structure-odor relationships of α-santalol derivatives with modified side chainsstructure-odorα-santalol衍生品与修改后的侧链的关系.pdfVIP

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structure-odor relationships of α-santalol derivatives with modified side chainsstructure-odorα-santalol衍生品与修改后的侧链的关系.pdf

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structure-odor relationships of α-santalol derivatives with modified side chainsstructure-odorα-santalol衍生品与修改后的侧链的关系

Molecules 2012, 17, 2259-2270; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Structure-Odor Relationships of α-Santalol Derivatives with Modified Side Chains Toshio Hasegawa 1,*, Hiroaki Izumi 1, Yuji Tajima 1 and Hideo Yamada 2 1 Department of Chemistry, Graduate School of Science and Engineering, Saitama University, Saitama 338-8570, Japan 2 Yamada-matsu Co., Ltd., Kyoto 602-8014, Japan * Author to whom correspondence should be addressed; E-Mail: toshihas@mail.saitama-u.ac.jp; Tel.: +81-48-858-3619; Fax: +81-48-858-3619. Received: 20 December 2011; in revised form: 16 February 2012 / Accepted: 20 February 2012 / Published: 22 February 2012 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 prep