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Basic information

  • Name:
  • Menadione

  • CAS No.:
  • 58-27-5

  • Molecular Structure:
  • Formula:
  • C11H8O2
  • Molecular Weight:
  • 172.18 .
  • Synonyms:
  • 1,4-Naphthalenedione,2-methyl-;2-Methyl-1,4-naphthalenedione;Kipca;VK3;Karcon;Kayklot;Kanone;Kayquinone;Memodol;Menaquinone 0;Kappaxin;Aquakay;2-Methylnaphthoquinone;Menadionum;Klottone;Kappaxin (TN);3-Methyl-1,4-naphthoquinone;K-Thrombyl;2-Methyl-1,4-naphthochinon [German];Synkay;Methyl-1,4-naphthoquinone;Methyl-1,4-naphthalenedione;Usaf ek-5185;Kappaxan (VAN);Mitenone;2-Methyl-1,4-naftochinon [Czech];Prestwick_313;Menadion;2-Methyl-1,4-naphthochinon;Vitamin K3;1,4-Naphthoquinone, 2-methyl-;Juva-K;1,4-Naphthalenedione, 2-methyl-;Riboflavin (Vitamin B2);Kolklot;Vitamin K2 (0);Hemodal;1, 4-Naphthoquinone, 2-methyl-;Koaxin;Menaphthone;Kaykot;Menaphthon;MNQ;Kaergona;2-methyl-1,4-dihydronaphthalene-1,4-dione;
  • EINECS:
  • 200-372-6
  • Density:
  • 1.225 g/cm3
  • Melting Point:
  • 105-107 °C(lit.)
  • Boiling Point:
  • 304.5 °C at 760 mmHg
  • Flash Point:
  • 113.8 °C
  • Solubility:
  • insoluble in water
  • Appearance:
  • bright yellow crystals
  • Hazard Symbols:
  • HarmfulXn,IrritantXi
  • Risk Codes:
  • 22-36/37/38-43
  • Safety Description:
  • 26-36-37/39-24 Details

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Chemistry

IUPAC Name: 2-methylnaphthalene-1,4-dione 
Empirical Formula: C11H8O2
Molecular Weight: 172.18g/mol
EINECS: 200-372-6
Structure of Menadione (CAS NO.58-27-5):

Index of Refraction: 1.592
Molar Refractivity: 47.6 cm3
Molar Volume: 140.5 cm3
Polarizability: 18.87×10-24cm3
Surface Tension: 46.4 dyne/cm
Density: 1.225 g/cm3
Flash Point: 113.8 °C
Enthalpy of Vaporization: 54.49 kJ/mol 
Melting Point: 105-107 °C(lit.)
Boiling Point: 304.5 °C at 760 mmHg
Vapour Pressure: 0.000871 mmHg at 25°C 
Solubility: oil: soluble
Form: crystalline
Color: yellow
Water Solubility: INSOLUBLE
Sensitive: Light Sensitive 
Stability: Stable. May be light sensitive. Incompatible with strong oxidizing agents. 
Product Categories: Biochemistry;Vitamins;Nutritional fortification substances;Vitamins and derivatives;Vitamin Ingredients;Miscellaneous Compounds 
Canonical SMILES: CC1=CC(=O)C2=CC=CC=C2C1=O
InChI: 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

Uses

 Menadione (CAS NO.58-27-5) is used as a source of vitamin K in the treatment of hypoprothrombinemia against vitamin K deficiency.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LDLo intraperitoneal 100mg/kg (100mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 43, Pg. 125, 1940.
mouse LD50 intraperitoneal 50mg/kg (50mg/kg)   National Technical Information Service. Vol. AD691-490,
mouse LD50 oral 500mg/kg (500mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 43, Pg. 125, 1940.
mouse LD50 subcutaneous 138mg/kg (138mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 75, Pg. 111, 1942.
rabbit LDLo oral 230mg/kg (230mg/kg) VASCULAR: OTHER CHANGES Journal of Pharmacology and Experimental Therapeutics. Vol. 75, Pg. 111, 1942.
rat LD50 intraperitoneal 75mg/kg (75mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes: HarmfulXn,IrritantXi
Risk Statements: 22-36/37/38-43
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R43:May cause sensitization by skin contact.
Safety Statements: 26-36-37/39-24
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37/39:Wear suitable gloves and eye/face protection. 
S24:Avoid contact with skin.
WGK Germany: 3
RTECS: QL9100000
F: 8
Poison by ingestion, intraperitoneal, and subcutaneous routes. Experimental teratogenic effects. Questionable carcinogen with experimental tumorigenic data. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Standards and Recommendations

IDENTIFICATION: Conforms
ASSAY: 98.5 - 101.5%
RESIDUE ON IGNITION: 0.1% max
LOSS ON DRYING: 0.5% max
HEAVY METALS: 20ppm max

Specification

  Menadione , its cas register number is 58-27-5. It also can be called 1,4-Naphthalenedione, 2-methyl- ; 2-Methyl-1,4-naphthochinon ; 2-Methylnaphthoquinone ; 3-Methyl-1,4-naphthoquinone ; Aquakay ; Aquinone ; Kayquinone ; Kipca ;
 Kipca-oil soluble ; Memodol ; Menaquinone ; Mitenon ; Mitenone ; Panosine ; Thyloquinone ; Vitamin K3 . Menadione (CAS NO.58-27-5) is a bright yellow crystals.

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