Octahydroxyanthraquinone

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.

Octahydroxyanthraquinone
Skeletal formula of octahydroxyanthraquinone
Skeletal formula of octahydroxyanthraquinone
Ball and stick model of octahydroxyanthraquinone
Ball and stick model of octahydroxyanthraquinone
Names
Preferred IUPAC name
1,2,3,4,5,6,7,8-Octahydroxyanthracene-9,10-dione
Other names
Octahydroxyanthracenedione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C14H8O10/c15-5-1-2(8(18)12(22)11(21)7(1)17)6(16)4-3(5)9(19)13(23)14(24)10(4)20/h17-24H ☒N
    Key: KOWBNNJAGJIIJW-UHFFFAOYSA-N ☒N
  • OC1=C(O)C(O)=C2C(=O)C3=C(O)C(O)=C(O)C(O)=C3C(=O)C2=C1O
  • OC1=C(O)C(O)=C(O)C2=C1C(C3=C(O)C(O)=C(O)C(O)=C3C2=O)=O
Properties
C14H8O12
Molar mass 368.206 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).
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Infobox references

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 (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. 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.
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