M5625

Menadion

crystalline

• Synonym(e): 2-Methyl-1,4-naphthochinon, Vitamin K₃
• Empirische Formel (Hill-System): C₁₁H₈O₂
• CAS-Nummer: 58-27-5
• Molekulargewicht: 172.18
• Beilstein: 1908453
• EG-Nummer: 200-372-6
• MDL-Nummer: MFCD00001681
• UNSPSC-Code: 12352205
• PubChem Substanz-ID: 24897023
• NACRES: NA.79

Eigenschaften

• Biologische Quelle: synthetic
• Qualitätsniveau: 200
• Assay: ≥98.0% (HPLC)
• Form: crystalline
• Methode(n): HPLC: suitable
• Farbe: faint green to green-yellow
• mp (Schmelzpunkt): 105-107 °C (lit.)
• Löslichkeit: oil: soluble
• Lagertemp.: 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
• InChIKey: MJVAVZPDRWSRRC-UHFFFAOYSA-N
• Angaben zum Gen: human ... NQO1(1728)

Beschreibung

Anwendung

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. Wirkung

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.

Sicherheitshinweise

• Piktogramme: GHS07,GHS09
• Signalwort: Warning
• H-Sätze: H302,H315,H317,H319,H335,H410
• P-Sätze: P261 - P273 - P280 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• Gefahreneinstufungen: Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3
• Zielorgane: Respiratory system
• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: dust mask type N95 (US), Eyeshields, Faceshields, Gloves