Organoleptic compounds

Patent metadata

Field	Value
Publication number	US-11286225-B2
Application number	US-201917268739-A
Country	US
Kind code	B2
Filing date	Aug 15, 2019
Priority date	Aug 17, 2018
Publication date	Mar 29, 2022
Grant date	Mar 29, 2022

Abstract

The present invention relates to novel ((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy) alcohols and their use as fragrance materials.

First claim

What is claimed is:

1. A compound having Formula I:

or an isomer thereof; wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of hydrogen and a C 1-12 linear or branched alkyl group, with the proviso that R 1 , R 2 , R 3 and R 4 together contain 1-12 carbon atoms.

2. The compound of claim 1 having Formula II:

or an isomer thereof; wherein R 1 ′, R 2 ′, R 3 ′ and R 4 ′ are independently selected from the group consisting of hydrogen and a C 1-6 linear or branched alkyl group, with the proviso that R 1 ′, R 2 ′, R 3 ′ and R 4 ′ together contain 1-6 carbon atoms.

3. The compound of claim 2 selected from the group consisting of
2-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)propan-1-ol;
1-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)propan-2-ol;
2-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)butan-1-ol;
1-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)butan-2-ol;
2-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)pentan-1-ol;
1-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)pentan-2-ol;
2-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)hexan-1-ol;
1-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)hexan-2-ol;
3-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)butan-2-ol;
an isomer thereof; and
a mixture thereof.

4. The compound of claim 3 is 2-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)pentan-1-ol, 1-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)pentan-2-ol, an isomer thereof or a mixture thereof.

5. A fragrance product containing the compound of claim 1 .

6. The fragrance product of claim 5 , wherein the fragrance product is selected from the group consisting of a perfume, a cologne, toilet water, a bar soap, a liquid soap, a shower gel, a foam bath, a cosmetic, a personal care product, a skin care product, a hair care product, a deodorant, an antiperspirant, a feminine care product, a baby care product, a family care product, a fabric product, an air care product, a fragrance delivery system, a cosmetic preparation, a cleaning product, a disinfectant, a washing agent, a dental and oral hygiene product, a health care and nutritional product and a food product.

7. A fragrance formulation comprising an olfactory acceptable amount of a compound having Formula I:

or an isomer thereof; wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of hydrogen and a C 1-12 linear or branched alkyl group, with the proviso that R 1 , R 2 , R 3 and R 4 together contain 1-12 carbon atoms.

8. The fragrance formulation of claim 7 , wherein the compound has Formula II:

or an isomer thereof; wherein R 1 ′, R 2 ′, R 3 ′ and R 4 ′ are independently selected from the group consisting of hydrogen and a C 1-6 linear or branched alkyl group, with the proviso that R 1 ′, R 2 ′, R 3 ′ and R 4 ′ together contain 1-6 carbon atoms.

9. The fragrance formulation of claim 8 , wherein the compound is selected from the group consisting of
2-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)propan-1-ol;
1-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)propan-2-ol;
2-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)butan-1-ol;
1-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)butan-2-ol;
2-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)pentan-1-ol;
1-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)pentan-2-ol;
2-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)hexan-1-ol;
1-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)hexan-2-ol;
3-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)butan-2-ol;
an isomer thereof; and
a mixture thereof.

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

11. The fragrance formulation of claim 7 , wherein the olfactory acceptable amount is from about 0.5 to about 25 weight percent of the fragrance formulation.

12. The fragrance formulation of claim 7 , wherein the olfactory acceptable amount is from about 1 to about 10 weight percent of the fragrance formulation.

13. The fragrance formulation of claim 7 further comprising a polymer.

14. The fragrance formulation of claim 13 , wherein the polymer is selected from the group consisting of polyacrylate, polyurea, polyurethane, polyacrylamide, polyester, polyether, polyamide, poly(acrylate-co-acrylamide), starch, silica, gelatin and gum Arabic, alginate, chitosan, polylactide, poly(melamine-formaldehyde), poly(urea-formaldehyde) and a combination thereof.

15. A method of improving, enhancing or modifying a fragrance formulation comprising the step of adding to the fragrance formulation an olfactory acceptable amount of a compound having Formula I:

or an isomer thereof; wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of hydrogen and a C 1-12 linear or branched alkyl group, with the proviso that R 1 , R 2 , R 3 and R 4 together contain 1-12 carbon atoms.

16. The method of claim 15 , wherein the compound has Formula II:

or an isomer thereof; wherein R 1 ′, R 2 ′, R 3 ′ and R 4 ′ are independently selected from the group consisting of hydrogen and a C 1-6 linear or branched alkyl group, with the proviso that R 1 ′, R 2 ′, R 3 ′ and R 4 ′ together contain 1-6 carbon atoms.

17. The method of claim 16 , wherein the compound is selected from the group consisting of
2-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)propan-1-ol;
1-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)propan-2-ol;
2-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)butan-1-ol;
1-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)butan-2-ol;
2-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)pentan-1-ol;
1-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)pentan-2-ol;
2-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)hexan-1-ol;
1-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)hexan-2-ol;
3-((4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecan-1-yl)oxy)butan-2-ol;
an isomer thereof; and
a mixture thereof.

18. The method of claim 15 , wherein the olfactory acceptable amount is from about 0.005 to about 50 weight percent of the fragrance formulation.

19. The method of claim 15 , wherein the olfactory acceptable amount is from about 0.5 to about 25 weight percent of the fragrance formulation.

20. The method of claim 15 , wherein the olfactory acceptable amount is from about 1 to about 10 weight percent of the fragrance formulation.

Assignees

• Int Flavors & Fragrances Inc

Inventors

• Veliath Elizabeth D
• Payne Richard K
• Narula Anubhav P S
• Jones Paul D
• Mertz Gary J
• Monteleone Michael G

Classifications

• C11B9/00 Primary

  Essential oils; Perfumes · CPC title

• A61Q13/00

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

• C07C43/196 Primary

  containing hydroxy or O-metal groups · CPC title

• C07C2603/78

  containing seven-membered rings · CPC title

• A61K8/34

  Alcohols · CPC title