Octahydroxyanthraquinone

Octahydroxyanthraquinone

Names
IUPAC name 1,2,3,4,5,6,7,8-Octahydroxy-9,10-anthracenedione
Other names Octahydroxyanthracenedione
Identifiers
CAS Number	169132-62-1
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:190016
ChEMBL	ChEMBL293801
ChemSpider	8016420
PubChem	9840703
InChI 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 Key: KOWBNNJAGJIIJW-UHFFFAOYSA-N
SMILES 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
Chemical formula	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).
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Infobox references

Octahydroxyanthraquinone is an organic compound with formula C
14H
8O
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
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: 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. 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.