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Molecules. 2012 Feb 22;17(2):2259-70. doi: 10.3390/molecules17022259.

Structure-odor relationships of α-santalol derivatives with modified side chains.

Author information

1
Department of Chemistry, Graduate School of Science and Engineering, Saitama University, Saitama 338-8570, Japan. toshihas@mail.saitama-u.ac.jp

Erratum in

  • Molecules. 2012;17(9):11292-3.

Abstract

(Z)-α-Santalol, which has a unique woody odor, is a main constituent of sandalwood essential oil. We investigated the structure-odor relationship of (Z)-α-santalol and its derivatives, focusing on the relationship between the structure of the side chain and the odor of the compounds. Various α-santalol derivatives (aldehydes, formates, and acetates) were synthesized from (Z)- and (E)-α-santalol, which were prepared from (+)-3-bromocamphor through modifications of a reported synthetic route. The Z- and E-isomers of α-santalols have different double-bond configurations in the side chain. Analogues with saturated side chains were also prepared from the corresponding α-santalols, and the odors of the all the prepared compounds were evaluated. We found that the odors of the Z-isomers (woody) were similar to those of the corresponding saturated compounds, but clearly different from the odors of the corresponding E-isomers (odorless, fresh, or fatty). These results indicate that the relative configuration of the side chain with respect to the santalane frame plays an important role in the odor of α-santalol. E-configuration in the side chain eliminates the woody odor character of α-santalol and its examined derivatives, whereas the Z-configuration or saturation of the carbon side chain does not.

PMID:
22357322
PMCID:
PMC6268821
DOI:
10.3390/molecules17022259
[Indexed for MEDLINE]
Free PMC Article

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