602-64-2

Basic information

• Product Name: ANTHRACENE BROWN
• Synonyms: chromefastbrownfc;mitsuianthracenebrown;Acid brown;Acid chrome brown G;Anthracene brown;Alizarol brown 18;Alizarol brown 18;1,2,3-trihydroxy-anthraqunone;1,2,3-Trihydroxy-9,10-anthraquinone;Antragallol;ANTHRACENE ACID BROWN G
• CAS NO: 602-64-2
• Molecular Formula: C₁₄H₈O₅
• Molecular Weight: 256.21
• EINECS: 210-022-4
• Product Categories: Aromatics;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 602-64-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 312-313°
• Boiling Point: 359.45°C (rough estimate)
• Flash Point: 241.7°C
• Appearance: /
• Density: 1.3683 (rough estimate)
• Vapor Pressure: 8.19E-09mmHg at 25°C
• Refractive Index: 1.4825 (estimate)
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 6.70±0.20(Predicted)
• Merck: 14,683
• CAS DataBase Reference: ANTHRACENE BROWN(CAS DataBase Reference)
• NIST Chemistry Reference: ANTHRACENE BROWN(602-64-2)
• EPA Substance Registry System: ANTHRACENE BROWN(602-64-2)

Safety Data

• RTECS: CB8198000
• Hazardous Substances Data: 602-64-2(Hazardous Substances Data)

Usage

Chemical Properties

Brown powder. Soluble in alcohol, ether, and glacial acetic acid; slightly soluble in water and chloroform. Sublimes at 290C.

Uses

Anthragallol is the most active inhibitor against xanthine oxidase.

Definition

ChEBI: A trihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1, 2 and 3.

Preparation

Commonly known as ?Anthragallol. (A)3,4,5-Trihydroxybenzoic acid and Benzoic acid and sulfuric acid heated; (b) in the presence of zinc chloride, heating gallic acid and Phthalic anhydride; (c) 2-Hydroxy-1,3-dinitroanthraquinone?reduction in strong alkaline solution; (d)1,3-Diamino-2-hydroxyanthracene-9,10-dione and hydrochloric acid heated under pressure. Note: The product is a free acid state paste; powdery product is sodium

Properties and Applications

Dark brown (chrome). (Sodium salt) was dissolved in water, slightly soluble in o-chlorophenol, (free acid) is insoluble in water, salt is not soluble in acetone, ethanol, benzene, carbon tetrachloride, cellosolve, chloroform, pyridine, toluene. The free acid in concentrated sulfuric acid is brown-red, sodium salt as a brown; diluted brown flocculent precipitate the free acid, sodium salt as an amber. Standard Ironing Fastness Light Fastness Fulling Persperation Fastness Soaping Water Alkali Acid ISO 5 5-6 3-4 2-3 5 5 5 AATCC Dry 3,wet 5 5 2-3 5 4 5

Standard

Ironing Fastness

Alkali

Acid

ISO

5

AATCC

Dry 3,wet 5

InChI:InChI=1/C14H8O5/c15-9-5-8-10(14(19)13(9)18)12(17)7-4-2-1-3-6(7)11(8)16/h1-5,15,18-19H

Upstream product

• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 65-85-0 benzoic acid 
• 10383-62-7 3-hydroxy-1,2-dimethoxyanthracene-9,10-dione 
• 7664-93-9 sulfuric acid 
• 5953-90-2 1,2,3-trimethoxyanthracene-9,10-dione 
• 10384-00-6 anthragallol-2,3-dimethyl ether 
• 7647-01-0 hydrogenchloride 
• 19852-76-7 2-hydroxy-1,3-dimethoxyanthracene-9,10-dione 
• 64-19-7 acetic acid 
• 85-44-9 phthalic anhydride 
• 87-66-1 2-hydroxyresorcinol 
• 1010-60-2 2-chloro-1,4-naphthoquinone 
• 78923-86-1 1,1,2,3-Tetrakis-1,3-butadiene 

Downstream Products

• 4554-99-8 (3-hydroxy-1,4-dioxo-1,4-dihydro-[2]naphthyl)-acetic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 361148-83-6 Ru(CO)2(P(C₄H₉)3)2(C₁₄H₅O₅H) 
• 361148-81-4 Ru(CO)2(P(C₆H₅)3)2(C₁₄H₅O₅H) 
• 120-12-7 anthracene 
• 84501-58-6 1,2,3-trihydroxy-anthraquinone; sodium salt 
• 72-48-0 1,2-dihydroxy-9,10-anthracenedione 

Relevant articles and documents

An anthraquinone scaffold for putative, two-face bim BH3 α-helix mimic

Bim BH3 peptide features an α-helix with hotspot residues on multiple faces. Compound 5 (6-bromo-2,3-dihydroxyanthracene-9,10-dione), which adopts a rigid-plan amphipathic conformation, was designed and evaluated as a scaffold to mimic two faces of Bim α-helix. It reproduced the functionalities of both D67 and I65 on two opposing helical sides. Moreover, it maintained the two-faced binding mode during further evolution. A putative BH3 α-helix mimic and nanomolar Bcl-2/Mcl-1 dual inhibitor, 6, was obtained based on the structure of 5.

Synthesis and activity of substituted anthraquinones against a human filarial parasite, Brugia malayi

Lymphatic filariasis (elephantiasis) is a global public health problem caused by the parasitic nematodes Wuchereria bancrofti and Brugia malayi. We have previously reported anthraquinones from daylily roots with potent activity against pathogenic trematode Schistosoma mansoni. Here we report the synthesis of novel anthraquinones A-S and their antifilrarial activity. Anthraquinones A-S were synthesized by a single-step Friedel-Crafts acylation reaction between phthalic anhydrides and substituted benzenes. The antifilarial properties of these synthetic anthraquinones were tested against microfilaria as well as adult male and female worms of B. malayi. The most active anthraquinone was K, which showed 100% mortality within 1, 5, and 3 days, respectively, against microfilaria and adult male and female worms at 5 ppm concentration. Albendazole, an oral drug currently used to treat parasitic infections, was used as a positive control. Methylated products of anthraquinones did not affect the microfilaria. Histological examination of treated adult female parasites showed most of the anthraquinones caused marked effects on intrauterine embryos.