The aim of this study was to investigate the antioxidant properties in vitro of three different vanillic dimers (Compounds 1a-c). They were synthesized through an oxidative coupling strategy in good yields. The targeted compounds were found to be highly active for the total antioxidant assay, as well as for the lipid peroxidation test. All investigated compounds exhibited superior or comparable antioxidant capacity in comparison to precursor vanillin, proving that the oxidative coupling is a great strategy to increase antioxidant behavior of vanillin derivatives