methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate

• ChemBase ID: 131825
• Molecular Formular: C21H34O2
• Molecular Mass: 318.49346
• Monoisotopic Mass: 318.25588033
• SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC
• Canonical SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• IUPAC Traditional name: methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• Synonyms: Arachidonic acid methyl ester; Methyl arachidonate

Database IDs

• CAS Number: 2566-89-4
• EC Number: 219-900-1
• MDL Number: MFCD00016775
• Beilstein Number: 1714445
• PubChem SID: 162226102; 24891434
• PubChem CID: 6421258

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 6.7330647
• LogD (pH = 7.4): 6.7330647
• Log P: 6.7330647
• Molar Refractivity: 104.7231 cm^3
• Polarizability: 39.259087 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• UN Number: 3183
• German water hazard class: 3
• Hazard Class: 4.2
• Packing Group: 3
• Risk Statements: 19
• GHS Pictograms: GHS02
• GHS Signal Word: Warning
• GHS Hazard statements: H252
• GHS Precautionary statements: P235 + P410
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 3183 4.2/PG 3
• Supplemental Hazard Statements: May form explosive peroxides.
• Storage Temperature: -20°C

Product Information

• Purity: ~90% (capillary GC); ≥99% (capillary GC)

DETAILS

Sigma Aldrich - A9298

包装
Sealed ampule under vacuum.
Biochem/physiol Actions
Unlike most unsaturated fatty acid methyl esters, methyl arachidonate 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 cyclooxygenase products, while lipoxygenase products mediate the effect at higher concentrations.1

Sigma Aldrich - A4175

包装
Sealed ampule.
Biochem/physiol Actions
Unlike most unsaturated fatty acid methyl esters, methyl arachidonate 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 cyclooxygenase products, while lipoxygenase products mediate the effect at higher concentrations.1