Skip to Content
Merck
All Photos(1)

Documents

M2939

Sigma-Aldrich

Methyl arachidonyl fluorophosphonate

≥98%, methyl acetate solution (10 mg/mL)

Synonym(s):

MAPF, Phosphonofluoridic acid, methyl-5Z,8Z,11Z,14Z-eicosatetraenyl ester

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C21H36FO2P
CAS Number:
188404-10-6
Molecular Weight:
370.48
EC Number:
201-185-2
MDL number:
MFCD03095722
UNSPSC Code:
41106300
PubChem Substance ID:
329817956
NACRES:
NA.77

Quality Level

200

Assay

≥98%

form

methyl acetate solution (10 mg/mL)

shipped in

dry ice

storage temp.

−70°C

SMILES string

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

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/b8-7-,11-10-,14-13-,17-16-

InChI key

KWKZCGMJGHHOKJ-ZKWNWVNESA-N

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.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H319,H336

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

Target Organs

Central nervous system

Supplementary Hazards

EUH066

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

3.2 °F - closed cup

Flash Point(C)

-16 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 1

1 of 1

Diethyl phosphite 98%

Sigma-Aldrich

D99234

Diethyl phosphite

Elizabeth R Cleverdon et al.
Bioorganic chemistry, 79, 98-106 (2018-05-09)
Ghrelin is a small peptide hormone that undergoes a unique posttranslational modification, serine octanoylation, to play its physiological roles in processes including hunger signaling and glucose metabolism. Ghrelin O-acyltransferase (GOAT) catalyzes this posttranslational modification, which is essential for ghrelin to
Rose Cairns et al.
Experimental cell research, 358(2), 397-410 (2017-07-18)
Annexin A6 (AnxA6) has been implicated in the regulation of endo-/exocytic pathways, cholesterol transport, and the formation of multifactorial signaling complexes in many different cell types. More recently, AnxA6 has also been linked to triglyceride storage in adipocytes. Here we
Yao-Fa Li et al.
In vitro cellular & developmental biology. Animal, 53(5), 421-429 (2017-04-30)
Prostaglandins (PGs) are oxygenated metabolites of arachidonic acid (AA) and two other C20 polyunsaturated fatty acids that serve as biochemical signals mediating physiological functions. We reported that PGs influence protein expression in insect cell lines, which prompted the question: do
Ryan M Wyatt et al.
The Journal of pharmacology and experimental therapeutics, 372(3), 339-353 (2019-12-11)
The serine hydrolase monoacylglycerol lipase (MAGL) is the rate-limiting enzyme responsible for the degradation of the endocannabinoid 2-arachidonoylglycerol (2-AG) into arachidonic acid and glycerol. Inhibition of 2-AG degradation leads to elevation of 2-AG, the most abundant endogenous agonist of the
Niina Aaltonen et al.
Biological procedures online, 22, 6-6 (2020-03-20)
Serine hydrolases (SHs) are a functionally diverse family of enzymes playing pivotal roles in health and disease and have emerged as important therapeutic targets in many clinical conditions. Activity-based protein profiling (ABPP) using fluorophosphonate (FP) probes has been a powerful
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service