13(r)hode

13(R)-HODE is the opposite enantiomer of the 13(S)-HODE produced when linoleic acid is incubated with soybean lipoxygenase. The presence of 13(R)-HODE in the supernatants and membranes of cultured bovine endothelial cells has been attributed to COX metabolism. 13(R)-HODE is a weak (IC50 = 2.7 μM) inhibitor of U-46619-induced platelet aggregation.

13(R)-HODE cholesteryl ester was originally extracted from atherosclerotic lesions. It remains uncertain whether the oxidized fatty acid portion of the molecule results from enzymatic lipoxygenation or from random lipid peroxidation. 13(R)-HODE cholesteryl ester can be used as a standard for analysis of chiral HODE cholesteryl esters.

9-OxoODE, formed through the oxidation of the allylic hydroxyl group in both 9(S)-HODE and 9(R)-HODE, is present in rabbit reticulocyte plasma and mitochondrial membranes as both 9- and 13-oxoODEs, constituting approximately 2% of the total linoleate residues. The majority of these oxidized linoleate residues are esterified to membrane lipids.