Synthesis and Antioxidant Activity of Caffeic Acid Derivatives

• Published in: Molecules (Basel, Switzerland) Vol. 23; no. 9; p. 2199
• Main Authors: Sidoryk, Katarzyna, Jaromin, Anna, Filipczak, Nina, Cmoch, Piotr, Cybulski, Marcin
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 30.08.2018; MDPI
• Subjects: Acetone; Acids; Aldehydes; antioxidant activity; Antioxidants; Antioxidants - chemical synthesis; Antioxidants - chemistry; Antioxidants - pharmacology; Boron; Caffeic acid; Caffeic Acids - chemical synthesis; Caffeic Acids - chemistry; Caffeic Acids - pharmacology; Cell Line; Cell Survival - drug effects; Communication; Condensates; Cytotoxicity; Demethylation; derivatives of caffeic acid; Fibroblasts; Humans; Investigations; Molecular Structure; Oxidation-Reduction - drug effects; phenolic acids; Reaction time; Skin; water medium; Wittig reaction; Yield; Wittig reaction; derivatives of caffeic acid; water medium; antioxidant activity; phenolic acids
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules23092199

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 , , and 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 , , and showed the highest activities. Moreover, all synthesized compounds displayed no cytotoxicity, and can therefore be used in the pharmaceutical or cosmetic industry.