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

Description

2-Hydroxyjuglone, also known as 2-hydroxy-1,4-naphthoquinone, is an organic compound derived from the naphthoquinone family. It possesses a hydroxyl group attached to the second carbon of the naphthalene ring, which contributes to its unique chemical properties and potential applications.

Uses

Used in Pharmaceutical Industry:
2-Hydroxyjuglone is used as a potential anti-cancer agent for its ability to inhibit cancer cell growth and proliferation. It is particularly effective against various types of cancer, including solid malignancies, due to its ability to interfere with essential cellular processes and signaling pathways in cancer cells.
Used in Chemical Synthesis:
2-Hydroxyjuglone is used as a reagent in the preparation of substituted 1,4-naphthoquinones, which are valuable compounds in the pharmaceutical and chemical industries. These substituted naphthoquinones have a wide range of applications, including their use as anti-cancer agents, due to their unique chemical structures and biological activities.

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

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

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.

Highly Efficient Synthesis and Structure–Activity Relationships of a Small Library of Substituted 1,4-Naphthoquinones

A platform of highly efficient synthetic methodologies has been established to access a focused library of substituted 1,4-naphthoquinones derivatives functionalized with a diversity of amino/hydroxy/alkyl groups. Furthermore, the structure–activity relationship deduced from antiproliferative activities and toxicities of this 1,4-naphthoquinone library and intracellular reactive oxygen species (ROS) level detections might warrant future potential of plumbagin (2) and compound 13 as promising basic structures to develop novel anti-cancer agents.

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