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D0879

Sigma-Aldrich

Diisopropylfluorophosphate

Synonym(s):
Diisopropyl phosphorofluoridate, Phosphoric acid diisopropyl ester fluoride, DFP, DIFP
Linear Formula:
[(CH3)2CHO]2POF
CAS Number:
Molecular Weight:
184.15
Beilstein:
1723307
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

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.)

Mode of action

protein synthesis | interferes

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

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

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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 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

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

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

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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...
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)
Recombinant human thrombomodulincsa+: a tool for analyzing Plasmodium falciparum adhesion to chondroitin-4-sulfate
Parzy D, et al.
Microbes and Infection, 2(7), 779-788 (2000)
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)
Asheebo Rojas et al.
Neurobiology of disease, 140, 104863-104863 (2020-04-14)
Seizures can be evident within minutes of exposure to an organophosphorus (OP) agent and often progress to status epilepticus (SE) resulting in a high mortality if left untreated. Effective medical countermeasures are necessary to sustain patients suffering from OP poisoning...

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