Rufigallol
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| 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 | |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
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| 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). | |
Rufigallol or 1,2,3,5,6,7-hexahydroxy-9,10-anthraquinone is an organic compound with formula C
14O
8H
8. It one of several hydroxyanthraquinones. It occurs naturally being derived from gallic acid.
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] It is prepared by acid-catalyzed condensation of a pair of gallic acid molecules.[2]
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.[3]
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
[edit]References
[edit]- ^ a b c 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
- ^ Bisoyi, Hari Krishna; Kumar, Sandeep (2007). "Microwave-assisted synthesis of rufigallol and its novel room-temperature liquid crystalline derivatives". Tetrahedron Letters. 48 (25): 4399–4402. doi:10.1016/j.tetlet.2007.04.094.
- ^ R. W. Winter, Kenneth A. Cornell, Linda L. Johnson, Marina Ignatushchenko, David J. Hinrichs, Michael K. Riscoe (1996), Potentiation of The Antimalarial Agent Rufigallol. Antimicrobial Agents and Chemotherapy, Vol. 40, No. 6, Pages 1408–1411Online version accessed on 2010-02-01.