12,13-DiHOME

Base Information

• Chemical Name: 12,13-DiHOME
• CAS No.: 263399-35-5
• Molecular Formula: C18H34O4
• Molecular Weight: 314.46000
• DSSTox Substance ID: DTXSID001273775
• Nikkaji Number: J470.613G
• Wikidata: Q27140059
• Metabolomics Workbench ID: 2266
• Mol file: 263399-35-5.mol

Synonyms:12,13-DiHOME;(+/-)12,13-Dihome;263399-35-5;12,13-dihydroxy-9Z-octadecenoic acid;12,13-DHOA;(9Z)-12,13-Dihydroxyoctadec-9-enoic acid;12,13-DHOME;(Z)-12,13-dihydroxyoctadec-9-enoic acid;9-Octadecenoic acid, 12,13-dihydroxy-, (9Z)-;Isoleukotoxin diol;12,13-dihydroxyoctadec-9-enoic acid;SCHEMBL2228623;CHEBI:72665;DTXSID001273775;(??)12(13)-DiHOME;LMFA02000230;AKOS040754637;HY-116003;(9Z)-12,13-Dihydroxy-9-octadecenoic acid;CS-0063434;threo-12,13-Dihydroxy-9(Z)-octadecenoic acid;J-016390;Q27140059

Chemical Property of 12,13-DiHOME

Chemical Property:

• Boiling Point: 476.0±30.0 °C(Predicted)
• PKA: 4.78±0.10(Predicted)
• PSA: 77.76000
• Density: 1.015±0.06 g/cm3(Predicted)
• LogP: 4.05010
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 15
• Exact Mass: 314.24570956
• Heavy Atom Count: 22
• Complexity: 289

Purity/Quality:

99% ^*data from raw suppliers

(±)12(13)-DiHOME ≥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)O)O
• Isomeric SMILES: CCCCCC(C(C/C=C\CCCCCCCC(=O)O)O)O
• Uses: (±)?-12,?13-?DIHOME is an exercise induced lipokine which has been shown to induce skeletal muscle fatty acid uptake. May be used in the treatment of neuropathic pain.

Technology Process of 12,13-DiHOME

There total 5 articles about 12,13-DiHOME 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) → 12,13-dihydroxy-9Z-octadecenoic acid (263399-35-5) + (±)-9,10-dihydroxy-12Z-octadecenoic acid (263399-34-4)

Guidance literature:

linoleic acid; With peroxygenase from tomato yeast extract; dihydrogen peroxide; at 30 ℃; for 1h; pH=6; Enzymatic reaction;

With recombinant Nicotiana benthamiana epoxide hydrolase 2.1; In aq. phosphate buffer; at 30 ℃; for 0.5h; Reagent/catalyst; Enzymatic reaction;

DOI:10.1016/j.phytochem.2013.02.020

Reference yield:

12-13-monoepoxy-9-octadecenoic acid (948310-68-7,16833-57-1,7576-35-4) → 12,13-dihydroxy-9Z-octadecenoic acid (263399-35-5)

Guidance literature:

DOI:10.1016/0031-9422(91)80030-5

Reference yield:

12,13-epoxy-(9Z)-octadecen-1-oic acid methyl ester (18652-40-9) → 12,13-dihydroxy-9Z-octadecenoic acid (263399-35-5)

Guidance literature:

With sodium acetate; acetic acid; at 80 ℃; for 2h;

upstream raw materials:

12-13-monoepoxy-9-octadecenoic acid

12,13-epoxy-(9Z)-octadecen-1-oic acid methyl ester

linoleic acid

Downstream raw materials:

(Z)-12,13-Bis-trimethylsilanyloxy-octadec-9-enoic acid methyl ester