Oxidation of ethyl hexadec‐1‐enyl ether, a plasmalogen model, in the presence of unsaturated esters

Abstract

Abstract To test the susceptibility of plasmalogen lipids to oxidation, a series of experiments was run on the model compound ethyl hexadec‐1‐enyl ether, which was prepared from hexadecanol by a multistep synthesis. Oxidation experiments were carried out on neat mixtures of the model ether with a variety of fatty esters in sealed vials under air. Disappearance of the ether, the fatty esters and, in one set of experiments, oxygen, was followed by gas chromatography. Ethyl stearate, which was inert to oxidation under the experimental conditions, served as internal standard. In the absence of polyunsaturate (linoleate or linolenate), alk‐1‐enyl ether underwent slow but measurable oxidation. In the presence of polyunsaturate, however, disappearance of the ether was greatly accelerated and proceeded at a rate comparable to that of the polyunsaturate. Reactions did not proceed in the absence of oxygen and were inhibited by antioxidant. The results suggest that oxidation of the alk‐1‐enyl ether functionality of plasmalogens should not be ignored as a factor that contributes to the oxidative instability of animal tissue or the development of rancidity in meat products.