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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

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.
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https://hal-agroparistech.archives-ouvertes.fr/hal-03630946
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Submitted on : Tuesday, April 5, 2022 - 12:30:14 PM
Last modification on : Friday, April 8, 2022 - 10:18:39 AM

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Benjamin Rioux, Cédric Peyrot, Matthieu Mention, Fanny Brunissen, Florent Allais. Sustainable Synthesis of p-Hydroxycinnamic Diacids through Proline-Mediated Knoevenagel Condensation in Ethanol: An Access to Potent Phenolic UV Filters and Radical Scavengers. Antioxidants , MDPI, 2020, 9 (4), pp.331. ⟨10.3390/antiox9040331⟩. ⟨hal-03630946⟩

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