17648-03-2

Basic information

• Product Name: 2,3-DIHYDRO-9,10-DIHYDROXY-1,4-ANTHRACENEDIONE
• Synonyms: 2,3-dihydro-9,10-dihydroxy-4-anthracenedione;4-Anthracenedione,2,3-dihydro-9,10-dihydroxy-1;9,10-DIHYDROXY-2,3-DIHYDRO-ANTHRACENE-1,4-DIONE;2,3DIHYDRO-1,4-DIHYDROXY-9,10-ANTHRACENEDIONE;2,3-DIHYDRO-9,10-DIHYDROXY-1,4-ANTHRACENEDIONE;1,4-DIHYDROXY-2,3-DIHYDRO ANTHRAQUINONE;2,3-dihydro-9,10-dihydroxyanthracene-1,4-dione;2,3-Dihydroxy-9,10-dihydroxy-1,4-anthracenedione
• CAS NO: 17648-03-2
• Molecular Formula: C₁₄H₁₀O₄
• Molecular Weight: 242.23
• EINECS: 207-507-8
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 17648-03-2.mol

Chemical Properties

• Melting Point: 154-157 °C(lit.)
• Boiling Point: 575.8 °C at 760 mmHg
• Flash Point: 316 °C
• Appearance: /
• Density: 1.511 g/cm³
• Vapor Pressure: 7.4E-14mmHg at 25°C
• Refractive Index: 1.744
• PKA: 7?+-.0.20(Predicted)
• CAS DataBase Reference: 2,3-DIHYDRO-9,10-DIHYDROXY-1,4-ANTHRACENEDIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIHYDRO-9,10-DIHYDROXY-1,4-ANTHRACENEDIONE(17648-03-2)
• EPA Substance Registry System: 2,3-DIHYDRO-9,10-DIHYDROXY-1,4-ANTHRACENEDIONE(17648-03-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 24/25-26
• WGK Germany: 3
• Hazardous Substances Data: 17648-03-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Aloe-emodin is used as a therapeutic agent for its anti-inflammatory, anti-bacterial, anti-viral, and anti-cancer properties. It is particularly effective in inhibiting the growth of tumor cells, making it a potential candidate for cancer treatment.
Used in Anti-cancer Applications:
Aloe-emodin is employed as an anti-cancer agent, targeting various types of cancer cells and exhibiting inhibitory effects on tumor growth and progression. Its potent inhibitory action on cancer cell proliferation has shown promising results in some studies, indicating its potential as a therapeutic agent for cancer treatment.
Used in Antioxidant Applications:
Aloe-emodin demonstrates antioxidant effects, which can help protect cells from oxidative stress and damage. This property makes it a potential candidate for the development of antioxidant therapies to combat various diseases and conditions associated with oxidative stress.
Used in Anti-fibrotic Applications:
Aloe-emodin has shown anti-fibrotic effects, making it a potential therapeutic agent for the treatment of fibrotic diseases. Its ability to inhibit the development of fibrosis could be beneficial in managing and treating conditions such as liver fibrosis, kidney fibrosis, and pulmonary fibrosis.
Used in Traditional Medicine:
Aloe-emodin has been used in traditional medicine for its various health benefits, including its anti-inflammatory, anti-bacterial, and anti-viral properties. Its long history of use and well-documented therapeutic effects make it a valuable component in traditional medicine practices.

InChI:InChI=1/C14H10O4/c15-9-5-6-10(16)12-11(9)13(17)7-3-1-2-4-8(7)14(12)18/h1-4,17-18H,5-6H2

Upstream product

• 571-60-8 1,4-Dihydroxynaphthalene 
• 543-20-4 succinoyl dichloride 
• 7647-01-0 hydrogenchloride 
• 73592-78-6 4-amino-anthracene-1,9,10-triol 
• 3443-92-3 4-(4-hydroxy-9,10-dioxo-9,10-dihydro-[1]anthrylamino)-toluene-3-sulfonic acid 
• 113719-50-9 1-hydroxy-4-nitro-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid 
• 151107-11-8 2-bromo-1-hydroxy-4-nitro-anthraquinone 
• 75829-97-9 1,4-Diethoxy-9,10-anthraquinone 
• 25060-18-8 2,3-dimethyl quinizarine 
• 392248-86-1 1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2,3-dicarboxylic acid 
• 5470-98-4 1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2,3-dicarbonitrile 
• 1709-63-3 anthracene-1,4,9,10-tetraone 
• 3179-85-9 4-(9,10-dioxo-4-p-toluidino-9,10-dihydro-[1]anthrylamino)-toluene-3-sulfonic acid 
• 4988-32-3 4-(4-amino-3-bromo-9,10-dioxo-9,10-dihydro-[1]anthrylamino)-toluene-3-sulfonic acid 

