methyl fluoro(icosa-5,8,11,14-tetraen-1-yl)phosphinate

• ChemBase ID: 128321
• Molecular Formular: C21H36FO2P
• Molecular Mass: 370.4815042
• Monoisotopic Mass: 370.24369524
• SMILES: FP(=O)(OC)CCCC/C=C/C/C=C/C/C=C/C/C=C/CCCCC
• Canonical SMILES: CCCCC/C=C/C/C=C/C/C=C/C/C=C/CCCCP(=O)(OC)F
• InChI: InChI=1S/C21H36FO2P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25(22,23)24-2/h7-8,10-11,13-14,16-17H,3-6,9,12,15,18-21H2,1-2H3
• InChIKey: KWKZCGMJGHHOKJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl fluoro(icosa-5,8,11,14-tetraen-1-yl)phosphinate; (icosa-5,8,11,14-tetraen-1-yl)(methoxy)phosphinoyl fluoride
• IUPAC Traditional name: methyl fluoro(icosa-5,8,11,14-tetraen-1-yl)phosphinate; icosa-5,8,11,14-tetraen-1-yl(methoxy)phosphinoyl fluoride
• Synonyms: MAPF; Phosphonofluoridic acid, methyl-5Z,8Z,11Z,14Z-eicosatetraenyl ester; Methyl arachidonyl fluorophosphonate; MAFP; Methoxy arachidonyl fluorophosphonate

Database IDs

• EC Number: 201-185-2
• MDL Number: MFCD03095722
• PubChem SID: 162222629
• PubChem CID: 10429254; 5353761
• CHEMBL: 113262
• Chemspider ID: 8604682
• Wikipedia Title: Methoxy_arachidonyl_fluorophosphonate

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 6.826752
• LogD (pH = 7.4): 6.826752
• Log P: 6.826752
• Molar Refractivity: 112.6768 cm^3
• Polarizability: 42.10538 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: methyl acetate solution
• Flash Point: -16 °C; 3.2 °F

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1231
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-36-66-67
• Safety Statements: 16-26-29-33
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H319-H336
• GHS Precautionary statements: P210-P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1231 3/PG 2
• Supplemental Hazard Statements: Repeated exposure may cause skin dryness or cracking.
• Storage Temperature: -70°C

Product Information

• Purity: ≥98%
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C21H36FO2P

DETAILS

Sigma Aldrich - M2939

Biochem/physiol Actions
MAFP is a selective, irreversible inhibitor of both calcium-dependent and calcium-independent cytosolic phospholipase A2, but not secretory phospholipase A2. MAFP is also a potent acetylcholinesterase inhibitor.
Preparation Note
To change the solvent, evaporate the methyl acetate under a gentle stream of nitrogen and immediately add the solvent of choice.