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Structure-Odor Relationships of αSantalol Derivatives with Modified Side Chains
Department of Chemistry, Graduate School of Science and Engineering, Saitama University, Saitama 338-8570, Japan
Yamada-matsu Co., Ltd., Kyoto 602-8014, Japan
* Author to whom correspondence should be addressed.
Received: 20 December 2011; in revised form: 16 February 2012 / Accepted: 20 February 2012 / Published: 22 February 2012
(This article belongs to the Special Issue Terpenoids
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.
Keywords: α-santalol; side chain; Z-isomer; E-isomer; odor
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Hasegawa, T.; Izumi, H.; Tajima, Y.; Yamada, H. Structure-Odor Relationships of αSantalol Derivatives with Modified Side Chains. Molecules 2012, 17, 2259-2270.
Hasegawa T, Izumi H, Tajima Y, Yamada H. Structure-Odor Relationships of αSantalol Derivatives with Modified Side Chains. Molecules. 2012; 17(2):2259-2270.
Hasegawa, Toshio; Izumi, Hiroaki; Tajima, Yuji; Yamada, Hideo. 2012. "Structure-Odor Relationships of αSantalol Derivatives with Modified Side Chains." Molecules 17, no. 2: 2259-2270.