Docosahexaenoic acid ethyl ester

Base Information

• Chemical Name: Docosahexaenoic acid ethyl ester
• CAS No.: 84494-72-4
• Molecular Formula: C₂₄H₃₆O₂
• Molecular Weight: 356.549
• Hs Code.: 2916196000
• Nikkaji Number: J382.980D,J599.432B
• NCI Thesaurus Code: C78086
• Mol file: 84494-72-4.mol

Synonyms:(all-Z)-isomer, no locants for unsaturation of 4,7,10,13,16,19-docosahexaenoic acid ethyl ester;4,7,10,13,16,19-docosahexaenoic acid ethyl ester;4,7,10,13,16,19-docosahexaenoic acid ethyl ester, (all-Z)-isomer;DH-ethyl ester;docosahexaenoic acid ethyl ester

Chemical Property of Docosahexaenoic acid ethyl ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.504
• Boiling Point: 443.5 °C at 760 mmHg
• Flash Point: 102.1 °C
• PSA: 26.30000
• Density: 0.914 g/cm³
• LogP: 7.02740
• Storage Temp.: −20°C
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 16
• Exact Mass: 356.271530387
• Heavy Atom Count: 26
• Complexity: 490

Purity/Quality:

≥98% ^*data from raw suppliers

Ethyl cis-4,7,10,13,16,19-Docosahexaenoate >97.0%(GC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)OCC
• Isomeric SMILES: CC/C=C/C/C=C/C/C=C/C/C=C/C/C=C/C/C=C/CCC(=O)OCC
• Uses: Docosahexanoic Acid Ethyl Ester is an omega-3 fatty acid found in marine fish oils and in many phospholipids. Major structural component of excitable membranes of the retina and brain; synthesized in the liver from α-linolenic acid. Nutritional supplement.

Technology Process of Docosahexaenoic acid ethyl ester

There total 22 articles about Docosahexaenoic acid ethyl 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:

→ all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate (81926-94-5,84494-72-4) + eicosapentaenoic acid ethyl ester (86227-47-6,84494-70-2)

Guidance literature:

Purification / work up;

Reference yield:

ethanol (64-17-5) + (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl chloride (98776-99-9,158754-21-3) → all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate (81926-94-5,84494-72-4)

Guidance literature:

With triethylamine; In hexane; at 0 - 20 ℃;

Reference yield:

docosahexaenoic acid (6217-54-5) + ethanol (64-17-5) + Diethyl carbonate (105-58-8,76619-83-5) → all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate (81926-94-5,84494-72-4)

Guidance literature:

With immobilized Candida antarctica Lipase B; In neat (no solvent); at 60 ℃; Green chemistry; Enzymatic reaction;

DOI:10.1016/j.molcatb.2012.04.009

upstream raw materials:

(4Z,7Z,10Z)-13-Oxo-trideca-4,7,10-trienoic acid ethyl ester

hex-5-en-2-yn-1-ol

(Z,Z)-1-hydroxynona-3,6-diene

Deca-4,7-diyne-1,2,10-triol

Downstream raw materials:

all-cis-4,7,10,13,16,19-docosahexaenoic acid methyl ester

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

docosahexaenoic acid

N-docosahexaenoylethanolamine

Refernces

• 1、 Selva, Elisabet,Soto, J. Javier,Nájera, Carmen,Foubelo, Francisco,Sansano, José M.. "Proline derivatives incorporating hydrophobic long-chain derived from natural and synthetic fatty acids". . p. 1378 - 1386. Retrieved 2019/02/05.
• 2、 Morrone,D'Antona,Biondi,Lambusta,Nicolosi. "Preparation of n-3 PUFAs ethyl esters by an efficient biocatalyzed solvent-free process". . p. 173 - 176. Retrieved 2012/11/06.