Methyl 12,13-epoxyoleate

Base Information

• Chemical Name: Methyl 12,13-epoxyoleate
• CAS No.: 18652-40-9
• Deprecated CAS: 186792-28-9
• Molecular Formula: C19H34O3
• Molecular Weight: 310.4715
• Nikkaji Number: J668.667B
• Mol file: 18652-40-9.mol

Synonyms:methyl 12,13-epoxyoleate;18652-40-9;9-Undecenoic acid, 11-(3-pentyloxiranyl)-, methyl ester, (Z)-;methyl vernoleate;SCHEMBL2825440;Oleic acid, 12,13-epoxy-, d(+)-, (z)-, methyl ester

Chemical Property of Methyl 12,13-epoxyoleate

Chemical Property:

• Vapor Pressure: 2.42E-06mmHg at 25°C
• Boiling Point: 391.7°Cat760mmHg
• Flash Point: 150.9°C
• PSA: 38.83000
• Density: 0.937g/cm³
• LogP: 5.18410
• Storage Temp.: ?20°C
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 310.25079494
• Heavy Atom Count: 22
• Complexity: 312

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC1C(O1)CC=CCCCCCCCC(=O)OC
• Isomeric SMILES: CCCCCC1C(O1)C/C=C\CCCCCCCC(=O)OC

Technology Process of Methyl 12,13-epoxyoleate

There total 11 articles about Methyl 12,13-epoxyoleate 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: 25.0%

Methyl linoleate (112-63-0) → methyl 8-(3-((3-pentyloxiran-2-yl)methyl)oxiran-2-yl)octanoate (2500-56-3) + 9,10-epoxy-(12Z)-octadecen-1-oic acid methyl ester (186792-27-8) + 12,13-epoxy-(9Z)-octadecen-1-oic acid methyl ester (18652-40-9) + methyl 9-hydroxy-9-(4-hydroxy-5-pentyltetrahydrofuran-2-yl)nonanoate

Guidance literature:

With tert.-butylhydroperoxide; MoO₃(2-(2-pyridyl)benzimidazole); at 70 ℃; for 24h; Inert atmosphere; Schlenk technique;

DOI:10.1002/ejic.201700286

Reference yield: 22.0%

Methyl linoleate (112-63-0) → (9Z)-11-[(2RS,3SR)-3-pentyloxyiranyl]undec-9-enoic acid methyl ester (2733-91-7,10547-36-1,18652-40-9,21019-42-1,38003-79-1,58800-38-7,58800-40-1,58800-42-3,105229-02-5) + (2RS,3SR)-3-[(2Z)-oct-2-enyl]oxiraneoctanoic acid methyl ester (6084-72-6,21019-43-2,40707-88-8,58800-37-6,58800-39-8,58800-41-2,146987-77-1,149405-48-1)

Guidance literature:

With 3,3-dimethyldioxirane; In tetrachloromethane; at 0 ℃;

DOI:10.1002/hlca.200690209

Reference yield: 20.0%

Methyl linoleate (112-63-0) → methyl 8-(3-((3-pentyloxiran-2-yl)methyl)oxiran-2-yl)octanoate (2500-56-3) + 9,10-epoxy-(12Z)-octadecen-1-oic acid methyl ester (186792-27-8) + 12,13-epoxy-(9Z)-octadecen-1-oic acid methyl ester (18652-40-9)

Guidance literature:

With tert.-butylhydroperoxide; MoO₃(2-(2-pyridyl)benzimidazole); at 70 ℃; for 6h; Inert atmosphere; Schlenk technique;

DOI:10.1002/ejic.201700286

upstream raw materials:

Methyl linoleate

linoleic acid

diazomethyl-trimethyl-silane

Downstream raw materials:

(E)-(9R,12R,13R)-9,12,13-Trihydroxy-octadec-10-enoic acid

12-13-monoepoxy-9-octadecenoic acid

12,13-dihydroxy-9Z-octadecenoic acid

methyl coriolate