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| CAS No.: | 58-27-5 |
|---|---|
| Name: | Menadione |
| Molecular Structure: | |
|
|
|
| Formula: | C11H8O2 |
| Molecular Weight: | 172.183 |
| 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: |
 Xn, Xi
|
| Risk Codes: | 22-36/37/38-43 |
| Safety: | 26-36-37/39-24 |
| PSA: | 34.14000 |
| LogP: | 2.01190 |
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| Conditions | Yield |
|---|---|
| With iodate form of Amberlyst A26 In dichloromethane at 20℃; for 2h; further reagent; | 100% |
| With sulfuric acid; sodium bromide In dichloromethane; water at 15℃; for 2.98h; Electrolysis; | 99% |
| With carbon dioxide; oxygen In water at 35 - 60℃; under 57005.7 - 62256.2 Torr; for 0.0833333h; Autoclave; | 96% |
| Conditions | Yield |
|---|---|
| With Co(salN-Medpt); oxygen In acetonitrile for 0.5h; | 100% |
| Stage #1: 2-methylnaphthalen-1-ol In acetonitrile at 74.84℃; Stage #2: With dihydrogen peroxide In acetonitrile for 0.75h; Reflux; chemoselective reaction; | 97.3% |
| With sulfuric acid; dihydrogen peroxide In water at 36 - 40℃; for 6h; Temperature; Solvent; Green chemistry; | 94.7% |
| Conditions | Yield |
|---|---|
| With dihydrogen peroxide; acetic acid In water at 75℃; for 5h; Product distribution / selectivity; | 100% |
| With C69H63Cl6N3O9(3-)*1.5Cu(2+); acetic acid In water at 40 - 100℃; for 14h; Catalytic behavior; Reagent/catalyst; Temperature; Concentration; | 93% |
| With dihydrogen peroxide; acetic acid In acetonitrile Catalytic behavior; Solvent; Reflux; | 93% |
- 58-27-5
menadione
| Conditions | Yield |
|---|---|
| With palladium 10% on activated carbon In acetone for 24h; Reflux; Inert atmosphere; | 100% |
| With sodium dichromate; sulfuric acid; acetic acid a) 80-90 deg C, 1 h, b) RT, 12 h; | 93% |
| With manganese(II) bromide; copper(I) bromide In dimethyl sulfoxide at 85℃; under 600.06 Torr; for 26h; Temperature; | 91.3% |
- 92071-59-5
C11H10O2
- 58-27-5
menadione
| Conditions | Yield |
|---|---|
| With palladium 10% on activated carbon In acetone Reflux; | 100% |
| Conditions | Yield |
|---|---|
| With sodium hydroxide In chloroform; water at 20℃; Product distribution / selectivity; | 100% |
| With water; sodium carbonate at 25℃; for 120h; Time; |
| Conditions | Yield |
|---|---|
| With carbon dioxide; oxygen In water at 37 - 80℃; under 60756.1 - 69757 Torr; for 0.125h; Pressure; Temperature; Autoclave; | 98.4% |
| With lithium perchlorate In acetonitrile; tert-butyl alcohol at 16 - 18℃; for 8.6h; electrolysis on Pt electrodes; | 94% |
| With chromium(VI) oxide; acetic acid at 20℃; |
- 16368-80-2
2-methyl-5,6,7,8-tetrahydronaphthalene-1,4-diol
- 58-27-5
menadione
| Conditions | Yield |
|---|---|
| With carbon dioxide; oxygen In water at 37 - 80℃; under 58505.9 - 72007.2 Torr; for 0.111111h; Autoclave; | 95.7% |
- 53772-19-3
1,4-dimethoxy-2-methylnaphthalene
- 58-27-5
menadione
| Conditions | Yield |
|---|---|
| With ammonium cerium(IV) nitrate In acetonitrile at 20℃; for 0.166667h; Oxidation; Demethylation; | 94% |
| With bis-[(trifluoroacetoxy)iodo]benzene In methanol; water at 20℃; for 0.5h; | 92% |
| With tert.-butylhydroperoxide; poly(bis-1,2-phenylene) diselenide In tert-butyl alcohol at 80℃; for 12h; | 90% |
| With ammonium persulfate; silver nitrate In water; acetonitrile for 18h; Ambient temperature; | 56% |
| Conditions | Yield |
|---|---|
| Stage #1: phthalic acid dimethyl ester; tert-butyl 3-cyanobutanoate With potassium tert-butylate In toluene at 100 - 105℃; for 3h; Green chemistry; Stage #2: With sodium hydroxide In water; toluene at 20 - 30℃; for 3h; Green chemistry; Stage #3: With hydrogenchloride In water; toluene at 60℃; for 3h; pH=2 - 2.5; Green chemistry; | 92.3% |
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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: 
Xn,
Xi
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.