Chemical properties Application Production
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Menadione

Chemical properties Application Production
Product Name
Menadione
CAS No.
58-27-5
Chemical Name
Menadione
Synonyms
VK3;Kipca;Juva-K;Kanone;Karcon;Kareon;Kaykot;Koaxin;Synkay;Aquakay
CBNumber
CB4494726
Molecular Formula
C11H8O2
Formula Weight
172.18
MOL File
58-27-5.mol
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Menadione Property

Melting point:
105-107 °C(lit.)
Boiling point:
262.49°C (rough estimate)
Density 
1.1153 (rough estimate)
refractive index 
1.5500 (estimate)
storage temp. 
room temp
solubility 
oil: soluble
form 
crystalline
color 
yellow
Odor
Slight odor
Water Solubility 
INSOLUBLE
Sensitive 
Light Sensitive
Merck 
14,5831
BRN 
1908453
Stability:
Stable. May be light sensitive. Incompatible with strong oxidizing agents.
InChIKey
MJVAVZPDRWSRRC-UHFFFAOYSA-N
CAS DataBase Reference
58-27-5(CAS DataBase Reference)
NIST Chemistry Reference
Menadione(58-27-5)
EPA Substance Registry System
Menadione (58-27-5)
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Safety

Hazard Codes 
Xn,Xi
Risk Statements 
22-36/37/38-43
Safety Statements 
26-36-37/39-24
WGK Germany 
3
RTECS 
QL9100000
8
TSCA 
Yes
HazardClass 
IRRITANT
HS Code 
29147000
Hazardous Substances Data
58-27-5(Hazardous Substances Data)
Toxicity
LD50 orally in mice: ~0.5 g/kg (Molitor, Robinson)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
47775
Product name
Menadione (K3)
Purity
analytical standard
Packaging
1000 mg
Price
$26.3
Updated
2021/03/22
Sigma-Aldrich
Product number
M5625
Product name
Menadione
Purity
crystalline
Packaging
25g
Price
$54.6
Updated
2021/03/22
Sigma-Aldrich
Product number
M0300000
Product name
Menadione
Purity
European Pharmacopoeia (EP) Reference Standard
Price
$190
Updated
2021/03/22
Sigma-Aldrich
Product number
1381006
Product name
Menadione
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$366
Updated
2020/08/18
TCI Chemical
Product number
M0373
Product name
2-Methyl-1,4-naphthoquinone
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$57
Updated
2021/03/22
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Menadione Chemical Properties,Usage,Production

Chemical properties

It appears as white crystalline or crystalline powder, being almost odorless and hygroscopic. Its color will change in case of light. It is easily soluble in water, slightly soluble in ethanol, but insoluble in ether and benzene.

Application

Biochemical research; clinical drugs belong to fat-soluble vitamins; it is clinically used as a hemostatic drug.
Vitamin K3 is mainly used as poultry feed enhancer at a dosage of 1-5mg/kg.
The goods can have addition reaction with sodium bisulfite to generate vitamin K3.
VK3. Used as raw material of feed additives; it can mainly promote the liver synthesis of prothrombin in livestock and poultry, and promote the liver synthesis of plasma coagulation factors as a hemostatic agent.
Traits: bright yellow crystal with very spicy smell. It is stable in the air and will be decomposed in sunlight. 1G can be dissolved in about 60ml ethanol, 10ml benzene and 50 ml vegetable oil. It is soluble in chloroform and carbon tetrachloride but insoluble in water. The ethanol solution was neutral to litmus paper. The solution will not be decomposed even when heated to 120 °C. It will be destroyed upon treatment with alkali and reducing agent. It is toxic with the half lethal dose (mouse, oral) being about 500 mG/kG. It is irritating. Its commodities still include sodium bisulfite manaquinone, appearing as white crystalline powder. It has no smell or with slightly special smell. It has hygroscopicity. It undergoes decomposition in case of light to turn into yellow or purple color. It is easily soluble in water, slightly soluble in ethanol, but almost insoluble in ether and benzene. Application: biochemical research

