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A correction was published on 21 September 2012, see Molecules 2012, 17(9), 11292-11293.

Molecules 2012, 17(2), 2259-2270; doi:10.3390/molecules17022259
Article

Structure-Odor Relationships of α­Santalol Derivatives with Modified Side Chains

1,* , 1, 1 and 2
Received: 20 December 2011; in revised form: 16 February 2012 / Accepted: 20 February 2012 / Published: 22 February 2012
(This article belongs to the Special Issue Terpenoids)
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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.
Keywords: α-santalol; side chain; Z-isomer; E-isomer; odor α-santalol; side chain; Z-isomer; E-isomer; odor
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Hasegawa, T.; Izumi, H.; Tajima, Y.; Yamada, H. Structure-Odor Relationships of α­Santalol Derivatives with Modified Side Chains. Molecules 2012, 17, 2259-2270.

AMA Style

Hasegawa T, Izumi H, Tajima Y, Yamada H. Structure-Odor Relationships of α­Santalol Derivatives with Modified Side Chains. Molecules. 2012; 17(2):2259-2270.

Chicago/Turabian Style

Hasegawa, Toshio; Izumi, Hiroaki; Tajima, Yuji; Yamada, Hideo. 2012. "Structure-Odor Relationships of α­Santalol Derivatives with Modified Side Chains." Molecules 17, no. 2: 2259-2270.


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