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Biosci Biotechnol Biochem


Title:"Analog synthesis of DAMASCENOLIDE(TM), an important aroma component of roses, and their odor properties"
Author(s):Miyazawa Y; Kawaguchi K; Katsuta R; Nukada T; Ishigami K;
Address:"R&D Center, T. Hasegawa Co., Ltd ., Kanagawa, Japan. Department of Chemistry for Life Sciences and Agriculture, Tokyo University of Agriculture , Tokyo, Japan"
Journal Title:Biosci Biotechnol Biochem
Year:2020
Volume:20200417
Issue:8
Page Number:1560 - 1569
DOI: 10.1080/09168451.2020.1753498
ISSN/ISBN:1347-6947 (Electronic) 0916-8451 (Linking)
Abstract:"DAMASCENOLIDE(TM) [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"
Keywords:"4-Butyrolactone/*analogs & derivatives/chemical synthesis/isolation & purification Chemistry Techniques, Synthetic Flowers/*chemistry Humans Isomerism Odorants/*analysis Rosa/*chemistry Smell/physiology Structure-Activity Relationship Volatile Organic Com;"
Notes:"MedlineMiyazawa, Yamato Kawaguchi, Kenji Katsuta, Ryo Nukada, Tomoo Ishigami, Ken eng England 2020/04/19 Biosci Biotechnol Biochem. 2020 Aug; 84(8):1560-1569. doi: 10.1080/09168451.2020.1753498. Epub 2020 Apr 17"

 
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Citation: El-Sayed AM 2024. The Pherobase: Database of Pheromones and Semiochemicals. <http://www.pherobase.com>.
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