For research use only. Not for therapeutic Use.
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.
| Catalog Number | R062726 |
| CAS Number | 2566-89-4 |
| Synonyms | (5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic Acid Methyl Ester; (all-Z)-5,8,11,14-Eicosatetraenoic Acid Methyl Ester; Methyl Arachidonate; Methyl 5Z,8Z,11Z,14Z-Eicosatetraenoate; Methyl all-cis-5,8,11,14-Eicosatetraenoate; Methyl cis,cis,cis,cis-Eicosa |
| Molecular Formula | C21H34O2 |
| Purity | ≥95% |
| Storage | -20°C |
| IUPAC Name | methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate |
| InChI | InChI=1S/C21H34O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21(22)23-2/h7-8,10-11,13-14,16-17H,3-6,9,12,15,18-20H2,1-2H3/b8-7-,11-10-,14-13-,17-16- |
| InChIKey | OFIDNKMQBYGNIW-ZKWNWVNESA-N |
| SMILES | CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC |
| Reference | 1. H. Katsuki and S. Okuda “Arachidonic acid as a neurotoxic and neurotrophic substance” Prog Neurobiol, vol. 46(6) pp. 607-636, 19952. R. Sanchez-Mejia and L. Mucke “Phospholipase A2 and arachidonic acid in Alzheimer/’s disease” Biochim Biophys Acta, vol. 1801(8) pp. 784-790, 20103. E. Bates “Eicosanoids, fatty acids and neutrophils: their relevance to the pathophysiology of disease” Prostaglandins Leukot Essent Fatty Acids, vol. 53pp.75–86, 19954. L. Levine “Proteasome inhibitors: Their effects on arachidonic acid release from cells in culture and arachidonic acid metabolism in rat liver cells” BMCPharmacology, vol. 4(15), 2004 |
