(±)13-HpODE (Synonyms: 13-Hydroperoxylinoleic acid; Linoleic acid 13-hydroperoxide)

(±)13-HpODE is a racemic mixture of hydroperoxides derived non-enzymatically from linoleic acid through the action of reactive oxygen species. Lipid hydroperoxides, including 13-HpODE, have limited direct biological actions, such as the activation of lipoxygenases. [1] Normally, (±)13-HpODE is rapidly reduced to (±)13-HODE, a compound which exhibits many biological activities. [2] Importantly, 13-HpODE can also be metabolized to unsaturated aldehydes that can, in turn, covalently bind to DNA, amino acids, and proteins.[3][4][5]

Reference:
[1]. Jones, G.D., Russell, L., Darley-Usmar, V.M., et al. Role of lipid hydroperoxides in the activation of 15-lipoxygenase. Biochemistry 35, 7197-7203 (1996).
[2]. Kühn, H. Biosynthesis, metabolization and biological importance of the primary 15-lipoxygenase metabolites 15-hydro(pero)xy-5Z,8Z,11Z,13E-eicosatetraenoic acid and 13-hydro(pero)xy-9Z,11E-octadecadienoic acid. Progress in Lipid Research 35, 203-226 (1996).
[3]. Williams, M.V., Wishnok, J.S., and Tannenbaum, S.R. Covalent adducts arising from the decomposition products lipid hydroperoxides in the presence of cytochrome C. Chemical Research in Toxicology 20(5), 767-775 (2007).
[4]. Iwahashi, H., Nishizaki, K., and Takagi, I. Cytochrome c catalyzes the formation of pentyl radical and octanoic acid radical from linoleic acid hydroperoxide. Biochemistry Journal 361, 57-66 (2002).
[5]. Kawai, Y., Kato, Y., Fujii, H., et al. Immunochemical detection of a novel lysine adduct using an antibody to linoleic acid hydroperoxide-modifies protein. Journal of Lipid Research 44, 1124-1131 (2003).