Epoxides: an underestimated lipid oxidation product.

Immense gains in understanding of mechanisms and effects of lipid oxidation have been achieved in the nearly 90 years over which lipid oxidation has been an active research focus. Even so, the substantial questions still being raised about lipid oxidation in this special issue show clearly that missing pieces remain and must be considered for full accounting of this important reaction in any system. In this context, epoxides are spotlighted as a critical overlooked product of lipid autoxidation - underestimated in analysis, underestimated in presence as a functionally active and competitive intermediate and product of lipid oxidation, and underestimated in potential contributions to impact of lipid oxidation on other molecules and cell functions. Logical reasons for ignoring or not finding epoxides are offered in historical development of lipid oxidation knowledge. Reactions generating lipid epoxides in autoxidation are reviewed, limitations in detecting and tracking epoxides are outlined to explain why epoxides may not be detected when they should be present, and justifications for increased research and analysis of epoxides are argued. The main goal is to provide a context for recognizing epoxides as critical products that must be accounted for in determining the state rather than extent of lipid oxidation and in tracking its consequences in oils, foods, personal care products, and tissues. A secondary goal is to stimulate new research using contemporary analyses to fill in the gaps of knowledge about epoxide formation, structure, and reactions in lipid autoxidation.