61434-48-8

Basic information

• Product Name: 2-(hydroxymethyl)-1,3-dimethoxyanthracene-9,10-dione
• Synonyms: 2-(Hydroxymethyl)-1,3-dimethoxy-9,10-anthraquinone; 9,10-anthracenedione, 2-(hydroxymethyl)-1,3-dimethoxy-
• CAS NO: 61434-48-8
• Molecular Formula: C₁₇H₁₄O₅
• Molecular Weight: 298.2901
• Mol File: 61434-48-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 531.6°C at 760 mmHg
• Flash Point: 200°C
• Density: 1.35g/cm³
• Vapor Pressure: 3.94E-12mmHg at 25°C
• Refractive Index: 1.628
• CAS DataBase Reference: 2-(hydroxymethyl)-1,3-dimethoxyanthracene-9,10-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(hydroxymethyl)-1,3-dimethoxyanthracene-9,10-dione(61434-48-8)
• EPA Substance Registry System: 2-(hydroxymethyl)-1,3-dimethoxyanthracene-9,10-dione(61434-48-8)

Safety Data

• Hazardous Substances Data: 61434-48-8(Hazardous Substances Data)

Upstream product

• 478-08-0 1,3-dihydroxy-2-hydroxymethyl-9,10-anthraquinone 
• 67-64-1 acetone 
• 77-78-1 dimethyl sulfate 
• 117-02-2 rubiadin 
• 608-25-3 2-methylbenzene-1,3-diol 
• 7416-31-1 rubiadin diacetate 
• 7460-43-7 rubiadin-1-methyl ether 
• 63965-62-8 2-(bromomethyl)-1,3-dimethoxyanthraquinone 
• 159663-54-4 2-methyl-1,3-dibromoanthraquinone 
• 22170-88-3 1,3-dimethoxy-2-methylanthraquinone 
• 477-83-8 damnacanthol 
• 95219-87-7 2-acetoxymethyl-1,3-dimethoxy-anthraquinone 
• 186581-53-3 diazomethane 

Relevant articles and documents

Synthesis of an anthraquinone derivative (DHAQC) and its effect on induction of G2/M arrest and apoptosis in breast cancer MCF-7 cell line

Anthraquinones are an important class of naturally occurring biologically active compounds. In this study, anthraquinone derivative 1,3-dihydroxy-9,10-anthraquinone-2-carboxylic acid (DHAQC) (2) was synthesized with 32% yield through the FriedelCrafts condensation reaction. The mechanisms of cytotoxicity of DHAQC (2) in human breast cancer MCF-7 cells were further investigated. Results from the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay showed that DHAQC (2) exhibited potential cytotoxicity and selectivity in the MCF-7 cell line, comparable with the naturally occurring anthraquinone damnacanthal. DHAQC (2) showed a slightly higher IC50 (inhibitory concentration with 50% cell viability) value in the MCF-7 cell line compared to damnacanthal, but it is more selective in terms of the ratio of IC50 on MCF-7 cells and normal MCF-10A cells. (selective index for DHAQC (2) was 2.3 and 1.7 for damnacanthal). The flow cytometry cell cycle analysis on the MCF-7 cell line treated with the IC50 dose of DHAQC (2) for 48 hours showed that DHAQC (2) arrested MCF-7 cell line at the G2/M phase in association with an inhibited expression of PLK1 genes. Western blot analysis also indicated that the DHAQC (2) increased BAX, p53, and cytochrome c levels in MCF-7 cells, which subsequently activated apoptosis as observed in annexin V/propidium iodide and cell cycle analyses. These results indicate that DHAQC (2) is a synthetic, cytotoxic, and selective anthraquinone, which is less toxic than the natural product damnacanthal, and which demonstrates potential in the induction of apoptosis in the breast cancer MCF-7 cell line.