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Department of Biochemistry, Memorial University of Newfoundland, St. Lipid oxidation is the major chemical reaction limiting the shelf-life of foods, and it also contributes to a wide range of pathologies, including aging and cancer. This chapter provides an interesting new perspective on broad aspects of lipid oxidation. It first reviews details of lipid oxidation reactions and mechanisms in the context of traditional free radical chain reactions and also in terms of multiple reaction pathways in which internal cyclization to epidioxides and epoxides, addition to double bonds, disproportionation, and scissions compete with hydrogen abstractions by lipid peroxyl and alkoxyl radicals.