| Identification | Back Directory | [Name]
9-Nitrooleate | [CAS]
875685-44-2 | [Synonyms]
9-Nitrooleate
9-Nitro Oleic Acid
(9E)-9-Nitro-9-octadecenoic Acid
9-Octadecenoic acid, 9-nitro-, (9E)- | [Molecular Formula]
C18H33NO4 | [MDL Number]
MFCD12912273 | [MOL File]
875685-44-2.mol | [Molecular Weight]
327.459 |
| Hazard Information | Back Directory | [Description]
Nitrated unsaturated fatty acids, such as 10- and 12-nitrolinoleate (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. 9-Nitrooleate is one of two regioisomers of nitrooleate, the other being 10-nitrooleate (OA-NO2; used for the mixture of isomers), which are formed by nitration of oleic acid in approximately equal proportions in vivo. 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. | [Uses]
9-Nitrooleic Acid is a bioactive, nitric-oxide derived fatty acid. 9-Nitrooleic Acid
II-induced hypertension. 9-Nitrooleic Acid is an endogenous PPAR agonist which may offer an effective and safe therapeutic intervention for obesity and obesity-related conditions. | [Uses]
9-Nitrooleic Acid is a bioactive, nitric-oxide derived fatty acid. 9-Nitrooleic Acid thats acts as an irreversible inhibitor of xanthine oxidoreductase. 9-Nitrooleic Acid is a novel antagonist of Ang II-induced hypertension. 9-Nitrooleic Acid is an endogenous PPAR agonist which may offer an effective and safe therapeutic intervention for obesity and obesity-related conditions. | [Definition]
ChEBI: (9E)-9-nitrooctadecenoic acid is a nitro fatty acid that is (9E)-octadec-9-enoic (elaidic) acid substituted by a nitro group at position 9. It has a role as a human metabolite. It is a long-chain fatty acid, a monounsaturated fatty acid and a nitro fatty acid. It is functionally related to an elaidic acid. | [storage]
Store at -20°C | [References]
[1] DONG GUN LIM. Nitrolinoleate, a nitric oxide-derived mediator of cell function: synthesis, characterization, and vasomotor activity.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2002, 99 25: 15941-15946. DOI: 10.1073/pnas.232409599
[2] FRANCISCO J SCHOPFER. Nitrolinoleic acid: an endogenous peroxisome proliferator-activated receptor gamma ligand.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2005, 102 7: 2340-2345. DOI: 10.1073/pnas.0408384102
[3] éMERSOM S. LIMA . Nitrated lipids decompose to nitric oxide and lipid radicals and cause vasorelaxation[J]. Free Radical Biology and Medicine, 2005, 39 4: Pages 532-539. DOI: 10.1016/j.freeradbiomed.2005.04.005
[4] 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
[5] PAUL R S BAKER. Fatty acid transduction of nitric oxide signaling: multiple nitrated unsaturated fatty acid derivatives exist in human blood and urine and serve as endogenous peroxisome proliferator-activated receptor ligands.[J]. The Journal of Biological Chemistry, 2005, 280 51: 42464-42475. DOI: 10.1074/jbc.m504212200 |
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