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 |
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MDPI AG
2020-04-01
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| Series: | Antioxidants |
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| Online Access: | https://www.mdpi.com/2076-3921/9/4/331 |
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| author | Benjamin Rioux Cédric Peyrot Matthieu M. Mention Fanny Brunissen Florent Allais |
| author_facet | Benjamin Rioux Cédric Peyrot Matthieu M. Mention Fanny Brunissen Florent Allais |
| author_sort | Benjamin Rioux |
| collection | DOAJ |
| description | <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. |
| first_indexed | 2024-03-10T20:23:41Z |
| format | Article |
| id | doaj.art-e223064e28604d609c0c63d9a2487c69 |
| institution | Directory Open Access Journal |
| issn | 2076-3921 |
| language | English |
| last_indexed | 2024-03-10T20:23:41Z |
| publishDate | 2020-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Antioxidants |
| spelling | doaj.art-e223064e28604d609c0c63d9a2487c692023-11-19T22:01:10ZengMDPI AGAntioxidants2076-39212020-04-019433110.3390/antiox9040331Sustainable Synthesis of <i>p</i>-Hydroxycinnamic Diacids through Proline-Mediated Knoevenagel Condensation in Ethanol: An Access to Potent Phenolic UV Filters and Radical ScavengersBenjamin Rioux0Cédric Peyrot1Matthieu M. Mention2Fanny Brunissen3Florent Allais4URD Agro-Biotechnologies Industrielles, CEBB, AgroParisTech, 51110 Pomacle, FranceURD Agro-Biotechnologies Industrielles, CEBB, AgroParisTech, 51110 Pomacle, FranceURD Agro-Biotechnologies Industrielles, CEBB, AgroParisTech, 51110 Pomacle, FranceURD Agro-Biotechnologies Industrielles, CEBB, AgroParisTech, 51110 Pomacle, FranceURD Agro-Biotechnologies Industrielles, CEBB, AgroParisTech, 51110 Pomacle, France<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.https://www.mdpi.com/2076-3921/9/4/331Knoevenagel condensationL-proline<i>p</i>-hydroxycinnamic diacidsferulic diacidcoumaric diacidcaffeic diacid |
| spellingShingle | Benjamin Rioux Cédric Peyrot Matthieu M. Mention Fanny Brunissen Florent Allais 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 Antioxidants Knoevenagel condensation L-proline <i>p</i>-hydroxycinnamic diacids ferulic diacid coumaric diacid caffeic diacid |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | Knoevenagel condensation L-proline <i>p</i>-hydroxycinnamic diacids ferulic diacid coumaric diacid caffeic diacid |
| url | https://www.mdpi.com/2076-3921/9/4/331 |
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