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Menadione

Basic information Chemical properties Application Production Safety Supplier Related

Menadione Basic information

Product Name:
Menadione
Synonyms:
  • enadione (1.05793)
  • weishengsK3
  • Phytomenadione EP Impurity A
  • MenadioneForBiochemistry
  • VITAMIN K3 = MENADIONE
  • Vitamin K3
  • menadione (k3)
  • MENADIONE,POWDER,USP
CAS:
58-27-5
MF:
C11H8O2
MW:
172.18
EINECS:
200-372-6
Product Categories:
  • Biochemistry
  • Vitamins
  • Nutritional fortification substances
  • Vitamins and derivatives
  • Vitamin Ingredients
  • Miscellaneous Compounds
  • Aromatics
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • RUMENSIN
  • Isolabel
  • Other APIs
  • Inhibitors
  • feeding additive raw materials
  • 58-27-5
Mol File:
58-27-5.mol
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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
LogP
2.200
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 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

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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

Menadione is a good hemostatic drug, its main function is to participate in the synthesis of thrombin, promote blood coagulation, can effectively prevent bleeding diseases, and also participate in the mineralization of bones. Menadione is also an important component of feed additives, an indispensable nutrient for the growth and development of livestock, and can also be used as plant growth regulators, promoters, herbicides, etc.

Production

Menadione is synthesized by oxidizing 2-methylnaphthalene with chromic anhydride and then reacting with sodium bisulfite.
Reaction: Dissolve 2-methylnaphthalene in glacial acetic acid, stir and cool to below 40°C, slowly add a mixture of chromic anhydride and an equal amount of water, and maintain the temperature at 35-40°C. After the addition, the temperature was kept at 40 °C for 0.5 h, then heated to 70 °C for 45 min, and then heated to 85 °C for 15 min. The reactant was poured into a large amount of water, and menadione was precipitated under constant stirring. After filtering, the filter cake was repeatedly washed with water until the aqueous solution had no sour taste, and then filtered to obtain Menadione. Yield 51%.

Description

Vitamin K is a general term referring to a group of naphthoquinone derivatives required in the diet for blood clotting. Menadione 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.

Chemical Properties

Bright-yellow crystals with a very faint acrid odour. Insoluble in water; soluble in benzene (1 g/10 mL), ethanol (1 g/60 mL), and vegetable oils (1g/50 mL); moderately soluble in carbon tetrachloride and chloroform. Stable in air; decomposed by sunlight; destroyed by alkalis and reducing agents.

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

Menadione is precursor to verious types of Vitamin K. It is of industrial importance as an intermediate in the synthesis of phylloquinone, and salts of its bisulfite adduct are used as stabilized forms in the animal feed industry. Commercially significant forms are menadione sodium bisulfite and menadione dimethyl pyrimidinol. Used as a micronutrient for livestock and pet foods.

Application

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. 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.

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: Menadione is a member of the class of 1,4-naphthoquinones that is 1,4-naphthoquinone which is substituted at position 2 by a methyl group. It is used as a nutritional supplement and for the treatment of hypoprothrombinemia. It has a role as a nutraceutical, a human urinary metabolite, an angiogenesis inhibitor, an EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor and an antineoplastic agent. It is a member of 1,4-naphthoquinones and a vitamin K.

Preparation

Menadione can be prepared by oxidizing 2-methylnaphthalene with chromic acid or hydrogen peroxide.

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.]

MenadioneSupplier

Hubei widely chemical technology Co., Ltd. Gold
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027-83991130 18627774460
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Products Intro
Product Name:2-Methyl-1,4-naphthoquinone
CAS:58-27-5
Purity:99.9% Package:1G 50G 1KG 25KG
Suzhou Laing Biological Technology Co., LTD Gold
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0512-62968256 18550502935
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Product Name:Menadione
CAS:58-27-5
Purity:98% Package:1kg;25kg
Hubei Wanye Zhongcheng Chemical Reagent Co., Ltd. Gold
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Product Name:Menadione
CAS:58-27-5
Purity:>98% Package:1KG/RMB 530;1KG10KG
Wuhan Dingxintong Pharmaceutical Co. , Ltd. Gold
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Products Intro
Product Name:2-Methyl-1,4-naphthoquinone
CAS:58-27-5
Purity:100 Package:98.5%—102.0% 可根据数量包装 Remarks:kg
Hubei wei shi reagent group ltd., company Gold
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Products Intro
Product Name:Menadione
CAS:58-27-5
Purity:98% Package:1瓶/RMB 585