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Sustainable Synthesis of p-Hydroxycinnamic Diacids through Proline-Mediated Knoevenagel Condensation in Ethanol: An Access to Potent Phenolic UV Filters and Radical Scavengers

URD Agro-Biotechnologies Industrielles, CEBB, AgroParisTech, 51110 Pomacle, France
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Antioxidants 2020, 9(4), 331; https://doi.org/10.3390/antiox9040331
Received: 6 April 2020 / Revised: 16 April 2020 / Accepted: 17 April 2020 / Published: 18 April 2020
(This article belongs to the Special Issue Sunscreens and Antioxidants)
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. View Full-Text
Keywords: Knoevenagel condensation; L-proline; p-hydroxycinnamic diacids; ferulic diacid; coumaric diacid; caffeic diacid; anti-UV; antioxidant Knoevenagel condensation; L-proline; p-hydroxycinnamic diacids; ferulic diacid; coumaric diacid; caffeic diacid; anti-UV; antioxidant
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MDPI and ACS Style

Rioux, B.; Peyrot, C.; Mention, M.M.; Brunissen, F.; Allais, F. Sustainable Synthesis of p-Hydroxycinnamic Diacids through Proline-Mediated Knoevenagel Condensation in Ethanol: An Access to Potent Phenolic UV Filters and Radical Scavengers. Antioxidants 2020, 9, 331. https://doi.org/10.3390/antiox9040331

AMA Style

Rioux B, Peyrot C, Mention MM, Brunissen F, Allais F. Sustainable Synthesis of p-Hydroxycinnamic Diacids through Proline-Mediated Knoevenagel Condensation in Ethanol: An Access to Potent Phenolic UV Filters and Radical Scavengers. Antioxidants. 2020; 9(4):331. https://doi.org/10.3390/antiox9040331

Chicago/Turabian Style

Rioux, Benjamin; Peyrot, Cédric; Mention, Matthieu M.; Brunissen, Fanny; Allais, Florent. 2020. "Sustainable Synthesis of p-Hydroxycinnamic Diacids through Proline-Mediated Knoevenagel Condensation in Ethanol: An Access to Potent Phenolic UV Filters and Radical Scavengers" Antioxidants 9, no. 4: 331. https://doi.org/10.3390/antiox9040331

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