An internal standard for the quantification of oleic acid
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Oleic Acid-13C5

Item No. 9004089

Technical Information
Formal Name
oleic-1,2,3,7,8-13C5 acid
CAS Number
1255644-48-4
Synonyms
  • 9Z-Octadecenoic Acid-13C5
  • C18:1(9Z)-13C5
  • cis-9-Octadecenoic Acid-13C5
  • FA 18:1-13C
Molecular Formula
C13[13C]5H34O2
Formula Weight
Purity
≥95%
Formulation
A 10 mg/ml solution in ethanol
Chloroform: SolubleDMF: >100 mg/mlDMSO: >100 mg/mlEthanol: >100 mg/mlPBS (pH 7.2): <100 µg/ml
SMILES
CCCCCCCC/C=C\[13CH2][13CH2]CCC[13CH2][13CH2][13C](O)=O
InChi Code
InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-/i11+1,12+1,16+1,17+1,18+1
InChi Key
ZQPPMHVWECSIRJ-TWKVKCSCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Oleic acid-13C5 is intended for use as an internal standard for the quantification of oleic acid (Item Nos. 90260 | 24659) 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 (Item Nos. 90010 | 90010.1 | 10006607).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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

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

    3. Naccache, P.H., Moiski, T.F., Volpi, M., et alModulation of rabbit neutrophil aggregation and degranulation by free fatty acids. J. 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 Signal 15(3), 215-232 (1997).