D0879

Diisopropylfluorophosphate

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

• Synonym(s): DFP, DIFP, Diisopropyl phosphorofluoridate, Phosphoric acid diisopropyl ester fluoride
• 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

Properties

• Product Name: Diisopropylfluorophosphate,
• SMILES string: CC(C)OP(F)(=O)OC(C)C
• InChI key: MUCZHBLJLSDCSD-UHFFFAOYSA-N
• InChI: 1S/C6H14FO3P/c1-5(2)9-11(7,8)10-6(3)4/h5-6H,1-4H3
• biological source: synthetic (organic)
• 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
• Quality Level: 100
• Gene Information: human ... ACHE(43), PTGS1(5742), PTGS2(5743)

Description

Analysis Note

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

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)[1]
• for inducing status epilepticus (SE) in adult rats[2]
• as an irreversible serine protease inhibitor in human neutrophil subcellular fractions[3]

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.

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.

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H300 + H310 + H330
• pcodes: P260 - P262 - P264 - P280 - P302 + P352 + P310 - P304 + P340 + P310
• 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
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter