Rufigallol

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
CAS Number	82-12-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:37500 ;
ChemSpider	59160 ;
PubChem CID	65737;
UNII	S977046N6I ;
CompTox Dashboard (EPA)	DTXSID1075359 ;
	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	304.210 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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]

References

^ ^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.

[azim-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] 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.

[winter-3] 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.

[1]

[2]

[3]

Rufigallol

See also

References