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'''Rufigallol''' or '''1,2,3,5,6,7-hexahydroxy-9,10-anthraquinone''' is an ] with formula {{chem|C|14|O|8|H|8}}, which can be viewed as a derivative of ] through the replacement of six ] atoms (H) by ] groups (OH). '''Rufigallol''' or '''1,2,3,5,6,7-hexahydroxy-9,10-anthraquinone''' is an ] with formula {{chem|C|14|O|8|H|8}}. It one of several ]s. It occurs naturally being derived from ].


The compound is soluble in ], from which it crystallizes as red needles that sublime without melting at 365 °C.<ref name=azim/> It can be obtained by treating ] with concentrated ] and then with ].<ref name=azim/> The compound is soluble in ], from which it crystallizes as red needles that sublime without melting at 365 °C.<ref name=azim/> It can be obtained by treating ] with concentrated ] and then with ].<ref name=azim/> It is prepared by acid-catalyzed condensation of a pair of ] molecules.<ref>{{cite journal |doi=10.1016/j.tetlet.2007.04.094 |title=Microwave-assisted synthesis of rufigallol and its novel room-temperature liquid crystalline derivatives |date=2007 |last1=Bisoyi |first1=Hari Krishna |last2=Kumar |first2=Sandeep |journal=Tetrahedron Letters |volume=48 |issue=25 |pages=4399–4402 }}</ref>


Rufigallol is particularly toxic to the ]l parasite '']'' and has a ] effect in combination with the ] drug ], which has structural similarities to rufigallol.<ref name=winter>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. accessed on 2010-02-01. <!-- Article has no DOI? {{doi|}}--></ref> Rufigallol is particularly toxic to the ]l parasite '']'' and has a ] effect in combination with the ] drug ], which has structural similarities to rufigallol.<ref name=winter>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 1408–1411 accessed on 2010-02-01. <!-- Article has no DOI? {{doi|}}--></ref>


Rufigallol forms a crimson-colored complex with ], ], ], ] and ], and this reaction has been used for the ] and ] determination of beryllium in low concentrations.<ref name=azim>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}}</ref> Rufigallol forms a crimson-colored complex with ], ], ], ] and ], and this reaction has been used for the ] and ] determination of beryllium in low concentrations.<ref name=azim>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}}</ref>

Latest revision as of 17:05, 29 August 2024

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
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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/h1-2,15-16,19-22HKey: 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/h1-2,15-16,19-22HKey: 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. It can be obtained by treating gallic acid with concentrated sulfuric acid and then with sodium hydroxide. It is prepared by acid-catalyzed condensation of a pair of gallic acid molecules.

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.

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.

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. 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.
  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.
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