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Star anise is an important fragrance material that has a characteristic anise-like odor. Although the main component of star anise is ( E)-anethole, which accounts for over 90% of the constituents, the odor of ( E)-anethole is different from that of the material itself. Here, we examined the aroma profile of star anise. GC-MS analysis of star anise extracts showed that it contains many compounds with structures similar to ( E)-anethole. Our results indicate that ( E)-anethole is the key compound in the odor of star anise, but structurally similar compounds play an important role in creating its odor. We examined the structure-odor relationship of ( E)-anethole, focusing on the methoxy and 1-propenyl substituents. Altering the 1-propenyl group changed the odors of all the anethole derivatives. Replacing the methoxy group with a hydrogen atom created compounds with similar fatty odors. This shows that the methoxy group is important for the characteristic odor of anethole. We synthesized anethole derivatives where the methoxy group was replaced with a methyl group. In both methoxy- and methyl-substituted anethole derivatives, altering the 1-propenyl group changed the odors of the derivatives. Therefore, the methoxy and methyl benzene moieties are important structural features for the odor of star anise. The structural characteristics of anethole are closely related to its odor expression.

Aroma Profile of Star Anise and the Structure-odor Relationship of Anethole