Key Documents

View All Documentation

P7626

Phenylmethanesulfonyl fluoride

Name: Phenylmethanesulfonyl fluoride
Brand: SIGMA

powder, ≥98.5% (GC)

Synonym(s):

α-Toluenesulfonyl fluoride, Benzylsulfonyl fluoride, PMSF, Phenylmethylsulfonyl fluoride

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):

C₇H₇FO₂S

CAS Number:

329-98-6

Molecular Weight:

174.19

Beilstein/REAXYS Number:

2088311

NACRES:

NA.77

PubChem Substance ID:

24898863

UNSPSC Code:

12352202

EC Number:

206-350-2

MDL number:

MFCD00007424

Technical Service

Need help? Our team of experienced scientists is here for you.

Let Us Assist

Properties

Product Name

Phenylmethanesulfonyl fluoride, ≥98.5% (GC)

biological source

synthetic

Quality Level

300

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

Description

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

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.

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

Biochem/physiol Actions

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