Menadiol

Base Information

• Chemical Name: Menadiol
• CAS No.: 481-85-6
• Molecular Formula: C11H10 O2
• Molecular Weight: 174.199
• European Community (EC) Number: 207-573-8
• UNII: VQ093653DO
• DSSTox Substance ID: DTXSID5023247
• Nikkaji Number: J30.357G
• Wikipedia: Menadiol
• Wikidata: Q192430
• NCI Thesaurus Code: C73595
• Metabolomics Workbench ID: 53280
• ChEMBL ID: CHEMBL1405447
• Mol file: 481-85-6.mol

Synonyms:2-methyl-1,4-naphthohydroquinone;2-methyl-1,4-naphthoquinol;dihydrovitamin K3;menadiol;menadiol diphosphate;menadiol diphosphate ion;menadiol diphosphate, monosodium salt;menadiol diphosphate, tetrasodium salt;menadiol, (-1)-ion;menadiol, monopotassium salt;naphtadon;reduced menadione;Synkavit;Synkavite

Chemical Property of Menadiol

Chemical Property:

• Vapor Pressure: 1.08E-06mmHg at 25°C
• Melting Point: 181℃
• Refractive Index: 1.5250 (estimate)
• Boiling Point: 391.6°Cat760mmHg
• PKA: 10.62±0.50(Predicted)
• Flash Point: 199.5°C
• PSA: 40.46000
• Density: 1.274g/cm³
• LogP: 2.55940
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 174.068079557
• Heavy Atom Count: 13
• Complexity: 181

Purity/Quality:

98% ^*data from raw suppliers

2-Methyl-1,4-naphthalenediol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=CC=CC=C2C(=C1)O)O

Technology Process of Menadiol

There total 29 articles about Menadiol 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%

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

Guidance literature:

With sodium dithionite; In diethyl ether; water;

Reference yield: 60.0%

1-acetoxybuta-1,3-diene (1515-76-0,35694-19-0,35694-20-3) + 2-Methyl-1,4-benzoquinone (553-97-9) → 2-methyl-1,4-naphthohydroquinone (481-85-6)

Guidance literature:

In benzene; at 120 ℃; for 30h;

Reference yield:

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

Guidance literature:

With hydrogen cation; Rate constant;

DOI:10.1021/jm00158a010

upstream raw materials:

menadione

Cholesteryl acetate

1-nitro-2-methylnaphthalene

1,4-dimethoxy-2-methylnaphthalene

Downstream raw materials:

1,4-bis-butyryloxy-2-methyl-naphthalene

2-(2-cyclohexyliden-ethyl)-3-methyl-[1,4]naphthoquinone

2-methyl-3-(3,7,11,15-tetramethyl-hexadec-2t,6t,10c,14-tetraenyl)-[1,4]naphthoquinone

2-methyl-3-(3,7,11,15-tetramethyl-hexadec-2t,6c,10t,14-tetraenyl)-[1,4]naphthoquinone

Refernces

• 1、 Cui, Xing-Ri,Saito, Ryota,Kubo, Takatsugu,Kon, Daijiro,Hirano, Yuich,Saito, Setsuo. "Preparations of anthraquinone and naphthoquinone derivatives and their cytotoxic effects". . p. 302 - 314. Retrieved 2011.
• 2、 Dobrinescu, Claudiu,Iorgulescu, Elena E.,Mihailciuc, Constantin,MacOvei, Dan,Wuttke, Stefan,Kemnitz, Erhard,Parvulescu, Vasile I.,Coman, Simona M.. "One-pot hydroacetylation of menadione (vitamin K3) to menadiol diacetate (vitamin K4) by heterogeneous catalysis". . p. 1301 - 1306. Retrieved 2012.
• 3、 Kimura, Kimito,Hirota, Yoshihisa,Kuwahara, Shigefumi,Takeuchi, Atsuko,Tode, Chisato,Wada, Akimori,Osakabe, Naomi,Suhara, Yoshitomo. "Synthesis of Novel Synthetic Vitamin K Analogues Prepared by Introduction of a Heteroatom and a Phenyl Group That Induce Highly Selective Neuronal Differentiation of Neuronal Progenitor Cells". . p. 2591 - 2596. Retrieved 2017.
• 4、 Koehn, Jordan T.,Magallanes, Estela S.,Peters, Benjamin J.,Beuning, Cheryle N.,Haase, Allison A.,Zhu, Michelle J.,Rithner, Christopher D.,Crick, Dean C.,Crans, Debbie C.. "A Synthetic Isoprenoid Lipoquinone, Menaquinone-2, Adopts a Folded Conformation in Solution and at a Model Membrane Interface". . p. 275 - 288. Retrieved 2018.
• 5、 Bolitho, Elizabeth M.,Coverdale, James P. C.,Sadler, Peter J.,Schünemann, Volker,Wolny, Juliusz A.,Worby, Nathan G.. "Quinone Reduction by Organo-Osmium Half-Sandwich Transfer Hydrogenation Catalysts". . p. 3012 - 3023. Retrieved 2021/09/13.
• 6、 Gong, Qijie,Yang, Fulai,Hu, Jiabao,Li, Tian,Wang, Pengfei,Li, Xiang,Zhang, Xiaojin. "Rational designed highly sensitive NQO1-activated near-infrared fluorescent probe combined with NQO1 substrates in vivo: An innovative strategy for NQO1-overexpressing cancer theranostics". . . Retrieved 2021/07/25.