cis-8,11,14-Eicosatrienoic acid methyl ester

Base Information

• Chemical Name: cis-8,11,14-Eicosatrienoic acid methyl ester
• CAS No.: 21061-10-9
• Molecular Formula: C21H36 O2
• Molecular Weight: 320.516
• Hs Code.: 2916190090
• UNII: LQD3YK782Q
• DSSTox Substance ID: DTXSID90334008
• Nikkaji Number: J110.961H
• Wikidata: Q27283125
• Mol file: 21061-10-9.mol

Synonyms:21061-10-9;cis-8,11,14-Eicosatrienoic acid methyl ester;Methyl dihomo-gamma-linolenate;8,11,14-Eicosatrienoic acid, methyl ester, (8Z,11Z,14Z)-;LQD3YK782Q;Dihomo-|A-linolenic acid methyl ester;Dihomo-gamma-linolenic acid methyl ester;Methyl dihomo-.gamma.-linolenate;Methyl 8,11,14-eicosatrienoate;Methyl eicosa-8,11,14-trienoate;UNII-LQD3YK782Q;methyl (8Z,11Z,14Z)-icosa-8,11,14-trienoate;Methyl 8,11,14-eicosatrienoate, (Z,Z,Z)-;Dihomo-.gamma.-Linolenic Acid methyl ester;DTXSID90334008;CHEBI:180989;QHATYOWJCAQINT-JPFHKJGASA-N;HMS3649L22;AS-80704;PD020400;Dihomo- gamma -Linolenic Acid methyl ester;HY-116015;CS-0063511;cis-8,11,14-Eicosatrienoic acid-methyl ester;Methyl eicosa-8,11,14-trienoate, (Z,Z,Z)-;(z,z,z)8,11,14-eicosatrienoic acid methyl ester;SR-01000946740;Methyl (8Z,11Z,14Z)-8,11,14-icosatrienoate #;SR-01000946740-1;Q27283125;8,11,14-Eicosatrienoic acid, methyl ester, (Z,Z,Z)-;cis-8,11,14-Eicosatrienoic acid methyl ester, >=99%

Chemical Property of cis-8,11,14-Eicosatrienoic acid methyl ester

Chemical Property:

• Vapor Pressure: 9.07E-07mmHg at 25°C
• Refractive Index: 1.4712 (589.3 nm 20℃)
• Boiling Point: 195-197℃ (0.6-1 Torr)
• Flash Point: 99.6°C
• PSA: 26.30000
• Density: 0.891g/cm³
• LogP: 6.52910
• Storage Temp.: −20°C
• XLogP3: 7.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 16
• Exact Mass: 320.271530387
• Heavy Atom Count: 23
• Complexity: 340

Purity/Quality:

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

cis-8,11,14-Eicosatrienoic acid methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CCC=CCCCCCCC(=O)OC
• Isomeric SMILES: CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC
• Uses: cis-8,11,14-Eicosatrienoic Acid Methyl Ester is the methyl ester derivative of cis-8,11,14-Eicosatrienoic Acid (E477930); a fatty acid with selective tumoricidal activity.

Technology Process of cis-8,11,14-Eicosatrienoic acid methyl ester

There total 3 articles about cis-8,11,14-Eicosatrienoic 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:

methanol (67-56-1) → methyl (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate (108698-02-8) + methyl vaccenate (1937-63-9,52380-33-3,6198-58-9) + methyl linoleate (16326-32-2) + methyl arachidonate (2566-89-4) + (Z)-9-hexadecenoic acid methyl ester (1120-25-8,3913-63-1) + Methyl oleate (112-62-9) + Methyl linoleate (112-63-0) + (11Z)-11-icosenoic acid methyl ester (2390-09-2,3946-08-5) + methyl linolenate (301-00-8) + methyl n-dodecanoate (111-82-0) + methyl myristoate (124-10-7) + pentadecanoic acid methyl ester (7132-64-1) + hexadecanoic acid methyl ester (112-39-0) + methyl margarate (1731-92-6) + Methyl stearate (112-61-8) + methyl arachidate (1120-28-1) + behenic acid methyl ester (929-77-1) + all-cis-8,11,14-eicosatrienoic acid methyl ester (21061-10-9) + (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid methyl ester (2734-47-6) + cis,cis,cis,cis-Docosa-7,10,13,16-tetraensaeuremethylester (13487-42-8) + myristoleic acid methyl ester (56219-06-8) + cis,trans-9,11-methyloctadecadienoate (35042-75-2)

Guidance literature:

With potassium hydroxide; water; In methanol; at 55 ℃; for 1.5h;

methanol; With sulfuric acid; In water; at 20 - 55 ℃; for 1.5h; Product distribution / selectivity;

Reference yield:

methanol (67-56-1) + sodium methylate (124-41-4) → methyl (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate (108698-02-8) + methyl vaccenate (1937-63-9,52380-33-3,6198-58-9) + methyl linoleate (16326-32-2) + methyl arachidonate (2566-89-4) + (Z)-9-hexadecenoic acid methyl ester (1120-25-8,3913-63-1) + Methyl oleate (112-62-9) + Methyl linoleate (112-63-0) + (11Z)-11-icosenoic acid methyl ester (2390-09-2,3946-08-5) + methyl linolenate (301-00-8) + methyl n-dodecanoate (111-82-0) + methyl myristoate (124-10-7) + pentadecanoic acid methyl ester (7132-64-1) + hexadecanoic acid methyl ester (112-39-0) + methyl margarate (1731-92-6) + Methyl stearate (112-61-8) + methyl arachidate (1120-28-1) + behenic acid methyl ester (929-77-1) + all-cis-8,11,14-eicosatrienoic acid methyl ester (21061-10-9) + (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid methyl ester (2734-47-6) + cis,cis,cis,cis-Docosa-7,10,13,16-tetraensaeuremethylester (13487-42-8) + myristoleic acid methyl ester (56219-06-8) + cis,trans-9,11-methyloctadecadienoate (35042-75-2)

Guidance literature:

at 55 ℃; for 1.5h; Product distribution / selectivity;

Reference yield:

(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid methyl ester (2734-47-6) → methyl arachidonate (2566-89-4) + (11Z)-11-icosenoic acid methyl ester (2390-09-2,3946-08-5) + all-cis-8,11,14-eicosatrienoic acid methyl ester (21061-10-9) + (11Z,14Z)-11,14-icosadienoic acid methyl ester (61012-46-2)

Guidance literature:

With hydrogen; In neat (no solvent); at 30 ℃; for 0.666667h; under 7500.75 Torr; Time; Reagent/catalyst; Autoclave;

DOI:10.1021/jacs.7b06957

upstream raw materials:

methanol

sodium methylate

(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid methyl ester

Downstream raw materials:

cis-8,11,14-eicosatrienoic acid

arachidonyl alcohol

Refernces

• 1、 -. "DIRECT METHOD AND REAGENT KITS FOR FATTY ACID ESTER SYNTHESIS". Page/Page column 18; 21-22; 29. . Retrieved 2008/12/07.