2549-78-2

Basic information

• Product Name: 1-Hydroxy-3-methylanthracene-9,10-dione
• Synonyms: 1-Hydroxy-3-methyl-9,10-anthracenedione;1-Hydroxy-3-methylanthracene-9,10-dione;Pachybasin;1-Hydroxy-3-Methylanthraquinone
• CAS NO: 2549-78-2
• Molecular Formula: C₁₅H₁₀O₃
• Molecular Weight: 238.24
• Product Categories: Aromatics, Heterocycles
• Mol File: 2549-78-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 178 °C(Solv: ethanol (64-17-5))
• Boiling Point: 453.1°C at 760 mmHg
• Flash Point: 241.9°C
• Appearance: /
• Density: 1.371g/cm³
• Vapor Pressure: 7.94E-09mmHg at 25°C
• Refractive Index: 1.676
• PKA: 7.22±0.20(Predicted)
• CAS DataBase Reference: 1-Hydroxy-3-methylanthracene-9,10-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Hydroxy-3-methylanthracene-9,10-dione(2549-78-2)
• EPA Substance Registry System: 1-Hydroxy-3-methylanthracene-9,10-dione(2549-78-2)

Safety Data

• Hazardous Substances Data: 2549-78-2(Hazardous Substances Data)

Usage

Description

1-Hydroxy-3-methylanthracene-9,10-dione, also known as 1-Hydroxy-3-methylanthraquinone, is an organic compound derived from anthraquinone. It is characterized by its unique chemical structure, which includes a hydroxyl group at the 1st position and a methyl group at the 3rd position, along with two carbonyl groups at the 9th and 10th positions. 1-Hydroxy-3-methylanthracene-9,10-dione has been found to exhibit various biological activities and applications in different fields.

Uses

Used in Mycoparasitic Coiling Regulation:
1-Hydroxy-3-methylanthracene-9,10-dione is used as a regulatory compound for the self-regulation of Trichoderma harzianum mycoparasitic coiling. It plays a role in the biological control of plant pathogens by enhancing the coiling behavior of Trichoderma harzianum, a beneficial fungus that can protect plants from various diseases caused by other fungi.

Synthesis Reference(s)

Journal of the American Chemical Society, 116, p. 7108, 1994 DOI: 10.1021/ja00095a014Synthesis, p. 255, 1994

InChI:InChI=1/C15H10O3/c1-8-6-11-13(12(16)7-8)15(18)10-5-3-2-4-9(10)14(11)17/h2-7,16H,1H3

Upstream product

• 85-44-9 phthalic anhydride 
• 108-39-4 3-methyl-phenol 

Downstream Products

• 25186-77-0 4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid 

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.

Synthesis and biological activity of anthrapyrazoles derivatives as potential antitumor agents

We have synthesized a series of anthrapyrazoles derivatives. The biological results indicated that these derivatives exhibited potent in vitro cytotoxicity against different cancer cell lines (human hepatocellular carcinoma HepG2 and BEL-7402, human colonic carcinoma HCT-116 and HT-29) and drug-resistant human hepatoma cell line (SMMC-7721). Among them, the polyamine-based anthrapyrazole derivatives 4c and 4f-g showed superior cytotoxicity than that of Mitoxantrone both on cancer cell lines and the drug-resistant subline. However, the DNA relaxation assay revealed that they had insignificant topoisomerase II inhibition. These results clearly indicate that polyamine side chains will have a profound effect on the cytotoxicity of anthrapyrazoles derivatives.