Quantum mechanical and experimental oxidation studies of pentadecylresorcinol, olivetol, orcinol and resorcinol.

Petra Leidinger, Christina Backes, Stefanie Rheinheimer, Andreas Keller, Eckart Meese

Index: Free Radic. Res. 28(4) , 359-68, (1998)

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Abstract

Resorcinols (pentadecylresorcinol, olivetol, orcinol and resorcinol) exhibit antioxidant properties in liposomal systems. Antioxidant potency depends on the length of the alkyl chain. Pentadecylresorcinol has been demonstrated to be the most active antioxidant, indicating significance of its alkyl chain in a lipid bilayer. Quantum DFT computations demonstrated that hydroxyl group attached to the ring is the first target for the hydrogen abstraction after formation of the radical. However, the carbons of the side chain could also participate in the antioxidant properties of the alkylresorcinols. Formation of the radical at the hydroxyl oxygen initiates changes in the electron density which destabilise the whole system and subsequently leads to oxidation of the ring. The detailed study of lipophilicity and electrostatic properties of resorcinols is discussed.