1,5-Dihydroxyanthraquinone

Chemical properties

Yellow to Green Solid

The Uses of 1,5-Dihydroxyanthraquinone

1,5-Dihydroxyanthraquinone is an anthraquinone derivative with suppressive effects against nitric oxide (NO) synthase. Potential antimalarial agent. Used in studies as a potential competitive non-peptidic inhibitor of HIV-1 protei nase.

The Uses of 1,5-Dihydroxyanthraquinone

Important intermediate in the manufacture of alizarin and indanthrene dyestuffs. Forms insoluble Ba and Ca lakes; has been proposed as analytical reagent for the detection of Ca.

The Uses of 1,5-Dihydroxyanthraquinone

1,5-Dihydroxyanthraquinone (anthrarufin) is an important intermediate for manufacturing disperse blue dyes. It is the key intermediates for manufacturing disperse blue dyes via dinitrodihydroxyanthraquinone and vat dyes via diaminoanthraquinones.

Definition

ChEBI: A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 5.

Synthesis

1,5-Dihydroxyanthraquinone is prepared from 1,5-anthraquinonedisulfonic acid by replacing the SO3H groups, and from 1,5-dinitroanthraquinone by directly replacing the nitro groups, e.g., in sulfolane with calcium oxide or, more effectively, via 1,5- dimethoxyanthraquinone and subsequent hydrolysis of the ether linkage.

Purification Methods

Purify anthrarufin by column chromatography on silica gel with CHCl3/Et2O as eluent, followed by recrystallisation from acetone. Alternatively recrystallise it from glacial acetic acid [Flom & Barbara J Phys Chem 89 4489 1985]. [Beilstein 7 III 2359, 8 IV 3268.]