cis-5,8,11,14,17-Eicosapentaenoic acid methyl ester

Base Information

• Chemical Name: cis-5,8,11,14,17-Eicosapentaenoic acid methyl ester
• CAS No.: 2734-47-6
• Molecular Formula: C21H32 O2
• Molecular Weight: 316.484
• Hs Code.: 2916190090
• European Community (EC) Number: 688-140-4
• UNII: 2O598O936I
• DSSTox Substance ID: DTXSID401016222
• Wikidata: Q27895957
• Metabolomics Workbench ID: 77363
• Mol file: 2734-47-6.mol

Synonyms:2734-47-6;Icosapent methyl;cis-5,8,11,14,17-Eicosapentaenoic acid methyl ester;methyl eicosapentaenoate;eicosapentaenoic acid methyl ester;methyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate;Methyl all-cis-5,8,11,14,17-eicosapentaenoate;Methyl all-cis-58111417-eicosapentaenoate;UNII-2O598O936I;Methyl cis-5,8,11,14,17-eicosapentaenoate;Methyl 5Z,8Z,11Z,14Z,17Z-eicosapentaenoate;5,8,11,14,17-Eicosapentaenoic acid, methyl ester, (all-Z)-;(5Z,8Z,11Z,14Z,17Z)-Methyl icosa-5,8,11,14,17-pentaenoate;2O598O936I;5,8,11,14,17-Eicosapentaenoic acid, methyl ester, (5Z,8Z,11Z,14Z,17Z)-;Methyl-(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate;(5Z,8Z,11Z,14Z,17Z)-eicosapentanoic acid methyl ester;all-cis-5,8,11,14,17-Eicosapentaenoic acid methyl ester;Methyl-(5Z,8Z,11Z,14Z,17Z)-eicosa-(5,8,11,14,17)-pentaenoate;MFCD02259226;SCHEMBL13129422;CIS-5,8,11,14,17-EICOSAPENTAENOICACIDMETHYLESTER;CHEBI:143585;QWDCYFDDFPWISL-JEBPEJKESA-N;DTXSID401016222;LMFA01031154;CS-W012027;HY-W011311;AS-70365;E78349;J-016746;cis-5,8,11,14,17-Eicosapentaenoic acidmethyl ester;Q27895957;METHYL (5Z,8Z,11Z,14Z,17Z)-EICOSAPENTAENOATE;methyl (Z,Z,Z,Z,Z)-5,8,11,14,17-eicosapentaenoate;all cis-5,8,11,14,17-Eicosapentaenoic acid methyl ester;5,8,11,14,17-Eicosapentaenoic acid, methyl ester, all-cis-;(5Z,8Z,11Z,14Z,17Z)-Methylicosa-5,8,11,14,17-pentaenoate;C21H32O2 (cis-eicosa-5,8,11,14,17-pentaenoic acid methyl ester);Methyl all-cis-5,8,11,14,17-eicosapentaenoate, analytical standard;Methyl all-cis-5,8,11,14,17-eicosapentaenoate, >=97% (capillary GC);Methyl all-cis-5,8,11,14,17-eicosapentaenoate, technical grade, >=90%;28061-45-2

Chemical Property of cis-5,8,11,14,17-Eicosapentaenoic acid methyl ester

Chemical Property:

• Vapor Pressure: 1.07E-06mmHg at 25°C
• Melting Point: -91℃
• Refractive Index: 1.4898 (589.3 nm 20℃)
• Boiling Point: 115-125℃ (0.005 Torr)
• Flash Point: 104 °C
• PSA: 26.30000
• Density: 0.912g/cm³
• LogP: 6.08110
• Storage Temp.: −20°C
• Solubility.: chloroform: 50 mg/mL, clear, colorless
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 14
• Exact Mass: 316.240230259
• Heavy Atom Count: 23
• Complexity: 412

Purity/Quality:

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

MethylEicosapentaenoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn,N
• Hazard Codes: F,Xn,N
• Statements: 11-38-50/53-65-67
• Safety Statements: 24/25-62-61-60-33-29-16-9-2

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC=CCC=CCC=CCC=CCCCC(=O)OC
• Isomeric SMILES: CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC
• Uses: Methyl eicosapentaenoate is the methyl ester derivative of Eicosapentaenoic acid (E477800). Methyl eicosapentaenoate is a highly unsaturated compound that is extracted from algae, and has some practical application in protecting stored grains against rice weevils.

Technology Process of cis-5,8,11,14,17-Eicosapentaenoic acid methyl ester

There total 6 articles about cis-5,8,11,14,17-Eicosapentaenoic 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:

methanol (67-56-1) + fish oil → methyl (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate (108698-02-8) + methyl linoleate (16326-32-2) + all-cis-4,7,10,13,16,19-docosahexaenoic acid methyl ester (2566-90-7,875288-77-0) + (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 cis-tetracos-15-enate (2733-88-2) + methyl n-dodecanoate (111-82-0) + methyl myristoate (124-10-7) + hexadecanoic acid methyl ester (112-39-0) + methyl margarate (1731-92-6) + Methyl stearate (112-61-8) + methyl arachidate (1120-28-1) + (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid methyl ester (2734-47-6) + myristoleic acid methyl ester (56219-06-8) + methyl (13Z,16Z)-docosadienoate (61012-47-3) + (11Z,14Z)-11,14-icosadienoic acid methyl ester (61012-46-2) + cis-10-heptadecenoic acid methyl ester (369657-02-3,75190-82-8)

Guidance literature:

fish oil; 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;

upstream raw materials:

methanol

sodium methylate

(2S)-1-O-5,8,11,14,17-eicosapentaenoyl-2-O-6,9,12-hexadecatrienoyl-3-O-[β-D-galactopyranosyl]glycerol

Downstream raw materials:

all cis-5,8,11,14,17-eicosapentaenoic acid

(5Z,8Z)-10-[(2S,3R)-((2Z,5Z)-3-Octa-2,5-dienyl)-oxiranyl]-deca-5,8-dienoic acid methyl ester

4-[(2S,3R)-((2Z,5Z,8Z,11Z)-3-Tetradeca-2,5,8,11-tetraenyl)-oxiranyl]-butyric acid methyl ester

(5Z,8Z,11Z)-13-[(2S,3R)-((Z)-3-Pent-2-enyl)-oxiranyl]-trideca-5,8,11-trienoic acid methyl ester

Refernces

• 1、 Andrianasolo, Eric H.,Haramaty, Liti,Vardi, Assaf,White, Eileen,Lutz, Richard,Falkowski, Paul. "Apoptosis-inducing galactolipids from a cultured marine diatom, Phaeodactylum tricornutum". experimental part. p. 1197 - 1201. Retrieved 2009/11/30.