Menadione CAS 58-27-5
Introduction：Basic information about Menadione CAS 58-27-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Menadione Basic informationChemical properties Application Production
| 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;feeding additive raw materials;Inhibitors;RUMENSIN;Isolabel;Other APIs;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;58-27-5 |
| Mol File: | 58-27-5.mol |
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 |
| biological source | synthetic (organic) |
| Water Solubility | INSOLUBLE |
| Sensitive | Light Sensitive |
| Merck | 14,5831 |
| BRN | 1908453 |
| Stability: | Stable. May be light sensitive. Incompatible with strong oxidizing agents. |
| Major Application | pharmaceutical (small molecule) |
| Cosmetics Ingredients Functions | FRAGRANCE |
| InChI | 1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3 |
| InChIKey | MJVAVZPDRWSRRC-UHFFFAOYSA-N |
| SMILES | CC1=CC(=O)c2ccccc2C1=O |
| 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) |
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 |
| F | 8 |
| TSCA | TSCA listed |
| HazardClass | IRRITANT |
| HS Code | 29147000 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Aquatic Acute 1 Aquatic Chronic 1 Eye Irrit. 2 Skin Irrit. 2 Skin Sens. 1 STOT SE 3 |
| Hazardous Substances Data | 58-27-5(Hazardous Substances Data) |
| Toxicity | LD50 orally in mice: ~0.5 g/kg (Molitor, Robinson) |
| 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 notoccur naturally but is a common synthetic form called menadione (2-methyl-1,4-naphthoquinone). This compound forms a water-soluble sodium bisulfite additionproduct, menadione sodium bisulfite, whose practical utility is limited by its instability in complex matrices such as feeds. However, in the presence of excess sodiumbisulfite, it crystallizes as a complex with an additional mole of sodium bisulfite(i.e., menadione sodium bisulfite complex), which has greater stability, therefore, isused widely as a supplement to poultry feeds. A third water-soluble compound ismenadione 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 (vitaminK3), and a variety of menaquinones (vitamin K2).These quinones promote the synthesis of proteins thatare involved in the coagulation of blood.These proteinsinclude prothrombin, factor VII (proconvertin), factorIX (plasma thromboplastin). The vitamin K quinones are obtainedfrom three major sources.Vitamin K is present in variousplants, especially green vegetables. The menaquinonesthat possess vitamin K2 activity are synthesizedby bacteria, particularly gram-positive organisms;the bacteria in the gut of animals produce useful quantitiesof this vitamin.Vitamin K3 is a chemically synthesizedquinone that possesses the same activity as vitaminK1. |
| 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 bleedingtime. This hypoprothrombinemia may lead to hemorrhagefrom the gastrointestinal tract, urinary tract, andnasal mucosa. In normal, healthy adults, deficiency israre. The two groups at greatest risk are newborn infantsand patients receiving anticoagulant therapy; hypoprothrombinemiapreexists in these two groups. Anydisease that causes the malabsorption of fats may leadto deficiency. Inhibition of the growth of intestinal bacteriafrom extended antibiotic therapy will result in decreasedvitamin 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 vitaminK are given to the mother before birth. Althoughkernicterus may result, this can be prevented by usingvitamin K. |
| Safety Profile | Poison by ingestion,intraperitoneal, and subcutaneous routes.Experimental teratogenic effects.Questionable carcinogen with experimentaltumorigenic data. Human mutation datareported. When heated to decomposition itemits 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 | Chromium(VI) oxide-->Sodium dichromate dihydrate-->Potassium dichromate-->1,3-Butadiene-->1-Methylnaphthalene-->2-Methylnaphthalene-->Methylnaphthalene-->Sulfuric acid-->3,3'-DIMETHYLNAPHTHIDINE-->Hydrogen peroxide-->Acetic acid |
| Preparation Products | 2-Naphthalenemethanol-->Menatetrenone-->2-methylnaphthalene-1,4-diyl dibenzoate |
