9(10)-Nitrooleate

9(10)-Nitrooleate is a mixture of the nitroalkene endogenous lipid signaling molecules 9-nitrooleate (Cay-10008042) and 10-nitrooleate (Cay-10008043). 9(10)-Nitrooleate is formed by nitration of oleic acid (Cay-90260, Cay-24659) by peroxynitrite, acidified nitrite, and myeloperoxidase in the presence of hydrogen peroxide (H2O2) and nitrite. It induces transactivation of peroxisome proliferator-activated receptor gamma (PPARgamma) or nuclear factor erythroid 2-related factor 2 (Nrf2) in reporter assays using MCF-7 cells when used at concentrations greater than or equal to 0.3 and greater than or equal to 3 µM, respectively. 9(10)-Nitrooleate also induces transactivation of PPARgamma, PPARdelta, or PPARalpha in reporter assays using CV-1 cells in a concentration-dependent manner. It induces adipogenesis in 3T3-L1 preadipocytes and glucose uptake in differentiated 3T3-L1 adipocytes when used at a concentration of 3 µM. In vivo, 9(10)-nitrooleate (500 µg/kg every six hours for 24 hours) decreases ischemia-induced increases in plasma levels of blood urea nitrogen, creatinine, and TNF-alpha and kidney levels of myeloperoxidase (Mpo) and IL-1beta and reduces tubular necrosis and tubule dilation in a mouse model of renal ischemia-reperfusion injury.Formal Name: 9-nitro-9E-octadecenoic acid, 10-nitro-9E-octadecenoate. CAS Number: 1092676-99-7. Synonyms: 9(10)-Nitrooleic Acid, OA-NO2, 9(10)-nitro-9-trans-Octadecenoic Acid. Molecular Formula: C18H33NO4 . C18H33NO4. Formula Weight: 654.9. Purity: >95% (1:1 mixture of isomers). Formulation: (Request formulation change), A solution in ethanol. Solubility: Ethanol: Slightly soluble: 0.1-1 mg/ml. SMILES: CCCCCCCC/C=C([N+]([O-])=O)\CCCCCCCC(O)=O.CCCCCCCC/C([N+]([O-])=O)=C\CCCCCCCC(O)=O. InChi Code: InChI=1S/2C18H33NO4/c1-2-3-4-5-8-11-14-17(19(22)23)15-12-9-6-7-10-13-16-18(20)21,1-2-3-4-5-6-8-11-14-17(19(22)23)15-12-9-7-10-13-16-18(20)21/h15H,2-14,16H2,1H3,(H,20,21),14H,2-13,15-16H2,1H3,(H,20,21)/b17-15+,17-14+. InChi Key: KKNNEUCJKHBLFK-BJZKJHGRSA-N.