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P7626

Sigma-Aldrich

Phenylmethanesulfonyl fluoride

powder, ≥98.5% (GC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C7H7FO2S
CAS Number:
329-98-6
Molecular Weight:
174.19
Beilstein:
2088311
EC Number:
206-350-2
MDL number:
MFCD00007424
UNSPSC Code:
12352202
PubChem Substance ID:
24898863
NACRES:
NA.77
Pricing and availability is not currently available.

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

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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.[1]
  • used as a supplement in nuclear protein extraction.[1][2]
  • inhibitor of cholesterol esterase (CE) and pseudocholinesterase (PCE).[3]
  • used for the collection of blood prior to centrifugation to quantify plasma ANP levels.[4]

Biochem/physiol Actions

Administration of PMSF produces analgesia unrelated to its anticholinesterase effect, and prolongs the analagesic effect of centrally administered β-endorphin.[5]

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

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Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H301,H314

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Estrogen receptors activate atrial natriuretic peptide in the rat heart.
Jankowski M, et al.
Proceedings of the National Academy of Sciences of the USA, 98(20), 11765-11770 (2001)
Salivary esterase activity and its association with the biodegradation of dental composites.
Finer Y and Santerre JP.
Journal of Dental Research, 83(1), 22-26 (2004)
Lise Boussemart et al.
Nature, 513(7516), 105-109 (2014-08-01)
In BRAF(V600)-mutant tumours, most mechanisms of resistance to drugs that target the BRAF and/or MEK kinases rely on reactivation of the RAS-RAF-MEK-ERK mitogen-activated protein kinase (MAPK) signal transduction pathway, on activation of the alternative, PI(3)K-AKT-mTOR, pathway (which is ERK independent)
Rui Chen et al.
The Journal of biological chemistry, 287(36), 30800-30811 (2012-07-19)
Hypoxia-inducible factors (HIFs) are oxygen-sensitive transcription factors. HIF-1α plays a prominent role in hypoxic gene induction. HIF-2α target genes are more restricted but include erythropoietin (Epo), one of the most highly hypoxia-inducible genes in mammals. We previously reported that HIF-2α
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Questions

1–6 of 6 Questions  

  1. At what temperature should the stock Product P7626, Phenylmethanesulfonyl fluoride (PMSF), be stored?

    1 answer

    1. A 200 mM PMSF solution in dry solvent has been reported to remain active for at least 9 months at
      2-8 °C. 100 mM PMSF solutions in isopropanol may be stored at –20 °C for several months. For more information please view the Product Data Sheet: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/348/427/p7626pis-ms.pdf

      Helpful?

  2. How should stock solutions of Product P7626,  Phenylmethanesulfonyl fluoride (PMSF), be stored?

    1 answer

    1. A 200 mM solution in dry solvent is stable for at least 9 months when stored at 2-8°C.

      Helpful?

  3. What is the Department of Transportation shipping information for this product?

    1 answer

    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

      Helpful?

  4. What is the effective amount of Product P7626,  Phenylmethanesulfonyl fluoride (PMSF), to be used?

    1 answer

    1. The effective concentration range is 0.1-1 mM. A final concentration of 5 mM was used for proteinase K inhibition.

      Helpful?

  5. What does Product P7626,  Phenylmethanesulfonyl fluoride (PMSF), inhibit?

    1 answer

    1. PMSF is a serine protease inhibitor, inhibiting the activity of enzymes such as thrombin, trypsin, papain, chymotrypsin and proteinase K. It also inhibits mammalian acetylcholinesterases.

      Helpful?

  6. How should Product P7626, Phenylmethanesulfonyl fluoride (PMSF), solutions be prepared?

    1 answer

    1. Stock solutions of 100-200 mM can be prepared in anhydrous isopropanol or anhydrous absolute ethanol. PMSF is unstable in the presence of water.

      Helpful?

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