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Abstract
Salicylidene‐D,L‐tyrosine ethyl ester and Cu(II)(SalTyrOEt)2 were synthesized, characterized, and chain‐breaking antioxidant and prooxidant reactivities determined in a 2,2′‐azoisobutyronitrile initiated linoleic acid peroxidation reaction. Kinetics of oxygen consumption were found to be comparable to the antioxidant reactivity of 2,6‐ditertiary‐butyl‐4‐hydroxytoluene, due to efficient removal of linoleic acid peroxyl radical with the formation of linoleic acid hydroperoxide, LOOH, and correlate with the presence of tyrosyl phenolic OH groups. Copper in Cu(II)(SalTyrOEt)2 accounts for prooxidant reactivity, catalyzing removal of LOOH, except at low concentrations when its antioxidant properties dominate. It is concluded that Cu(II)(SalTyrOEt)2 is a unique antioxidant with prooxidant reactivity.
This work was supported by the International Science Technology Center (A‐361‐00 Project). We thank Dr. Prof. L. Tavadyan, Institute of Chemical Physics, NAS of Armenia, for his helpful discussions; Dr. G. Sedrakyan and L. Haroutunyan for their technical assistance and Dr. T. Stepanyan, Molecular Structure Research Center, Spectroscopy Laboratory, NAS of Armenia, for her assistance in obtaining FTIR spectra.