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A convenient synthesis of 14 C‐labelled resveratrol
Author(s) -
Zeng Dongli,
Mi Qixi,
Sun Hongfang,
Wang Haifang
Publication year - 2004
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.806
Subject(s) - chemistry , resveratrol , phytoalexin , yield (engineering) , formic acid , demethylation , wittig reaction , sodium formate , organic chemistry , polyphenol , formate , nuclear chemistry , catalysis , biochemistry , antioxidant , materials science , dna methylation , gene expression , metallurgy , gene
Resveratrol ( trans ‐3,4′,5‐trihydroxystilbene) is a naturally occurring phytoalexin and polyphenol existing in grapes and various plants. It shows remarkable beneficial bioactivities in the prevention of cancer, inflammation and platelet aggregation, etc. This paper reports the synthesis of [ β ‐ 14 C]‐ trans‐ resveratrol using 14 C‐formic acid (exchanged with sodium 14 C‐formate) and 3,5‐dihydroxybenzoic acid as the starting materials. [ 14 C‐formyl]‐4‐methoxybenzaldehyde and diethyl 3,5‐dimethoxy benzylphosphonate reacted following the Wittig–Horner reaction to give trans ‐3,4′,5‐[ β ‐ 14 C]‐trimethoxystilbene. The final product was obtained through the demethylation of trans ‐3,4′,5‐[ β ‐ 14 C]‐trimethoxystilbene and identified by TLC and UV spectroscopy. Adoption of the whole procedure provided 14 C‐resveratrol with a specific radioactivity of 40.8 µCi/mmol, chemical yield of 15.3% and radiochemical yield of 12.5%. Copyright © 2004 John Wiley & Sons, Ltd.