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Bioscience Biotechnology and Biochemistry
Article . 2020 . Peer-reviewed
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Studies on analogs of DAMASCENOLIDETM: Part 3. Synthesis and odor evaluation of dimethylated, cyclopropanated, and other analogs of DAMASCENOLIDETM

Authors: Yamato Miyazawa; Kenji Kawaguchi; Ryo Katsuta; Tomoo Nukada; Ken Ishigami;

Studies on analogs of DAMASCENOLIDETM: Part 3. Synthesis and odor evaluation of dimethylated, cyclopropanated, and other analogs of DAMASCENOLIDETM

Abstract

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 24 analogs of 1 as part of our new aroma compound developing project. To accumulate more information on structure–odor relationships, 10 more promising analogs such as dimethylated and cyclopropanated analogs were synthesized and subjected to odor evaluation. As a result, it was found that dimethylation of the furanone ring affected the odor. It was also found that cyclopropanation of 1 affected the odor, whereas cyclopropanation of the double bond isomer of 1 did not significantly affect the odor. The effects on the odor caused by ring size expansion and replacement of the side chain were also investigated.

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Keywords

Cyclopropanes, Structure-Activity Relationship, Isomerism, Odorants, Furans, Rosa, Methylation

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citations
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
1
Average
Average
Average
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