QUANTUM-MECHANICAL AND EXPERIMENTAL OXIDATION STUDIES OF PENTADECYLRESORCINOL, OLIVETOL, ORCINOL AND RESORCINOL

Resorcinols (pentadecylresorcinol, olivetol, orcinol and resorcinol) e xhibit antioxidant properties in liposomal systems. Antioxidant potenc y depends on the length of the alkyl chain. Pentadecylresorcinol has b een demonstrated to be the most active antioxidant, indicating signifi cance of its alkyl chain in a lipid bilayer. Quantum DFT computations demonstrated that hydroxyl group attached to the ring is the first tar get for the hydrogen abstraction after formation of the radical. Howev er, the carbons of the side chain could also participate in the antiox idant properties of the alkylresorcinols. Formation of the radical at the hydroxyl oxygen initiates changes in the electron density which de stabilise the whole system and subsequently leads to oxidation of the ring. The detailed study of lipophilicity and electrostatic properties of resorcinols is discussed.