Menadione

Base Information

• Chemical Name: Menadione
• CAS No.: 58-27-5
• Molecular Formula: C11H8O2
• Molecular Weight: 172.183
• Hs Code.: 29147000
• European Community (EC) Number: 200-372-6
• NSC Number: 758200,4170
• UNII: 723JX6CXY5
• DSSTox Substance ID: DTXSID4021715
• Nikkaji Number: J4.591H
• Wikipedia: Menadione
• Wikidata: Q192471
• NCI Thesaurus Code: C66086
• Pharos Ligand ID: WVQKKNPRLQ3J
• Metabolomics Workbench ID: 37914
• ChEMBL ID: CHEMBL590
• Mol file: 58-27-5.mol

Synonyms:2-Methyl-1,4-naphthalenedione;2-Methyl-1,4-naphthoquinone;2-Methylnaphthoquinone;Bisulfite, Menadione;Bisulfite, Menadione Sodium;Menadione;Menadione bisulfite;Menadione sodium bisulfite;Menadione sodium bisulfite, trihydrate;Sodium Bisulfite, Menadione;Vicasol;Vikasol;Vitamin K 3;Vitamin K3;Vitamin K3 sodium bisulfite

Chemical Property of Menadione

Chemical Property:

• Appearance/Colour: bright yellow crystals
• Melting Point: 105-107 °C(lit.)
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 304.5 °C at 760 mmHg
• Flash Point: 113.8 °C
• PSA: 34.14000
• Density: 1.225 g/cm³
• LogP: 2.01190
• Storage Temp.: Store at RT.
• Sensitive.: Light Sensitive
• Solubility.: oil: soluble
• Water Solubility.: INSOLUBLE
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 172.052429494
• Heavy Atom Count: 13
• Complexity: 289

Purity/Quality:

99% ^*data from raw suppliers

VitaminK3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-43
• Safety Statements: 26-36-37/39-24

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Vitamins and Derivatives
• Canonical SMILES: CC1=CC(=O)C2=CC=CC=C2C1=O
• Recent ClinicalTrials: Menadione Topical Lotion in Treating Skin Discomfort and Psychological Distress in Patients With Cancer Receiving Panitumumab, Erlotinib Hydrochloride, or Cetuximab
• 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.
• 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).
• 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.
• 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.
• Therapeutic Function: Prothrombogenic vitamin
• 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.

Technology Process of Menadione

There total 163 articles about Menadione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2-methyl-5,6,9,10-tetrahydro-1,4-naphthoquinone → menadione (58-27-5,34524-96-4)

Guidance literature:

With palladium 10% on activated carbon; In acetone; for 24h; Reflux; Inert atmosphere;

DOI:10.1002/ejoc.201100740

Reference yield: 100.0%

2-methyl-1,4-naphthohydroquinone (481-85-6) → menadione (58-27-5,34524-96-4)

Guidance literature:

With iodate form of Amberlyst A₂₆; In dichloromethane; at 20 ℃; for 2h; further reagent;

Reference yield: 100.0%

2-Methylnaphthalene (91-57-6,34468-07-0) → menadione (58-27-5,34524-96-4)

Guidance literature:

With dihydrogen peroxide; acetic acid; In water; at 75 ℃; for 5h; Product distribution / selectivity;

upstream raw materials:

diazomethane

2-methyl-1,4-naphthohydroquinone

1-methoxy-4-nitronaphthalene

acetone

Downstream raw materials:

2-(4-methoxyphenyl)-3-methylnaphthalene-1,4-dione

2-methyl-3-methylthio-1,4-naphthoquinone

2‐benzyl‐3‐methylnaphthalene‐1,4‐dione

2-methyl-1,4-naphthohydroquinone

Refernces

• 1、 Urus, Serhan,Keles, Mustafa,Serindag, Osman. "Catalytic synthesis of 2-methyl-1,4-naphthoquinone (vitamin K3) over silica-supported aminomethyl phosphine-Ru(II), Pd(II), and Co(II) complexes". . p. 1416 - 1424. Retrieved 2010.
• 2、 Chambers,Chambers. "". . p. 2922,2923. Retrieved 1966.
• 3、 Tabushi et al.. "". . p. 6456. Retrieved 1977.
• 4、 Uru?, Serhan,?aylar, Mahmut,Ko?er, Ferudun. "Synthesis of crab type Aminomethyldiphosphine-Oxovanadium(IV) complexes supported on magnetic Nano particles: Selective and recoverable catalysts in vitamin K3 synthesis". . . Retrieved 2018.
• 5、 Gogin, L. L.,Zhizhina, E. G.. "Preparation of Vitamin K3 in Mo–V–P Heteropoly Acid Solutions by Diene Synthesis". . p. 276 - 282. Retrieved 2020.
• 6、 M?ller, Konstanze,Wienh?fer, Gerrit,Westerhaus, Felix,Junge, Kathrin,Beller, Matthias. "Oxidation of 1,2,4-trimethylbenzene (TMB), 2,3,6-trimethylphenol (TMP) and 2-methylnaphthalene to 2,3,5-trimethylbenzoquinone (TMBQ) and menadione (vitamin K3)". . p. 68 - 75. Retrieved 2011.
• 7、 Cohen,Lapidot. "". . p. 1210. Retrieved 1967.
• 8、 Li, Fanfan,Liu, Guoji,Xu, Li,Yu, Yi,Zang, Zhouxuan. "Highly efficient selective oxidation of 2-methylnaphthalene to vitamin K3 over mesoporous Al/Ti-SBA-15 catalysts: The effect of acid sites and textural property". . . Retrieved 2020.
• 9、 Kholdeeva, Oxana A.,Zalomaeva, Olga V.,Shmakov, Alexander N.,Melgunov, Maxim S.,Sorokin, Alexander B.. "Oxidation of 2-methyl-1-naphthol with H2O2 over mesoporous Ti-MMM-2 catalyst". . p. 62 - 68. Retrieved 2005.
• 10、 -. "Method for preparing 2-methyl-1,4-naphthoquinone under supercritical conditions". Paragraph 0030-0032. . Retrieved 2021/02/06.