Downstream Products

• 86722-66-9 disperse blue 3 
• 62758-81-0 1-(4-amino-anilino)-4-(2-hydroxy-ethylamino)-anthraquinone 
• 19286-75-0 1-hydroxy-4-phenylaminoanthraquinone 
• 2944-12-9 1,4-bis(phenylamino)anthracene-9,10-dione 
• 111527-60-7 4-anilino-anthracene-1,9,10-triol 
• 154164-00-8 2-[1-(4-Chloro-phenyl)-2-nitro-ethyl]-1,4-dihydroxy-anthraquinone 

Relevant articles and documents

Synthesis of 1,4-Anthracene-9,10-dione derivatives and their regulation of nitric oxide, IL-1β and TNF-α in activated RAW264.7 cells

Mitoxantrone is an anthracenedione antineoplastic and immunosuppressive agent approved for multiple sclerosis treatment. Novel mono- and disubstituted anthraquinone derivatives, analogues of mitoxantrone, were synthesized through the addition of lipophilic amino alcohols and evaluated for their effect on IL-1β, TNF-α and nitric oxide production by LPS/IFN-γ-stimulated RAW264.7 cells. The disubstituted 1,4-anthracene-9,10-dione 10 showed significant inhibition of nitric oxide, TNF-α and IL-1β production at the concentration of 5 μg/mL, with a much lower cytotoxicity than mitoxantrone. The monosubstituted 3, 4, 11, 12 and 13 also displayed a moderate to good inhibitory capacity on IL-1β production. However, the methylated compounds 11, 12 and 13 failed to inhibit the TNF-α production, and compound 13 was the only one to decrease the production of nitric oxide. None of these derivatives was toxic at the tested concentrations. Compounds 10 and 13 had better inhibitory capacity of the inflammatory mediators analyzed, with reliable viability of the cells.

A new kind of H-acid monoazo-anthraquinone reactive dyes with surprising colour

A new kind of reactive dyes containing both monoazo and anthraquinone chromophores was obtained by using 1,4-bis((4-aminophenyl)amino)anthrancene- 9,10-dione as diazo component and 1-amino-8-naphthol-3,6-disulfonicacid (H-acid) derivatives as coupling components. The dyes were characterized by UV-Vis, IR, MS, 1H NMR and 13C NMR. The results showed that the maximum absorption wavelengths of the dyes were all about 590 nm, which indicated that they were a kind of blue dyes. 1H NMR and 13C NMR results revealed that there were two kinds of tautomerisms in dye structure and a new conjugated system formed between the anthraquinone ring and the phenyl azo linkage. Density functional theory (DFT) calculations also proved the formation of the new larger conjugated system from which the blue colour was generated. The fixations of the dyes on cotton were over 88% and the light fastness reached 5 grade.

A new InCl3-catalyzed reduction of anthrones and anthraquinones by using aluminum powder in aqueous media

InCl3-catalyzed reduction of anthrones and anthraquinones was investigated under different conditions. A new synthetic method for anthracenes in aqueous media under mild conditions is described.

Parimycin: Isolation and structure elucidation of a novel cytotoxic 2,3-dihydroquinizarin analogue of γ-indomycinone from a marine Streptomycete isolate

In our screening of actinomycetes from the marine environment for bioactive components, a new antibiotic with a novel structure designated as parimycin was obtained from the culture broth of Streptomyces sp. isolate B8652. The structure of the new antibiotic was determined by spectroscopic methods and by comparison of the NMR data with those of the structurally related γ-indomycinone.

New 1,4-anthracene-9,10-dione derivatives as potential anticancer agents

The amino-substituted anthracene-9,10-dione (9,10-anthraquinone) derivatives represent one of the most important classes of potential anticancer agents. To better understand the basic rules governing DNA sequence specificity, we have recently synthesized a new class of d- and l- aminoacyl-anthraquinone derivatives. We have tested these new compounds as cytotoxic agents, and we have correlated their activity with the configuration of the chiral aminoacyl moiety. Molecular modeling studies have been performed to compare the test drugs in terms of steric overlapping. (C) 2000 Elsevier Science S.A.

A Direct Route for the Regioselective Synthesis of Hydroxylated Aromatic Cycloalkanediones

A "one-pot" regioselective synthesis of hydroxylated aromatic cycloalkanediones 1 from phenols or their methyl ethers and aliphatic dicarboxylic acid chlorides is reported.

An EPR Study of a Model System for the Initial Oxygen Activation Process Caused by Adriamycin-Iron System

1,4-Dihydroxyanthraquinone, a model compound for Adriamycin, is reduced by Fe2+-ADP complex to generate semiquinone, while by Fe2+-phosphate complex to hydroquinone.The difference is explained in terms of the higher redox potential of the latter reducing agent.Similar reduction reactions were observed in the case of the drug.