Menadione epoxide

Base Information

• Chemical Name: Menadione epoxide
• CAS No.: 15448-59-6
• Molecular Formula: C₁₁H₈O₃
• Molecular Weight: 188.183
• NSC Number: 65669
• DSSTox Substance ID: DTXSID80934995
• Nikkaji Number: J103.791I
• ChEMBL ID: CHEMBL3220796
• Mol file: 15448-59-6.mol

Synonyms:2,3-epoxy-2,3-dihydro-2-methyl-1,4-naphthoquinone;menadione epoxide;menadione oxide;menadione-2,3-epoxide;NSC 65669;NSC-65669;vitamin K3 2,3-oxide

Chemical Property of Menadione epoxide

Chemical Property:

• Vapor Pressure: 2.74E-05mmHg at 25°C
• Melting Point: 100-101 °C
• Boiling Point: 357.4°Cat760mmHg
• Flash Point: 162.3°C
• PSA: 46.67000
• Density: 1.406g/cm³
• LogP: 1.22310
• Storage Temp.: ?20°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 188.047344113
• Heavy Atom Count: 14
• Complexity: 323

Purity/Quality:

99%min ^*data from raw suppliers

Vitamin K3 2,3-epoxide ≥98.5% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12C(O1)C(=O)C3=CC=CC=C3C2=O
• Uses: Menadione 2,3-Epoxide is a Vitamin K derivative found to induce selective tumor cytotoxicty in neublastoma as well as induce apotosis through activiation of ROS-dependent ERK and JNK protein phosphorylation.

Technology Process of Menadione epoxide

There total 6 articles about Menadione epoxide 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) → 2,3-epoxy-2-methyl-2,3-dihydro-1,4-naphthoquinone (15448-59-6,61840-91-3,82864-14-0,105016-62-4)

Guidance literature:

With dihydrogen peroxide; fipronilβ-cyclodextrin; In water; at 25 ℃; for 96h; pH 9; other reagents (t-BuOOH, NaOCl, PhC(CH₃)2OOH), MCPBA), other solvents (DMF, DMSO), addition of base (NaOH, NaHCO₃, Na₂CO₃);

DOI:10.1021/jo00310a018

Reference yield: 60.0%

2-methylnaphthalen-1-ol (7469-77-4) → 2,3-epoxy-2-methyl-2,3-dihydro-1,4-naphthoquinone (15448-59-6,61840-91-3,82864-14-0,105016-62-4) + menadione (58-27-5,34524-96-4) + 1,2-dihydro-2-tert-butylperoxo-2-methyl-1-oxonaphthalene (1113019-39-8)

Guidance literature:

With tert.-butylhydroperoxide; In acetonitrile;

DOI:10.1039/b821534k

Reference yield:

2-Methylnaphthalene (91-57-6,34468-07-0) → 2,3-epoxy-2-methyl-2,3-dihydro-1,4-naphthoquinone (15448-59-6,61840-91-3,82864-14-0,105016-62-4) + menadione (58-27-5,34524-96-4) + 3,3’-dimethyl-1,1’-binaphthalenylidene-4,4’-dione (14453-57-7)

Guidance literature:

With dihydrogen peroxide; In water; acetonitrile; at 80 ℃; for 24h; under 760.051 Torr; Temperature; Solvent;

DOI:10.1016/j.cattod.2014.12.026

upstream raw materials:

2-methyl-1,4-naphthohydroquinone

menadione

2-methylnaphthalen-1-ol

2-Methylnaphthalene

Downstream raw materials:

3-methyl-2-(phenylthio)-1,4-naphthoquinone

2-methyl-3-(4-bromophenylthio)-1,4-naphthalenedione

phthiocol

menadione

Refernces

• 1、 Maksimchuk, Nataliya V.,Ivanchikova, Irina D.,Cho, Kyung Ho,Zalomaeva, Olga V.,Evtushok, Vasiliy Yu.,Larionov, Kirill P.,Glazneva, Tatiana S.,Chang, Jong-San,Kholdeeva, Oxana A.. "Catalytic Performance of Zr-Based Metal–Organic Frameworks Zr-abtc and MIP-200 in Selective Oxidations with H2O2". . p. 6985 - 6992. Retrieved 2021/03/17.
• 2、 Maksimchuk, Nataliya V.,Evtushok, Vasilii Yu.,Zalomaeva, Olga V.,Maksimov, Gennadii M.,Ivanchikova, Irina D.,Chesalov, Yuriy A.,Eltsov, Ilia V.,Abramov, Pavel A.,Glazneva, Tatyana S.,Yanshole, Vadim V.,Kholdeeva, Oxana A.,Errington, R. John,Solé-Daura, Albert,Poblet, Josep M.,Carbó, Jorge J.. "Activation of H2O2over Zr(IV). Insights from Model Studies on Zr-Monosubstituted Lindqvist Tungstates". . p. 10589 - 10603. Retrieved 2021/09/02.