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Cited by 44Chemical Synthesis and ReactionsMulticomponent Synthesis of HeterocyclesSynthesis of Organic Compounds

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

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Rioux, Benjamin, Peyrot, Cédric, Mention, Matthieu M., Brunissen, Fanny, Allais, Florent·2020·Antioxidants
DOI 10.3390/antiox9040331PMC PMC7222392
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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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  • Sinapic diacid (160) and caffeic diacid (161) displayed the best photoprotective characteristics among p-hydroxycinnamic diacids (158-161).

    “Based in natural-inspired p-hydroxycinnamic acids, p-hydroxycinnamic diacids were prepared (158–161), being sinapic diacid (160) and caffeic diacid (161) the derivatives that displayed the best photoprotective characteristics [141].”

    From UV Filters: Challenges and Prospects (2022) · cites this paper as [141]

    The Results and Discussion identifies caffeic diacid as the most promising UV filter, but says coumaric and caffeic diacids had the best photostability; coumaric also had the highest absorbance. Sinapic and caffeic diacids were the strongest radical scavengers, so the claim conflates antioxidant performance with the paper’s comparison of photoprotective UV properties. Page numbers are unavailable in our copy. (LLM, conf=0.88)

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References 44 · Cited by 44

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Authors
Rioux, B., Peyrot, C., Mention, M. M., Brunissen, F., & Allais, F.
Affiliations
AgroParisTech (FR)
Corresponding author
Allais, Florent
ORCID
Venue
Antioxidants
Publisher
MDPI AG
Published
2020-04-18
Volume
9
Issue
4
Pages
331
ISSN
2076-3921 (ISSN-L)
DOI
10.3390/antiox9040331
PMC
PMC7222392
OpenAlex
W3017241784
Cited by
44
References
44
Citations by year
2026: 8 · 2025: 6 · 2024: 5 · 2023: 5 · 2022: 10 · 2021: 8 · 2020: 2
FWCI
2.42
Type
journal article
Language
en
Open access
Licence
Locations
  • Antioxidants (publishedVersion, cc-by)
  • PubMed Central (publishedVersion, cc-by)
  • PubMed (publishedVersion)
  • HAL (submittedVersion, other-oa)
  • Zenodo (CERN European Organization for Nuclear Research) (submittedVersion, cc-by)
  • DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
Funders
  • Agence Nationale de la Recherche (ANR-17-CE07-0046)
  • H2020 Future and Emerging Technologies (828753)
Topics
  • Physical Sciences › Chemistry › Organic Chemistry › Chemical Synthesis and Reactions
  • Physical Sciences › Chemistry › Organic Chemistry › Multicomponent Synthesis of Heterocycles
  • Health Sciences › Medicine › Pharmacology › Synthesis of Organic Compounds
Keywords
Knoevenagel condensation, proline catalysis, ethanol solvent, sustainable synthesis, UV filters, radical scavengers, antioxidant activity, photostability, phenolic compounds

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