Rufigallol

Rufigallol

Names
IUPAC name 1,2,3,5,6,7-Hexahydroxyanthracene-9,10-dione
Other names Rufigallic acid; 1,2,3,5,6,7-Hexahydroxy-9,10-anthraquinone; 1,2,3,5,6,7-Hexahydroxyanthracene-9,10-dione
Identifiers
CAS Number	82-12-2
ChEBI	CHEBI:37500
ChemSpider	59160
Jmol interactive 3D	Image
PubChem	65737
InChI InChI=1S/C14H8O8/c15-5-1-3-7(13(21)11(5)19)10(18)4-2-6(16)12(20)14(22)8(4)9(3)17/h1-2,15-16,19-22H Key: NEIMTOOWBACOHT-UHFFFAOYSA-N InChI=1/C14H8O8/c15-5-1-3-7(13(21)11(5)19)10(18)4-2-6(16)12(20)14(22)8(4)9(3)17/h1-2,15-16,19-22H Key: NEIMTOOWBACOHT-UHFFFAOYAS
SMILES C1=C2C(=C(C(=C1O)O)O)C(=O)C3=CC(=C(C(=C3C2=O)O)O)O
Properties
Chemical formula	C14H8O8
Molar mass	304.21 g·mol^−1
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

Rufigallol or 1,2,3,5,6,7-hexahydroxy-9,10-anthraquinone is an organic compound with formula C
14O
8H
8, which can be viewed as a derivative of anthraquinone through the replacement of six hydrogen atoms (H) by hydroxyl groups (OH).

The compound is soluble in dioxane, from which it crystallizes as red needles that sublime without melting at 365 °C.^[1] It can be obtained by treating gallic acid with concentrated sulfuric acid and then with sodium hydroxide.^[1]

Rufigallol is particularly toxic to the malarial parasite Plasmodium falciparum and has a synergistic effect in combination with the antimalarial drug exifone, which has structural sumilarities to rufigallol.^[2]

Rufigallol forms a crimson-colored complex with beryllium, aluminum, thorium, zirconium and hafnium, and this reaction has been used for the spot and spectrophotometric determination of beryllium in low concentrations.^[1]

See also

• Quinone
• Hydroxyanthraquinone
• Hexahydroxyanthraquinone
• Octahydroxyanthraquinone

References

1. M. A. Azim and A. A. Ayaz (1969), Spectrophotometric determination of beryllium. Microchimica Acta Volume 57, Number 1, pages 153-159 doi:10.1007/BF01216677
2. R. W. WINTER, KENNETH A. CORNELL, LINDA L. JOHNSON, MARINA IGNATUSHCHENKO,DAVID J. HINRICHS and MICHAEL K. RISCOE (1996), Potentiation of the Antimalarial Agent Rufigallol. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, Vol. 40, No. 6, pages 1408–1411. Online version accessed on 2010-02-01.