Structure-Odor Relationships of α­Santalol 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.

Cytotoxicity and Genotoxicity Assessment of Sandalwood Essential Oil in Human Breast Cell Lines MCF‐7 and MCF‐10A

“…The chemical composition of SEO has been studied in detail. At least 300 chemical constituents have been identified, of which ( Z )- α -santalol and ( Z )- β -santalol are the most abundant [ 2 ]. SEO is used in the food industry as a flavoring ingredient and also in the cosmetic and perfume industry [ 3 ].…”

Structural Factors in the Odor of α-Santalol Derivatives

“…We have previously reported the synthesis and odors of several E-and Z-isomers with different functional groups for part B [3]. The results are shown in Figure 2 and Table 1.…”

Prolonged anxiolytic‐like activity of sandalwood (Santalum album L.) oil in stress‐loaded mice

“…album include antimicrobial and repellent effects against acari, and chemopreventative effects on skin papillomas, etc. Research investigating the aroma of sandalwood oil has focused on identifying/characterizing the olfactory receptor involved, and the profile of the aroma, etc. Other research has involved the analysis of sandalwood oil compounds in mouse blood samples, the sedative effect of an extract or essential oil from sandalwood in mice, and the evaluation of sandalwood oil effects on humans after transdermal absorption, etc.…”