M5625

Menadione

crystalline

• Synonym(s): 2-Methyl-1,4-naphthoquinone, Vitamin K₃
• Empirical Formula (Hill Notation): C₁₁H₈O₂
• CAS Number: 58-27-5
• Molecular Weight: 172.18
• Beilstein: 1908453
• EC Number: 200-372-6
• MDL number: MFCD00001681
• UNSPSC Code: 12352205
• PubChem Substance ID: 24897023
• NACRES: NA.79

Properties

• 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)

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.

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 Information

• Pictograms: GHS07,GHS09
• Signal Word: Warning
• Hazard Statements: H302,H315,H317,H319,H335,H410
• Precautionary Statements: P261 - P273 - P280 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• 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 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