(9Z,12Z)-(8R)-8-Hydroperoxyoctadeca-9,12-dienoic acid

Base Information

• Chemical Name: (9Z,12Z)-(8R)-8-Hydroperoxyoctadeca-9,12-dienoic acid
• CAS No.: 143343-95-7
• Molecular Formula: C₁₈H₃₂O₄
• Molecular Weight: 312.45
• DSSTox Substance ID: DTXSID101222963
• Nikkaji Number: J646.349E
• Wikidata: Q27116103
• Metabolomics Workbench ID: 2149
• Mol file: 143343-95-7.mol

Synonyms:8-HPODE;8-hydroperoxylinoleic acid

Chemical Property of (9Z,12Z)-(8R)-8-Hydroperoxyoctadeca-9,12-dienoic acid

Chemical Property:

• Vapor Pressure: 2.24E-10mmHg at 25°C
• Boiling Point: 459.5°Cat760mmHg
• Flash Point: 155.2°C
• Density: 1.002g/cm³
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 15
• Exact Mass: 312.23005950
• Heavy Atom Count: 22
• Complexity: 310

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCC=CCC=CC(CCCCCCC(=O)O)OO
• Isomeric SMILES: CCCCC/C=C\C/C=C\[C@@H](CCCCCCC(=O)O)OO

Technology Process of (9Z,12Z)-(8R)-8-Hydroperoxyoctadeca-9,12-dienoic acid

There total 2 articles about (9Z,12Z)-(8R)-8-Hydroperoxyoctadeca-9,12-dienoic 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:

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) → 1-octen-3-ol (3391-86-4) + 2-octen-1-al (2548-87-0,20664-46-4,2363-89-5) + 10-hydroperoxyoctadeca-8,12-dienoic acid (107616-75-1) + 10-ODA (79868-90-9) + 10-keto-octadeca-8,12-dienoic acid (107616-76-2) + 10-hydroxyoctadeca-8,12-dienoic acid (107616-77-3) + 8-hydroxyoctadeca-9,12-dienoic acid + 8-hydroperoxyoctadeca-9,12-dienoic acid (143343-95-7) + 12,13-epoxy-10-hydroxyoctadec-8-enoic acid + 2-octenol (22104-78-5)

Guidance literature:

With PpoC from Aspergillus nidulans; at 20 ℃; for 0.5h; pH=8; aq. buffer; Enzymatic reaction;

DOI:10.1042/BJ20091096

Reference yield:

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) → 8R-hydroperoxy-9Z,12Z-octadecadienoic acid (143343-95-7) + C18H32O4 + C18H32O4

Guidance literature:

With dioxygenase cytochrome P₄₅₀ from Fusarium oxysporum; enantiospecific reaction; Enzymatic reaction;

DOI:10.1007/s11745-015-4078-9

upstream raw materials:

linoleic acid

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