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9-Nitrooleate
Cayman Chemical Item Number 10008042
Description
Nitrated unsaturated fatty acids, such as 10- and 12-nitrolinoleic acid (LNO2), cholesteryl nitrolinoleate, and nitrohydroxylinoleate, represent a new class of endogenous lipid-derived signalling molecules. LNO2 isomers serve as potent endogenous ligands for PPARγ and can also decompose or be metabolized to release nitric oxide.1↗,2↗,3↗,4↗ 9-Nitrooleic acid is one of two regioisomers of nitrooleic acid, the other being 10-nitrooleic acid (OA-NO2; used for the mixture of isomers), which are formed by nitration of oleic acid in approximately equal proportions in vivo.5↗ 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.5↗
Synonyms 9-nitro-9-trans-Octadecenoic Acid
Formal Name 9-nitro-9E-octadecenoic acid
CAS Number 875685-44-2
Molecular Formula C18H33NO4
Formula Weight 327.5
Formulation A solution in ethanol
Purity ≥98%
λmax 255 nm
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES CCCCCCCC/C=C([N+]([O-])=O)\CCCCCCCC(O)=O
InCHI Code 1S/C18H33NO4/c1-2-3-4-5-6-8-11-14-17(19(22)23)15-12-9-7-10-13-16-18(20)21/h14H,2-13,15-16H2,1H3,(H,20,21)/b17-14+
InCHI Key CQOAKBVRRVHWKV-SAPNQHFASA-N |