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M5625 Sigma-Aldrich

Menadione

crystalline

Synonym: 2-Methyl-1,4-naphthoquinone, Vitamin K3

  • CAS Number 58-27-5

  • Empirical Formula (Hill Notation) C11H8O2

  • Molecular Weight 172.18

  •  Beilstein/REAXYS Number 1908453

  •  EC Number 200-372-6

  •  MDL number MFCD00001681

  •  PubChem Substance ID 24897023

  •  NACRES NA.79

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Properties

Related Categories Biochemicals and Reagents, Cell Biology, Cell Signaling and Neuroscience, Cell Stress, Lipids,
Quality Level   200
biological source   synthetic
assay   ≥98.0% (HPLC)
form   crystalline
application(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)

Description

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.

Packaging

25, 100 g in glass bottle

Biochem/physiol Actions

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.

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.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
QL9100000
Protocols & Articles
Peer-Reviewed Papers
15

References

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