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Kyoto, Japan

Hasegawa T.,Saitama University | Izumi H.,Saitama University | Yamada H.,Yamada matsu Co.
Natural Product Communications | Year: 2013

α-Santalol is a sesquiterpene that is a major constituent of sandalwood (Santalum album L.), and is responsible for its distinctive woody odor. We replaced the polycyclic moiety and hydroxyl group of α-santalol with other moieties, and we compared the odors of the E/Z-isomers and their saturated analogues. Our previous study of the structure-odor relationships of α-santalols bearing hydroxyl, formyl, formyloxy, and acetoxy functional groups showed there was a similarity in odor between the Z-isomer and its saturated analogue. We synthesized α-santalols with a benzyl group in place of the hydroxyl group, because many benzyl compounds have strong characteristic odors. We found similar odors for the E-isomer and its saturated analogue. In contrast, the odors of the α- santalol derivatives with a hydroxyl, formyl, formyloxy, or acetoxy group were different. We also replaced the bulky polycyclic moiety with a linear alkyl chain. The polycyclic moiety was the most important structural factor in the characteristic sandalwood odor. The synthesis of derivatives and the evaluation of their odor allowed us to identify the key structural factors in the odor of α-santalol.

Miyagawa M.,Toho University | Satou T.,Toho University | Yukimune C.,Toho University | Ishibashi A.,Toho University | And 4 more authors.
Phytotherapy Research | Year: 2014

The fruit of Illicium verum Hook. f. (star anise) is used by many as a spice. The fragrance of I. verum fruit is characteristically anise-like. In this study, hexane-extracted I. verum fruit oil (IVO), trans-anethole as the main component, and related compounds (propiophenone, 4′-methoxy-propiophenone, trans-β-methylstyrene) were analyzed in order to clarify the emotional effect of inhaling the fragrance of I. verumfruit.As a result, although 4 μL/L air IVO did not exhibit an anxiolytic-like effect, 1 μL/L air trans-anethole exhibited a significant effect (p<0.05). Moreover, the anxiolytic-like effect of 1 μL/L air trans-anethole was significantly greater than 1 μL/L air propiophenone and 1 μL/L air 4′-methoxy-propiophenone (p<0.05). Thus, the anxiolytic-like effect of transanethole was confirmed, and it is proposed that the methoxyl group and 1-propenyl group in the para position of the benzene ring are necessary for the effect. Copyright © 2014 John Wiley & Sons, Ltd.

Satou T.,Toho University | Miyagawa M.,Toho University | Seimiya H.,Saitama University | Yamada H.,Yamada matsu Co. | And 2 more authors.
Flavour and Fragrance Journal | Year: 2014

The fragrance of Santalum album L. (sandalwood) has been used as a sedative. However, few reports have investigated the anxiolytic activity of sandalwood fragrance. Therefore, in this study, we examined the anxiolytic-like activity of hexane-extracted sandalwood oil (SAO). Male ICR mice, aged 5weeks at the start of each experiment, were used. To mimic its clinical use, the effect of SAO after stress loading was investigated. Mice were individually housed in cages for 1week and subjected to loaded water-immersion stress for 24h. Next, SAO inhalation (i.h.) was initiated 90min prior to the elevated plus maze (EPM) test. As a result, significant anxiolytic-like activity was observed at 4μl/l air SAO i.h. In contrast, anxiolytic-like activity was not observed in non-stressed control mice. Additionally, mice were subjected to SAO i.h prior to water-immersion stress for 24h in order to investigate its prolonged effect. As a result, significant anxiolytic-like activity was observed at 4μl/l air SAO i.h. In contrast, anxiolytic-like activity was not observed in non-stressed control mice. The above results indicate that the anxiolytic-like activity of SAO i.h. is revealed under stress conditions and is prolonged for at least 24h. Since the main components of SAO are (Z)-α-santalol (51.1%) and (Z)-β-santalol (28.5%), it is proposed that they are involved in mediating the characteristic anxiolytic-like activity of SAO. © 2013 John Wiley & Sons, Ltd.

Hasegawa T.,Saitama University | Izumi H.,Saitama University | Tajima Y.,Saitama University | Yamada H.,Yamada matsu Co.
Molecules | Year: 2012

(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.

Hasegawa T.,Saitama University | Toriyama T.,Saitama University | Ohshima N.,Saitama University | Tajima Y.,Saitama University | And 4 more authors.
Flavour and Fragrance Journal | Year: 2011

Sandalwood (Santalum album L.) is a traditional incense, and its essential oil is used in fragrances. The hexane extract from Indian sandalwood chips had a sandalwood odour similar to sandalwood chips, but it clearly differed from that of commercial essential oil. By fractional distillation of the extract under reduced pressure, a fraction was obtained that had a sandalwood-like odour and contained several unknown formyl compounds as the main constituents. Santalyl formates were isolated as new components from this fraction by chromatography and characterized by 1H- and 13C-NMR spectroscopy. These constituents were less abundant in the commercial essential oil than in the hexane extract. Santalyl formates were synthesized from the corresponding alcohols. Copyright © 2010 John Wiley & Sons, Ltd.

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