A trihydroxyanthraquinone or trihydroxyanthracenedione is any of several isomeric organic compounds with formula , formally derived from anthraquinone by replacing three hydrogen atoms by hydroxyl groups. They include several historically important dyes. Wahl, Andre; Atack, F. W (1919) The Manufacture Of Organic Dyestuffs. G. Bell And Sons, Limited. Online version accessed on 2010-01-22. Hugh Alister McGuigan (1921), An introduction to chemical pharmacology; pharmacodynamics in relation to chemistry. P. Blakiston's son, Philadelphia. Online version at archive.org, accessed on 2010-01-30. The isomers may differ in the parent anthraquinone isomer and/or of the three hydroxyl groups.
In general there are 56 ways of choosing three out of the 8 hydrogens. However, if the underlying core is symmetrical, some of these choices will give identical molecules.
Isomers From 9,10-anthraquinone Due to the symmetry of the 9,10-anthraquinone core, there are only 14 isomers. CRC (1996), Dictionary of organic compounds, Volume 1 CRC Press Online version at books.google.com, accessed on 2010-01-22.
1,2,3-Trihydroxyanthraquinone (anthragallol) 1,2,4-Trihydroxyanthraquinone (purpurin), a component of madder root dye. 1,2,5-Trihydroxyanthraquinone (oxyanthrarufin) 1,2,6-Trihydroxyanthraquinone (flavopurpurin) 1,2,7-Trihydroxyanthraquinone (isopurpurin, anthrapurpurin) 1,2,8-Trihydroxyanthraquinone (oxychrysazin) 1,3,5-Trihydroxyanthraquinone 1,3,6-Trihydroxyanthraquinone 1,3,7-Trihydroxyanthraquinone 1,3,8-Trihydroxyanthraquinone 1,4,5-Trihydroxyanthraquinone 1,4,6-Trihydroxyanthraquinone M. L. Crossley (1918), 1,4,6-TRIHYDROXYANTHRAQUINONE J. Am. Chem. Soc., volume 40 issue 2, pages 404–406 1,6,7-Trihydroxyanthraquinone 2,3,6-Trihydroxyanthraquinone
See also Hydroxyanthraquinone Dihydroxyanthraquinone Tetrahydroxyanthraquinone Pentahydroxyanthraquinone Hexahydroxyanthraquinone Heptahydroxyanthraquinone Octahydroxyanthraquinone
References