CIS-15-OCTADECENOIC ACID METHYL ESTER

Base Information

• Chemical Name: CIS-15-OCTADECENOIC ACID METHYL ESTER
• CAS No.: 10411-39-9
• Molecular Formula: C₁₉H₃₆O₂
• Molecular Weight: 296.494
• Hs Code.: 2916190090
• Mol file: 10411-39-9.mol

Synonyms:15-Octadecenoicacid, methyl ester, (Z)- (8CI,9CI); Methyl cis-15-octadecenoate

Chemical Property of CIS-15-OCTADECENOIC ACID METHYL ESTER

Chemical Property:

• Melting Point: 10 °C
• Boiling Point: 364.3±11.0 °C(Predicted)
• PSA: 26.30000
• Density: 0.8724 g/cm3(Temp: 30 °C)
• LogP: 6.19690
• Storage Temp.: −20°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of CIS-15-OCTADECENOIC ACID METHYL ESTER

There total 4 articles about CIS-15-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: 80.0%

15-oxo-pentadecanoic acid methyl ester (1931-69-7) + n-propyltriphenylphosphonium bromide (6228-47-3) → methyl 15(Z)-octadecenoate (10411-39-9)

Guidance literature:

n-propyltriphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

15-oxo-pentadecanoic acid methyl ester; In tetrahydrofuran; at -78 - 20 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.1007/s11745-009-3378-3

Reference yield:

10-bromodecanoic acid methyl ester (26825-94-5) + (3Z)-8-bromooct-3-ene (76971-26-1) → 1,18-octadecanoic acid dimethyl ester (42235-38-1) + methyl 15(Z)-octadecenoate (10411-39-9) + 3,13-hexadecadiene

Guidance literature:

With manganese; (1,2-dimethoxyethane)dichloronickel(II); 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine; In N,N-dimethyl-formamide; at 40 ℃; for 4h;

DOI:10.1002/aocs.12484

Reference yield:

15-hydroxylpentadecanoic acid (4617-33-8) → methyl 15(Z)-octadecenoate (10411-39-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / acetone; water / 4 h / Reflux

2.1: pyridinium chlorochromate; silica gel / dichloromethane / 2 h / Inert atmosphere

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

3.2: 0.5 h / -78 °C / Inert atmosphere

With sodium hexamethyldisilazane; silica gel; potassium carbonate; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; acetone; 3.2: |Wittig Olefination;

DOI:10.1021/acs.joc.7b00264

upstream raw materials:

15-oxo-pentadecanoic acid methyl ester

n-propyltriphenylphosphonium bromide

15-hydroxylpentadecanoic acid

methyl 15-hydroxypentadecanoate

Downstream raw materials:

(Z)-octadec-15-enoic acid

Refernces

• 1、 Rawling, Tristan,Duke, Colin C.,Cui, Pei H.,Murray, Michael. "Facile and stereoselective synthesis of (Z)-15-octadecenoic acid and (Z)-16-nonadecenoic acid: Monounsaturated omega-3 fatty acids". . p. 159 - 165. Retrieved 2010.