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P7626

Sigma-Aldrich

Phenylmethanesulfonyl fluoride

≥98.5% (GC)

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Synonym(s):
α-Toluenesulfonyl fluoride, Benzylsulfonyl fluoride, PMSF, Phenylmethylsulfonyl fluoride
Empirical Formula (Hill Notation):
C7H7FO2S
CAS Number:
Molecular Weight:
174.19
Beilstein/REAXYS Number:
2088311
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic

Quality Level

assay

≥98.5% (GC)

form

powder

mp

91-94 °C

solubility

dry solvents (ethanol, methanol, and 2-propanol): 200 mM (Stock solution are stable for months at 4°C.)
H2O: unstable

SMILES string

FS(=O)(=O)Cc1ccccc1

InChI

1S/C7H7FO2S/c8-11(9,10)6-7-4-2-1-3-5-7/h1-5H,6H2

InChI key

YBYRMVIVWMBXKQ-UHFFFAOYSA-N

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This Item
788305233293482
Phenylmethanesulfonyl fluoride ≥98.5% (GC)

P7626

Phenylmethanesulfonyl fluoride

Phenylmethanesulfonyl fluoride ≥99.0% (T)

78830

Phenylmethanesulfonyl fluoride

Phenylmethylsulfonyl Fluoride Phenylmethylsulfonyl Fluoride, CAS 329-98-6, is an irreversible inhibitor of serine proteases. It causes sulfonylation of the active-site serine residues.

52332

Phenylmethylsulfonyl Fluoride

biological source

synthetic

biological source

synthetic

biological source

-

biological source

microbial, synthetic

Quality Level

300

Quality Level

200

Quality Level

200

Quality Level

200

form

powder

form

powder or crystals

form

crystalline solid

form

liquid

solubility

dry solvents (ethanol, methanol, and 2-propanol): 200 mM (Stock solution are stable for months at 4°C.), H2O: unstable

solubility

anhydrous isopropanol: soluble 35 mg/mL, clear to faintly hazy, colorless to faintly yellow (Heating required)

solubility

ethanol: soluble, isopropanol: soluble, methanol: soluble

solubility

-

mp

91-94 °C

mp

92-95 °C

mp

-

mp

-

General description

Phenylmethanesulfonyl fluoride (PMSF) is a widely used serine protease inhibitor, effective against such enzymes as chymotrypsin, thrombin, and trypsin. PMSF acts as an inhibitor via sulfonation of the hydroxyl residues of serine residues at the reactive sites of serine proteases.

Application

PMSF is often used in lysis buffer to assist in preserving proteins of interest during protein isolation and sample preparation, by inhibiting proteases that would otherwise degrade proteins after cell or tissue lysis. PMSF is unstable in aqueous media. Thus stock solutions of PMSF are generally prepared in anhydrous organic solvents (e.g. 100% ethanol, or anhydrous isopropanol) prior to use in aqueous media.

Noted general features and benefits of PMSF include the following:
  • Inhibits serine proteases such as trypsin and chymotrypsin
  • Also inhibits cysteine proteases (reversible by reduced thiols) and mammalian acetylcholinesterase
  • Not as effective or as toxic as DFP
  • Effective concentration 0.1-1 mM
  • Half-life = 1 hr. at pH 7.5
Phenylmethanesulfonyl fluoride has been used in following applications:
  • cell fractionation.
  • used as a supplement in nuclear protein extraction.
  • inhibitor of cholesterol esterase (CE) and pseudocholinesterase (PCE).
  • used for the collection of blood prior to centrifugation to quantify plasma ANP levels.

Biochem/physiol Actions

Administration of PMSF produces analgesia unrelated to its anticholinesterase effect, and prolongs the analagesic effect of centrally administered β-endorphin.

related product

pictograms

CorrosionSkull and crossbones

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Skin Corr. 1B

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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C Pinsky et al.
Life sciences, 31(12-13), 1193-1196 (1982-09-20)
Intraperitoneal (IP) injection of the serine proteinase inhibitor phenylmethylsulfonyl fluoride (PMSF) produced dose-dependent analgesia in Sprague-Dawley rats. AD50 was 2.9 +/- 1.4 (S.E.) mg kg-1, the analgesia was antagonized by naloxone but unaffected by atropine. PMSF significantly enhanced the analgesic
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