Rufigallol

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).

Rufigallol
Skeletal formula of rufigallol
Ball-and-stick model of rufigallol
Names
Preferred 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
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • 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 ☒N
    Key: NEIMTOOWBACOHT-UHFFFAOYSA-N ☒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
  • C1=C2C(=C(C(=C1O)O)O)C(=O)C3=CC(=C(C(=C3C2=O)O)O)O
Properties
C14H8O8
Molar mass 304.210 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

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 similarities to rufigallol.[2]

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

See also

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.
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