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
VITAMIN K3;VITAMIN K;VK3;2-METHYL-1,4-NAPHTHOQUINONE;Menadion;2-METHYL-1,4-NAPHTHAQUINONE;Aquakay;Aquinone;Vitmin K3;menadione (k3)
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
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

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
Danger
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H335May cause respiratory irritation

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
M5625
Product name
Menadione
Purity
crystalline
Packaging
25g
Price
$67.6
Updated
2024/03/01
Sigma-Aldrich
Product number
47775
Product name
Menadione (K3)
Purity
analytical standard
Packaging
1000mg
Price
$34
Updated
2024/03/01
Sigma-Aldrich
Product number
1381006
Product name
Menadione
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$174.4
Updated
2024/03/01
TCI Chemical
Product number
M0373
Product name
2-Methyl-1,4-naphthoquinone
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$76
Updated
2024/03/01
TCI Chemical
Product number
M0373
Product name
2-Methyl-1,4-naphthoquinone
Purity
>98.0%(HPLC)(T)
Packaging
250g
Price
$567
Updated
2024/03/01
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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

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.]

Menadione Preparation Products And Raw materials

Raw materials

Preparation Products

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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
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Menadione (Vitamin K3) 58-27-5
Price
US $0.00/Kg/Bag
Min. Order
1KG
Purity
98.5%~101.0%; USP32
Supply Ability
5000kg/month
Release date
2021-06-03
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

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