Production

There are two production processes. 1. Methyl naphthalene is obtained from the oxidization of chromic anhydride. 2-methyl naphthalene is dissolved in glacial acetic acid, stirred and cooled to temperature below 40 ℃. Slowly add the mixture of chromic anhydride and the same amount of water so that the temperature can be maintained at 35-40 ℃. After the completion of the addition, maintain the temperature at 40 ℃ for 0.5 h, the temperature was then raised to 70 ℃ for 45min, and further heated to 85 ℃ for 15min. Pour the reactants into a lot of water and stir continuously to precipitate out the 2-naphthoquinone. Filter and rinse the filter cake repeatedly with water, until the aqueous solution has no sour. Filter to get the 2-menenoquinone with a yield of 51%. 2-methyl naphthalene can also be made from sodium dichromate and potassium dichromate with the oxidation yield being roughly the same. 2. Cyclohexanone has cyclization reaction with butadiene to get 2-methyl naphthalene hydroquinone, followed by oxidation with chromic acid to obtain the final product. Dissolve the toluquinone in glacial acetic acid; send the butadiene to the required amount at temperature below 20 ℃; stand for 20 hours; heat to release the remaining butadiene and continue to heat to about 110 °C for refluxing of 3 hours. Then recycle 30% of glacial acetic acid through vacuum distillation and cooled to temperature below 40 ℃; slowly add the mixture of chromic acid and the same amount of water so that the temperature is maintained at 65-70 ℃. After the completion of the addition, maintain the temperature at 70-80 degree for 1h to obtain the menadione.
O-methyl naphthoquinone is used as raw material. It undergoes oxidation with glacial acetic acid and chromic anhydride, followed by addition with sodium bisulfite in ethanol to derive it.

Chemical Properties

Bright yellow crystals

Physical properties

Appearance: phylloquinone is a yellow oil at room temperature, but the other vitamers K are yellow crystals. Solubility: the vitamers K and MK and most forms of menadione are insoluble in water, slightly soluble in ethanol, and readily soluble in ether, chloroform, fats, and oils. Stability: the vitamers K are sensitive to light and alkali, but are relatively stable to heat and oxidizing environments.
Menadione, the formal parent compound of the menaquinone series does not occur naturally but is a common synthetic form called menadione (2-methyl-1,4- naphthoquinone). This compound forms a water-soluble sodium bisulfite addition product, menadione sodium bisulfite, whose practical utility is limited by its instability in complex matrices such as feeds. However, in the presence of excess sodium bisulfite, it crystallizes as a complex with an additional mole of sodium bisulfite (i.e., menadione sodium bisulfite complex), which has greater stability, therefore, is used widely as a supplement to poultry feeds. A third water-soluble compound is menadione pyridinol bisulfite (MPB).

Originator

Kappaxin,Sterling Winthrop

Uses

Precursor to verious types of Vitamin K. Used as a micronutrient for livestock and pet foods.

Uses

prothrombogenic agent

Uses

antibacterial

Uses

The primary known function of vitamin K is to assist in the normal clotting of blood, but it may also play a role in normal bone calcification.

Uses

vitamin K helps promote blood clotting and has been used medically to reduce the possibility of bruising after surgery. It is being incorporated into cosmetic preparations, particularly those used for treating dark circles. It could also be used in acne products, and there are studies underway on its efficacy for the treatment of spider veins.

Uses

Menadione (Vitamin K) is a fat-soluble vitamin that is essential for blood clotting. It is destroyed by irradiation during processing but has no appreciable loss during storage. It occurs in spinach, cabbage, liver, and wheat bran.

Indications

Vitamin K activity is associated with several quinones, including phylloquinone (vitamin K1), menadione (vitamin K3), and a variety of menaquinones (vitamin K2). These quinones promote the synthesis of proteins that are involved in the coagulation of blood.These proteins include prothrombin, factor VII (proconvertin), factor IX (plasma thromboplastin). The vitamin K quinones are obtained from three major sources.Vitamin K is present in various plants, especially green vegetables. The menaquinones that possess vitamin K2 activity are synthesized by bacteria, particularly gram-positive organisms; the bacteria in the gut of animals produce useful quantities of this vitamin.Vitamin K3 is a chemically synthesized quinone that possesses the same activity as vitamin K1.

Definition

ChEBI: A member of the class of 1,4-naphthoquinones that is 1,4-naphthoquinone which is substituted at position 2 by a methyl group.

