(10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoic acid

Base Information

• Chemical Name: (10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoic acid
• CAS No.: 5502-91-0
• Molecular Formula: C₁₈H₃₂O₄
• Molecular Weight: 312.45
• Hs Code.: 2918990090
• UNII: R9G4SN7TYX
• DSSTox Substance ID: DTXSID901347925
• Nikkaji Number: J711.800G
• Metabolomics Workbench ID: 39102
• Mol file: 5502-91-0.mol

Synonyms:5502-91-0;(10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoic acid;R9G4SN7TYX;( inverted exclamation markA)9-HpODE;(+/-)9-HpODE;(10E,12Z)-9-Hydroperoxy-10,12-octadecadienoic acid;Linoleic acid 9-hydroperoxide, (+/-)-;(E,Z)-9-Hydroperoxy-10,12-octadecadienoic acid;10,12-Octadecadienoic acid, 9-hydroperoxy-, (E,Z)-;UNII-R9G4SN7TYX;9-HOO;(??)9-HpODE;SCHEMBL4103652;CHEBI:177850;DTXSID901347925;AKOS040755339;HY-118149A;9-hydroperoxy-10E,12Z-octadecadienoic acid;CS-0181940;LINOLEIC ACID 9-HYDROPEROXIDE, (RS)-;J-500104;10,12-Octadecadienoic acid, 9-hydroperoxy-, (10E,12Z)-;9-HYDROPEROXY-TRANS-10,CIS-12-OCTADECADIENOIC ACID;9-HYDROPEROXY-10,12-OCTADECADIENOIC ACID, (10E,12Z)-(+/-)-

Chemical Property of (10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoic acid

Chemical Property:

• Vapor Pressure: 6.77E-10mmHg at 25°C
• Boiling Point: 447.7°Cat760mmHg
• Flash Point: 150.1°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%min ^*data from raw suppliers

(±)9-HpODE ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CC=CC(CCCCCCCC(=O)O)OO
• Isomeric SMILES: CCCCC/C=C\C=C\C(CCCCCCCC(=O)O)OO

Technology Process of (10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoic acid

There total 30 articles about (10E,12Z)-9-hydroperoxyoctadeca-10,12-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: 90.0%

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) → C18H32O4 (122046-44-0) + 9(S)-hydroperoxyoctadeca-10Z,12E-dienoic acid (5502-91-0,7324-20-1,26911-36-4,28396-96-5,39692-45-0,63121-49-3,65941-74-4,67597-24-4,90760-93-3,100018-30-2,104759-96-8,122046-44-0,123410-63-9,29774-12-7)

Guidance literature:

ΔNt-NspLOX; Enzyme kinetics;

DOI:10.1016/j.phytochem.2008.03.002

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) + (9R,S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid (5502-91-0) + 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) → (9R,S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid (5502-91-0) + (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid (33964-75-9,18320-18-8)

Guidance literature:

With Pleurotus sapidus recombinant lipoxygenase type 1; sodium hydroxide; In water; at 35 ℃; pH=7; Kinetics; Enzymatic reaction;

DOI:10.1016/j.molcatb.2012.11.004

upstream raw materials:

linoleic acid

methyl 9-(R,S)-hydroperoxy-10-trans,12-cis-octadecadienoate

[11(S)-²H]linoleic acid

Methyl linoleate

Downstream raw materials:

9-hydroxynonanoic acid

(8E,1'E,3'Z)-9-(1',3'-nonadienyloxy)-8-nonenoic acid

azelaic acid semialdehyde

(Z)-3-nonenal

Refernces

• 1、 Do, Quynh,Lee, David D.,Dinh, Andrew N.,Seguin, Ryan P.,Zhang, Rutan,Xu, Libin. "Development and Application of a Peroxyl Radical Clock Approach for Measuring Both Hydrogen-Atom Transfer and Peroxyl Radical Addition Rate Constants". supporting information. p. 153 - 168. Retrieved 2020/12/23.
• 2、 Gorina, Svetlana S.,Grechkin, Alexander N.,Iljina, Tatiana M.,Mukhtarova, Lucia S.,Smirnova, Elena O.,Toporkova, Yana Y.. "The CYP74B and CYP74D divinyl ether synthases possess a side hydroperoxide lyase and epoxyalcohol synthase activities that are enhanced by the site-directed mutagenesis". . . Retrieved 2020/09/16.