Oleic Acid-13C5 (Synonyms: 9Z-Octadecenoic Acid-13C5, C18:1(9Z)-13C5, cis-9-Octadecenoic Acid-13C5)

Oleic acid-¹³C₅ is intended for use as an internal standard for the quantification of oleic acid by GC- or LC-MS. Oleic acid is a monounsaturated fatty acid and a major component of membrane phospholipids that has been found in human plasma, cell membranes, and adipose tissue.^1,2 It contributes approximately 17% of the total fatty acids esterified to phosphatidylcholine, the major phospholipid class in porcine platelets.¹ Oleic acid inhibits collagen-stimulated platelet aggregation by approximately 90% when used at a concentration of 10 µg/ml. It also inhibits fMLF-induced neutrophil aggregation and degranulation by 55 and 68%, respectively, when used at a concentration of 5 µM, similar to arachidonic acid .³ Oleic acid (60 µM) induces release of intracellular calcium in human platelets.⁴ In vivo, oleic acid increases TNF-α, IL-8, IL-6, and IL-1β production, neutrophil accumulation, and apoptotic and necrotic cell death in mouse lung and has been used to induce lung injury in a mouse model of acute respiratory distress syndrome (ARDS).²

1.Wahle, K.W., and Peacock, L.I.Effects of isomeric cis and trans eighteen carbon monounsaturated fatty acids on porcine platelet functionBiochim. Biophys. Acta1301(1-2)141-149(1996) 2.GonÇalves-de-Albuquerque, C.F., Silva, A.R., Burth, P., et al.Acute respiratory distress syndrome: Role of oleic acid-triggered lung injury and inflammationMediators Inflamm.260465(2015) 3.Naccache, P.H., Moiski, T.F., Volpi, M., et al.Modulation of rabbit neutrophil aggregation and degranulation by free fatty acidsJ. Leukoc. Biol.36(3)333-340(1984) 4.Siafaka-Kapadai, A., Hanahan, D.J., and Javors, M.A.Oleic acid-induced Ca2+ mobilization in human platelets: Is oleic acid an intracellular messenger•J. Lipid Mediat. Cell Signal15(3)215-232(1997)