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Merck

178385

Sigma-Aldrich

Apocynin

≥98% (GC), powder, NADPH oxidase inhibitor, Calbiochem®

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:
Molecular Weight:
166.17
MDL number:
UNSPSC Code:
51111800
NACRES:
NA.77

Product Name

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

Quality Level

description

Merck USA index - 14, 741

Assay

≥98% (GC)

form

powder

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

off-white to brown

solubility

DMSO: 10 mg/mL
ethanol: 20 mg/mL

shipped in

ambient

storage temp.

−20°C

SMILES string

O(C)c1c(ccc(c1)C(=O)C)O

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 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

Preparation Note

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

Disclaimer

Toxicity: Irritant (B)

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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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Kendra M Prutton et al.
Free radical biology & medicine, 196, 11-21 (2023-01-14)
Cellular redox state directs differentiation of induced pluripotent stem cells (iPSC) by energy metabolism control and ROS generation. As oxidative stress and mitochondrial dysfunction have been extensively reported in Down syndrome (DS), we evaluated mitochondrial phenotypes and energy metabolism during
Yangyang Ding et al.
Nature communications, 14(1), 4829-4829 (2023-08-11)
Human MutT Homolog 1 (MTH1) is a nucleotide pool sanitization enzyme that hydrolyzes oxidized nucleotides to prevent their mis-incorporation into DNA under oxidative stress. Expression and functional roles of MTH1 in platelets are not known. Here, we show MTH1 expression
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STAR protocols, 3(1), 101053-101053 (2022-01-11)
Reactive oxygen species (ROS) are important physiological molecules, and identifying agonists for ROS production can yield useful tools for future research. Here we present an optimized protocol for high-throughput screening for agonists that induce ROS production. We describe the use

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