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Octahydroxyanthraquinone

Octahydroxyanthraquinone is an organic compound with formula C
14H
8O
10, formally derived from anthraquinone by replacement of 8 hydrogen atoms by hydroxyl groups.

The compound was obtained in 1911 by Georg von Georgievics[1][2] and can be obtained through oxidation of rufigallol (1,2,3,5,6,7-hexahydroxyanthraquinone) with boric acid and mercuric oxide in sulfuric acid at 250 °C (482 °F).[3]

Esters of octahydroxyanthraquinone, where all eight hydroxyls are replaced by straight-chain 1-alkanecarboxylate groups H
3C-(CH
2)n-COO-, with n between 6 and 14, are liquid crystals and have been studied for possible LCD applications.[3]

Octahydroxyanthraquinone is active against the malaria parasite, but rufigallol (1,2,3,5,6,7-hexahydroxyanthraquinone) is 22 times more potent.[4]

References

  1. ^ Georgievics, G. v. (1911). "Darstellung und Eigenschaften des Octooxyanthrachinons". Monatshefte für Chemie. 32 (5): 347–352. doi:10.1007/BF01518160. S2CID 97848374.
  2. ^ Wahl, Andre; Atack, F. W (1919) The Manufacture Of Organic Dyestuffs. G. Bell And Sons, Limited. Online version accessed on 2010-01-22.
  3. ^ a b Kumar, Sandeep (2008). "Rufigallol-based self-assembled supramolecular architectures". Phase Transitions. 81: 113–128. doi:10.1080/01411590701601610. S2CID 59445187.
  4. ^ Winter, R (1995). "Hydroxy-anthraquinones as antimalarial agents". Bioorganic & Medicinal Chemistry Letters. 5 (17): 1927–1932. doi:10.1016/0960-894X(95)00326-O.