Merck
All Photos(3)

M5625

Sigma-Aldrich

Menadione

crystalline

Synonym(s):
Vitamin K3, 2-Methyl-1,4-naphthoquinone
Empirical Formula (Hill Notation):
C11H8O2
CAS Number:
Molecular Weight:
172.18
Beilstein:
1908453
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.79

Quality Level

biological source

synthetic

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)

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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.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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