Analog synthesis of DAMASCENOLIDETM, an important aroma component of roses, and their odor properties.

Analog synthesis of DAMASCENOLIDETM, an important aroma component of roses, and their odor properties. Biosci Biotechnol Biochem. 2020 Apr 17;:1-10 Authors: Miyazawa Y, Kawaguchi K, Katsuta R, Nukada T, Ishigami K Abstract DAMASCENOLIDETM [1, 4-(4-methylpent-3-en-1-yl)furan-2(5H)-one], which has a citrus-like odor, is an important aroma component of roses. We have previously reported on the synthesis and odor evaluation of double-bond isomers of 1 and concluded that the position and the geometric isomerism of the double-bond had a significant effect on the odor. For the purpose of deepening knowledge about structure-odor relationships, we synthesized 13 analogs of compound 1 and evaluated their odors. As a result, it was found that the presence of two double-bonds and branched methyl group at the terminal position in the side chain was essential in order to have a citrus-like odor. Substitution of the side chain with appropriate length at the appropriate 4-position of the 2(5H)-furanone ring was also an important factor in determining the quality of the odor. PMID: 32303150 [PubMed - as supplied by publisher]
Source: Bioscience, Biotechnology, and Biochemistry - Category: Biochemistry Authors: Tags: Biosci Biotechnol Biochem Source Type: research