Dataset Information

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

ABSTRACT: (Z)-?-Santalol, which has a unique woody odor, is a main constituent of sandalwood essential oil. We investigated the structure-odor relationship of (Z)-?-santalol and its derivatives, focusing on the relationship between the structure of the side chain and the odor of the compounds. Various ?-santalol derivatives (aldehydes, formates, and acetates) were synthesized from (Z)- and (E)-?-santalol, which were prepared from (+)-3-bromocamphor through modifications of a reported synthetic route. The Z- and E-isomers of ?-santalols have different double-bond configurations in the side chain. Analogues with saturated side chains were also prepared from the corresponding ?-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 ?-santalol. E-configuration in the side chain eliminates the woody odor character of ?-santalol and its examined derivatives, whereas the Z-configuration or saturation of the carbon side chain does not.

SUBMITTER: Hasegawa T

PROVIDER: S-EPMC6268821 | biostudies-other | 2012 Feb

REPOSITORIES: biostudies-other

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

Hasegawa Toshio T Izumi Hiroaki H Tajima Yuji Y Yamada Hideo H

Molecules (Basel, Switzerland) 20120222 2

(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 ...[more]

PMID: 22357322

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Dataset Information

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

Publications

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

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