ARACHIDONIC ACID ETHYL ESTER

Base Information

• Chemical Name: ARACHIDONIC ACID ETHYL ESTER
• CAS No.: 1808-26-0
• Molecular Formula: C₂₂H₃₆O₂
• Molecular Weight: 332.527
• UNII: 3NU6034AW3
• DSSTox Substance ID: DTXSID301016455
• Nikkaji Number: J103.655F
• Wikidata: Q27158140
• Mol file: 1808-26-0.mol

Synonyms:5,8,11,14-Eicosatetraenoicacid, ethyl ester, (all-Z)-; Arachidonic acid, ethyl ester (6CI,7CI,8CI); Ethylarachidonate

Chemical Property of ARACHIDONIC ACID ETHYL ESTER

Chemical Property:

• Vapor Pressure: 3.35E-07mmHg at 25°C
• Boiling Point: 418.1°Cat760mmHg
• Flash Point: 100.7°C
• PSA: 26.30000
• Density: 0.899g/cm³
• LogP: 6.69520
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Very Slightly)
• XLogP3: 7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 16
• Exact Mass: 332.271530387
• Heavy Atom Count: 24
• Complexity: 389

Purity/Quality:

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

Ethyl Arachidonate| ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CCC=CCC=CCCCC(=O)OCC
• Isomeric SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCC
• Uses: Arachidonic acid (AA) is an unsaturated omega-6 fatty acid constituent of the phospholipids of cell membranes. Phospholipase A2 releases AA from the membrane phospholipids in response to inflammation. Arachidonic Acid ethyl ester is an emollient with healing and smoothing properties that is also reported as appropriate for use in indoor tanning preparations. It is the ester of ethyl alcohol and arachidonic acid. A modified form of ethyl arachidonate can reduce the possibility of irritation that can result from using straight ethyl arachidonate.

Technology Process of ARACHIDONIC ACID ETHYL ESTER

There total 3 articles about ARACHIDONIC 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: 67.0%

ethanol (64-17-5) + 2-((5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy)propane-1,3-diyl dibutyrate (1274596-36-9) → ethyl arachidonate (95285-77-1,1808-26-0) + 2-arachidonoyl glycerol (53847-30-6)

Guidance literature:

With immobilized Candida antarctica; at 20 ℃; for 2h; Enzymatic reaction;

DOI:10.1016/j.tetlet.2011.01.047

Reference yield:

arachidonic acid-containing triglyceride oil → ethyl arachidonate (95285-77-1,1808-26-0)

Guidance literature:

Reference yield:

ethanol (64-17-5) + all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → ethyl arachidonate (95285-77-1,1808-26-0)

Guidance literature:

With Candida antarctica B lipase; In hexane; at 55 ℃; for 1h; Enzymatic reaction;

DOI:10.1002/ejoc.201501263

upstream raw materials:

ethanol

2-((5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy)propane-1,3-diyl dibutyrate

all cis 5,8,11,14-eicosatetraenoic acid

Downstream raw materials:

all cis 5,8,11,14-eicosatetraenoic acid

2-pentylfuran

(E)-2-Octenal

1-octen-3-ol

Refernces

• 1、 Vadivel, Subramanian K.,Whitten, Kyle M.,Makriyannis. "Chemoenzymatic synthesis of 2-arachidonoylglycerol, an endogenous ligand for cannabinoid receptors". . p. 1149 - 1150. Retrieved 2011.
• 2、 -. "Composition having action preventing or alleviating symtoms or diseases due to aging of blood vessels". Page/Page column 6. . Retrieved 2008/06/13.