| |
| 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. |
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) |
| Provider |
Language |
| SigmaAldrich |
English |
| ACROS |
English |
| ALFA |
English |
| |
| 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. |
| Description |
A general term referring to a group of naphthoquinone derivatives required in the diet for blood clotting. Vitamin K5 or medadione and its derivatives are synthetic, lipid-soluble compounds. |
| 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 |
| General Description |
Menadione is a prothrombogenic compound and belongs to the Vitamin K class of compounds, which are necessary for the biosynthesis of prothrombin and other blood clotting factors. It is used as a model quinone in cell culture and in vivo investigations. It is obtained as a catabolic product of phylloquinone and circulating precursor of tissue menaquinone-4 in rats.
|
| Hazard |
Irritant to skin and mucous membranes, especially the alcoholic solution. |
| Biochem/physiol Actions |
Menadione is an oxidative stress inducer. |
| 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 |
|
| Tag:Menadione(58-27-5) Related Product Information |
|
|
China (Mainland)
Premiumsupplier 
