(icosa-5,8,11,14-tetraen-1-yl)(methoxy)phosphinoyl fluoride|icosa-5,8,11,14-tetraen-1-yl(methoxy)phosphinoyl fluoride|MAFP|Methoxy arachidonyl fluorophosphonate|methyl fluoro(icosa-5,8,11,14-tetraen...

Molecular Formula

C₂₁H₃₆FO₂P

Molecular Mass

370.4815042

Exact Mass

370.24369524

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

Canonic Smiles

CCCCC/C=C/C/C=C/C/C=C/C/C=C/CCCCP(=O)(OC)F

Isomeric Smiles

FP(=O)(OC)CCCC/C=C/C/C=C/C/C=C/C/C=C/CCCCC

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

6.826752

LogD (pH = 7.4)

6.826752

Log P

6.826752

Molar Refractivity

112.6768

Polarizability

42.10538

Polar Surface Area

26.3

Rotatable Bonds

Lipinski's Rule of Five

false

Commercial Catalog

Sigma Aldrich

M2939

IUPAC name

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

Synonyms

MAFPMethoxy arachidonyl fluorophosphonatePhosphonofluoridic acid, methyl-5Z,8Z,11Z,14Z-eicosatetraenyl esterMAPFMethyl arachidonyl fluorophosphonate

IUPAC Traditional name

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

PubChem CID

Chemspider ID

MDL Number

PubChem SID

Product Information

Empirical Formula (Hill Notation)

C21H36FO2P

Shipped in

dry ice

Purity

≥98%

GHS Hazard statements

H225-H319-H336

MSDS Link

Download link

Personal Protective Equipment

Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Storage Temperature

-70°C

European Hazard Symbols

Irritant (Xi)

Flammable (F)

German water hazard class

GHS Signal Word

Danger

Risk Statements

11-36-66-67

Packing Group

GHS Pictograms

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Flammable gases, category 1

Flammable aerosols, categories 1,2

Flammable liquids, categories 1,2,3

Self-reactive substances and mixtures, Types B,C,D,E,F

Pyrophoric liquids, category 1

Pyrophoric solids, category 1

Self-heating substances and mixtures

Substances and mixtures, which in contact with water, emit flammable gases, categories 1,2,3

Organic peroxides, Types B,C,D,E,F

UN Number

1231

GHS Precautionary statements

P210-P261-P305+P351+P338

Safety Statements

16-26-29-33

Hazard Class

Supplemental Hazard Statements

Repeated exposure may cause skin dryness or cracking.

RID/ADR

UN 1231 3/PG 2

Physical Property

Apperance

methyl acetate solution

Flash Point

-16 °C

3.2 °F

No Data Available

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No Data Available

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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.