M5625

Menadione

crystalline

• Synonyme(s) : 2-Methyl-1,4-naphthoquinone, Vitamin K₃
• Formule empirique (notation de Hill) : C₁₁H₈O₂
• Numéro CAS: 58-27-5
• Poids moléculaire : 172.18
• UNSPSC Code: 12352205
• NACRES: NA.79
• PubChem Substance ID: 24897023
• EC Number: 200-372-6
• Beilstein/REAXYS Number: 1908453
• MDL number: MFCD00001681

Propriétés

• biological source: synthetic
• Quality Segment: 200
• 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 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.

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.

Informations sur la sécurité

• 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
• Classe de stockage: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves