ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Bisphenols analogues derived from natural phenols: synthesis and evaluation of antioxidant capacity

Evgeny V. Buravlev and Oksana G. Shevchenko

Institute of Chemistry of Komi Science Centre of the Ural Branch of the Russian Academy of Sciences, Syktyvkar, Russian Federation

E-mail: eugeneburavlev@gmail.com

Received: 14 April 2023  Accepted: 14 June 2023

Abstract:

A series of symmetric methylenebisphenols based on sesamol (1), 2-methoxybenzene-1,4-diol (2), eugenol (3), carvacrol (4), and thymol (5) was synthesized using the condensation reaction between these phenols and paraformaldehyde. We carried out a comparative evaluation of the antioxidant properties of both parent compounds 1–5 and the products derived from them. The conversion of sesamol (1), eugenol (3), and thymol (5) to the corresponding methylenebisphenols is associated with a significant increase in the antioxidant activity (AOA) of the synthesized compounds, measured by the degree of inhibition of Fe²⁺/ascorbate-induced fatty acid oxidation of mouse brain lipids. The derivatives are superior to the original natural phenols in terms of their ability to improve the survival of red blood cells (RBCs) of lab mice and protect their hemoglobin from oxidation under the conditions of hemolysis induced by 2,2′-azobis(2-amidinopropane) dihydrochloride (AAPH) or hydrogen peroxide. In terms of several parameters, the activity of the synthesized products exceeded that of the synthetic antioxidant 2,6-di-tert-butyl-4-methylphenol (BHT).

Graphical abstract

Keywords: Bisphenols; Methylenebisphenols; Natural phenols; Oxidative hemolysis; Antioxidant activity; Synthesis design

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-023-02930-0

Chemical Papers 77 (10) 6169–6182 (2023)