M5625
Menadione
crystalline
Synonym(s):
2-Methyl-1,4-naphthoquinone, Vitamin K3
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About This Item
Empirical Formula (Hill Notation):
C11H8O2
CAS Number:
Molecular Weight:
172.18
UNSPSC Code:
12352205
NACRES:
NA.79
PubChem Substance ID:
EC Number:
200-372-6
Beilstein/REAXYS Number:
1908453
MDL number:
biological source
synthetic
Quality Level
assay
≥98.0% (HPLC)
form
crystalline
technique(s)
HPLC: suitable
color
faint green to green-yellow
mp
105-107 °C (lit.)
solubility
oil: soluble
storage temp.
room temp
SMILES string
CC1=CC(=O)c2ccccc2C1=O
InChI
1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3
InChI key
MJVAVZPDRWSRRC-UHFFFAOYSA-N
Gene Information
human ... NQO1(1728)
Application
Menadione has been used for the generation of reactive oxygen species (ROS), followed by flow cytometry analysis. It has also been used in microbiological evaluation, such as to detect fastidious microorganisms.
Biochem/physiol Actions
Menadione is an aromatic polycyclic ketone. It serves as a precursor for vitamin K synthesis. Menadione is converted to menaquinone-4, an active metabolite of vitamin K3. Menadione mediates cell death, by inducing the production of reactive oxygen species through the futile redox cycling.
Menadione (Vitamin K3) is a synthetic analogue of of 1,4-naphthoquinone with a methyl group in the 2-position. Menadione is used as a phosphatase inhibitor and an inhibitor of mitochondrial DNA polymerase γ (pol γ). Menadione can be used as an oxidative injury (free radical generator) inducing agent.
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Warning
Hazard Classifications
Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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Investigation of cultivable bacteria isolated from longstanding retreatment-resistant lesions of teeth with apical periodontitis
Signoretti Fernanda GC, et al.
Journal of Endodontics, 39(10), 1240-1244 (2013)
H Thor et al.
The Journal of biological chemistry, 257(20), 12419-12425 (1982-10-25)
The cytotoxic effects of many quinones are thought to be mediated through their one-electron reduction to semiquinone radicals, which subsequently enter redox cycles with molecular oxygen to produce active oxygen species and oxidative stress. The two-electron reduction of quinones to
Menadione triggers cell death through ROS-dependent mechanisms involving PARP activation without requiring apoptosis
Loor G, et al.
Free Radical Biology & Medicine, 49(12), 1925-1936 (2010)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| M5625-25G | 04061835546831 |
| M5625-100G | 04061835546824 |