| 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 |
| 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" |