Manufacturing Process

Dissolve 100 g of β-methylnaphthalene in 500 g of carbon tetrachloride. Dissolve 500 g of commercial sodium dichromate in 175 g of hot water. Pour these two solutions into a 3-liter 3-necked flask, equipped with an efficient stirrer, a reflux condenser, and a dropping funnel. The flask should be put into a water bath held at 50°C. The contents of the flask agitated as violently as possible at adding (through the dropping funnel) 896 g of 77% (by weight) sulfuric acid. The rate of dropping depends on the efficiency of the reflux condenser. If the reaction tends to get out of hand due to overheating, cold water should be run into the water bath. After the addition of acid has been completed, keep the water bath at 70°C, for 1% to 2 hours. Then stop the agitation, cool the mixture and decant therefrom as much of the carbon tetrachloride layer as possible. Pour water into the flask; add 100 g more of carbon tetrachloride and stir for an additional ten minutes. The carbon tetrachloride layer will now settle to the bottom. The acid layer can be decanted and discarded, or worked up for those components desired. A complete separation of the acid from the carbon tetrachloride is effected by means of a separatory funnel. All of the carbon tetrachloride solutions are pooled and filtered to clarity through filter paper. The carbon tetrachloride may be distilled off from the quinone in a vacuum, using a water bath heated to 50°C.
The quinone is concentrated to a point where crystallization begins. Thereupon the concentrated solution is transferred to a beaker and allowed to crystallize at room temperature. Further crops of crystals are obtained by allowing the mother liquor to cool in an icebox, or by reducing it still further. If the β-methylnaphthalene starting material was pure, the 2-methyl-1,4- naphthoquinone obtained will have a melting point of 100°-104°C, without further purification. Vacuum sublimation has been found most effective to produce quinones of a very high purity. There is a rapid method of oxygenation of β-methylnaphthalene: 3 g of β-methylnaphthalene is dissolved in 180 grams of carbon tetrachloride. To this is added 15 grams of commercial sodium dichromate dissolved in 6 grams of hot water. The above solutions are placed in a 1-liter 3-necked flask equipped with an efficient stirrer, a dropping funnel, and a distilling condenser of large bore. The mixture is agitated energetically, and 25 grams of 77% sulfuric acid added through the dropping funnel. The time of addition need not be over 30 seconds. The flask is not subjected to exterior cooling, as the distilling carbon tetrachloride should hold the heat to the proper temperature, which should not exceed 85°C. After five minutes the reaction may be discontinued and the product handled similarly to the method outlined in above. The yield of 2-methyl-1,4-naphthoquinone will be around 80% of theoretical by the use of this rapid method.

brand name

Kappaxin (Sterling Winthrop); Kayquinone.

Therapeutic Function

Prothrombogenic vitamin

Hazard

Irritant to skin and mucous membranes, especially the alcoholic solution.

Pharmacology

The typical role of vitamin K is to maintain normal blood coagulation function. Its role is related to the metabolic processes.

Clinical Use

Vitamin K deficiency results in increased bleeding time. This hypoprothrombinemia may lead to hemorrhage from the gastrointestinal tract, urinary tract, and nasal mucosa. In normal, healthy adults, deficiency is rare. The two groups at greatest risk are newborn infants and patients receiving anticoagulant therapy; hypoprothrombinemia preexists in these two groups. Any disease that causes the malabsorption of fats may lead to deficiency. Inhibition of the growth of intestinal bacteria from extended antibiotic therapy will result in decreased vitamin K synthesis and possible deficiency.

Side effects

Toxicity of vitamin K has not been well defined. Jaundice may occur in a newborn if large dosages of vitamin K are given to the mother before birth. Although kernicterus may result, this can be prevented by using vitamin K.

Safety Profile

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.

Purification Methods

Recrystallise it from 95% EtOH, or MeOH after filtration. It forms bright yellow crystals which are decomposed by light. Its solubility in EtOH is 1.7% and in *C6H6 it is 10%. It IRRITATES mucous membranes and skin. [Fieser J Biol Chem 133 391 1940, Beilstein 7 IV 2430.]

Menadione Preparation Products And Raw materials

Raw materials

Preparation Products

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Menadione Suppliers

Hubei widely chemical technology Co., Ltd.
Tel
027-83991130-
Fax
027-83991130
Email
1718093273@qq.com
Country
China
ProdList
1978
Advantage
58
Wuhan Dingxintong Pharmaceutical Co. , Ltd.
Tel
027-52344656-
Fax
QQ 2796190295
Email
15871722230@163.com
Country
China
ProdList
946
Advantage
58
Beijing Comparison Pharmaceutical Technology Co., Ltd
Tel
010-52878169-
Email
sales@bjcomparison.com
Country
China
ProdList
2949
Advantage
58
Hubei huizepu Pharmaceutical Technology Co., Ltd
Tel
027-59212684-
Fax
QQ:2188308251
Email
p19107121455@163.com
Country
China
ProdList
1266
Advantage
58
Hubei Chenxin Pharmaceutical Co., Ltd.
Tel
Fax
QQ:2544920688
Email
like1076463918@163.com
Country
China
ProdList
2188
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
21-61259100-
Fax
86-21-61259102
Email
sh@meryer.com
Country
China
ProdList
40264
Advantage
62
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15877
Advantage
69
future industrial shanghai co., ltd
Tel
400-0066-400;021-60496031
Fax
021-55660885
Email
sales@jonln.com;sales@jonln.com
Country
China
ProdList
1999
Advantage
65
Alfa Aesar
Tel
400-610-6006; 021-67582000
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30159
Advantage
84
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View Lastest Price from Menadione manufacturers

WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Menadione/Vitamin K3 58-27-5
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2020-09-28
Baoji Guokang Bio-Technology Co., Ltd.
Product
Menadione 58-27-5
Price
US $110.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
100kg
Release date
2021-06-08
Hebei Yirun Sega Biological Technology Co. Ltd
Product
Vitamin K3 58-27-5
Price
US $15.00/KG
Min. Order
500KG
Purity
99%
Supply Ability
5ton/Month
Release date
2021-11-08

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