Related Searches: Menadione

Menadione(CAS No. 58-27-5)

Menadione C11H8O2 (cas 58-27-5) Molecular Structure

58-27-5 Structure

Identification and Related Records

【Name】
Menadione
【CAS Registry number】
58-27-5
【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(EC#)】
200-372-6
【Molecular Formula】
C11H8O2 (Products with the same molecular formula)
【Molecular Weight】
172.18
【Inchi】
InChI=1/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3
【Canonical SMILES】
CC1=CC(=O)C2=CC=CC=C2C1=O
【MOL File】
58-27-5.mol

Chemical and Physical Properties

【Appearance】
Bright yellow crystals
【Density】
1.225 g/cm3
【Melting Point】
105-108℃
【Boiling Point】
304.5 °C at 760 mmHg
【Flash Point】
113.8 °C
【Water】
INSOLUBLE
【Solubilities】
Soluble
【Color/Form】
yellow
【Stability】
Stable. May be light sensitive. Incompatible with strong oxidizing agents.
【Storage temp】
Store at RT.
【Spectral properties】
MAX ABSORPTION (ALC): 246 NM (LOG E= 4.28); 262 NM (LOG E= 4.23) SHOULDER; 333 NM (LOG E= 3.42); SADTLER REF NUMBER: 8077 (IR, PRISM)
IR: 8522 (Sadtler Research Laboratories IR Grating Collection)
UV: 2183 (Sadtler Research Laboratories Spectral Collection)
NMR: 3217 (Sadtler Research Laboratories Spectral Collection)
MASS: 6783 (NIST/EPA/MSDC Mass Spectral Database, 1990 version)
【Computed Properties】
Molecular Weight:172.18002 [g/mol]
Molecular Formula:C11H8O2
XLogP3:2.2
H-Bond Donor:0
H-Bond Acceptor:2
Rotatable Bond Count:0
Tautomer Count:3
Exact Mass:172.05243
MonoIsotopic Mass:172.05243
Topological Polar Surface Area:34.1
Heavy Atom Count:13
Formal Charge:0
Complexity:289
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Ring Count:2
Effective Rotor Count:0
Conformer Sampling RMSD:0.4
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R22;R36/37/38;R43
【Safety Statements 】
S24;S26;S37/39
【HazardClass】
IRRITANT
【Safety】

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.

【Sensitive】
Light Sensitive
【Skin, Eye, and Respiratory Irritations】
Irritant to the skin and mucous membranes, especially the alcoholic solution.
【Formulations/Preparations】
MENADIONE, NF (VIT K3)...AVAIL IN ORAL ADMIN IN TABLETS CONTAINING 2, 5, OR 10 MG, & AS STERILE SOLN OF MENADIONE IN OIL (USUALLY 2, 10, OR 25 MG/ML) DESIGNED FOR IM ADMIN.
MENADIONE SODIUM BISULFITE, NF (HYKINONE)...WHITE CRYSTALLINE, HYGROSCOPIC POWDER. ...SOL IN WATER...MARKETED IN 5-MG TABLETS & IN AMPULS... 5-10 MG/ML. MENADIOL SODIUM DIPHOSPHATE INJECTION, NF (KAPPADIONE, SYNKAVITE)...AMPULS...5, 10, OR 37.5 MG/ML. MENADIOL SODIUM DIPHOSPHATE TABLETS, NF...5 MG...
MENADIOL SODIUM DIPHOSPHATE INJECTION, NF (KAPPADIONE, SYNKAVITE), IS MARKETED IN AMPULS CONTAINING 5, 10, OR 37.5 MG/ML. MENADIOL SODIUM DIPHOSPHATE TABLETS, NF, CONTAIN 5 MG OF SALT FOR ORAL USE.
Commercially significant forms are menadione sodium bisulfite and menadione dimethyl pyrimidinol.
Menadione is available as a 2, 5, and 10 mg tablet and as a 2 and 10 mg/mL injection (in oil).
Trade names for menadione include: Aquakay, Aquinone, Austrovit-K Depot, Hemodal, K-Thrombyl, K-Vitan, Kaergona, Kanone, Kaom Belgarum, Kappaxan, Kappaxin, Karanum, Karcon, Kareon, Kativ-G, Kavitamin, Kayklot, Kaykot, Kayquinone, Kipca, Kipca-Oil Soluble, Klottone, Koaxin, Kolklot, Menadion, Menaphthon, Menaphthone, Menaquinone 0, Mitenon, Mitenone, MNQ, Neo-Zimema-K, Panosine, Prokayvit, Synkay, Thyloquinone, Vikaman, Vita-Noxi K, and Vitavel-K.
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies discontinued drug products. Menadione is included on this list.
【Protective Equipment and Clothing】
Irritant to the skin and mucous membranes, especially the alcoholic solution.
【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.

