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Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').
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Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chem
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| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 37502
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| ChemSpiderID = 170598

Revision as of 22:32, 5 August 2011

1,3-Dihydroxyanthraquinone
Skeletal formula
Ball-and-stick model
Names
IUPAC name
1,3-dihydroxyanthracene-9,10-dione
Other names
Purpuroxanthin; Xanthopurpurin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
  • InChI=1S/C14H8O4/c15-7-5-10-12(11(16)6-7)14(18)9-4-2-1-3-8(9)13(10)17/h1-6,15-16H checkY
    Key: WPWWKBNOXTZDQJ-UHFFFAOYSA-N checkY
  • InChI=1/C14H8O4/c15-7-5-10-12(11(16)6-7)14(18)9-4-2-1-3-8(9)13(10)17/h1-6,15-16H
    Key: WPWWKBNOXTZDQJ-UHFFFAOYAR
  • O=C2c1ccccc1C(=O)c3c2cc(O)cc3O
Properties
C14H8O4
Molar mass 240.21 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

1,3-Dihydroxyanthraquinone, also called purpuroxanthin or xanthopurpurin is an organic compound with formula C
14
H
8
O
4
that occurs in the plant Rubia cordifolia (Indian madder).[1] It is one of ten dihydroxyanthraquinone isomers. Its molecule can be viewed as deriving from anthraquinone by replacement of two hydrogen atoms (H) by hydroxyl groups (-OH).

Xanthopurpurin occurs in small amounts (as a glycoside) in the root of the common madder plant, Rubia tinctorum, together with alizarin, purpurin and other anthraquinone derivatives.[2]

Properties

Xanthopurpurin is insoluble in hexane but soluble in chloroform. It can be obtained from solutions in the latter as reddish crystals that melt at 270–273 °C.[1]

Like many dihydroxy- and trihydroxyanthraquinones, it has a purgative action, although only 1/6 as effective as 1,2,7-trihidroxyanthraquinone (anthrapurpurin).[3]

See also

References

  1. ^ a b Padma S. Vankar, Rakhi Shanker, Debajit Mahanta and S.C. Tiwari (2008), Ecofriendly sonicator dyeing of cotton with Rubia cordifolia Linn. using biomordant. Dyes and Pigments, Volume 76, Issue 1, Pages 207-212. doi:10.1016/j.dyepig.2006.08.023
  2. ^ Goverdina C. H. Derksen, Harm A. G. Niederländer and Teris A. van Beek (2002), Analysis of anthraquinones in Rubia tinctorum L. by liquid chromatography coupled with diode-array UV and mass spectrometric detection. Journal of Chromatography A, Volume 978, Issues 1-2, Pages 119-127, doi:10.1016/S0021-9673(02)01412-7
  3. ^ Hugh Alister McGuigan (1921), An introduction to chemical pharmacology; pharmacodynamics in relation to chemistry. P. Blakiston's son, Philadelphia. Online version at archive.org, accessed on 2010-01-30.

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