Sustainable Synthesis of <i>p</i>-Hydroxycinnamic Diacids through Proline-Mediated Knoevenagel Condensation in Ethanol: An Access to Potent Phenolic UV Filters and Radical Scavengers
<i>p</i>-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...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2020-04-01
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| Series: | Antioxidants |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2076-3921/9/4/331 |
| Summary: | <i>p</i>-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 <i>p</i>-hydroxycinnamic diacids were not only potent radical scavengers but also efficient UV filters exhibiting high photostability. |
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| ISSN: | 2076-3921 |