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Keywords = p-hydroxycinnamic diacids

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14 pages, 2638 KiB  
Article
Sustainable Synthesis of p-Hydroxycinnamic Diacids through Proline-Mediated Knoevenagel Condensation in Ethanol: An Access to Potent Phenolic UV Filters and Radical Scavengers
by Benjamin Rioux, Cédric Peyrot, Matthieu M. Mention, Fanny Brunissen and Florent Allais
Antioxidants 2020, 9(4), 331; https://doi.org/10.3390/antiox9040331 - 18 Apr 2020
Cited by 31 | Viewed by 6520
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Sunscreens and Antioxidants)
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