title: Structure-odor relationships of α-santalol derivatives with modified side chains.
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.
authors.affiliation: Department of Chemistry, Graduate School of Science and Engineering, Saitama University, Saitama 338-8570, Japan. toshihas@mail.saitama-u.ac.jp
authors.forename: Toshio
authors.initials: T
authors.lastname: Hasegawa
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Izumi
authors.forename: Yuji
authors.initials: Y
authors.lastname: Tajima
authors.forename: Hideo
authors.initials: H
authors.lastname: Yamada
mesh_terms: D007536:Isomerism; D009812:Odorants; D010938:Plant Oils / Q000737:chemistry*; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D010938:Plant Oils; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C043206:santalol; C076763:sandalwood oil