Structure-Odor Relationships of α­Santalol Derivatives with Modified Side Chains

Molecules

Toshio Hasegawa¹  Hiroaki Izumi¹  Yuji Tajima¹ 

[1] ¹Department of Chemistry, Graduate School of Science and Engineering, Saitama University, Saitama 338-8570, Japan ²Yamada-matsu Co., Ltd., Kyoto 602-8014, Japan

关键词: α-santalol;    side chain;    Z-isomer;    E-isomer;    odor;   

DOI  :  10.3390/molecules17022259

来源: mdpi

【 摘 要 】

(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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.