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Molecules 2018, 23(9), 2199; https://doi.org/10.3390/molecules23092199

Synthesis and Antioxidant Activity of Caffeic Acid Derivatives

1
Pharmaceutical Research Institute, 8 Rydygiera Street, 01-793 Warsaw, Poland
2
Department of Lipids and Liposomes, Faculty of Biotechnology, University of Wroclaw, 14a Joliot-Curie Street, 50-383 Wroclaw, Poland
*
Author to whom correspondence should be addressed.
Received: 1 August 2018 / Revised: 26 August 2018 / Accepted: 28 August 2018 / Published: 30 August 2018
(This article belongs to the Special Issue Medicinal Chemistry in Europe)
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Abstract

A series of caffeic acid derivatives were synthesized via a modified Wittig reaction which is a very important tool in organic chemistry for the construction of unsaturated carbon–carbon bonds. All reactions were performed in water medium at 90 °C. The aqueous Wittig reaction worked best when one unprotected hydroxyl group was present in the phenyl ring. The olefinations in the aqueous conditions were also conducted with good yields in the presence of two unprotected hydroxyl groups. When the number of the hydroxyl groups was increased to three, the reaction yields were worse, and the derivatives 12, 13, and 18 were obtained with 74%, 37%, and 70% yields, respectively. Nevertheless, the Wittig reaction using water as the essential medium is an elegant one-pot synthesis and a greener method, which can be a safe alternative for implementation in organic chemistry. The obtained compounds were tested for their antioxidant activity, and 12, 13, and 18 showed the highest activities. Moreover, all synthesized compounds displayed no cytotoxicity, and can therefore be used in the pharmaceutical or cosmetic industry. View Full-Text
Keywords: phenolic acids; derivatives of caffeic acid; Wittig reaction; water medium; antioxidant activity phenolic acids; derivatives of caffeic acid; Wittig reaction; water medium; antioxidant activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Sidoryk, K.; Jaromin, A.; Filipczak, N.; Cmoch, P.; Cybulski, M. Synthesis and Antioxidant Activity of Caffeic Acid Derivatives. Molecules 2018, 23, 2199.

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