Carvacrol, a monoterpene phenol, is the major component of the essential oils of oregano and thyme. The compound exhibits a wide range of biological activities including anticancer, antibacterial, antimicrobial, insecticidal and antioxidant properties. Various derivatives of carvacrol have been previously prepared, which resulted in enhancement or retention of biological activity relative to the parent compound, often with a decrease in toxicity. In the current study, ten heterocyclic thioether derivatives of carvacrol were prepared for antioxidant evaluation. Carvacrol was converted to its methyl ether, followed by Friedel-Crafts acylation to form a chloroacetophenone. Subsequent alkylation using thiolates as nucleophiles afforded the heterocyclic thioether derivatives in moderate to excellent yields. The antioxidant activity of carvacrol and the thioether derivatives was measured by the CUPric Reducing Antioxidant Capacity (CUPRAC) assay method, using ascorbic acid as a positive control. The thioether derivatives of carvacrol showed comparable reducing capacity to ascorbic acid, but were less effective than carvacrol.

Synthesis and antioxidant evaluation of thioether derivatives of carvacrol

2019 Spring National Meeting

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