Structural Modification of Epigallocatechin-3-gallate to (2<i>R</i>,3<i>R</i>)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chroman-3-yl <span style="font-variant: small-caps">l</span>-valinate in Four Steps

Abstract

Tea is a daily drink for most people, and one of its major ingredients, epigallocatechin-3-gallate (EGCG), has been widely recognized as a potent antioxidant with diverse biological activities. However, its low stability and bioavailability hinder its further clinical applications. In this study, we designed and synthesized a novel EGCG-valine derivative 4 by replacing the gallic acid with a valine moiety in four steps. The structural elucidation of derivative 4 was performed using NMR, IR, mass, and UV spectroscopies. Additionally, the physicochemical properties of 4 were predicted by SwissADME, showing improved drug-like parameters and intestinal absorption compared to the parent compound EGCG.

Keywords

• EGCG
• structural modification
• valine