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A convenient synthesis of 14C-labelled resveratrol

✍ Scribed by Dongli Zeng; Qixi Mi; Hongfang Sun; Haifang Wang

Publisher: John Wiley and Sons
Year: 2004
Tongue: French
Weight: 105 KB
Volume: 47
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.806

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✦ Synopsis

Abstract

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.

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