A novel endogenous lipid signalling molecule
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Labeled Version(s)
105579-Nitrooleate-d17
Parent Compound(s)
90260Oleic Acid 24659Oleic Acid (sodium salt)
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9-Nitrooleate

Item No. 10008042

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9-nitro-9E-octadecenoic acid
CAS Number
875685-44-2
Synonyms
  • 9-Nitrooleic Acid
  • 9-nitro-9-trans-Octadecenoic Acid
Molecular Formula
C18H33NO4
Formula Weight
327.5
Purity
≥98%
Formulation (Request formulation change)
A 500 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
Ethanol: 50 mg/ml
λmax
255 nm
SMILES
CCCCCCCC/C=C([N+]([O-])=O)\CCCCCCCC(O)=O
InChi Code
InChI=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
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    50 µg

    $35

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    100 µg

    $67

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    500 µg

    $315

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    1 mg

    $595

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    Product Description

    Nitrated unsaturated fatty acids, such as 10- and 12-nitrolinoleate (LNO2; Item No. 10037), 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-Nitrooleate is one of two regioisomers of nitrooleate, the other being 10-nitrooleate (Item No. 10008043) (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 the differentiation of 3T3-L1 preadiopcytes to adipocytes at 3 µM.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description 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 γ 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(4), 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. The Journal of Biological Chemisty 280(51), 42464-42475 (2005).

    Product Citations

    Wang, H., Sun, J., Jia, Z., et al. Nitrooleic acid attenuates lipid metabolic disorders and liver steatosis in DOCA-salt hypertensive mice. PPAR Res. 2015, 480348 (2015).

    Wang, H., Liu, H., Jia, Z., et al. Effects of endogenous PPAR agonist nitro-oleic acid on metabolic syndrome in obese zucker rats. PPAR Res. 601562 (2010).

    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).