129-15-7

Usage

General Description

Pale yellow needles or light yellow solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-methyl-1-nitroanthraquinone is easily reduced. 2-methyl-1-nitroanthraquinone is also readily oxidized.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition 2-methyl-1-nitroanthraquinone emits toxic fumes of nitrogen oxides.

Fire Hazard

Flash point data for 2-methyl-1-nitroanthraquinone are not available; however, 2-methyl-1-nitroanthraquinone is probably combustible.

Safety Profile

Confirmed carcinogen with experimental carcinogenic and neoplastigenic data. Moderately toxic by intraperitoneal route. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C15H9NO4/c1-8-6-7-11-12(13(8)16(19)20)15(18)10-5-3-2-4-9(10)14(11)17/h2-7H,1H3

Upstream product

• 84-54-8 2-methylanthracene-9,10-dione 
• 84-65-1 9,10-phenanthrenequinone 
• 82-28-0 disperse orange 11 
• 7664-93-9 sulfuric acid 
• 108-88-3 toluene 
• 85-44-9 phthalic anhydride 

Downstream Products

• 82-24-6 1-aminoanthraquinone-2-carboxylic acid 
• 36139-44-3 anthra[1,2-c]isoxazole-6,11-dione 
• 128-67-6 1-nitroanthraquinone-2-carboxylic acid 
• 6941-85-1 2-dibromomethyl-1-nitro-anthraquinone 
• 82-28-0 disperse orange 11 
• 82-23-5 1-chloro-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid 
• 84-54-8 2-methylanthracene-9,10-dione 
• 92439-31-1 2-methylanthraquinone-1-sulfonic acid 
• 70173-75-0 3-methyl-1⁽²⁾H-dibenz[cd,g]indazol-6-one 
• 7400-93-3 1-hydroxy-9,10-dioxoanthracene-2-carboxylic acid 
• 129-35-1 1-chloro-2-methylanthraquinone 
• 81-26-5 2,2'-dimethyl-1,1'-bianthraquinone 
• 6336-80-7 1-amino-3-bromo-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid 
• 82-45-1 1-amino-9,10-anthracenedione 

Relevant academic research and scientific papers

Novel anthraquinone compounds inhibit colon cancer cell proliferation via the reactive oxygen species/JNK pathway

A series of amide anthraquinone derivatives, an important component of some traditional Chinese medicines, were structurally modified and the resulting antitumor activities were evaluated. The compounds showed potent anti-proliferative activities against eight human cancer cell lines, with no noticeable cytotoxicity towards normal cells. Among the candidate compounds, 1-nitro-2-acyl anthraquinone-leucine (8a) showed the greatest inhibition of HCT116 cell activity with an IC50 of 17.80 μg/mL. In addition, a correlation model was established in a three-dimensional quantitative structure-activity relationship (3D-QSAR) study using Comparative Molecular Field Analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA). Moreover, compound 8a effectively killed tumor cells by reactive oxygen species (ROS)-JNK activation, causing an increase in ROS levels, JNK phosphorylation, and mitochondrial stress. Cytochrome c was then released into cytoplasm, which, in turn activated the cysteine protease pathway and ultimately induced tumor cell apoptosis, suggesting a potential use of this compound for colon cancer treatment.

Design, Synthesis, Molecular Docking, and Biological Evaluation of New Emodin Anthraquinone Derivatives as Potential Antitumor Substances

The emodin anthraquinone derivatives are generally used in traditional Chinese medicine due to their various pharmacological activities. In the present study, a series of emodin anthraquinone derivatives have been designed and synthesized, among which 1,3-dihydroxy-6,8-dimethoxyanthracene-9,10-dione is a natural compound that has been synthesized for the very first time, and 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione is a compound that has never been reported earlier. Interestingly, while total seven of these compounds showed neuraminidase inhibitory activity in influenza virus with inhibition rate more than 50 %, specific four compounds exhibited significant inhibition of tumor cell proliferation. The further results demonstrate that 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione showed the best anticancer activity among all the synthesized compounds by inducing highest apoptosis rate to HCT116 cancer cells and arresting their G0/G1 cell cycle phase, through elevation of intracellular level of reactive oxygen species (ROS). Moreover, the binding of 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione with BSA protein has thoroughly been investigated. Altogether, this study suggests the neuraminidase inhibitory activity and antitumor potential of the new emodin anthraquinone derivatives.

Efficiency of ultrafiltration purification of solutions of polymeric colorants by inorganic base addition

The ultrafiltration purification of aqueous solutions of polymeric colorants, wherein low molecular weight impurities are removed in an ultrafiltrate leaving a purified polymeric colorant-bearing retentate, is carried out with improved efficiency when during at least 2 diavolumes of ultrafiltration, the pH of the retentate is maintained above about pH 9.0.