| Identification | Back Directory | [Name]
9,12-Octadecadienoic acid, 12-nitro-, (9Z,12E)- | [CAS]
774603-05-3 | [Synonyms]
12-Nitrolinoleate
9,12-Octadecadienoic acid, 12-nitro-, (9Z,12E)- | [Molecular Formula]
C18H31NO4 | [MOL File]
774603-05-3.mol | [Molecular Weight]
325.44 |
| Chemical Properties | Back Directory | [Boiling point ]
452.2±33.0 °C(Predicted) | [density ]
1.016±0.06 g/cm3(Predicted) | [solubility ]
Ethanol: Soluble: = 10 mg/ml | [pka]
4.78±0.10(Predicted) |
| Hazard Information | Back Directory | [Description]
12-Nitrolinoleate is an agonist of peroxisome proliferator-activated receptor γ (PPARγ) and a nitrated form of linoleic acid (Item Nos. 90150 | 90150.1 | 21909).1 It is formed upon exposure to acidified nitrite and is found in human red blood cells and plasma.2 12-Nitrolinoleate induces PPARγ-dependent gene expression in a reporter assay using MCF-7 cells expressing human PPARγ (EC50 = 0.045 µM). It inhibits LPS-induced secretion of IL-6, TNF-α, and chemokine (C-C motif) ligand 2 (CCL2) in THP-1 and RAW 264.7 macrophages when used at a concentration of 2.5 µM.3 12-Nitrolinoleate inhibits LPS-induced NF-κB transcriptional activity in a reporter assay using RAW 264.7 macrophages and TNF-α-induced increases in vascular cell adhesion molecule-1 (VCAM-1) in human umbilical vein endothelial cells (HUVECs). It increases the levels of heme oxygenase-1 (HO-1) in primary human aortic endothelial cells when used at concentrations of 1, 5, or 10 µM.4WARNING This product is not for human or veterinary use. | [References]
[1] RICHARD L. ALEXANDER. Differential Potencies of Naturally Occurring Regioisomers of Nitrolinoleic Acid in PPARγ Activation†[J]. Biochemistry Biochemistry, 2008, 48 2: 492-498. DOI: 10.1021/bi8016747
[2] PAUL R S BAKER. Red cell membrane and plasma linoleic acid nitration products: synthesis, clinical identification, and quantitation.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2004, 101 32: 11577-11582. DOI: 10.1073/pnas.0402587101
[3] TAIXING CUI. Nitrated fatty acids: Endogenous anti-inflammatory signaling mediators.[J]. The Journal of Biological Chemistry, 2006, 281 47: 35686-35698. DOI: 10.1074/jbc.m603357200
[4] MARCIENNE M WRIGHT. Fatty acid transduction of nitric oxide signaling: nitrolinoleic acid potently activates endothelial heme oxygenase 1 expression.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2006, 103 11: 4299-4304. DOI: 10.1073/pnas.0506541103 |
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