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Common Name

Oleic acid

Systematic Name

9Z-octadecenoic acid

Synonyms

9-octadecylenic acid
cis-9-octadecenoic acid
cis-Oleic acid
cis-Oleate
Oleate
Elaic acid
Elaidoic acid
C18:1n-9
Rapinic acid
9(Z)-OME

LM ID

LMFA01030002

Formula

C₁₈H₃₄O₂

Exact Mass

Calculate m/z

282.25588

Sum Composition

FA 18:1

Status

Curated

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Classification

Biological Context

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

This information has been provided by Cayman Chemical

References

1. Naccache, P.H., Moiski, T.F., Volpi, M., et al. Modulation of rabbit neutrophil aggregation and degranulation by free fatty acids. J. Leukoc. Biol. 36(3), 333-340 (1984).

2. Wahle, K.W., and Peacock, L.I. Effects of isomeric cis and trans eighteen carbon monounsaturated fatty acids on porcine platelet function. Biochim. Biophys. Acta 1301(1-2), 141-149 (1996).

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 Signal 15(3), 215-232 (1997).

4. Gonçalves-de-Albuquerque, C.F., Silva, A.R., Burth, P., et al. Acute respiratory distress syndrome: Role of oleic acid-triggered lung injury and inflammation. Mediators Inflamm. 260465 (2015).