Octahydroxyanthraquinone

Octahydroxyanthraquinone
Names
IUPAC name
1,2,3,4,5,6,7,8-Octahydroxy-9,10-anthracenedione
Other names
Octahydroxyanthracenedione
Identifiers
169132-62-1 YesY
ChEBI CHEBI:190016 N
ChEMBL ChEMBL293801 N
ChemSpider 8016420 N
Jmol interactive 3D Image
Image
PubChem 9840703
Properties
C14H8O12
Molar mass 368.21 g·mol−1
log P -0.291
Acidity (pKa) 5.358
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Octahydroxyanthraquinone is an organic compound with formula C
14
H
8
O
12
, 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
3
C
-(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: 347. doi:10.1007/BF01518160.
  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. 1 2 Kumar, Sandeep (2008). "Rufigallol-based self-assembled supramolecular architectures". Phase Transitions 81: 113. doi:10.1080/01411590701601610.
  4. Winter, R (1995). "Hydroxy-anthraquinones as antimalarial agents". Bioorganic & Medicinal Chemistry Letters 5: 1927. doi:10.1016/0960-894X(95)00326-O.
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