Synthesis of phenolic components of Grains of Paradise |
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Authors: | Hiroyuki Hattori Tohru Mitsunaga Derrick LJ Clive |
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Institution: | 1. The United Graduate School of Agricultural Science, Gifu University, 1-1 Yanagido, 10 501-1193 Gifu, Japan;2. Chemistry Department, University of Alberta, Edmonton, Alberta T6G 2G2, Canada |
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Abstract: | Two vanilloids, (5E)-8-(4-hydroxy-3-methoxyphenyl)oct-5-en-4-one (1) and 4-3-hydroxydecyl]-2-methoxyphenol (2), isolated from the dried seeds of Grains of Paradise (Aframomum melegueta), were synthesized; the latter compound was made as the S-enantiomer and the material derived from the seeds was found to be a 1:1.7 mixture of the R and S isomers. The synthetic route used should allow the preparation of analogs having extended alkyl chains and consequently different lipophilicity, and 3, a homolog of 2, was also prepared. |
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Keywords: | Corresponding author Grains of Paradise Anti-obesity Malic acid Wittig reaction Horner-Wadsworth-Emmons olefination Hydrogenolysis |
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