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Menadione Powder CAS 58-27-5
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Menadione Powder CAS 58-27-5

Menadione Powder CAS 58-27-5

Product Code: BM-2-3-043
English Name: Menadione
CAS No.: 58-27-5
Molecular formula: c11h8o2
Molecular weight: 172.18
EINECS No.: 200-372-6
MDL No.:MFCD00001681
Hs code: 28273985
Analysis items: HPLC>99.0%, LC-MS
Main market: USA, Australia, Brazil, Japan, Germany, Indonesia, UK, New Zealand , Canada etc.
Manufacturer: BLOOM TECH Changzhou Factory
Technology service: R&D Dept.-4

Shaanxi BLOOM Tech Co., Ltd. is one of the most experienced manufacturers and suppliers of menadione powder cas 58-27-5 in China. Welcome to wholesale bulk high quality menadione powder cas 58-27-5 for sale here from our factory. Good service and reasonable price are available.

 

Menadione powder, also known as Vitamin K3, is an organic compound with the chemical formula of c11h8o2, CAS 58-27-5. It is a yellow crystalline powder, almost odorless, hygroscopic and discoloured when exposed to light. It has a slight pungent smell. It is stable in air and decomposes in sunlight. 1g of the product is soluble in about 60ml ethanol, 10ml benzene, 50ml vegetable oil, chloroform and carbon tetrachloride. Soluble in water. Ethanol solution is neutral to litmus test paper. The solution will not decompose when heated to 120 ℃. It will be destroyed in case of alkali and reductant. Insoluble in ether and benzene. Clinically, it is a coagulant, which can be used to treat hemorrhagic diseases caused by vitamin K deficiency, such as neonatal hemorrhage, vitamin K deficiency caused by intestinal malabsorption, and prothrombin hypoemia.

 

Product Introduction

 

Chemical Formula

C11H8O2

Exact Mass

172

Molecular Weight

172

m/z

172 (100.0%), 173 (11.9%)

Elemental Analysis

C, 76.73; H, 4.68; O, 18.58

CAS 58-27-5 Menadione structure | Shaanxi BLOOM Tech Co., Ltd

Menadione | Shaanxi BLOOM Tech Co., Ltd

Applications

 

Menadione powder, also known as vitamin K3, with the chemical formula C11H8O2, is a white crystalline powder that is prone to moisture and clumping. It has good water solubility but is sensitive to light. It is a synthetic vitamin K analogue with wide applications in various fields such as biomedicine, chemical engineering, cosmetics, and pet food.

Menadione field | Shaanxi BLOOM Tech Co., Ltd

Biomedical field

1. Procoagulant drugs
Methylnaphthoquinone, as a procoagulant drug, has important clinical applications. It is an auxiliary factor in the synthesis of prothrombin and other coagulation factors (VII, IX, X) by the liver, which helps to normalize the blood clotting process. Methylnaphthoquinone is mainly used to treat hemorrhagic diseases caused by vitamin K deficiency, such as neonatal bleeding, vitamin K deficiency caused by intestinal malabsorption, and hypophrombinemia. Specific application scenarios include:

Treatment of hemorrhagic diseases: menaquinone can be used to treat bleeding in the lungs, stomach, hemorrhoids, trauma, and nose. It can also be used for bleeding in oral surgery, bone resection surgery, and abdominal organ surgery. For complex conditions such as functional uterine bleeding and excessive menstruation, menaquinone is also a part of the treatment.
Prevention and treatment of neonatal hemorrhagic diseases: menaquinone can be used for the treatment and prevention of neonatal hemorrhagic diseases.

Menadione disease | Shaanxi BLOOM Tech Co., Ltd
Menadione uses | Shaanxi BLOOM Tech Co., Ltd

In surgical procedures where severe parenchymal bleeding may occur, menaquinone can also be used preventively.

Treatment of Vitamin K Deficiency: Vitamin K deficiency includes obstructive jaundice, hepatitis, cirrhosis, long-term diarrhea, etc. Methylnaphthoquinone can improve vitamin K absorption disorders caused by poor bile excretion and treat diseases such as obstructive jaundice.
Treatment after overdose of vitamin K antagonist drugs: After overdose of vitamin K antagonist drugs (such as warfarin, benzodiazepine, and acenocoumarin), menaquinone can be used to correct hypophrombinemia.

Spasmodic and analgesic drugs:
Methylnaphthoquinone also has antispasmodic and analgesic effects, and can be used to treat pain caused by gastrointestinal spasms, biliary tract roundworms, or gallstones. Intramuscular injection of menaquinone, 8-16mg each time, can effectively alleviate pain symptoms.

Surgical adjuvant medication:
Medication of naphthoquinone for 2-3 days before and after surgery can promote intestinal peristalsis and advance the start of defecation, which is helpful for postoperative recovery.

Menadione treatment | Shaanxi BLOOM Tech Co., Ltd
Menadione medical | Shaanxi BLOOM Tech Co., Ltd

Other medical applications:
Rescuing poisoning caused by rodenticide "enemy rat sodium": When rescuing poisoning caused by rodenticide "enemy rat sodium", it is advisable to use high-dose menaquinone.
Diuretic and hypotensive functions: Metaquinone also has diuretic and hypotensive functions, which may have a certain adjuvant therapeutic effect on patients with hypertension and edema.

Chemical industry field

1. Colorants or food additives:
Methyl naphthoquinone has specific chemical properties that make it suitable for use as a coloring agent or food additive. However, for safety reasons, vitamin K3 has not been approved for use in human food (which has been proven to be harmful to the human body), but it may be used as a coloring agent or additive in the production of certain chemical products.

2. Biomedical research and technological innovation:
Menaquinone has also been applied in the development of biomedical research projects and innovation of cutting-edge biological technologies.

Menadione industrial | Shaanxi BLOOM Tech Co., Ltd
Menadione reagent | Shaanxi BLOOM Tech Co., Ltd

Researchers can use the specific chemical properties of naphthoquinone for drug development, biological activity testing, and other research.

3. Foreign Trade and Academic Exchange:
Methyl naphthoquinone is exported through foreign trade transactions or foreign trade companies to supply international research institutions with project development, academic experience exchange, and production and development of new products by foreign terminal biological companies. This will help promote the scientific research and application development of naphthoquinone worldwide.

Cosmetics field

1. Skin conditioner:
Naphthoquinone can be used as a skin conditioner in cosmetics. It has certain antibacterial properties and has inhibitory effects on various bacteria such as Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus. In addition, menaquinone has strong absorption in the UVB region and can be used for sunscreen products; It also has the function of whitening the skin and improving uneven skin tone. However, there is also some controversy surrounding the use of naphthoquinone in cosmetics, as its safety and efficacy need further validation.

2. Antibacterial ingredients:

Menadione skin | Shaanxi BLOOM Tech Co., Ltd
Menadione bacteria | Shaanxi BLOOM Tech Co., Ltd

Methyl naphthoquinone has inhibitory effects on various bacteria, including Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Candida albicans, Pseudomonas aeruginosa, Propionibacterium acnes, and Bacillus subtilis. The minimum inhibitory concentrations (MICs) were 4.0 μ g/ml, 4.0 μ g/ml, 2.0 μ g/ml, 64.0 μ g/ml, 4.0 μ g/ml, 2.0 μ g/ml, and 16.0 μ g/ml, respectively. This broad-spectrum antibacterial activity makes menaquinone useful in cosmetics for the prevention and treatment of diseases such as acne and skin cellulitis.
3. Inhibit dandruff generation:
Adding menaquinone to hair water can inhibit the formation of dandruff. This has certain help in improving scalp health and reducing dandruff problems.

Pet food field

1. Vitamin K supplements:
Menadione powder is usually added to commercial pet food as an inexpensive vitamin K supplement. Manufacturers claim that menaquinone is "more stable" and has "more nutritional value" than natural vitamin K, and even consider it "safe". The factors they considered include: the shelf life of naphthoquinone is longer than that of natural vitamin K; Natural vitamin K is prone to loss during processing; Pets with intestinal diseases can hinder the production of vitamin K by gut bacteria;

Menadione cell | Shaanxi BLOOM Tech Co., Ltd
Menadione risks | Shaanxi BLOOM Tech Co., Ltd

Not all manufacturers add leafy green vegetables to their ingredients; only when the amount added exceeds 1000 times is it toxic and considered safe within a reasonable range; The cost of vitamin K is low and the economic benefits are cost-effective.

2. Disputes and Risks
However, the application of naphthoquinone in pet food is also controversial and risky. Opponents argue that menaquinone has never been studied or specifically approved for long-term use in pet food; Due to serious side effects, including permanent damage and death, food and supplements for human use have been banned in many European countries;

Due to the high toxicity of synthetic vitamin K, the US FDA has banned synthetic vitamin K from over-the-counter supplements. Vitamin K ₁ and K ₂ are metabolized through the lymphatic system, utilizing pancreatic enzymes and bile acids, and regulated by the liver, while the metabolic pathways of naphthoquinone may be different; Naphthoquinone can greatly weaken the immune system; May cause skin allergic reactions; It will accumulate in the body for a long time and be detected in eggs, meat, and milk of animals that consume naphthoquinone derivatives.

Menadione pet | Shaanxi BLOOM Tech Co., Ltd
Menadione anti | Shaanxi BLOOM Tech Co., Ltd

Other potential applications

1. Anti cancer and anti-inflammatory properties (in vitro study):
Although vitamin K (including naphthoquinone) is harmful to humans, it has shown anti-cancer and anti-inflammatory properties in vitro studies. For example, the synergistic effect of vitamin C and vitamin K ≮ can inhibit and kill the growth of human breast cancer and prostate cancer cells; Vitamin K3 inhibits the growth of Helicobacter pylori in infected human gastric cells by reducing the replication ability of bacteria.

However, these benefits have not been proven in humans and there are toxic side effects.
2. Drug development and testing:
Menaquinone can also be used as a tool compound in drug development and testing. Researchers can use its specific chemical properties for drug activity testing, drug metabolism research, and more.

Menadione application | Shaanxi BLOOM Tech Co., Ltd

Manufacture Information

Menadione powder is prepared by oxidation and addition with o-methylnaphthoquinone as raw material.

Methyl naphthalene is oxidized with chromic anhydride:

Dissolve 2-methylnaphthalene in glacial acetic acid, stir and cool to below 40 ℃, slowly add the mixture of chromic anhydride and equal amount of water to maintain the temperature at 35-40 ℃. After addition, keep the temperature at 40 ℃ for 0.5h, raise the temperature to 70 ℃ for 45min, and then raise the temperature to 85 ℃ for 15min. Pour the reactant into a large amount of water and precipitate 2-menadione under continuous stirring. Filter, wash the filter cake repeatedly with water until the aqueous solution has no sour taste, and filter it dry to obtain 2-menadione. The yield was 51%. 2-methylnaphthalene can also be oxidized with sodium dichromate and potassium dichromate, and the yield is roughly the same.

Combination and chromic acid oxidation:

Toluene quinone is cyclized with butadiene to obtain 2-methylnaphthalene hydroquinone, which is then oxidized by chromic acid. Toluene quinone is added to glacial acetic acid to dissolve, butadiene is added, and the required amount is passed below 20 ℃. After 20 hours of airtight standing, heat to make the remaining butadiene escape, continue to heat to about 110 ℃, reflux for 3 hours, and then distill under reduced pressure to recover about 30% glacial acetic acid. Then cool it to below 40 ℃, slowly add the mixture of chromic acid and equal amount of water to keep the temperature at 65-70 ℃, after adding, keep it at 70-80 ℃ for 1h to produce menadione.

Optimized process:

Optimize the production process of vitamin K3. The optimized reaction conditions can be obtained by comparing the effects of raw material ratio, reaction temperature, reaction time and other factors on the yield of products. The experiment shows that under the best technological conditions (the mass ratio of 2-methyl-1,4-aminoquinone (2-mnq) to NaHSO3 is 1:1.5; M (2-mnq):v water / (g/ml) =1.5; M (2-mnq):v ethanol / (g/ml) =4.0; The reaction temperature is 52 ~ 55 ℃; The reaction time was 1H), and the yield of vitamin K3 was stable above 75%.

Menadione synthesis | Shaanxi BLOOM Tech Co., Ltd

Determination of vitamin K3

1. Spectrophotometry:

In the weak alkaline medium with pH of 8.7 ~ 9.5, vitamin K3 (VK3) can cause the fading reaction of methyl green. Its maximum fading wavelength is 630nm, and two new absorption peaks appear in the ultraviolet region, and its fading degree( Δ A) It is in direct proportion to the concentration of VK3 in the range of 0.11 ~ 2.40mg/l, and can be used for the spectrophotometric determination of VK3. The method has high sensitivity, and its apparent molar absorption coefficient ε 630=2.13 × 105L·mol-1·cm-1; Detection limit for VK3 (3 σ) Is 32.0 μ g/L. The method has good selectivity and can be used for the determination of VK3 in some pharmaceutical preparations and blood drugs.

2. Extraction spectrophotometry:

The reaction of vitamink3 (VK3) with basic dyes butyl rhodamine B (BRB), ethyl violet (EV) and methylene blue (MB) to form ion pair associate was studied, and the optimal reaction conditions were determined. A simple, rapid, selective and sensitive analytical method for the determination of VK3 was established. VK3 reacts with BRB, EV and MB to form ion pair Association compounds that can be extracted by organic solvents. The ion pair Association compounds have maximum absorption at 568, 613 and 658nm respectively, and their apparent Moore coefficients are 2.92 respectively × 104,6.96 × 104 and 4.85 × 104L·mol-1·cm-1;

 

The composition of ion pair Association compounds is 1:1, and the stability constants are 9.5 respectively × 105,1.9 × 106 and 7.8 × 105; The drug concentration in the range of 0.0083 ~ 13, 0.029 ~ 6.6 and 0.015 ~ 9.6 mg/l conforms to beer's law; The recovery is 96% - 103%. This method can be successfully applied to the determination of VK3 in pharmaceutical preparations.

3. Gas chromatography:

The compound multidimensional additive or premixed feed contains more vitamin E and Menadione powder. Because vitamin E is easy to be oxidized, it mainly exists in the form of its acetate. The content of vitamin E acetate is usually determined by high-performance liquid chromatography, colorimetry, fluorescence, etc. the samples need to be saponified, extracted, washed, concentrated and other pretreatment. The operation is cumbersome and takes a long time. In the production process, the quality of the products cannot be monitored in time, which makes the production and detection disconnected.

Frequently Asked Questions
 
 

What is menadione used for?

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Menadione is a fat-soluble vitamin precursor which is used for the prevention and control of bleeding associated with a low blood level of prothrombin or factor VII. It is also used for the treatment of patients with Vitamin K deficiency (too little vitamin K in the body).

Is menadione safe for humans?

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Menadione (vitamin K3 or 2-methyl-1,4-naphthoquinone) is a fat-soluble vitamin K analog that promotes the hepatic biosynthesis of blood clotting factors. Although menadione is considered to be unsafe for human use, it has been used as a vitamin K supplement.

What is another name for vitamin K3?

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Menadione

Menadione is a natural organic compound with the formula C6H4(CO)2C2H(CH3). It is an analog of 1,4-naphthoquinone with a methyl group in the 2-position. It is sometimes called vitamin K3. Use is allowed as a nutritional supplement in animal feed because of its vitamin K activity.

Which vitamin is menadione?

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Vitamin K3

Menadione (Vitamin K3) is a fat-soluble vitamin precursor that is converted into menaquinone in the liver. Vitamin K1 and K2 are the naturally occurring types of vitamin K.

What are the side effects of menadione?

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Liver toxicity, hemolytic anemia, allergic reactions, skin issues, gastrointestinal problems, blood clotting disturbances, and neurological symptoms are all possible side effects that should not be overlooked.

 

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