cis-5,8,11-Eicosatrienoic acid methyl ester

Base Information

• Chemical Name: cis-5,8,11-Eicosatrienoic acid methyl ester
• CAS No.: 14602-39-2
• Molecular Formula: C₂₁H₃₆O₂
• Molecular Weight: 320.516
• UNII: 8Y3T4RA34E
• Nikkaji Number: J1.120.304C
• Wikidata: Q27271187
• Mol file: 14602-39-2.mol

Synonyms:14602-39-2;cis-5,8,11-Eicosatrienoic acid methyl ester;8Y3T4RA34E;5,8,11-Eicosatrienoic acid, methyl ester, (5Z,8Z,11Z)-;methyl (5Z,8Z,11Z)-icosa-5,8,11-trienoate;Methyl 5,8,11-eicosatrienoate, (5Z,8Z,11Z)-;UNII-8Y3T4RA34E;Methyl (Z,Z,Z)-5,8,11-eicosatrienoate;5,8,11-Eicosatrienoic acid, methyl ester, (Z,Z,Z)-;Mead acid methyl ester;AESHPAQQBZWZMS-NWFXIAEYSA-N;CHEBI:190340;2463-03-8;PD020805;methylcis,cis,cis-5,8,11-eicosatrienoate;Methyl 5(Z),8(Z),11(Z)-Eicosatrienoate;(5Z,8Z,11Z)-methyl 5,8,11-eicosatrienoate;cis-5,8,11-Eicosatrienoic acid, methyl ester;J-008181;Q27271187;(5Z,8Z,11Z)-5,8,11-Icosatrienoic acid methyl ester;5,8,11-Eicosatrienoicacid,methyl ester,(5Z,8Z,11Z)-;cis-5,8,11-Eicosatrienoic acid methyl ester, ~10 mg/mL in methanol, >=90%

Chemical Property of cis-5,8,11-Eicosatrienoic acid methyl ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.475
• Boiling Point: 405.1 °C at 760 mmHg
• Flash Point: 99.7 °C
• PSA: 26.30000
• Density: 0.891 g/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%Min ^*data from raw suppliers

cis-5,8,11-Eicosatrienoic acid methyl ester ~10mg/mL in methanol, ≥90% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,F
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC=CCC=CCC=CCCCC(=O)OC
• Isomeric SMILES: CCCCCCCC/C=C\C/C=C\C/C=C\CCCC(=O)OC
• Description: Mead acid is a 20-carbon ω-9 polyunsaturated fatty acid. Its level is elevated in plasma during essential fatty acid deficiency in humans. 5(Z),8(Z),11(Z)-Eicosatrienoic Acid methyl ester (Mead acid methyl ester) is typically used as a standard for the analysis of fatty acids, when the fatty acids have been transesterified to methyl esters before analysis.

Technology Process of cis-5,8,11-Eicosatrienoic acid methyl ester

There total 6 articles about cis-5,8,11-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: 73.0%

Icosa-5,8,11-triynoic acid methyl ester (62285-67-0) → methyl 5Z,8Z,11Z eicosatrienoate (14602-39-2)

Guidance literature:

With hydrogen; ethylenediamine; sodium tetrahydroborate; nickel diacetate; In ethanol;

DOI:10.1016/0040-4039(92)89024-7

Reference yield:

1-bromoundec-2-yne (18495-28-8) → methyl 5Z,8Z,11Z eicosatrienoate (14602-39-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / copper(I) iodide, sodium carbonate, tetra-n-butylammonium chloride / dimethylformamide / 23 h / 20 °C

2: 86 percent / CBr₄, PPh₃ / CH₂Cl₂ / 1.5 h / 0 °C

3: 51 percent / copper(I) iodide, sodium carbonate, tetra-n-butylammonium chloride / dimethylformamide / 23 h / 20 °C

4: 73 percent / H₂, H₂N(CH₂)2NH₂ / Ni(OAc)2*4H₂O, NaBH₄ / ethanol

With copper(l) iodide; carbon tetrabromide; tetrabutyl-ammonium chloride; hydrogen; sodium carbonate; ethylenediamine; triphenylphosphine; sodium tetrahydroborate; nickel diacetate; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(92)89024-7

Reference yield:

1-bromo-tetradeca-2,5-diyne (13488-18-1) → methyl 5Z,8Z,11Z eicosatrienoate (14602-39-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / copper(I) iodide, sodium carbonate, tetra-n-butylammonium chloride / dimethylformamide / 23 h / 20 °C

2: 73 percent / H₂, H₂N(CH₂)2NH₂ / Ni(OAc)2*4H₂O, NaBH₄ / ethanol

With copper(l) iodide; tetrabutyl-ammonium chloride; hydrogen; sodium carbonate; ethylenediamine; sodium tetrahydroborate; nickel diacetate; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(92)89024-7

upstream raw materials:

diazomethane

5,8,11-eicosatriynoic acid

Icosa-5,8,11-triynoic acid methyl ester

1-bromoundec-2-yne

Refernces