Methyl arachidonate - Moligand™, ≥99%(GC) , CAS No.2566-89-4

CAS: 2566-89-4 Cat. No.: M138567 Molecular Weight: 318.49 Beilstein Registry Number: 1714445 EC Number: 219-900-1

GRADE & PURITY Moligand™, ≥99%(GC)

Synonyms

(5Z,8Z,11Z,14Z)-icosatetraenoate methyl ester | AKOS000201174 | cis-5,8,11,14-Eicosatetraenoic acidmethyl ester | (5Z,8Z,11Z,14Z)-Methylicosa-5,8,11,14-tetraenoate | 5,8,11,14-Eicosatetraenoic acid, methyl ester, (all-Z)- (8CI); Arachidonic acid, methyl e

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Arachidonic Acid methyl ester 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.
The keystone essential fatty acid at the origin of the arachidonic acid cascade.

Specifications

Synonyms

(5Z, 8Z, 11Z, 14Z)-icosatetraenoate methyl ester | AKOS000201174 | cis-5, 8, 11, 14-Eicosatetraenoic acidmethyl ester | (5Z, 8Z, 11Z, 14Z)-Methylicosa-5, 8, 11, 14-tetraenoate | 5, 8, 11, 14-Eicosatetraenoic acid, methyl ester, (all-Z)- (8CI); Arachidonic acid, methyl e

Specifications & Purity

Moligand™, ≥99%(GC)

Biochemical and Physiological Mechanisms

Unlike most unsaturated fatty acid methyl esters, arachidonic acid methyl ester is a potent activator of protein kinase C at 5 50 μM. At the low end of the effective concentration range, the effect is due to the cyclooxygenase product, while the lipoxygen

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Purity

≥99%(GC)

Names and Identifiers

• Pubchem Sid: 488195755
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488195755
• Canonical Smiles: CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC
• IUPAC Name: methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• InChIKey: OFIDNKMQBYGNIW-ZKWNWVNESA-N
• 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-
• Isomeric SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC
• Molecular Weight: 318.49
• Beilstein: 1714445
• Reaxy-Rn: 22931884
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=22931884&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Fatty Acyls
      • Subclass Fatty acid esters

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Fatty Acyls
• Subclass: Fatty acid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Fatty acid methyl esters
• Alternative Parents: Methyl esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Fatty acid methyl ester - Methyl ester - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as fatty acid methyl esters. These are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group.
• External Descriptors: fatty acid methyl ester

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in heptane (10 mg/ml), ethanol, DMSO, DMF, and ethanol:PBS(pH 7.2)(1:1) (~0.5 mg/ml).
• Sensitivity: Moisture sensitive
• Refractive Index: 1.49
• Boil Point(°C): 403.94 °C
• Molecular Weight: 318.500 g/mol
• XLogP3: 6.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 318.256 Da
• Monoisotopic Mass: 318.256 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 375.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 4
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 4
• Covalently-Bonded Unit Count: 1

References

1. Jinghan Cui, Wenjie Yu, Qifang Sun, Qiuning Wang, Jinwang Li, Xiali Guo, Yanling Song, Yan Li, Liping Luo.  (2025)  Response of quality differences of winter wheat from different origins to meteorological factors based on metabolomics.  FOOD CHEMISTRY,      [PMID:41391413] [10.1016/j.foodchem.2025.147539]