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.
Highlights
Sandalwood (Santalum album L.) is a valuable and expensive material because of the difficulty involved in growing sandalwood trees, from which the essential oil and incense are obtained
We found that the odors of the Z-isomers were similar to those of the corresponding saturated compounds, but clearly different from the odors of the corresponding E-isomers
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
Summary
Sandalwood (Santalum album L.) is a valuable and expensive material because of the difficulty involved in growing sandalwood trees, from which the essential oil and incense are obtained. The structure-odor relationships of (Z)-β-santalol and its related compounds have been investigated in detail [5,6,7,8]. We reported that the odor of sandalwood chips is formed by a combination of santalols and their aldehyde and formate derivatives [9]. We investigated the relationship between the structure and odor of (Z)-α-santalol (1) (Figure 1) and its derivatives bearing modified side chains. To examine whether E-/Z-configuration alone or other structural elements of the aliphatic side chain of α-santalol and its derivative have an influence on the woody odor note, we focus our attention on the similarities and differences in odor between molecules with different side chain geometries (Z-isomer, E-isomer, and saturated side chain) and functional groups on the side chain
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