A mixture of 9-nitrooleate and 10-nitrooleate
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9(10)-Nitrooleate

Item No. 33896

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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
A 1 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
Ethanol: 50 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
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    100 µg

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    Product Description

    9(10)-Nitrooleate is a mixture of the nitroalkene endogenous lipid signaling molecules 9-nitrooleate (Item No. 10008042) and 10-nitrooleate (Item No. 10008043). 9(10)-Nitrooleate is formed by nitration of oleic acid (Item Nos. 90260 | 24659) by peroxynitrite, acidified nitrite, and myeloperoxidase in the presence of hydrogen peroxide (H2O2) and nitrite.1 It induces transactivation of peroxisome proliferator-activated receptor γ (PPARγ) 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.2 9(10)-Nitrooleate also induces transactivation of PPARγ, PPARδ, or PPARα in reporter assays using CV-1 cells in a concentration-dependent manner.1 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-α and kidney levels of myeloperoxidase (Mpo) and IL-1β and reduces tubular necrosis and tubule dilation in a mouse model of renal ischemia-reperfusion injury.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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. The Journal of Biological Chemisty 280(51), 42464-42475 (2005).

    2. Bates, D.J.P., Smitherman, P.K., Townsend, A.L., et al. Nitroalkene fatty acids mediate activation of Nrf2/ARE-dependent and PPARγ-dependent transcription by distinct signaling pathways and with significantly different potencies. Biochemistry 50(36), 7765-7773 (2011).

    3. Liu, H., Jia, Z., Soodvilai, S., et al. Nitro-oleic acid protects the mouse kidney from ischemia and reperfusion injury. Am. J. Physiol. Renal. Physiol. 295(4), F942-F949 (2008).