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.

Quick facts Names, Identifiers ...

Octahydroxyanthraquinone

Names
Preferred IUPAC name 1,2,3,4,5,6,7,8-Octahydroxyanthracene-9,10-dione
Other names Octahydroxyanthracenedione
Identifiers
CAS Number	169132-62-1 Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:190016 N
ChEMBL	ChEMBL293801 N
ChemSpider	8016420 N
PubChem CID	9840703
UNII	62VN682KQG Y
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 N Key: KOWBNNJAGJIIJW-UHFFFAOYSA-N 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	C14H8O10
Molar mass	336.208 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 YN ?) Infobox references

Close

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]