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P7626

Sigma-Aldrich

Phenylmethanesulfonyl fluoride

≥98.5% (GC)

Synonym(s):
α-Toluenesulfonyl fluoride, Benzylsulfonyl fluoride, PMSF, Phenylmethylsulfonyl fluoride
Empirical Formula (Hill Notation):
C7H7FO2S
CAS Number:
Molecular Weight:
174.19
Beilstein:
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
523327883093482
assay

≥98.5% (GC)

assay

≥99% (GC)

assay

≥99.0% (T)

assay

-

form

powder

form

crystalline solid

form

powder or crystals

form

liquid

mp

91-94 °C

mp

-

mp

92-95 °C

mp

-

solubility

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

solubility

ethanol: soluble, isopropanol: soluble, methanol: soluble

solubility

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

solubility

-

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

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral - Skin Corr. 1B

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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