Chemical Properties
Yellow to Green Solid
Uses
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.
Uses
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.
Uses
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.
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.]
