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D0879

Sigma-Aldrich

Diisopropylfluorophosphate

Sinónimos:

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

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About This Item

Fórmula lineal:
[(CH3)2CHO]2POF
Número de CAS:
55-91-4
Peso molecular:
184.15
Beilstein:
1723307
Número CE:
200-247-6
Número MDL:
MFCD00008873
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
24893303
NACRES:
NA.77

origen biológico

synthetic (organic)

Nivel de calidad

100

presión de vapor

0.58 mmHg ( 20 °C)

formulario

liquid

índice de refracción

n20/D 1.385 (lit.)

bp

62 °C/9 mmHg (lit.)

mp

−82 °C (lit.)

solubilidad

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.)

densidad

1.06 g/mL at 25 °C (lit.)

espectro de actividad antibiótica

Gram-negative bacteria
Gram-positive bacteria

Modo de acción

protein synthesis | interferes

temp. de almacenamiento

2-8°C

cadena 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

Clave InChI

MUCZHBLJLSDCSD-UHFFFAOYSA-N

Información sobre el gen

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

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Aplicación

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

Acciones bioquímicas o fisiológicas

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.

Nota de análisis

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

Otras notas

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.

Pictogramas

Skull and crossbones
GHS06

Palabra de señalización

Danger

Frases de peligro

H300 + H310 + H330

Clasificaciones de peligro

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

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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)
A molecular probe for the highly selective chromogenic detection of DFP, a mimic of Sarin and Soman nerve agents.
Raúl Gotor et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(43), 11994-11997 (2011-09-17)
Yonggang Li et al.
Toxicology and applied pharmacology, 262(2), 194-204 (2012-05-16)
Current medical countermeasures against organophosphate (OP) nerve agents are effective in reducing mortality, but do not sufficiently protect the CNS from delayed brain damage and persistent neurological symptoms. In this study, we examined the efficacy of neuregulin-1 (NRG-1) in protecting
A V Terry et al.
Neurotoxicology and teratology, 34(1), 1-8 (2011-10-26)
The acute toxicity of organophosphates (OPs) has been studied extensively; however, much less attention has been given to the subject of repeated exposures that are not associated with overt signs of toxicity (i.e., subthreshold exposures). The objective of this study
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Analytical Enzyme Chymotrypsin: Chymotrypsin is produced in the acinar cells of the pancreas as the inactive precursor, chymotrypsinogen.

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Trypsin is an enzyme in the serine protease class that consists of a polypeptide chain of 223 amino acid residues. Multiple sources, grades and formulations of trypsin specifically designed for research applications are available.

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