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M2939

Sigma-Aldrich

Methyl arachidonyl fluorophosphonate

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

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C21H36FO2P
Número de CAS:
188404-10-6
Peso molecular:
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

signalword

Danger

Hazard Classifications

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

target_organs

Central nervous system

supp_hazards

EUH066

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

3.2 °F - closed cup

flash_point_c

-16 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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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
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