4923-55-1

Basic information

• Product Name: 2-hydroxyjuglone
• Synonyms: 2-hydroxyjuglone;2,5-Dihydroxy-1,4-naphthalenedione;2,5-Dihydroxy-1,4-naphthoquinone;2,5-Dihydroxynaphthalene-1,4-dione;2-HJ
• CAS NO: 4923-55-1
• Molecular Formula: C₁₀H₆O₄
• Molecular Weight: 190.153
• Mol File: 4923-55-1.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 430°Cat760mmHg
• Flash Point: 228°C
• Appearance: /
• Density: 1.639g/cm³
• Vapor Pressure: 3.71E-08mmHg at 25°C
• Refractive Index: 1.731
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-hydroxyjuglone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxyjuglone(4923-55-1)
• EPA Substance Registry System: 2-hydroxyjuglone(4923-55-1)

Safety Data

• Hazardous Substances Data: 4923-55-1(Hazardous Substances Data)

Usage

Uses

2,5-Dihydroxynaphthalene-1,4-dione is a useful reagent in the preparation of substituted 1,?4-?naphthoquinones, a potential anti-cancer agent.

InChI:InChI=1/C10H6O4/c11-6-3-1-2-5-9(6)7(12)4-8(13)10(5)14/h1-4,11-12H

Upstream product

• 71186-96-4 2-hydroxy-5-methoxynaphthalene-1,4-dione 
• 90771-97-4 2,3-Dihydro-naphtho-purpurin 
• 109621-28-5 5-hydroxy-2-(phenylamino)naphthalene-1,4-dione 
• 64-17-5 ethanol 
• 15255-29-5 2,3-epoxy-5-hydroxy-2,3-dihydro-1,4-naphthoquinone 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 18855-92-0 3-chlorojuglone 
• 15254-76-9 8-hydroxy-2-methoxynaphthalene-1,4-dione 
• 83-56-7 1,5-dihydroxynaphthalene 
• 4923-57-3 2-chlorojuglone 
• 15127-94-3 2-methoxy-5-hydroxy-1,4-naphthoquinone 
• 18512-17-9 2-(dimethylamino)-5-hydroxy-1,4-naphthalenedione 
• 49598-85-8 scytalone 
• 52431-65-9 3-Bromojuglone 

Downstream Products

• 123297-90-5 (–)-5-hydroxy-2-(1'-hydoxyethyl)naphtho[2,3-b]furan-4,9-dione 
• 1021299-35-3 (S)-NQ₈₀₁ MTPA ester 
• 62042-67-5 2,5-Dihydroxy-3-methyl-[1,4]naphthochinon 
• 123297-90-5 5-hydroxy-2-(1-hydroxyethyl)naphtho<2.3-b>furan-4,9-dione 
• 13378-90-0 6-Acetyl-2-hydroxy-juglon 
• 88497-92-1 diodantunezone 
• 137039-30-6 5-hydroxy-2-phenyl-1,4-naphthoquinone 

Relevant articles and documents

OXYDATION DU NAPHTALENEDIOL-1,5 PAR LE SUPEROXYDE DE POTASSIUM EN PHASE HETEROGENE

The oxydation of 1,5-dihydroxynaphthalene by potassium superoxide is essentially an interfacial solid/liquid reaction, which leads to 2,5- and 3,5-dihydroxy-1,4-naphthoquinones.The reaction proceeds in two steps through the formation of 5-hydroxy-1,4-naphthoquinone.The mechanism of the reaction is discussed.

Investigation of chemical reactivity of 2-alkoxy-1,4-naphthoquinones and their anticancer activity

To establish the structure-activity relationship of 5-hydroxy-1,4-naphthoquinones toward anticancer activity, a series of its derivatives were prepared and tested for the activity (IC50 in μM) against three cell lines; colo205 (colon adenocarcinoma), T47D (breast ductal carcinoma) and K562 (chronic myelogenous leukemia). Among them 2 (IC50: 2.3; 2.0; 1.4 μM), 6 (IC50: 1.9; 2.2; 1.3 μM), 9 (IC50: 0.7; 1.7; 0.9 μM) and 10 (IC50:1.7; 1.0; 1.2 μM) showed moderate to excellent activity. Our perception toward the DNA substitution of alkoxy groups at the C2 position of these naphthoquinones for the anticancer activity led us to investigate their reactivity of substitution toward dimethylamine as a nucleophile. The ease of the substitution of alkoxy groups at the C2 position with dimethylamine is strongly accelerated by hydroxyl group at C5 position and is well correlated with the found anticancer activity results.

Synthesis and cytotoxic activity of a small naphthoquinone library: First synthesis of juglonbutin

A synthetic protocol has been designed to synthesize grecoketidone (2k), 5-hydroxylapachol (2g), and the recently discovered natural products juglonbutin (2o) and its derivatives, leading to a small library of different 1,4-naphthoquinones with the intention of finding new active compounds. Within our collection, 2-O-alkylated naphthoquinones with an ester functionality in the side-chain and a free OH group at C-5 showed the best activities. Compounds 2f, 2m, and 2n showed GI50 values against 12 tumor cell lines in the lower micromolar range and juglonbutin (2o) showed remarkably efficient inhibition of the glycogen synthase kinase 3β with an IC50 value of 2.03 μM. Furthermore, studies on the mode of action of the most active cytotoxic compounds have been carried out. To the best of our knowledge, this is the first report on the synthesis of juglonbutin (2o) and its biological activity. Copyright