Trihydroxyanthraquinone
A trihydroxyanthraquinone or trihydroxyanthracenedione is any of several isomeric organic compounds with formula (C12H5(OH)3)(CO)2, formally derived from anthraquinone by replacing three hydrogen atoms by hydroxyl groups. They include several historically important dyes.[1][2] 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
[edit]From 9,10-anthraquinone
[edit]Due to the symmetry of the 9,10-anthraquinone core, there are only 14 isomers.[3]
- 1,2,3-Trihydroxyanthraquinone (anthragallol)[2]
- 1,2,4-Trihydroxyanthraquinone (purpurin), a component of madder root dye.
- 1,2,5-Trihydroxyanthraquinone (oxyanthrarufin)
- 1,2,6-Trihydroxyanthraquinone (flavopurpurin)[2]
- 1,2,7-Trihydroxyanthraquinone (isopurpurin, anthrapurpurin)[2]
- 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[4]
- 1,6,7-Trihydroxyanthraquinone
- 2,3,6-Trihydroxyanthraquinone
See also
[edit]- Hydroxyanthraquinone
- Dihydroxyanthraquinone
- Tetrahydroxyanthraquinone
- Pentahydroxyanthraquinone
- Hexahydroxyanthraquinone
- Heptahydroxyanthraquinone
- Octahydroxyanthraquinone[1]
References
[edit]- ^ a b Wahl, Andre; Atack, F. W (1919) The Manufacture Of Organic Dyestuffs. G. Bell And Sons, Limited. Online version accessed on 2010-01-22.
- ^ a b c d 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.
- ^ CRC (1996), Dictionary of organic compounds, Volume 1 CRC Press Online version at books.google.com, accessed on 2010-01-22.
- ^ M. L. Crossley (1918), 1,4,6-TRIHYDROXYANTHRAQUINONE J. Am. Chem. Soc., volume 40 issue 2, pages 404–406 doi:10.1021/ja02235a011
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