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
• Numéro Beilstein : 1908453
• Numéro CE : 200-372-6
• Numéro MDL: MFCD00001681
• Code UNSPSC : 12352205
• ID de substance PubChem : 24897023
• Nomenclature NACRES : NA.79

Propriétés

• Source biologique: synthetic
• Pureté: ≥98.0% (HPLC)
• Forme: crystalline
• Technique(s): HPLC: suitable
• Couleur: faint green to green-yellow
• Pf: 105-107 °C (lit.)
• Solubilité: oil: soluble
• Température de stockage: room temp
• Chaîne SMILES: 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
• Clé InChI: MJVAVZPDRWSRRC-UHFFFAOYSA-N
• Informations sur le gène: 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.

Actions biochimiques/physiologiques

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.

Informations sur la sécurité

• Pictogrammes: GHS07,GHS09
• Mention d'avertissement: Warning
• Mentions de danger: H302,H315,H317,H319,H335,H410
• Conseils de prudence: P261 - P273 - P280 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• Classification des risques: Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3
• Organes cibles: Respiratory system
• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: dust mask type N95 (US), Eyeshields, Faceshields, Gloves