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D0879

Sigma-Aldrich

Diisopropylfluorophosphate

Synonyme(s) :

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

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About This Item

Formule linéaire :
[(CH3)2CHO]2POF
Numéro CAS:
55-91-4
Poids moléculaire :
184.15
Numéro Beilstein :
1723307
Numéro CE :
200-247-6
Numéro MDL:
MFCD00008873
Code UNSPSC :
12352200
ID de substance PubChem :
24893303
Nomenclature NACRES :
NA.77

Source biologique

synthetic (organic)

Niveau de qualité

100

Pression de vapeur

0.58 mmHg ( 20 °C)

Forme

liquid

Indice de réfraction

n20/D 1.385 (lit.)

Point d'ébullition

62 °C/9 mmHg (lit.)

Pf

−82 °C (lit.)

Solubilité

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.)

Densité

1.06 g/mL at 25 °C (lit.)

Spectre d'activité de l'antibiotique

Gram-negative bacteria
Gram-positive bacteria

Mode d’action

protein synthesis | interferes

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

MUCZHBLJLSDCSD-UHFFFAOYSA-N

Informations sur le gène

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

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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

Actions biochimiques/physiologiques

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.

Remarque sur l'analyse

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

Autres remarques

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.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H300 + H310 + H330

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

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)
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)
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)
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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