A trihydroxyanthraquinone or trihydroxyanthracenedione is any of several isomeric organic compounds with formula C
14H
8O
5, 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

From 9,10-anthraquinone

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

References

  1. 1 2 Wahl, Andre; Atack, F. W (1919) The Manufacture Of Organic Dyestuffs. G. Bell And Sons, Limited. Online version accessed on 2010-01-22.
  2. 1 2 3 4 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.
  3. ↑ CRC (1996), Dictionary of organic compounds, Volume 1 CRC Press Online version at books.google.com, accessed on 2010-01-22.
  4. ↑ 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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