Fragrance and methods for production of 5-epi-β-vetivone, 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one, and 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-1,6-dien-8-one
The present invention is directed to novel methods for production of 5-epi-β-vetivone, 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one and 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-1,6-dien-8-one, which are useful for their fragrant qualities. In one embodiment the present invention describes a method for production of 5-epi-β-vetivone by the use of premnaspirodiene as starting material. In another embodiment the present invention describes a method for production of 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one and 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-1,6-dien-8-one by the use of premnaspirodiene as starting material. In yet another embodiment the present invention describes a novel method for production of premnaspirodiene from a terpene substrate. Use of the fragrant components or any composition containing the component can be advantageously employed in the perfumery industry.
1. A fragrance composition, comprising:
a compound having the structure:
in an amount effective to impart fragrance, wherein the composition is free of beta-vetivone.
2. The fragrance composition of claim 1 , wherein the compound is present in an amount of at least 0.01% by weight.
3. The fragrance composition of claim 1 which comprises an amount of the compound of Formula (1) effective to impart fragrance in combination with conventional fragrance ingredients.
4. A perfumed product, comprising a compound having the structure of Formula (1):
free of beta-vetivone.
5. The perfumed product of claim 4 , wherein the product is a household product, laundry product, body care product or cosmetic product.
6. The perfumed product of claim 5 , wherein the household product is a solid or liquid detergent, a fabric softener, an air freshener, a fabric freshener, an ironing water, a paper, a wipe or a bleach.
7. The perfumed product of claim 5 , wherein the body care product is a perfume, a cologne or after-shave lotion, a perfumed soap, a shower or bath salt, mousse, oil or gel, a hygiene product, a hair care product, a shampoo, a deodorant or antiperspirant.
8. A perfuming composition, comprising a compound of Formula (1):
in an amount sufficient to give a fragrance to the composition, wherein the composition is free of beta-vetivone.
9. The perfuming composition of claim 8 that comprises at least one perfumery carrier, perfumery base, or perfumery adjuvant.
10. A fragrance application, comprising a compound of Formula (1):
wherein the application is free of beta-vetivone.
11. The fragrance application of claim 10 wherein the fragrance application is a household product, laundry product, body care product or cosmetic product.
12. The fragrance application of claim 11 , wherein the household product is a solid or liquid detergent, a fabric softener, an air freshener, a fabric refresher, an ironing water, a paper, a wipe or a bleach.
13. The fragrance application of claim 11 , wherein the body care product is a perfume, a cologne or after-shave lotion, a perfumed soap, a shower or bath salt, mousse, oil or gel, a hygiene product, a hair care product, a shampoo, a deodorant or antiperspirant.
14. A method of imparting a woody, grapefruit, or vetivert odor to a fragrance, comprising providing a compound of Formula (1):
free of beta-vetivone to the fragrance.
15. A method of imparting a woody, grapefruit, or vetivert odor to a fragrance composition, comprising providing a compound of Formula (1):
free of beta-vetivone to the fragrance composition.
16. A method of imparting, improving, enhancing or modifying a fragrance formulation, comprising adding an olfactory acceptable amount of a compound of Formula (1):
free of beta-vetivone to the fragrance formulation.
17. The method of claim 16 , wherein the olfactory acceptable amount is from about 0.005 to about 10 weight percent of the fragrance formulation.
18. The method of claim 17 , wherein the olfactory acceptable amount is from about 0.5 to about 8 weight percent of the fragrance formulation.
19. The method of claim 18 , wherein the olfactory acceptable amount is from about 1 to about 7 weight percent of the fragrance formulation.
20. A mixture, comprising:
a compound of Formula (1):
free of beta-vetivone; and
an auxiliary ingredient compatible with the compound of Formula (1), wherein the weight ratio of the compound of Formula (1) is in the range of from about 1:1 up to about 1:5.
21. A fragrance modifying composition, comprising:
a compound of Formula (1):
free of beta-vetivone; and
an auxiliary ingredient compatible with the compound of Formula (1), wherein the weight ratio of the compound of Formula (1) is in the range of from about 1:1 up to about 1:5.
22. A perfume composition, comprising:
a compound of Formula (1):
free of beta-vetivone; and
at least one compatible adjuvant, wherein the ratio of the compound of Formula (1) is in the range of from about 1:1 up to about 1:5.
23. A cologne composition, comprising:
a compound of Formula (1):
free of beta-vetivone; and
at least one compatible adjuvant, wherein the ratio of the compound of Formula (1) is in the range of from about 1:1 up to about 1:5.
24. A method of formulating a perfumed product, comprising incorporating into at least one compatible perfumery carrier, perfumery base, or perfumery adjuvant a compound of Formula (1):
free of beta-vetivone.
25. The method of claim 24 , further comprising an auxiliary ingredient compatible with the compound of Formula (1).
26. A compound of Formula (1):
that is isolated, purified, and free of beta-vetivone.
27. A compound of Formula (1):
that is isolated, purified, and free of beta-vetivone that is produced by the process of:
(a) subjecting (−)-premnaspirodiene to oxidation of an allylic carbon to form (−)-solavetivone; and
(b) subjecting the (−)-solavetivone to acid-catalyzed isomerization to form 5-epi-beta-vetivone; wherein time and temperature conditions for step (b) are such that the predominant product is 5-epi-beta-vetivone.
28. A compound of Formula (1):
that is isolated, purified, and free of beta-vetivone and that is produced by the process of:
(a) providing a terpene substrate to a host cell transformed or transfected with a vector comprising a sequence encoding a Hyoscyamus muticus premnaspirodiene synthase gene;
(b) culturing the host cell under conditions suitable to produce (−)-premnaspirodiene from the terpene substrate;
(c) isolating the (−)-premnaspirodiene;
(d) subjecting the isolated (−)-premnaspirodiene to oxidation of an allylic carbon to form (−)-solavetivone; and
(e) subjecting the (−)-solavetivone formed in step (d) to acid-catalyzed isomerization to form 5-epi-beta-vetivone; wherein time and temperature conditions for step (e) are such that the predominant product is 5-epi-beta-vetivone.