ChemicalBook >  Product Catalog >  API >  Vitamins and Minerals medicines >  Vitamin C drugs >  Menadione

Menadione

Basic information Chemical properties Application Production Safety Related Supplier

Menadione Basic information

Product Name:
Menadione
CAS:
58-27-5
MF:
C11H8O2
MW:
172.18
EINECS:
200-372-6
Mol File:
58-27-5.mol
More
Less

Menadione Chemical Properties

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. 
Store at RT.
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)
More
Less

Safety Information

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)

MSDS

More
Less

Menadione Usage And Synthesis

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

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.

brand name

Kappaxin (Sterling Winthrop); Kayquinone.

Hazard

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

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.]

More
Less

MenadioneSupplierMore

Hubei widely chemical technology Co., Ltd. Gold
Tel:
027-83991130
Email:
1718093273@QQ.COM
Products Intro:
Product Name:2-Methyl-1,4-naphthoquinone
CAS:58-27-5
Purity:99.9% Package:1G 50G 1KG 25KG
Hubei Hongyuanda Biotechnology Co., Ltd. Gold
Tel:
Email:
3505191060@qq.com
Products Intro:
CAS:58-27-5
Purity:99%
Wuhan Dingtong Pharmaceutical Co., Ltd Gold
Tel:
027-59207795-
Email:
18327179646@163.com
Products Intro:
Product Name:Menadione
CAS:58-27-5
Purity:>98%
Hubei huizepu Pharmaceutical Technology Co., Ltd Gold
Tel:
1776-2444226-
Email:
17762444226@163.com
Products Intro:
Product Name:Menadione
CAS:58-27-5
Purity:>98%
J & K SCIENTIFIC LTD.
Tel:
010-82848833- ;010-82848833-
Email:
jkinfo@jkchemical.com;market6@jkchemical.com
Products Intro:
Product Name:2-Methyl-1,4-naphthoquinone, 98%
CAS:58-27-5
Purity:98% Package:100G;25G;5G
Basic information Chemical properties Application Production Safety Related Supplier