Chemo-, photo- and enzyme-catalyzed dimerization of resveratrol under batch reaction conditions

Resveratrol represents an important natural polyphenol with high potential for structural modification through oxidative coupling and dimerization reactions. The synthesis of resveratrol dimers has attracted increasing interest due to their increased structural complexity, enhanced stability, and altered physicochemical properties compared to the parent molecule, as well as their potential for improved biological activity and selectivity. In addition, dimerization enables the development of sustainable synthetic methodologies under mild reaction conditions. In this study, (photo)chemical and enzyme-catalyzed dimerization of resveratrol was investigated in batch reactor systems using different oxidative and catalytic approaches. The chemical synthesis was performed using two dimerization strategies, including photochemical dimerization under UV irradiation and oxidative coupling. In parallel, enzyme-catalyzed reactions using horseradish peroxidase were evaluated as environmentally friendly alternatives to conventional synthetic methods. The influence of reaction conditions, oxidants, catalyst type, and solvent composition on dimer formation and product selectivity was systematically investigated. The obtained results demonstrated that chemo-, photo- and enzymatic methodologies enabled successful formation of structurally diverse resveratrol dimers under batch conditions. Oxidative reaction pathways strongly affected product distribution and selectivity, while enzyme-catalyzed transformations provided milder and more selective synthesis conditions. The synthesized dimers were identified and characterized using HPLC-DAD and NMR analysis, enabling comparison of reaction efficiency and selectivity among the investigated systems.