10-Nitrolinoleic acid

Base Information

• Chemical Name: 10-Nitrolinoleic acid
• CAS No.: 774603-04-2
• Molecular Formula: C₁₈H₃₁NO₄
• Molecular Weight: 325.448
• DSSTox Substance ID: DTXSID201261386
• Metabolomics Workbench ID: 1883
• Nikkaji Number: J2.344.973K
• Wikidata: Q27115831
• Mol file: 774603-04-2.mol

Synonyms:10-nitro-9,12-octadecadienoic acid;9-nitrolinoleic acid;nitrolinoleic acid

Chemical Property of 10-Nitrolinoleic acid

Chemical Property:

• Vapor Pressure: 1.94E-09mmHg at 25°C
• Refractive Index: 1.492
• Boiling Point: 452.2°C at 760 mmHg
• PKA: 4.77±0.10(Predicted)
• Flash Point: 174°C
• PSA: 83.12000
• Density: 1.016g/cm³
• LogP: 6.01210
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 14
• Exact Mass: 325.22530847
• Heavy Atom Count: 23
• Complexity: 383

Purity/Quality:

99%min ^*data from raw suppliers

10-Nitrolinoleate ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC(=CCCCCCCCC(=O)O)[N+](=O)[O-]
• Isomeric SMILES: CCCCC/C=C\C/C(=C\CCCCCCCC(=O)O)/[N+](=O)[O-]
• Description: 10-Nitrolinoleate is a nitrated fatty acid and a peroxisome proliferator-activated receptor γ (PPARγ) agonist. It is formed from linoleic acid (Item Nos. 90150 | 90150.1 | 21909) upon exposure to acidified nitrite.

Technology Process of 10-Nitrolinoleic acid

There total 3 articles about 10-Nitrolinoleic 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: 82.0%

allyl (9E,12Z)-10-nitrooctadeca-9,12-dienoate (1051325-65-5) → (9E,12Z)-10-nitrooctadeca-9,12-dienoic acid (774603-04-2)

Guidance literature:

With formic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 80 ℃; for 24h;

DOI:10.1021/jo801364v

Reference yield: 73.0%

(9E,12Z)-methyl 10-nitrooctadeca-9,12-dienoate (774603-02-0) → (9E,12Z)-10-nitrooctadeca-9,12-dienoic acid (774603-04-2)

Guidance literature:

With lipozyme TL; In acetone; at 20 ℃; for 24h; pH=7.4; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1021/jo1007493

Reference yield: 12.0%

linoleic acid (60-33-3,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) → (9E,12Z)-9-nitrooctadeca-9,12-dienoic acid (903503-65-1) + (9E,12Z)-10-nitrooctadeca-9,12-dienoic acid (774603-04-2)

Guidance literature:

linoleic acid; With Phenylselenyl bromide; In tetrahydrofuran; at -78 ℃; for 0.166667h;

With silver(I) nitrite; mercury dichloride; In tetrahydrofuran; acetonitrile; at -78 - 20 ℃; for 3.5h;

With dihydrogen peroxide; In chloroform; at 4 - 20 ℃; for 1h; Further stages.;

DOI:10.1021/jo801364v

upstream raw materials:

allyl (9E,12Z)-10-nitrooctadeca-9,12-dienoate

linoleic acid

(9E,12Z)-methyl 10-nitrooctadeca-9,12-dienoate

Refernces

• 1、 Manini, Paola,Capelli, Luigia,Reale, Samantha,Arzillo, Marianna,Crescenzi, Orlando,Napolitano, Alessandra,Barone, Vincenzo,D'Ischia, Marco. "Chemistry of nitrated lipids: Remarkable instability of 9-nitrolinoleic acid in neutral aqueous medium and a novel nitronitrate ester product by concurrent autoxidation/nitric oxide-release pathways". . p. 7517 - 7525. Retrieved 2008/12/22.