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1,3,8-Trihydroxyanthraquinone

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1,3,8-Trihydroxyanthraquinone
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name 1,3,8-Trihydroxyanthracene-9,10-dione
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C14H8O5/c15-6-4-8-12(10(17)5-6)14(19)11-7(13(8)18)2-1-3-9(11)16/h1-5,15-17HKey: VVEKCQAFOLKNKB-UHFFFAOYSA-N
SMILES
  • O=C1C2=C(C=C(O)C=C2O)C(C3=CC=CC(O)=C31)=O
Properties
Chemical formula C14H8O5
Molar mass 256.213 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

1,3,8-Trihydroxyanthraquinone is an organic compound. It is one of many trihydroxyanthraquinone isomers, formally derived from anthraquinone by replacement of three hydrogen atoms by hydroxyl (OH) groups.

The compound occurs in some microorganisms and in alcoholic extracts of the wood of the South American plant Senna reticulata (mangerioba grande or maria mole in Portuguese), used in the local folk medicine for liver problems and rheumatism. The extract also contained, among other products chrysophanol (1,8-dihydroxy-3-methylanthraquinone), physcion (1,8-dihydroxy-3-methyl-6-methoxyanthraquinone), aloe-emodin (3-carbinol-1,8-dihydroxyanthraquinone), lunatin (3-methoxy-1,6,8-trihydroxyanthraquinone), emodin (6-methyl-1,3,8-trihydroxyanthraquinone), and chrysophanol-10,10'-bianthrone.

The substance is soluble in ethanol and chloroform but not in n-hexane, and melts at 283 °C.

See also

References

  1. ^ SANTOS, Rogério Nunes dos; SILVA, Maria Goretti de Vasconcelos, and BRAZ FILHO, Raimundo (2008). Constituintes químicos do caule de Senna reticulata Willd. (Leguminoseae) ("Chemical constituents isolated from the wood of Senna reticulata Willd") Química Nova , volume 31 issue 8, pages 1979--1981 (in Portuguese). doi:10.1590/S0100-40422008000800011 "It is the first report of 1,3,8-trihydroxyanthraquinone and 3-methoxy-1,6,8-trihydroxyanthraquinone in higher plants."
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