Octahydroxyanthraquinone

Octahydroxyanthraquinone
Skeletal formula of octahydroxyanthraquinone	Ball and stick model of 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 (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:190016 ;
ChEMBL	ChEMBL293801 ;
ChemSpider	8016420 ;
PubChem CID	9840703;
CompTox Dashboard (EPA)	DTXSID40431697 ;
	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	368.206 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

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

Georgievics, G. v. (1911). "Darstellung und Eigenschaften des Octooxyanthrachinons". Monatshefte für Chemie. 32 (5): 347–352. doi:10.1007/BF01518160.
Wahl, Andre; Atack, F. W (1919) The Manufacture Of Organic Dyestuffs. G. Bell And Sons, Limited. Online version accessed on 2010-01-22.
Kumar, Sandeep (2008). "Rufigallol-based self-assembled supramolecular architectures". Phase Transitions. 81: 113–128. doi:10.1080/01411590701601610.
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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[1] Georgievics, G. v. (1911). "Darstellung und Eigenschaften des Octooxyanthrachinons". Monatshefte für Chemie. 32 (5): 347–352. doi:10.1007/BF01518160.

[manu-2] Wahl, Andre; Atack, F. W (1919) The Manufacture Of Organic Dyestuffs. G. Bell And Sons, Limited. Online version accessed on 2010-01-22.

[sankum-3] Kumar, Sandeep (2008). "Rufigallol-based self-assembled supramolecular architectures". Phase Transitions. 81: 113–128. doi:10.1080/01411590701601610.

[winter-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.