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Oleic Acid-d17

Cayman Chemical Item Number 9000432

Oleic Acid-d17

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Description

Oleic acid-d17 contains 17 deuterium atoms at the 11, 11’, 12, 12’, 13, 13’, 14, 14’, 15, 15’, 16, 16’, 17, 17’, 18, 18, and 18 positions. It is intended for use as an internal standard for the quantification of oleic acid by GC- or LC-mass spectrometry. Oleic acid is a monounsaturated fatty acid and is one of the major components of membrane phospholipids. Oleic acid contributes about 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.1 fMLF-induced neutrophil aggregation and degranulation is inhibited by 55% and 68%, respectively, using 5 µM oleic acid. This inhibition is comparable to that observed using arachidonic acid under the same conditions.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 Acta 1301 141-149 (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 Biol 36 333-340 (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 Signal 15 215-232 (1997).

Formal Name 9Z-​octadecenoic-​11,​11,​12,​12,​13,​13,​14,​14,​15,​15,​16,​16,​17,​17,​18,​18,​18-​d17 acid
Molecular Formula C18H17D17O2
Formula Weight 299.6
Formulation A solution in methyl acetate
Purity ≥99% deuterated forms (d1-d17)
Stability 6 months
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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[2H]​C(C([2H]​)​([2H]​)​[2H]​)​([2H]​)​C([2H]​)​([2H]​)​C([2H]​)​([2H]​)​C([2H]​)​([2H]​)​C([2H]​)​([2H]​)​C([2H]​)​([2H]​)​C([2H]​)​([2H]​)​/C=C\CCCCCCCC(O)​=O
Size Global Purchasing
1 mg See a distributor in your region for pricing
5 mg See a distributor in your region for pricing
10 mg See a distributor in your region for pricing
50 mg See a distributor in your region for pricing

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Warning This product is not for human or veterinary use.

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FAQs

It appears that there is a heterogenous mixture of deuterated species in your deuterated standards; is this normal?

Yes, this is typical of our deuterated products. Our deuterated products contain less than 1 % d0. However, the labeled compounds are not 100% of the deuterated form listed on our product insert. For example, upon analysis of 2-arachidonoyl glycerol-d8 it is expected to see masses associated with the d7, d6, d5 etc.

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