M5625

Menadione

crystalline

• Synonyma: 2-Methyl-1,4-naphthoquinone, Vitamin K₃
• Empirický vzorec (Hillův zápis): C₁₁H₈O₂
• Číslo CAS: 58-27-5
• Molekulová hmotnost: 172.18
• Beilstein/REAXYS Number: 1908453
• EC Number: 200-372-6
• MDL number: MFCD00001681
• UNSPSC Code: 12352205
• PubChem Substance ID: 24897023
• NACRES: NA.79

Vlastnosti

• 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)

Popis

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.

Bezpečnostní informace

• pictograms: GHS07,GHS09
• signalword: Warning
• hcodes: H302,H315,H317,H319,H335,H410
• pcodes: 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: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves