2-Methyl-1,4-naphthoquinone
2-Methyl-1,4-naphthoquinone
CAS: 58-27-5
Molecular Formula: C11H8O2
2-Methyl-1,4-naphthoquinone - Names and Identifiers
| Name | 2-Methyl-1,4-naphthoquinone |
| Synonyms | Menadione Vitamin K3 menaphthone weishengsK3 Vitamin K_3 Vitamin K2(0) menadione (k3) enadione (1.05793) Menadione (1.05793) MENADIONE,POWDER,USP MenadioneForBiochemistry 2-Methyl-1,4-naphthoquinone Phytomenadione EP Impurity A 2-Methyl-1,4-dihydronaphthalene-1,4-dione |
| CAS | 58-27-5 |
| EINECS | 200-372-6 |
| InChI | InChI=1/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3 |
| InChIKey | MJVAVZPDRWSRRC-UHFFFAOYSA-N |
2-Methyl-1,4-naphthoquinone - Physico-chemical Properties
| Molecular Formula | C11H8O2 |
| Molar Mass | 172.18 |
| Density | 1.1153 (rough estimate) |
| Melting Point | 105-107°C(lit.) |
| Boling Point | 262.49°C (rough estimate) |
| Water Solubility | INSOLUBLE |
| Solubility | Soluble in ethanol (1G/60 ML), benzene (1G/10 ML), chloroform, carbon tetrachloride and vegetable oil (1G/50 ML), etc., insoluble in water |
| Appearance | yellow viscous oily liquid |
| Color | yellow |
| Odor | Slight odor |
| Merck | 14,5831 |
| BRN | 1908453 |
| Storage Condition | room temp |
| Stability | Stable. May be light sensitive. Incompatible with strong oxidizing agents. |
| Sensitive | Light Sensitive |
| Refractive Index | 1.5500 (estimate) |
| MDL | MFCD00001681 |
| Physical and Chemical Properties | Melting point 105-108°C water-soluble INSOLUBLE |
| Use | Feed additive raw materials, mainly can promote the synthesis of prothrombin in the liver of livestock and poultry, and promote the synthesis of plasma coagulation factors in the liver |
2-Methyl-1,4-naphthoquinone - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R43 - May cause sensitization by skin contact |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S37/39 - Wear suitable gloves and eye/face protection S24 - Avoid contact with skin. |
| WGK Germany | 3 |
| RTECS | QL9100000 |
| FLUKA BRAND F CODES | 8 |
| TSCA | Yes |
| HS Code | 29147000 |
| Hazard Class | IRRITANT |
| Toxicity | LD50 orally in mice: ~0.5 g/kg (Molitor, Robinson) |
2-Methyl-1,4-naphthoquinone - Reference
| Reference Show more | 1. Zhang Yubin, Li Pingzi, Lei Yun, etc. Study on NADH mitochondria-mediated regeneration of yak meat based on lactate-LDH [J]. Journal of Agricultural Machinery, 2020, v.51(06):360-366. 2. Bear bean, Xie pen-jun, Sun Zhi-da. Protective effect of naphthoquinone MK-4 on carotenoid oxidation in simulated gastric juice [J]. Journal of Huazhong Agricultural University, 2020, v.39(02):108-117. 3. Jing Lan, Zhu Yuzhang, Wang Huamin, cow Xiaofan, Zhang Jian, high strength. Comparison of the stability of heterologously expressed Indigoidine in Escherichia coli and Indigo [J]. Microbiology, 2021,48(01):1-13. 4. Cheng Yuxin. Regulatory effect and mechanism of blueberry pomace fermented by Lactobacillus casei on intestinal barrier function in mice fed with high fat diet [D]. Huazhong Agricultural University, 2020. 5. Cheng Yuxin. Regulatory effect and mechanism of blueberry pomace fermented by Lactobacillus casei on intestinal barrier function in mice fed with high fat diet [D]. Huazhong Agricultural University, 2020. |
2-Methyl-1,4-naphthoquinone - Nature
Open Data Verified Data
white to light yellow crystalline powder, no or slightly odorous. Hygroscopic, decomposed in light. Soluble in water, ethanol-soluble, insoluble in ether or benzene.
Last Update：2024-01-02 23:10:35
2-Methyl-1,4-naphthoquinone - Preparation Method
Open Data Verified Data
with O-methyl naphthoquinone as raw material, prepared by oxidation and addition.
Last Update：2022-01-01 10:10:44
2-Methyl-1,4-naphthoquinone - Use
Open Data Verified Data
can promote the synthesis of prothrombin in the liver of livestock and poultry, and promote the synthesis of plasma coagulation factors in the liver.
Last Update：2022-01-01 10:10:45
2-Methyl-1,4-naphthoquinone - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | vitamin K3 is white or off-white crystalline powder, caking after moisture absorption, soluble in water and hot ethanol, insoluble in ice ethanol, insoluble in benzene and aqueous solution PH4.7-7. Stable at room temperature, easy to decompose when exposed to light. Vitamin K3 is a procoagulant, which can be used to treat some hemorrhagic diseases caused by vitamin K deficiency. Vitamin K3 is also called menadione, which can promote the formation of prothrombin, also has a diuretic effect, can reduce blood pressure, sometimes vitamin K3 is used as a coloring agent or food additives. |
| Source | vitamin K3 is derived from artificial synthesis. |
| physiological function and role | the specific function and role of vitamin K3 include the following aspects: first, promote blood coagulation, vitamin K3 is able to turn fibrinogen into fibrin. Two, involved in energy metabolism, vitamin K3 is an important component of the respiratory chain of cells is an intermediate product of oxidative phosphorylation in vivo. Three, increase muscle elasticity, vitamin K3 can promote intestinal peristalsis, stimulate the secretion of digestive glands, so that the digestive tract function is normal. Vitamin K3 is also used in clinic, mainly for the treatment of hypertension, Hiccup, acute pharyngitis eye obstruction. |
| Food contraindication | There are also many foods that cannot be consumed with vitamin K3. Such as fungus, black fungus can hinder blood coagulation, it is contrary to the role of vitamin K3, and rabbit meat, Hawthorn, rabbit meat lecithin content is higher, inhibit platelet aggregation, therefore, it weakens the function of vitamin K3. Similarly, Hawthorn has the effect of promoting blood circulation, and can not be consumed with vitamin K3. |
| usage limit | GB 14880-94: infant food, 420-750, V. G/kg. |
| note | when using vitamin K3 Note: 1. Can cause Nausea, Vomit and other gastrointestinal reactions. 2. High dose can cause hemolytic anemia, hyperbilirubinemia and jaundice in newborns and premature infants. Acute hemolytic anemia can be induced in patients with glucose -6-phosphate dehydrogenase deficiency. 3. May cause liver damage. Use with caution in patients with severe liver disease. |
| adverse reaction | vitamin K3 adverse reaction: 1. Visible local swelling and pain. 2, large doses can cause neonatal, premature hemolytic anemia, hyperbilirubinemia and jaundice. In patients with erythrocyte 6-phosphate dehydrogenase deficiency can induce acute hemolytic anemia. 3, the use of large doses can cause liver damage. Patients with hepatic insufficiency may switch to Vitamin K1. |
| Use | biochemical research, clinical medicine is fat-soluble vitamin, clinical as hemostatic. vitamin K3 is mainly used as a poultry feed fortifier. Dosage 1-5 mg/kg. VK3. Feed additive raw materials, mainly can promote the synthesis of prothrombin in the liver of livestock and poultry, and promote the synthesis of plasma coagulation factors in the liver, as a hemostatic agent. character: bright yellow crystal, with a very slightly spicy smell. Stable in air, decomposed in sunlight. 1g soluble in about 60ml ethanol, 10ml benzene, 50ml vegetable oil, soluble in chloroform and carbon tetrachloride. Insoluble in water. Ethanol solution was neutral to litmus paper. The solution did not decompose even when heated to 120 °c. In the case of alkali and reducing agent is destroyed. Toxic, median lethal dose (mice, oral) about 500mg/kG. Irritating. There are commercial sodium bisulfite Menadione, white crystalline powder. No odor or micro-special odor. Hygroscopic. Easily decomposed and turned yellow or purple when exposed to light. Soluble in water, ethanol-soluble, almost insoluble in ether and benzene. Purpose: biochemical research biochemical research. The product with sodium bisulfite addition of vitamin K3. |
| production method | with O-methyl naphthoquinone as raw material, after acetic acid and acetic anhydride oxidation in ethanol and sodium bisulfite addition. There are two production processes. Methyl naphthalene was obtained by oxidation with chromic anhydride. 2-methylnaphthalene was dissolved in glacial acetic acid, cooled to below 40 °c with stirring, and a mixture of chromic anhydride and an equal amount of water was slowly added to maintain the temperature at 35-40 °c. After addition, heat preservation at 40 ℃ for 0.5h, heating to 70 ℃ for 45min, then heating to 85 ℃ for 15min, pour the reactants into a large amount of water, 2-menadione was precipitated with constant stirring. Filter, the filter cake is washed repeatedly with water until the aqueous solution has no sour taste, and is filtered to obtain 2-menadione. The yield was 51%. 2-methylnaphthalene can also be oxidized with approximately the same yield using sodium dichromate and potassium dichromate. 2. 2-methylnaphthyl hydroquinone is obtained by cyclization of toluoquinone with butadiene, followed by oxidation with chromic acid. The methylbenzoquinone was added to glacial acetic acid to dissolve, and butadiene was introduced to the desired amount below 20 °c. After standing closed for 20h, the remaining butadiene was allowed to escape by heating and refluxed at about 110 ° C. For 3H. About 30% of glacial acetic acid was recovered by distillation under reduced pressure. Then, it is cooled to below 40 ° C., and a mixed solution of chromic acid and an equal amount of water is slowly added so that the temperature is maintained at 65-70 ° C. After addition, it is maintained at 70-80 for 1H to form menadione. 2-methylnaphthalene was oxidized by chromic anhydride and then reacted with sodium bisulfite. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:49:11
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