A convenient synthesis of 14C-labelled resveratrol

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-14C]-trans-resveratrol using 14C-formic acid (exchanged with sodium 14C-formate) and 3,5-dihydroxybenzoic acid as the starting materials. [14C-formyl]-4-methoxybenzaldehyde and diethyl 3,5-dimethoxy benzylphosphonate reacted following the Wittig-Horner reaction to give trans-3,4′,5-[β-14C]-trimethoxystilbene. The final product was obtained through the demethylation of trans-3,4′ ,5-[β-14C]-trimethoxystilbene and identified by TLC and UV spectroscopy. Adoption of the whole procedure provided 14C-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.