13-Hpode

Base Information

• Chemical Name: 13-Hpode
• CAS No.: 23017-93-8
• Deprecated CAS: 97672-38-3,18320-18-8,5502-90-9
• Molecular Formula: C₁₈H₃₂O₄
• Molecular Weight: 312.45
• UNII: DPF3WUY4S4
• DSSTox Substance ID: DTXSID101266533
• Metabolomics Workbench ID: 87209
• Mol file: 23017-93-8.mol

Synonyms:13-HPOD;13-HPODE;13-hydroperoxy-9,11-octadecadienoic acid;13-hydroperoxy-9,11-octadecadienoic acid, (Z,E)-isomer

Chemical Property of 13-Hpode

Chemical Property:

• Vapor Pressure: 5.53E-10mmHg at 25°C
• Boiling Point: 449.9°Cat760mmHg
• Flash Point: 151°C
• PSA: 66.76000
• Density: 1.002g/cm³
• LogP: 5.35260
• XLogP3: 5.4
• 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:

99% ^*data from raw suppliers

(±)13-HpODE ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC=CCCCCCCCC(=O)O)OO
• Isomeric SMILES: CCCCCC(/C=C/C=C\CCCCCCCC(=O)O)OO
• Uses: (±)13-HpODE, is a racemic mixture of hydroperoxides derived non-enzymatically from linoleic acid through the action of reactive oxygen species.

Technology Process of 13-Hpode

There total 16 articles about 13-Hpode 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: 100.0%

methyl 9Z,11E-13-hydroperoxyoctadecadienoate (60900-56-3) → (9Z,11E)-13-hydroperoxyoctadeca-9,11-dienoic acid (5502-90-9,7324-21-2,28529-44-4,33964-75-9,40878-62-4,63121-48-2,73036-16-5,90760-91-1,90760-92-2,97672-38-3,104832-62-4,123410-62-8,126873-57-2,23017-93-8,18320-18-8)

Guidance literature:

With potassium hydroxide; In methanol; for 0.0833333h; Ambient temperature;

DOI:10.1248/cpb.41.1863

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) → (R,S)-coriolic acid (10219-69-9,29623-28-7,29899-88-5,32819-31-1,73804-64-5,81445-95-6,114297-05-1,114818-04-1,114818-05-2,127911-29-9,128821-19-2,5204-88-6,149341-86-6,18104-45-5) + (9Z,11E)-13-hydroperoxyoctadeca-9,11-dienoic acid (5502-90-9,7324-21-2,28529-44-4,33964-75-9,40878-62-4,63121-48-2,73036-16-5,90760-91-1,90760-92-2,97672-38-3,104832-62-4,123410-62-8,126873-57-2,23017-93-8,18320-18-8) + 9‐oxo‐10E,12Z‐octadecanoic acid (54232-59-6) + 13-oxo-9Z,11E-octadecadienoic acid (54739-30-9)

Guidance literature:

Further byproducts given. Yields of byproduct given; pea (Pisum sativum) lipoxygenase;

DOI:10.1021/jf00050a014

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) → (R,S)-coriolic acid (10219-69-9,29623-28-7,29899-88-5,32819-31-1,73804-64-5,81445-95-6,114297-05-1,114818-04-1,114818-05-2,127911-29-9,128821-19-2,5204-88-6,149341-86-6,18104-45-5) + (10E,12Z)-9-hydroxy-10,12-octadecadienoic acid (73543-67-6) + (9Z,11E)-13-hydroperoxyoctadeca-9,11-dienoic acid (5502-90-9,7324-21-2,28529-44-4,33964-75-9,40878-62-4,63121-48-2,73036-16-5,90760-91-1,90760-92-2,97672-38-3,104832-62-4,123410-62-8,126873-57-2,23017-93-8,18320-18-8) + (9E,11E,13R,S)-13-hydroperoxy-9,11-octadecadienoic acid (63121-48-2,18320-18-8) + 9‐oxo‐10E,12Z‐octadecanoic acid (54232-59-6) + 13-oxo-9Z,11E-octadecadienoic acid (54739-30-9)

Guidance literature:

at 2 - 5 ℃; for 480h; autoxidation;

upstream raw materials:

linoleic acid

methyl 9Z,11E-13-hydroperoxyoctadecadienoate

(9E,11E,13R,S)-13-hydroperoxy-9,11-octadecadienoic acid

1,2-Dilinoleoyl-sn-glycerol-3-phosphorylcholine

Downstream raw materials:

(R,S)-coriolic acid

(9E,11E,13R,S)-13-hydroperoxy-9,11-octadecadienoic acid

(9R,S,10E,12E)-9-hydroperoxy-10,12-octadecadienoic acid

12-[1′(E)-hexenyloxy]-9(Z),11(E)-dodecadienoic acid

Refernces

• 1、 Takigawa, Yuta,Koshiishi, Ichiro. "Catalytic production of oxo-fatty acids by lipoxygenases is mediated by the radical-radical dismutation between fatty acid alkoxyl radicals and fatty acid peroxyl radicals in fatty acid assembly". . p. 258 - 264. Retrieved 2020/11/26.
• 2、 Simplicio, Fernanda I.,Seabra, Amedea B.,De Souza, Gabriela F. P.,De Oliveira, Marcelo G.. "In vitro inhibition of linoleic acid peroxidation by primary S-Nitrosothiols". experimental part. p. 1885 - 1895. Retrieved 2011/01/12.