DOCOSAHEXAENOIC ACID METHYL ESTER

Base Information

• Chemical Name: DOCOSAHEXAENOIC ACID METHYL ESTER
• CAS No.: 2566-90-7
• Molecular Formula: C23H34 O2
• Molecular Weight: 342.522
• Hs Code.: 29161900
• DSSTox Substance ID: DTXSID401016115
• Nikkaji Number: J590H
• Wikidata: Q72486595
• Mol file: 2566-90-7.mol

Synonyms:4,7,10,13,16,19-Docosahexaenoicacid, methyl ester, (all-Z)- (8CI); Methyl 4,7,10,13,16,19-cis-docosahexanenoate;Methyl all-cis-4,7,10,13,16,19-docosahexaenoate; Methylcis,cis,cis,cis,cis,cis-docosa-4,7,10,13,16,19-hexaenoate; Methyldocosahexaenoate

Chemical Property of DOCOSAHEXAENOIC ACID METHYL ESTER

Chemical Property:

• Vapor Pressure: 1.35E-07mmHg at 25°C
• Refractive Index: 1.4959 (589.3 nm 20℃)
• Boiling Point: 429.9°C at 760 mmHg
• Flash Point: 18 °C
• PSA: 26.30000
• Density: 0.921 g/mL at 25 °C(lit.)
• LogP: 6.63730
• Storage Temp.: −20°C
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 342.255880323
• Heavy Atom Count: 25
• Complexity: 476

Purity/Quality:

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

cis-4,7,10,13,16,19-Docosahexaenoic acid methyl ester ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)OC
• Isomeric SMILES: CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)OC
• Uses: Docosahexaenoic Acid methyl ester is a type of biodiesel with industrial applications. Used as a reagent in cholesterol photooxidation.

Technology Process of DOCOSAHEXAENOIC ACID METHYL ESTER

There total 28 articles about DOCOSAHEXAENOIC 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: 100.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + docosahexaenoic acid (6217-54-5) → all-cis-4,7,10,13,16,19-docosahexaenoic acid methyl ester (2566-90-7,875288-77-0)

Guidance literature:

In diethyl ether;

DOI:10.1021/jo00228a050

Reference yield: 97.0%

methanol (67-56-1) + all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate (81926-94-5,84494-72-4) → all-cis-4,7,10,13,16,19-docosahexaenoic acid methyl ester (2566-90-7,875288-77-0)

Guidance literature:

With disodium hydrogenphosphate; for 24h; Reflux;

DOI:10.1016/j.bioorg.2020.103653

Reference yield: 76.0%

(Z,Z)-10-oxodeca-4,7-dienoic acid methyl ester (169900-28-1) + (Z,Z,Z)-dodeca-3,6,9-trienyltriphenylphosphonium bromide → all-cis-4,7,10,13,16,19-docosahexaenoic acid methyl ester (2566-90-7,875288-77-0)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -80 ℃;

DOI:10.1021/jo00125a065

upstream raw materials:

diazomethane

Docosa-4,7,10,13,16,19-hexainsaeure

methanol

docosahexaenoic acid

Downstream raw materials:

(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaen-1-ol

(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaen-1-ol

methyl 3-(3-((2Z,5Z,8Z,11Z,14Z)-heptadeca-2,5,8,11,14-pentaen-1-yl)oxiran-2-yl)propanoate

all-cis-methyl 19,20-epoxydocosapentaenoate

Refernces

• 1、 Giner, José-Luis,Ceballos, Harriette,Tang, Ying-Zhong,Gobler, Christopher J.. "Sterols and Fatty Acids of the Harmful Dinoflagellate Cochlodinium polykrikoides". . p. 249 - 252. Retrieved 2016/02/27.
• 2、 -. "METHOD FOR THE SYNTHESIS OF DHA". Page/Page column 63-65. . Retrieved 2012/10/08.