9-NitrooleateAn activator of PPARγ

9-Nitrooleate (CAS 875685-44-2)

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Synonym: 9-Nitrooleic Acid
Application: An activator of PPARγ
CAS Number: 875685-44-2
Purity: >98%
Molecular Weight: 327.5
Molecular Formula: C18H33NO4
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* Refer to Certificate of Analysis for lot specific data (including water content).
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9-Nitrooleate is one of two regioisomers of nitrooleic acid, the other being 10-nitrooleic acid (OA-NO2, used for the mixture of isomers), are formed by nitration of oleic acid in approximately equal proportions. Peroxynitrite, acidified nitrite, and myeloperoxidase, in the presence of H2O2 and nitrite, all mediate the nitration of oleic acid. OA-NO2 is found in human plasma as the free acid and esterified in phospholipids at concentrations of 619 ± 52 nM and 302 ± 369 nM, respectively. OA-NO2 activates PPARγ approximately 7-fold at a concentration of 1 µM and effectively promotes differentiation 3T3-L1 preadipocytes to adipocytes at 3 µM.


References

1 Lim, D.G., Sweeney, S., Bloodsworth, A., et al. Nitrolinoleate, a nitric oxide-derived mediator of cell function: Synthesis, characterization, and vasomotor activity. Proc Natl Acad Sci USA 99(25) 15941-15946 (2002). 2 Schopfer, F.J., Lin, Y., Baker, P.R.S., et al. Nitrolinoleic acid: An endogenous peroxisome proliferator-activated receptor g ligand. Proc Natl Acad Sci USA 102(7) 2340-2345 (2005). 3 Lima, E.S., Bonini, M.G., Augusto, O., et al. Nitrated lipids decompose to nitric oxide and lipid radicals and cause vasorelaxation. Free Radic Biol Med 39 532-539 (2005). 4 Baker, P.R.S., Schopfer, F.J., Sweeney, S., et al. Red cell membrane and plasma linoleic acid nitration products: Synthesis, clinical identification, and quantitation. Proc Natl Acad Sci USA 101(32) 11577-11582 (2004). 5 Baker, P.R., Lin, Y., Schopfer, F.J., et al. Fatty acid transduction of nitric oxide signaling. Multiple nitrated unsaturated acid derivatives exist in human blood and urine serve as endogenous peroxisome proliferator-activated receptor ligands. J Biol Chem 280(51) 42464-42475 (2005).

Formulation :
A solution in ethanol
Physical State :
Liquid
Solubility :
Soluble in ethanol, DMSO (~1 mg/ml), and DMF (~1 mg/ml). Insoluble in water at 25° C.
Storage :
Store at -20° C
Boiling Point :
78° C
Refractive Index :
n20D 1.48 (Predicted)
IC50 :
PPAR γ: IC50 = 0.98 µM (human); ANKTM1: EC5050 = 1 µM (human); PPAR α: IC50 >15 µM (human)
pK Values :
pKa: 4.77 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
24836820
MDL Number :
MFCD12912273
SMILES :
CCCCCCCCC(=CCCCCCCCC(=O)O)[N+](=O)[O-]

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Certificate of Analysis

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