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D0879

Diisopropylfluorophosphate

synthetic (organic), serine proteases and acetylcholinesterase inhibitor, liquid

Synonym(s):

DFP, DIFP, Diisopropyl phosphorofluoridate, Phosphoric acid diisopropyl ester fluoride

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About This Item

Linear Formula:
[(CH3)2CHO]2POF
CAS Number:
55-91-4
Molecular Weight:
184.15
NACRES:
NA.77
PubChem Substance ID:
24893303
UNSPSC Code:
12352200
EC Number:
200-247-6
MDL number:
MFCD00008873
Beilstein/REAXYS Number:
1723307
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Product Name

Diisopropylfluorophosphate,

biological source

synthetic (organic)

Quality Level

100

vapor pressure

0.58 mmHg ( 20 °C)

form

liquid

refractive index

n20/D 1.385 (lit.)

bp

62 °C/9 mmHg (lit.)

mp

−82 °C (lit.)

solubility

anhydrous isopropanol: 0.1-0.5 M (stable for months if stored at -70 °C), H2O: 1.5% at 25 °C (very unstable (at pH 7.5, half-life = 1 hr); decomposed by alkali.)

density

1.06 g/mL at 25 °C (lit.)

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

CC(C)OP(F)(=O)OC(C)C

InChI

1S/C6H14FO3P/c1-5(2)9-11(7,8)10-6(3)4/h5-6H,1-4H3

InChI key

MUCZHBLJLSDCSD-UHFFFAOYSA-N

Gene Information

human ... ACHE(43), PTGS1(5742), PTGS2(5743)

Application

Diisopropylfluorophosphate has been used:
  • in combination with inactivated thrombin in Affi-Gel 10 column for the purification of recombinant human thrombomodulin with its chondroitin sulfate chain (shrTMCSA)
  • for inducing status epilepticus (SE) in adult rats
  • as an irreversible serine protease inhibitor in human neutrophil subcellular fractions

Biochem/physiol Actions

Potent inhibitor of serine proteases and acetylcholinesterase; inhibits cathepsin G, cholinesterase, coagulation factor Xa, leucocyte elastase, pancreatic elastase, tissue kallikrein, plasmin, subtilisin, and thrombin. Inhibits apoptosis induced by ricin and bacterial toxins.
Potent inhibitor of serine proteases such as trypsin and chymotrypsin, and of acetylcholinesterase; also inhibits cathepsin G, cholinesterase, coagulation factor Xa, leucocyte elastase, pancreatic elastase, tissue kallikrein, plasmin, subtilisin, and thrombin. Inhibition of acetylcholinesterase makes this compound especially toxic. Inhibits apoptosis induced by ricin and bacterial toxins.

Analysis Note

Typically used at a concentration of 0.10 mM. A safer alternative inhibitor for serine protease is phenylmethylsulfonyl fluoride (PMSF).

Other Notes

Stored properly at 2-8°C, in an unopened bottle, DIFP should be stable for a minimum of two years. DIFP
is unstable when exposed to moisture. DIFP will develop a dark yellow color upon decomposition.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 1 Oral - Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Information

监管及禁止进口产品

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Certificates of Analysis (COA)

Lot/Batch Number
MKDB1391
MKDB1390
MKDB4331
MKCX9985
MKCX8492

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Protocols

Thrombin from Bovine Plasma

Thrombin is an endolytic serine protease that selectively cleaves the Arg–Gly bonds of fibrinogen to form fibrin and release fibrinopeptides A and B.

牛血浆凝血酶

凝血酶是一种内溶性丝氨酸蛋白酶，可选择性裂解纤维蛋白原的精氨酸-甘氨酸键，从而形成纤维蛋白并释放纤维蛋白肽A和B。

Articles

Chymotrypsin

Analytical Enzyme Chymotrypsin: Chymotrypsin is produced in the acinar cells of the pancreas as the inactive precursor, chymotrypsinogen.

Elastase Function and Importance

Elastase application index for understanding leukocyte elastase, a 29KDa serine endoprotease.

Identification of a novel splice variant isoform of TREM-1 in human neutrophil granules
Baruah S, et al.
Journal of Immunology, 195(12), 5725-5731 (2015)
Inhibition of the prostaglandin EP2 receptor is neuroprotective and accelerates functional recovery in a rat model of organophosphorus induced status epilepticus
Rojas A, et al.
Neuropharmacology, 93, 15-27 (2015)
Özge Karayel et al.
Molecular & cellular proteomics : MCP, 19(9), 1546-1560 (2020-07-01)
Pathogenic mutations in the Leucine-rich repeat kinase 2 (LRRK2) are the predominant genetic cause of Parkinson's disease (PD). They increase its activity, resulting in augmented Rab10-Thr73 phosphorylation and conversely, LRRK2 inhibition decreases pRab10 levels. Currently, there is no assay to
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Global Trade Item Number

SKUGTIN
D0879-1G04061833558164