(+)-[12S,13R]-EPOXY-CIS-9-OCTADECENOIC ACID METHYL ESTER

Base Information

• Chemical Name: (+)-[12S,13R]-EPOXY-CIS-9-OCTADECENOIC ACID METHYL ESTER
• CAS No.: 2733-91-7
• Molecular Formula: C19H34 O3
• Molecular Weight: 310.477
• Hs Code.: 2918990090
• Mol file: 2733-91-7.mol

Synonyms:9-Undecenoicacid, 11-(3-pentyloxiranyl)-, methyl ester, [2S-[2a(Z),3a]]-; 9-Undecenoic acid, 11-[(2S,3R)-3-pentyloxiranyl]-, methyl ester,(9Z)- (9CI); Oleic acid, 12,13-epoxy-, methyl ester, (12S,13R)-(+)- (8CI);(+)-Vernolic acid methyl ester; Methyl vernolate; Vernolic acid methyl ester

Chemical Property of (+)-[12S,13R]-EPOXY-CIS-9-OCTADECENOIC ACID METHYL ESTER

Chemical Property:

• Vapor Pressure: 2.42E-06mmHg at 25°C
• Boiling Point: 391.7°C at 760 mmHg
• Flash Point: 150.9°C
• PSA: 38.83000
• Density: 0.937g/cm³
• LogP: 5.18410
• Storage Temp.: −20°C

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (+)-Vernolic Acid Methyl Ester, is a derivative of Vernolic Acid (E589430), which is the cis epoxide derived from the C12–C13 alkene of linoleic acid, and an isomer of coronaric acid. Vernolic acid is the key component in vernonia oil, which is produced in abundance by the genera Vernonia and Euphorbia and is a potentially useful biofeedstock.

Technology Process of (+)-[12S,13R]-EPOXY-CIS-9-OCTADECENOIC ACID METHYL ESTER

There total 8 articles about (+)-[12S,13R]-EPOXY-CIS-9-OCTADECENOIC ACID METHYL ESTER 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: 45.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 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) → methyl (9Z,12S,13R)-12,13-epoxy-9-octadecenoate (2733-91-7)

Guidance literature:

linoleic acid; With cytochrome P₄₅₀BM₃; wild type; potassium carbonate; NADPH; at 20 ℃; for 0.25h; pH=7.4;

diazomethane; In methanol; diethyl ether;

DOI:10.1016/S0040-4039(01)00694-3

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: 2.4%

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

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 1.33333h;

upstream raw materials:

Methyl linoleate

diazomethane

linoleic acid

methanol

Downstream raw materials:

cis-9-octadecenoamide

N,N-dimethyl-(12S,13R)-epoxy-cis-9-octadecenyl amide

Palmitamide

stearamide

Refernces

• 1、 Johnson, Nikki S.,Ayorinde, Folahan O.. "Vernonia oil: Conversion to a mixture of tertiary amines including N,N-Dimethyl-(12S,13R)-Epoxy-cis-9-Octadecenyl amine". scheme or table. p. 1425 - 1430. Retrieved 2011/11/11.
• 2、 Falck,Reddy,Haines, Donovan C.,Reddy, Komandla Malla,Krishna,Graham, Sandra,Murry, Barbara,Peterson, Julian A.. "Practical, enantiospecific syntheses of 14,15-EET and leukotoxin B (vernolic acid)". . p. 4131 - 4133. Retrieved 2007/10/03.