9(S)-HODE-13C18 (Synonyms: (+)-α-Dimorphecolic Acid)

9(S)-HODE-¹³C₁₈ is intended for use as an internal standard for the quantification of 9(S)-HODE by GC- or LC-MS. 9(S)-HODE is a monohydroxy fatty acid formed from linoleic acid primarily by lipoxygenases with a 9-HpODE intermediate.^1,2,3,4 It is an agonist of PPARγ, inducing transcription of AF-2 in a reporter assay when used at a concentration of 20 µM, and enhances the production of primary human chorionic gonadotropin (hCG) in trophoblasts.⁵ 9(S)-HODE is also an agonist of transient receptor potential vanilloid 1 (TRPV1), TRP ankyrin 1 (TRPA1), and TRP melastatin 8 (TRPM8), increasing intracellular calcium levels in HEK293 cells (EC₅₀s = 21, 31.9, and 43.6 µM, respectively, for the human receptors).⁶ It inhibits the migration of primary porcine aortic endothelial cells and phytohemagglutinin-induced migration of human mononuclear cells when used at concentrations ranging from 0.01 to 1 µM.⁷

1.Vick, B.A.Oxygenated fatty acids of the lipoxygenase pathwayLipid Metabolism in Plants167-191(1993) 2.Reinaud, O., Delaforge, M., Boucher, J.L., et al.Oxidative metabolism of linoleic acid by human leukocytesBiochem. Biophys. Res. Commun.161(2)883-891(1989) 3.Kim, E., Rundhaug, J.E., Benavides, F., et al.An antitumorigenic role for murine 8S-lipoxygenase in skin carcinogenesisOncogene24(7)1174-1187(2005) 4.Hamberg, M.Stereochemistry of oxygenation of linoleic acid catalyzed by prostaglandin-endoperoxide H synthase-2Arch. Biochem. Biophys.349(2)376-380(1998) 5.Schild, R.L., Schaiff, W.T., Carolson, M.G., et al.The activity of PPARγ in primary human trophoblasts is enhanced by oxidized lipidsJ. Clin. Endocrinol. Metab.87(3)1105-1110(2002) 6.De Petrocellis, L., Moriello, A.S., Imperatore, R., et al.A re-evaluation of 9-HODE activity at TRPV1 channels in comparison with anandamide: enantioselectivity and effects at other TRP channels and in sensory neuronsBr. J. Pharmacol.167(8)1643-1651(2012) 7.Pankonin, G., Mahmood, S.A., Kuhn, H., et al.Inhibition of cell migrations by the linoleic acid oxygenation product 9S-hydroxy 10E,12Z octadecadienoic acid (9-HODE)Biomed. Biochim. Acta.47(12)K17-21(1988)