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178385

Sigma-Aldrich

Apocynin

A cell-permeable, anti-inflammatory phenolic compound that acts as a potent and selective inhibitor of NADPH oxidase.

Synonym(s):

Apocynin, 4-Hydroxy-3-methoxyacetophenone, Acetovanillone, NADPH Oxidase Inhibitor V, NOX Inhibitor V

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About This Item

Empirical Formula (Hill Notation):
C9H10O3
CAS Number:
498-02-2
Molecular Weight:
166.17
MDL number:
MFCD00008747
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (GC)

form

powder

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white to off-white

solubility

DMSO: 10 mg/mL
ethanol: 20 mg/mL

shipped in

ambient

storage temp.

−20°C

InChI

1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3

InChI key

DFYRUELUNQRZTB-UHFFFAOYSA-N

General description

A cell-permeable, anti-inflammatory phenol that acts as a potent and selective inhibitor of NADPH oxidase. Also blocks peroxynitrite formation in murine macrophages. Reported to increase glutathione synthesis through the activation of AP-1. Shown to prevent phagocytosis of myelin by macrophages (10 mM).
A cell-permeable, anti-inflammatory phenolic compound that acts as a potent and selective inhibitor of NADPH oxidase. Shown to block peroxynitrite formation in murine macrophages. Reported to increase glutathione synthesis through activation of AP-1. Also reported to prevent phagocytosis of myelin by macrophages (10 mM).

Biochem/physiol Actions

Cell permeable: yes
Primary Target
NADPH oxidase
Product does not compete with ATP.
Reversible: no

Packaging

Packaged under inert gas

Warning

Toxicity: Irritant (B)

Reconstitution

Following reconstitution aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Abid, M.R., et al. 2000. FEBS Lett.486, 252.
Muijsers, R.B., et al. 2000. Br. J. Pharmacol.130, 932.
Lapperre, T.S., et al. 1999. FEBS Lett.443, 235.
Supinski, G., et al. 1999, J. Appl. Physiol.87, 776.
van der Goes, A., et al. 1998. J. Neuroimmunol.92, 67.
Hart, B.A., and Simmons, J.M. 1992. Biotechnol. Ther.3, 3.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

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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