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.

(Bio)chemical Labelling Tools for Studying Absorption & Metabolism of Dietary Phenols - An Overview

“…The resulting N-methylformanilide 123 was submitted to a Bouveault reaction, to give [ 14 C]-panisaldehyde 124 [82]. The resulting N-methylformanilide 123 was submitted to a Bouveault reaction, to give [ 14 C]-panisaldehyde 124 [82].…”

Catalyst-Free N-Formylation of Amines Using Formic Acid as a Sustainable C1 Source

“…The requirement of separating catalysts from products complicates the synthesis process. In addition, Wang and Choi et al , reported the N-formylation of amines using formic acid in the absence of catalyst. However, the reaction required the use of stoichiometric dicyclohexylcarbodiimide as dehydrant, and a restricted substrate scope was acquired.…”

“…Based on the results of controlled experiments and previous research, − a possible reaction mechanism has been proposed (Scheme ). Initially, the lone pair on the N atoms of aniline attacks the activated C atom of HCOOH, producing formate, which then dehydrates to yield the corresponding formamide.…”