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Sigma
Diisopropylfluorophosphate
D0879
DOWNLOAD MSDS (PDF)Synonym: DFP, DIFP, Diisopropyl phosphorofluoridate, Phosphoric acid diisopropyl ester fluoride
CAS Number: 55-91-4
Linear Formula: [(CH3)2CHO]2POF
Molecular Weight: 184.15
Beilstein Registry Number: 1723307
EC Number: 200-247-6
MDL number: MFCD00008873
PubChem Substance ID: 24893303
Properties
| Related Categories | A to C, Acetylcholinesterase, Analytical Enzymes, Apoptosis Enzymes, Bioactive Small Molecules, |
| vapor pressure | 0.58 mmHg ( 20 °C) |
| refractive index | n |
| bp | 62 °C/9 mmHg(lit.) |
| mp | −82 °C(lit.) |
| solubility | anhydrous isopropanol: soluble0.1-0.5 M (stable for months if stored at -70 °C) |
| H2O: soluble1.5% 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.) |
| storage temp. | 2-8°C |
| Gene Information | Research your gene in Your Favorite Gene powered by Ingenuity human ... 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).
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.
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.
Price and Availability
Documents
Certificate of Analysis
Certificate of Origin
| Gene Information |
| Structure Search |  |
| Pressure-Temperature Nomograph |  |
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Safety Information
| Symbol |  GHS06 |
| Signal word | Danger |
| Hazard statements | H300-H310-H330 |
| Precautionary statements | P260-P264-P280-P284-P301 + P310-P302 + P350 |
| Personal Protective Equipment | Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter |
| Hazard Codes | T+ |
| Risk Statements | 26/27/28 |
| Safety Statements | 36/37/39-45 |
| RIDADR | UN 3382 6.1/PG 1 |
| WGK Germany | 3 |
| RTECS | TE5075000 |
Technical information & documentation associated with this product is available in the Safety & Documentation tab.
References
Cohen, J.A., et al. Meth. Enzymol. 11, 686, (1967)
Wilson, B.W. and Walker, C.R., Regulation of newly synthesized acetylcholinesterase in muscle cultures treated with diisopropylfluorophosphate. Proc. Natl. Acad. Sci. U. S. A. 71, 3194-3198, (1974) Abstract
, Beynon, R.J. and Bond, J.S., ed. Proteolytic Enzymes: A Practical Approach, (1989), 239-243
Powers, J.C. and Harper, J.W., Barrett, A.J., ed. Protease Inhibitors, (1986), 55-112
Oda, T., et al., Diisopropylfluorophosphate (DFP) inhibits ricin-induced apoptosis of MDCK cells. Biosci. Biotechnol. Biochem. 62, 325-333, (1998) Abstract
Terry, A.V., et al., Repeated, Intermittent Exposures To Diisopropylfluorophosphate In Rats: Protracted Effects On Cholinergic Markers, Nerve Growth Factor-related Proteins, And Cognitive Function. Neuroscience 176, 237-53, (2011) Abstract
Li, Y., et al., Spatiotemporal Pattern Of Neuronal Injury Induced By DFP In Rats: A Model For Delayed Neuronal Cell Death Following Acute OP Intoxication. Toxicol. Appl. Pharmacol. 253, 261-9, (2011) Abstract
Merck 14,5176
Beil. 1,IV,1480
Aldrich MSDS 1, 723:B / Corp MSDS 1 (1), 1297:C / IR-Spectra (2), 491:C / IR-Spectra (3), 554:C / NMR-Reference 2 (2), 872:D / RegBook 1 (1), 1117:D / Sax 6, 1667 / Structure Index 1, 173:A:2
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