2,3,5,8-Tetrahydroxy-6-methyl-1,4-naphthalenedione

Base Information

• Chemical Name: 2,3,5,8-Tetrahydroxy-6-methyl-1,4-naphthalenedione
• CAS No.: 41768-12-1
• Molecular Formula: C11H8O6
• Molecular Weight: 0
• Mol file: 41768-12-1.mol

Synonyms:1,4-NAPHTHALENEDIONE,2,3,5,8-TETRAHYDROXY-6-METHYL;2,3,5,8-Tetrahydroxy-6-methylnaphthalene-1,4-dione;Methylspinazaline;Methylspinazarin;

Chemical Property of 2,3,5,8-Tetrahydroxy-6-methyl-1,4-naphthalenedione

Chemical Property:

• Vapor Pressure: 1.29E-18mmHg at 25°C
• Boiling Point: 670.9°C at 760 mmHg
• Flash Point: 373.6°C
• PSA: 115.06000
• Density: 1.759g/cm³
• LogP: 0.83430

Purity/Quality:

99% ^*data from raw suppliers

Methylspinazarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Methylspinazarin is a naphthoquinone bacterial metabolite that has been found in Streptomyces and is an inhibitor of catechol O-methyltransferase (COMT; IC50 = 0.8 μg/ml). It is selective for COMT over tyrosine hydroxylase, DOPA decarboxylase, and dopamine-β-hydroxylase at 100 μg/ml. Methylspinazarin decreases blood pressure in spontaneously hypertensive rats when administered at a dose of 50 mg/kg.

Technology Process of 2,3,5,8-Tetrahydroxy-6-methyl-1,4-naphthalenedione

There total 2 articles about 2,3,5,8-Tetrahydroxy-6-methyl-1,4-naphthalenedione 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: 88.0%

2-amino-3,5,8-trihydroxy-6-methyl-1,4-dihydronaphthalene-1,4-dione (1184950-97-7) + 3-amino-2,5,8-trihydroxy-6-methyl-1,4-dihydronaphthalene-1,4-dione (1184950-98-8) → methylspinazarin (41768-12-1)

Guidance literature:

With formic acid; sulfuric acid; dimethyl sulfoxide; In water; for 0.5h; Reflux;

DOI:10.1016/j.tetlet.2016.06.056

Reference yield: 67.0%

citraconic acid anhydride (616-02-4) + 1,2,3,4-tetramethoxybenzene (21450-56-6) → methylspinazarin (41768-12-1)

Guidance literature:

With aluminium trichloride; sodium chloride; at 180 - 190 ℃; for 0.0833333h;

upstream raw materials:

citraconic acid anhydride

1,2,3,4-tetramethoxybenzene

2-amino-3,5,8-trihydroxy-6-methyl-1,4-dihydronaphthalene-1,4-dione

3-amino-2,5,8-trihydroxy-6-methyl-1,4-dihydronaphthalene-1,4-dione

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