1,3,8-Trihydroxyanthraquinone

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1,3,8-Trihydroxyanthraquinone
1,3,8-Trihydroxyanthraquinone.svg
1,3,8-trihydroxyanthraquinone-3D-balls.png
Names
Preferred IUPAC name
1,3,8-Trihydroxyanthracene-9,10-dione
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • 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/h1-5,15-17H
    Key: VVEKCQAFOLKNKB-UHFFFAOYSA-N
  • O=C1C2=C(C=C(O)C=C2O)C(C3=CC=CC(O)=C31)=O
Properties
C14H8O5
Molar mass 256.210 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 [1] 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. [1]

The substance is soluble in ethanol and chloroform but not in n-hexane, and melts at 283 °C. [1]

See also

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Methoxy group Functional group consisting of a methyl group bound to oxygen

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Anthraquinones

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Phenanthrenoid

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Emodin Chemical compound

Emodin (6-methyl-1,3,8-trihydroxyanthraquinone) is a chemical compound, of the anthraquinone family, that can be isolated from rhubarb, buckthorn, and Japanese knotweed. Emodin is particularly abundant in the roots of the Chinese rhubarb, knotweed and knotgrass as well as Hawaii ‘au‘auko‘i cassia seeds or coffee weed. It is specifically isolated from Rheum Palmatum L. It is also produced by many species of fungi, including members of the genera Aspergillus, Pyrenochaeta, and Pestalotiopsis, inter alia. The common name is derived from Rheum emodi, a taxonomic synonym of Rheum australe, and synonyms include emodol, frangula emodin, rheum emodin, 3-methyl-1,6,8-trihydroxyanthraquinone, Schuttgelb, and Persian Berry Lake.

Aloe emodin

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Chrysophanol Chemical compound

Chrysophanol, also known as chrysophanic acid, is a fungal isolate and a natural anthraquinone. It is a C-3 methyl substituted chrysazin of the trihydroxyanthraquinone family.

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Lunatin Chemical compound

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Lichexanthone Chemical compound found in some lichens

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References

  1. 1 2 3 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 [online], 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."