【Octanol/Water Partition Coefficient】
log Kow = 2.20 @ pH 7.4
【Report】

Reported in EPA TSCA Inventory.

【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

It is obtained from 2-methylnaphthalene in 70-90% yield by oxidation with chromic acid. Slightly lower yields are obtained with chromium trioxide in conjunction with crown ethers.
【Usage】
Precursor to verious types of Vitamin K. Used as a micronutrient for livestock and pet foods.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Agents that prevent fibrinolysis or lysis of a blood clot or thrombus. Several endogenous antiplasmins are known. The drugs are used to control massive hemorrhage and in other coagulation disorders.
- Organic substances that are required in small amounts for maintenance and growth, but which cannot be manufactured by the human body.
【Therapeutic Uses】
The synthetic water soluble forms of vitamin K (menadione, menadiol) have long since been considered inferior to vitamin K1 (phytonadione) in the treatment of drug-induced hypoprothrombinemia.
Menadione (vitamin K3) a redox cycling quinone, is a clinically important chemotherapeutic agent. ... [Laux I, Nel A; Clin Immunol 101 (3): 335-44 (2001)]
【Biomedical Effects and Toxicity】
Menadione and its water soluble derivatives ... are absorbed even in the absence of bile ... /and/ enter the bloodstream directly.
Eighteen hr after intracardiac admin of (3)H-menadione ... to rats fed diet deficient in vit k, 78% of (3)H had been excreted in urine, 3% in feces, and 29% remained in animals. Biliary excretion ... observed in dogs, & 5-10% of (14)c had been excreted by this route 12 hr after oral dose of (14)C-menadione.
Vit k accum in liver, spleen, and lungs. /however/ significant amounts are not stored in body for long periods.
VET: ... Menadione or vit k3 absorbed is converted to k2 for utilization, otherwise it is rapidly eliminated via urine.
The pharmacokinetics of menadione (vitamin K3)... were studied in rabbits after iv injection of 75 mg menadiol sodium diphosphate (Synkayvite). ... Plasma clearance was 0.822 L/min. Systemic clearance in RBCs was 0.407 L/min. Apparent volume of distribution was 30.833 L in plasma and 20.488 L in RBCs. Area under the concn-time curve was 32.453 ug min/ml for plasma and 67.219 ug min/ml for RBCs. /Menadiol sodium diphosphate/ [Hu OY et al; Biopharm. Drug Dispos. 17: 493-499 (1996)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 370(SRC), determined from a log Kow of 2.20(2) and a regression-derived equation(3), indicates that menadione is expected to have moderate mobility in soil(SRC). Volatilization of menadione from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.1X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Menadione is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.9X10-4 mm Hg(SRC), determined from a fragment constant method(5).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 370(SRC), determined from a log Kow of 2.20(2) and a regression-derived equation(3), indicates that menadione is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.1X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 1.4(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), menadione, which has an estimated vapor pressure of 1.9X10-4 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), will exist in the vapor phase in the ambient atmosphere. Vapor-phase menadione is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 33 hrs(SRC), calculated from its rate constant of 1.1X10-11 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). Menadione is decomposed by sunlight(4).

Supplier Location

Top Suppliers

Diamond member Nanjing Bangnuo Biotechnology Co., Ltd
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-1732-7098554
Diamond member Wuhan Fortuna Chemical Co., Ltd.
Country:ChinaChina
Business Type:Manufacturer
Telephone:0086-27-59207850
Diamond member Hubei XinRunde Chemical Co., Ltd
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-188-74586545
Diamond member Wuhan H.X.K Fine Chemicals Co.,LTD
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-27-59721024
Diamond member Hangzhou Dayangchem Co., Ltd.
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-571-88938639
Diamond member Hangzhou Utanpharma biology co,.Ltd
Country:ChinaChina
Business Type:Trading Company
Telephone:86-571-87758773
Diamond member shijiazhuang guizheng trade co.,ltd
Country:ChinaChina
Business Type:Trading Company
Telephone:86-312-18103315327
Diamond member Nanjing Chemlin Chemical Co., Ltd.
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-25-83697070
Diamond member Jinlan Pharm-Drugs Technology Co., Limited
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-571-85829152
Diamond member Yichang yongnuopharm co.,ltd
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-717-4128488

Quick Search

Cas    Name

Related products

Menadione nicotinamide bisulfite

2-Methoxysulfonyltetralin-1,4-dione; pyridine-3-carboxamide;1,2,3,4-Tetrahydro-2-methyl-1,4-dioxonaphthalene-2-sulphonic acid,compound with nicotin-3-...

Menadione sodium bisulfite

1,2,3,4-Tetrahydro-2-methyl-1,4-dioxo-2-naphthalenesulfonic acid sodium salt;2,3-Dihydro-2-methyl-1,4-naphthoquinone-2-sulfonate sodium;Golagen K;Hyki...