Oleic acid is a monounsaturated fatty acid and is one of the major components of membrane phospholipids. It contributes about 17% of the total fatty acids esterified to phosphatidylcholine in porcine platelets.1 Oleic acid ethyl ester is a neutral, more lipid-soluble form of oleic acid. As the free acid, it inhibits collagen-stimulated platelet aggregation by approximately 90% at a concentration of 10 µg/ml.1 It inhibits fMLF-induced neutrophil aggregation and degranulation by 55% and 68%, respectively, at 5 µM.2 Oleic acid, whether applied extracellularly (EC50 = ~60 µM) to human platelets or released from membrane phospholipids, causes an increase in intracellular calcium levels.3
1
Wahle, K.W.J., and Peacock, L.I.L. Effects of isomeric cis and trans eighteen carbon monounsaturated fatty acids on porcine platelet function. Biochim Biophys Acta1301141-149(1996).
2
Naccache, P.H., Moiski, T.F.P., Volpi, M., et al. Modulation of rabbit neutrophil aggregation and degranulation by free fatty acids. J Leukoc Biol36333-340(1984).
3
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 Signal15215-232(1997).
Synonyms
Ethyl Oleate
Formal Name
9Z-octadecenoic acid, ethyl ester
CAS Number
111-62-6
Molecular Formula
C20H38O2
Formula Weight
310.5
Formulation
A solution in ethanol
Purity
>98%
Stability
1 year
Storage
-20°C
Shipping
Wet ice
in continental US; may vary elsewhere
SMILES
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CCCCCCCC/C=C\CCCCCCCC(OCC)=O
Background Reading
Wahle, K.W.J., and Peacock, L.I.L. Effects of isomeric cis and trans eighteen carbon monounsaturated fatty acids on porcine platelet function. Biochim Biophys Acta1301141-149(1996).
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 Signal15215-232(1997).
Naccache, P.H., Moiski, T.F.P., Volpi, M., et al. Modulation of rabbit neutrophil aggregation and degranulation by free fatty acids. J Leukoc Biol36333-340(1984).
Oleic Acid ethyl ester is available in the following screening
libraries: