Sustainable Synthesis of p-Hydroxycinnamic Diacids through Proline-Mediated Knoevenagel Condensation in Ethanol: An Access to Potent Phenolic UV Filters and Radical Scavengers
Benjamin Rioux, Cédric Peyrot, Matthieu M. Mention, Fanny Brunissen, Florent Allais
Abstract
p-Hydroxycinnamic diacids are reaction intermediates of the classical Knoevenagel–Doebner condensation between malonic acid and benzaldehydes. As they are generally obtained in low yields, they remain relatively under-studied and under-exploited. Herein, we developed and optimized a sustainable synthetic procedure allowing the production of these compounds in good to high yields (60–80%) using proline as the catalyst and ethanol as the solvent. Study of their antioxidant and anti-UV activities revealed that these p-hydroxycinnamic diacids were not only potent radical scavengers but also efficient UV filters exhibiting high photostability.
Topics & Concepts
Knoevenagel condensationChemistryHydroxycinnamic acidOrganic chemistryCatalysisAntioxidantEthanolMalonic acidSolventOxidative Organic Chemistry ReactionsSynthesis of Organic CompoundsMulticomponent Synthesis of Heterocycles