6003-12-9

Basic information

• Product Name: 1,2-Dimethoxyanthracene-9,10-dione
• Synonyms: 1,2-Dimethoxyanthracene-9,10-dione;1,2-Dimethoxyanthraquinone
• CAS NO: 6003-12-9
• Molecular Formula: C₁₆H₁₂O₄
• Molecular Weight: 268.27
• Mol File: 6003-12-9.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2-Dimethoxyanthracene-9,10-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Dimethoxyanthracene-9,10-dione(6003-12-9)
• EPA Substance Registry System: 1,2-Dimethoxyanthracene-9,10-dione(6003-12-9)

Safety Data

• Hazardous Substances Data: 6003-12-9(Hazardous Substances Data)

Usage

General Description

1,2-Dimethoxyanthracene-9,10-dione, also known as Anthraquinone, is a chemical compound with the molecular formula C16H12O4. It is a yellow solid that is commonly used as a dye intermediate and as a raw material for the synthesis of various other organic compounds. Anthraquinone is also employed in the manufacturing of pharmaceuticals, insecticides, and explosives. It is known for its versatile reactivity, being involved in a wide range of chemical reactions and being used in diverse applications across different industries. Anthraquinone is also found naturally in plants, particularly in the roots and rhizomes of certain species, where it functions as a defense mechanism against herbivores and pathogens.

Upstream product

• 186581-53-3 diazomethane 
• 67-56-1 methanol 
• 6003-11-8 1-hydroxy-2-methoxyanthraquinone 
• 72-48-0 1,2-dihydroxy-9,10-anthracenedione 
• 80-48-8 methyl p-toluene sulfonate 
• 108-86-1 bromobenzene 
• 569-31-3 meconin 
• 1010-60-2 2-chloro-1,4-naphthoquinone 
• 159420-50-5 1,2-dimethoxy-1-trimethylsilyloxy-1,3-butadiene 
• 132814-35-8 dimethoxyanthracene 
• 74-88-4 methyl iodide 
• 1629-51-2 diacetylalizarin 
• 82-39-3 1-methoxyanthracene-9,10-dione 
• 7664-93-9 sulfuric acid 

Downstream Products

• 80034-23-7 1,2-dimethoxy-9,10-bis(phenylethynyl)anthracene 
• 6003-11-8 1-hydroxy-2-methoxyanthraquinone 
• 80034-13-5 1,2-dimethoxy-9,10-bis(phenylethynyl)-9,10-dihydroanthracene-9,10-diol 

Relevant articles and documents

Evaluation of a series of 9,10-anthraquinones as antiplasmodial agents

Background: A phytochemical study on medicinal plants used for the treatment of fever and malaria in Africa yielded metabolites with potential antiplasmodial activity, many of which are Anthraquinones (AQ). AQs have similar sub-structure as naphthoquinones and xanthones, which were previously reported as novel antiplasmodial agents. Objective: The present study aimed to investigate the structural requirements of 9,10-anthraquinones with hydroxy, methoxy and methyl substituents to exert strong antiplasmodial activity and to investigate their possible mode of action. Methods: Thirty-one AQs were synthesized through Friedel-Crafts reaction and assayed for antiplasmodial activity in vitro against Plasmodium falciparum (3D7). The selected compounds were tested for toxicity and probed for their mode of action against β-hematin dimerization through HRP2 and lipid catalyses. The most active compounds were subjected to a docking study using AutoDock 4.2. Results: The active AQs have similar common structural characteristics. However, it is difficult to establish a structure-activity relationship as certain compounds are active despite the absence of the structural features exhibited by other active AQs. They have either ortho- or meta-arranged substituents and one free hydroxyl and/or carbonyl groups. When C-6 is substituted with a methyl group, the activity of AQs generally increased. 1,3-DihydroxyAQ (15) showed good antiplasmodial activity with an IC50 value of 1.08 μM, and when C-6 was substituted with a methyl group, 1,3-dihydroxy-6-methylAQ (24) showed stronger antiplasmodial activity with an IC50 value of 0.02μM, with better selectivity index. Compounds 15 and 24 showed strong HRP2 activity and mild toxicity against hepatocyte cells. Molecular docking studies showed that the hydroxyl groups at the ortho (23) and meta (24) positions are able to form hydrogen bonds with heme, of 3.49 A and 3.02 A, respectively. Conclusion: The activity of 1,3-dihydroxy-6-methylAQ (24) could be due to their inhibition against the free heme dimerization by inhibiting the HRP2 protein. It was further observed that the anthraquinone moiety of compound 24 bind in parallel to the heme ring through hydrophobic interactions, thus preventing crystallization of heme into hemozoin.

Preparation of Anthraquinones from 10-Hydroxy-9-anthracenecarbonitriles Obtained from a Novel Aryne Annulation Reaction

A new method for brief regioselective synthesis of anthraquinones via the reaction of anions of ethyl cyanoacetate or the anions of 2-(carbethoxyaryl)acetonitriles with arynes is described.

The preparation of anthraquinones and anthracyclinones via the reaction of haloarenes and cyanophthalides under aryne-forming conditions

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