81-61-8

Basic information

• Product Name: 1,2,5,8-TETRAHYDROXYANTHRAQUINONE
• Synonyms: CI 58500;CI NO 58500;LABOTEST-BB LT00129956;ALIZARIN CYANINE 3R;ALIZARIN BORDEAUX;1,2,5,8-TETRAHYDROXYANTHRAQUINONE;QUINALIZARINE;QUINALIZARIN
• CAS NO: 81-61-8
• Molecular Formula: C₁₄H₈O₆
• Molecular Weight: 272.21
• EINECS: 201-366-6
• Product Categories: Miscellaneous
• Mol File: 81-61-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: >275°
• Boiling Point: 375.27°C (rough estimate)
• Flash Point: 280.6 °C
• Appearance: red/
• Density: 1.4292 (rough estimate)
• Vapor Pressure: 2.59E-11mmHg at 25°C
• Refractive Index: 1.5230 (estimate)
• Storage Temp.: room temp
• Water Solubility: 2.586mg/L(25 oC)
• BRN: 1889617
• CAS DataBase Reference: 1,2,5,8-TETRAHYDROXYANTHRAQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,5,8-TETRAHYDROXYANTHRAQUINONE(81-61-8)
• EPA Substance Registry System: 1,2,5,8-TETRAHYDROXYANTHRAQUINONE(81-61-8)

Safety Data

• Hazard Codes: Xn,N
• Statements: 36/37/38-50-22
• Safety Statements: 26-36-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 81-61-8(Hazardous Substances Data)

Usage

Uses

1,2,5,8-TETRAHYDROXYANTHRAQUINONE is Al salts dark red, cotton mordanted with Cr salts bluish-violet. No longer used as a dye, except occasionally in printing cotton.

Preparation

Quinalizarin. 1,2-Dihydroxyanthracene-9,10-dione or 1,4-Dihydroxyanthracene-9,10-dione with great excess fuming sulfuric acid oxidation and hydrolysis.

Definition

ChEBI: A tetrahydroxyanthraquinone having the four hydroxy groups at the 1-, 2-, 5- and 8-positions.

Biochem/physiol Actions

Quinalizarin is a potent (IC50 = 110 nM), ATP-competitive, and highly selective (IC50 >1μM against CK1 and 72 other kinases) casein Kinase II (CK2) inhibitor.

Properties and Applications

violet (chromium), dark red light purple (aluminum). Soluble in ethanol. In concentrated sulfuric acid for blue purple, dilution after dark red precipitation. Standard Ironing Fastness Light Fastness Fulling Persperation Fastness Soaping Water Alkali Acid ISO 6 4-5 5 4-5

Standard

Ironing Fastness

Alkali

Acid

Purification Methods

Crystallise the quinone from acetic acid or nitrobenzene. It can be sublimed in vacuo. The Cu salt forms red crystals. [Beilstein 8 H 549, 8 I 755, 8 II 584.]

InChI:InChI=1/C14H8O6/c15-6-3-4-7(16)11-10(6)12(18)5-1-2-8(17)13(19)9(5)14(11)20/h1-4,15-17,19H

Upstream product

• 518-90-1 3,4-dimethoxy-phthalic acid 
• 123-31-9 hydroquinone 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 7664-93-9 sulfuric acid 
• 13460-50-9 metaboric acid 
• 72-48-0 1,2-dihydroxy-9,10-anthracenedione 
• 14597-12-7 3,6-dimethoxyphthalic anhydride 
• 120-80-9 benzene-1,2-diol 

Downstream Products

• 123-31-9 hydroquinone 
• 120-12-7 anthracene 
• 121151-80-2 triphenylgermyl 1,2,5,8-tetrahydroxy-9,10-anthraquinone adduct 
• 61169-36-6 1,2,4,5,6,8-hexahydroxy-9,10-anthraquinone 
• 120951-83-9 1,2,5,8-Tetrakis-benzyloxy-anthraquinone 
• 5413-65-0 1,2,4,5,8-pentahydroxy-9,10-anthraquinone 
• 6373-25-7 1,2,4,5,7,8-hexahydroxy-anthraquinone 

Relevant articles and documents

Method for dyeing keratinous fibres using a monohydroxyindole or dihydroxyindole and a non-oxidizing aromatic carbonyl derivative and dyeing agent

The present invention relates to a method for dyeing keratinous fibers, characterized in that the following are applied to the fibers: a) a composition (A) containing, in a medium appropriate for dyeing, at least one monohydroxyindole or dihydroxyindole, this application being preceded or followed by the application of b) a composition (B) containing, in a medium appropriate for dyeing, at least one aromatic carbonyl derivative chosen from hydroxyacetophenones, hydroxybenzophenones, 2-hydroxy-1,4-benzoquinones, hydroxy-1,4-naphthoquinones,amino-1,4-naphthoquinones,hydroxy-9,10-anthraquinones and amino-9,10-anthraquinones. It also relates to the dyeing agents for carrying it out.