9-nitro-9E-octadecenoic acid

Base Information

• Chemical Name: 9-nitro-9E-octadecenoic acid
• CAS No.: 875685-44-2
• Molecular Formula: C18H33NO4
• Molecular Weight: 327.464
• ChEMBL ID: CHEMBL550762
• DSSTox Substance ID: DTXSID301316471
• Metabolomics Workbench ID: 1886
• Nikkaji Number: J2.361.801J,J2.786.923H
• Pharos Ligand ID: CC7HNYX5M7J8
• Wikidata: Q27087939
• Mol file: 875685-44-2.mol

Synonyms:9-nitro-9E-octadecenoic acid;(E)-9-nitrooctadec-9-enoic Acid;875685-44-2;9-Nitrooleic acid;nitrooleic acid;Nitroleic Acid;9-Nitrooleate;9-Nitro Oleic Acid;CHEMBL550762;(9E)-9-nitrooctadecenoic acid;CHEBI:86329;9-Octadecenoic acid, 9-nitro-, (9E)-;(9E)-Nitro Oleic Acid;9-nitro-9E-Octadecenoate;(9E)-9-Nitrooctadecenoate;(e)-9-Nitrooctadec-9-enoate;GTPL6296;SCHEMBL1015108;CQOAKBVRRVHWKV-SAPNQHFASA-N;DTXSID301316471;(e)-9-nitro-octadec-9-enoic acid;(9E)-9-nitrooctadec-9-enoic acid;BDBM50295048;LMFA01120004;AKOS040755478;NS00096526;SR-01000946992;SR-01000946992-1;Q27087939

Chemical Property of 9-nitro-9E-octadecenoic acid

Chemical Property:

• PSA: 83.12000
• LogP: 6.23610
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 15
• Exact Mass: 327.24095853
• Heavy Atom Count: 23
• Complexity: 347

Purity/Quality:

99% ^*data from raw suppliers

9-Nitrooleic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC=C(CCCCCCCC(=O)O)[N+](=O)[O-]
• Isomeric SMILES: CCCCCCCC/C=C(\CCCCCCCC(=O)O)/[N+](=O)[O-]
• 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. 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.

Technology Process of 9-nitro-9E-octadecenoic acid

There total 39 articles about 9-nitro-9E-octadecenoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

(E)-prenyl 9-nitrooctadec-9-enoate → Nitrooleic Acid (875685-44-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 23 ℃; for 3h; Reagent/catalyst;

DOI:10.1002/ejoc.202100247

Reference yield: 95.0%

(E)-9-nitro-octadec-9-enoic acid allyl ester (911029-52-2) → Nitrooleic Acid (875685-44-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; In tetrahydrofuran; for 24h; Heating;

DOI:10.1021/ol0613463

Reference yield: 77.1%

(E)-methyl 9-nitrooctadec-9-enoate (16700-68-8) → Nitrooleic Acid (875685-44-2)

Guidance literature:

With hydrogenchloride; In water; for 48h; Inert atmosphere; Reflux;

DOI:10.1055/s-0037-1611530

upstream raw materials:

(E)-methyl 9-nitrooctadec-9-enoate

(E)-9-nitro-octadec-9-enoic acid allyl ester

cis-Octadecenoic acid

9-bromononanoic acid allyl ester

Refernces

• 1、 Dietz, Ulrich,Frank, Andrea,Lehr, Alexander,Münch, Winfried,Nubbemeyer, Udo. "Synthesis of 1-Palmitoyl-2-((E)-9- and (E)-10-nitrooleoyl)- sn -glycero-3-phosphatidylcholines". supporting information. p. 3295 - 3304. Retrieved 2019/08/28.
• 2、 Hock, Katharina J.,Grimmer, Jennifer,G?bel, Dominik,Gasaya, George Gichogo T.,Roos, Jessica,Maucher, Isabelle V.,Kühn, Benjamin,Fettel, Jasmin,Maier, Thorsten J.,Manolikakes, Georg. "Modular Regiospecific Synthesis of Nitrated Fatty Acids". . p. 615 - 636. Retrieved 2017/01/25.