claim 10, wherein the olfactory acceptable amount is from about 0.1 to about 25 weight percent of the fragrance formulation.

15. The method of claim 10, wherein the olfactory acceptable amount is from about 0.5 to about 10 weight percent of the fragrance formulation.