Methyl arachidonate

Base Information

• Chemical Name: Methyl arachidonate
• CAS No.: 2566-89-4
• Molecular Formula: C21H34 O2
• Molecular Weight: 318.5
• Hs Code.: 2916190090
• European Community (EC) Number: 219-900-1
• UNII: 22AF6IJ1IJ
• DSSTox Substance ID: DTXSID801015890
• Nikkaji Number: J589D
• Wikidata: Q27085332
• Mol file: 2566-89-4.mol

Synonyms:Methyl arachidonate;2566-89-4;Arachidonic acid methyl ester;Methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate;(5Z,8Z,11Z,14Z)-Methyl icosa-5,8,11,14-tetraenoate;arachidonate methyl ester;UNII-22AF6IJ1IJ;22AF6IJ1IJ;5,8,11,14-Eicosatetraenoic acid, methyl ester, (all-Z)-;Methyl all-cis-5,8,11,14-eicosatetraenoate;EINECS 219-900-1;METHYLARACHIDONATE;Arachidonic acid methyl;D0C9DS;Arachidonic acid methylester;SCHEMBL23820;Arachidonic acid-methyl ester;GTPL5222;CHEBI:78033;DTXSID801015890;Methyl arachidonate, >=99% (GC);CS-W012013;HY-W011297;AC-33774;AS-78027;BP-29804;Methyl arachidonate, ~90% (capillary GC);F70472;(5Z,8Z,11Z,14Z)-icosatetraenoate methyl ester;1-O-methyl (5Z,8Z,11Z,14Z)-eicosatetraenoate;1-O-methyl-(5Z,8Z,11Z,14Z)-eicosatetraenoate;cis-5,8,11,14-Eicosatetraenoic acidmethyl ester;Methyl all-cis-5,8,11,14-eicosatetraenoic acid;cis-5,8,11,14-Eicosatetraenoic acid, methyl ester;J-016096;METHYL (5Z,8Z,11Z,14Z)-EICOSATETRAENOATE;(5Z,8Z,11Z,14Z)-Icosatetraenoic acid methyl ester;1-O-Methyl (5Z,8Z,11Z,14Z)-eicosatetraenoic acid;Q27085332;5,8,11,14-Eicosatetraenoic acid, methyl ester, cis-;(5Z,8Z,11Z,14Z)-Methylicosa-5,8,11,14-tetraenoate;5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, METHYL ESTER;5,8,11,14-Eicosatetraenoicacid,methyl ester,(5Z,8Z,11Z,14Z)-;5,8,11,14-Eicosatetraenoic acid, methyl ester, (5Z,8Z,11Z,14Z)-

Chemical Property of Methyl arachidonate

Chemical Property:

• Vapor Pressure: 9.81E-07mmHg at 25°C
• Refractive Index: 1.4875 (589.3 nm 20℃)
• Boiling Point: 403.9 °C at 760 mmHg
• Flash Point: 102 °C
• PSA: 26.30000
• Density: 0.901 g/cm³
• LogP: 6.30510
• Storage Temp.: −20°C
• Solubility.: chloroform: 50 mg/mL, clear, colorless
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 318.255880323
• Heavy Atom Count: 23
• Complexity: 375

Purity/Quality:

GC ≥98% ^*data from raw suppliers

Arachidonic Acid Methyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn,N
• Hazard Codes: F,Xn,N
• Statements: 19-67-65-50/53-38-11
• Safety Statements: 9-16-29-33-60-61-62

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC
• Isomeric SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC
• Uses: Arachidonic acid is the keystone essential fatty acid at the origin of the arachidonic acid cascade. It is converted by cyclooxygenase, lipoxygenase, and epoxygenase enzymes into more than one hundred fifty different potent primary autacoid metabolites in species ranging from fungi to plants to mammals. Arachidonic acid is stored in tissue phospholipids in esterified form, where it comprises a small but critically controlled percentage of the polyunsaturated fatty acid pool. Arachidonic acid content is frequently measured by the saponification of the lipid fraction followed by methyl esterification and gas chromatographic analysis of the resulting FAME (fatty acid methyl ester) compounds. Arachidonic acid methyl ester can also be incorporated into dietary regimens or fed to cultured cells as a source of exogenous arachidonate.

Technology Process of Methyl arachidonate

There total 43 articles about Methyl arachidonate 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) + all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → methyl arachidonate (2566-89-4)

Guidance literature:

In methanol; at 0 ℃; for 0.333333h;

DOI:10.1016/S0960-894X(03)00348-2

Reference yield: 70.0%

8-oxo-oct-5-cis-enoic acid methyl ester (80764-54-1) + ((3Z,6Z)-dodeca-3,6-dien-1-yl)triphenylphosphonium bromide (83606-41-1) → methyl arachidonate (2566-89-4)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/S0040-4039(99)01498-7

Reference yield: 52.0%

methanol (67-56-1) + Peroxyarachidonsaeure (21290-17-5) → methyl arachidonate (2566-89-4) + methyl 14,15-epoxyeicosa-cis-5,8,11-trienoate (70219-56-6)

Guidance literature:

Peroxyarachidonsaeure; With 1,1'-carbonyldiimidazole; In dichloromethane; at 20 ℃; for 0.333333h; Inert atmosphere;

With urea hydrogen peroxide adduct; lithium salt of imidazole; In diethyl ether; dichloromethane; at 0 ℃; for 0.05h; Inert atmosphere;

methanol; Further stages;

DOI:10.1080/00397911.2014.956369

upstream raw materials:

diazomethane

1-chloro-nonadeca-4c,7c,10c,13c-tetraene

carbon dioxide

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

Downstream raw materials:

methyl arachidate

arachidonyl alcohol

arachidonic acid pyrrolidide

15-oxoeicosatetraenoic acid

Refernces

• 1、 Isaeva, E. V.,Levin, E', D.. "AMOUNTS OF ARACHIDONIC ACID IN THE BUDS OF Populus balzamifera IN THE COURSE OF THE ANNUAL CYCLE". . p. 426 - 428. Retrieved 1987.
• 2、 Hess, Sandra K.,Schunck, Natalie S.,Goldbach, Verena,Ewe, Daniela,Kroth, Peter G.,Mecking, Stefan. "Valorization of Unconventional Lipids from Microalgae or Tall Oil via a Selective Dual Catalysis One-Pot Approach". supporting information. p. 13487 - 13491. Retrieved 2017/10/05.
• 3、 Xie, Fuchun,Li, Bingbing X.,Alkayed, Nabil J.,Xiao, Xiangshu. "Synthesis of 14,15-EET from Arachidonic Acid Using Urea-Hydrogen Peroxide as the Oxidant". . p. 105 - 110. Retrieved 2015/10/20.