82-24-6

Basic information

• Product Name: 1-amino-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylicaci
• Synonyms: 1-amino-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylicaci;1-amino-9,10-dioxo-9,10-dihydro-2-anthracenecarboxylicacid;9,10-dihydro-1-amino-9,10-dioxo-2-anthracenecarboxylicaci;1-amino-9,10-dihydro-9,10-dioxoanthracene-2-carboxylic acid;1-Aminoanthraquinone-2-Carboxylic Acid;1-Amino-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid;2-Anthracenecarboxylic acid, 1-amino-9,10-dihydro-9,10-dioxo-;2-Anthraquinonecarboxylic acid, 1-amino-
• CAS NO: 82-24-6
• Molecular Formula: C₁₅H₉NO₄
• Molecular Weight: 267.23626
• EINECS: 201-406-2
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 82-24-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 291°C
• Boiling Point: 410.42°C (rough estimate)
• Flash Point: 302.1°C
• Appearance: /
• Density: 1.2671 (rough estimate)
• Vapor Pressure: 4.22E-14mmHg at 25°C
• Refractive Index: 1.6231 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-amino-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylicaci(CAS DataBase Reference)
• NIST Chemistry Reference: 1-amino-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylicaci(82-24-6)
• EPA Substance Registry System: 1-amino-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylicaci(82-24-6)

Safety Data

• Hazardous Substances Data: 82-24-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthesis, p. 528, 1976 DOI: 10.1055/s-1976-24108

Purification Methods

It is used for the detection of Al, Mg Cd, Zn, Mn, Cu, Hg, Fe, Co, Ni and Pb. The methyl ester gives red needles from AcOH, m 228o. The ethyl ester, m 198o, crystallises also as red needles from AcOH. [Locher & Fietz Helv Chim Acta 10 667 1927, Beilstein 14 II 419, 14 III 168.]

InChI:InChI=1/C15H9NO4/c16-12-10(15(19)20)6-5-9-11(12)14(18)8-4-2-1-3-7(8)13(9)17/h1-6H,16H2,(H,19,20)/p-1

Upstream product

• 89174-90-3 1,3-dihydroanthra<1,2-c>isoxazole-3,6,11-trione 
• 36139-44-3 anthra[1,2-c]isoxazole-6,11-dione 
• 74214-86-1 2-bromomethyl-1-nitro-anthraquinone 
• 108-88-3 toluene 
• 85-44-9 phthalic anhydride 
• 13432-32-1 1-amino-2,4-dichloroanthraquinone 
• 117-07-7 1-amino-2-chloro-9,10-anthraquinone 
• 3300-23-0 1-amino-2-bromoanthraquinone 
• 873388-39-7 2'-amino-2,4'-carbonyl-di-benzoic acid 
• 98-95-3 nitrobenzene 
• 128-67-6 1-nitroanthraquinone-2-carboxylic acid 
• 82-23-5 1-chloro-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid 
• 7664-41-7 ammonia 
• 497-19-8 sodium carbonate 

Downstream Products

• 4182-49-4 1-amino-N-cyclohexyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxamide 
• 75535-00-1 1-amino-N-(2-methoxyphenyl)-9,10-dioxo-9,10-dihydroanthracene-2-carboxamide 
• 138058-33-0 3-Phenyl-1H-naphtho<2,3-h>quinazoline-2,4,7,12-tetrone 
• 82-23-5 1-chloro-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid 
• 7400-93-3 1-hydroxy-9,10-dioxoanthracene-2-carboxylic acid 
• 2058-02-8 1-amino-4-nitroanthraquinone-2-carboxylic acid 
• 6363-90-2 1-Amino-4-bromoanthraquinone-2-carboxylic acid 

Relevant articles and documents

CHARACTERISTIC FEATURES OF THE REACTION OF 3(5)-AMINO-5(3)-METHYLPYRAZOLE WITH 1-NITROANTHRAQUINONE-2-CARBOXYLIC ACID

In the reaction of 3(5)-amino-5(3)-methylpyrazole with 1-nitroanthraquinone-2-carboxylic acid in sulfolane at 150 deg C, 2-methylpyrazolonaphthoquinazoline-5,10.13-trione is formed with an admixture of 1-aminoanthraquinone-2-carboxylic acid and 1-aminoanthraquinone.Under similar conditions, from 4-amino-1,5-dimethylpyrazole, only 1-(1,5-dimethyl-4-pyrazolylamino)anthraquinone-2-carboxylic acid is formed.

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.

TRANSFORMATIONS OF 1-AZIDO-2-ANTHRAQUINONECARBOXYLIC ACID AND ITS ESTERS

When heated in nonpolar solvents, 1-azido-2-alkoxycarbonylanthraquinones are converted into 3-alkoxycarbonylanthra-6-isoxazolones.The product from the thermolysis of 1-azido-2-anthraquinonecarboxylic acid is 1,3-dihydroanthraisoxazole-3,6,11-trione.