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通过脯氨酸介导的克脑文盖尔缩合反应在乙醇中可持续合成对羟基肉桂二酸:一种获得高效酚类紫外线过滤器和自由基清除剂的方法。

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

作者信息

Rioux Benjamin, Peyrot Cédric, Mention Matthieu M, Brunissen Fanny, Allais Florent

机构信息

URD Agro-Biotechnologies Industrielles, CEBB, AgroParisTech, 51110 Pomacle, France.

出版信息

Antioxidants (Basel). 2020 Apr 18;9(4):331. doi: 10.3390/antiox9040331.

Abstract

-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 -hydroxycinnamic diacids were not only potent radical scavengers but also efficient UV filters exhibiting high photostability.

摘要

羟基肉桂二酸是丙二酸和苯甲醛之间经典的克诺文纳格尔-多布纳缩合反应的中间体。由于它们通常产率较低,因此相对研究较少且开发不足。在此,我们开发并优化了一种可持续的合成方法,以脯氨酸为催化剂、乙醇为溶剂,能够以良好至高的产率(60-80%)生产这些化合物。对其抗氧化和抗紫外线活性的研究表明,这些羟基肉桂二酸不仅是有效的自由基清除剂,还是具有高光稳定性的高效紫外线过滤器。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7de4/7222392/66c123d32f65/antioxidants-09-00331-g001.jpg

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