Sandal fragrances
View Patent ↗A compound of formula (Ia) or (Ib), wherein in each of formulae (Ia) and (Ib) R 1 and R 2 , independently of one another, are H or CH 3 , and the use thereof as a sandalwood fragrance.
1. Compound of formula (Ia) or (Ib)
wherein in each of the formulae (Ia) and (Ib) R 1 and R 2 , independently of one another, are H or CH 3 .
2. Compound according to claim 1 , wherein the compound is present in the form of
(a) a pure optically active enantiomer,
(b) a racemic mixture of different enantiomers of the diastereoisomeric enantiomer pairs, or
(c) an optically active mixture of different enantiomers.
3. Compound according to claim 1 , wherein:
R 1 is CH 3 , and
R 2 is H.
4. Mixture comprising a compound of formula (Ia) and a compound of formula (Ib)
wherein in each of the formulae (Ia) and (Ib) R 1 and R 2 , independently of one another, are H or CH 3 .
5. Mixture according to claim 4 , R 1 and R 2 in the compound of formula (Ia) are the same as in the compound of formula (Ib).
6. Mixture according to claim 5 , comprising or wherein both in the compound of formula (Ia) and in the compound of formula (Ib)
R 1 is CH 3 , and
R 2 is H.
7. Fragrance composition having a sandalwood odour, comprising a compound according to claim 1 .
8. Fragrance composition according to claim 7 further comprising a carrier or substrate which is in direct contact with said compound.
9. Process for the preparation of a compound according to claim 1 , comprising:
reducing a compound of formula (IXa) or (IXb)
wherein R 1 represents H or CH 3 , to form a compound according to claim 1 wherein R 2 is H.
10. Process according to claim 9 further comprising methylating said compound by nucleophilic addition of an organometallic compound of methyl anion nature to said compound to form a compound wherein R 2 is CH 3 .
11. Process for the preparation of a compound of formula (Ia)
wherein
R 1 represents H or CH 3 , and
R 2 represents H, comprising the following steps:
forming an aldehyde of formula (IXa) wherein R 2 ═H by an epoxide ring-opening reaction of a compound of formula (XIV) and
reducing said aldehyde of formula (IXa) to form a compound of formula (Ia) wherein R 1 , R 2 ═H, or
methylating said aldehyde of formula (IXa) by nucleophilic addition of an organometallic compound of methyl anion nature to the aldehyde, to form said compound of formula (Ia) wherein R 1 ═CH 3 , and R 2 ═H.
12. Method of producing, enhancing or modifying a sandalwood odour in a formulation, comprising the following steps:
mixing one or more compounds according to claim 1 with said formulation in an amount that is sufficient (a) to produce a sandalwood odour in the resulting mixture, (b) to enhance an existing sandalwood odour in said formulation.