2,6-dihydroxyanthraquinone

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Structural formula
Structure of 2,6-dihydroxyanthraquinone
General
Surname 2,6-dihydroxyanthraquinone
other names
  • Anthraflavin
  • Anthraflavic acid
  • 2,6-dihydroxy-9,10-anthracenedione
  • 2,6-dihydroxy-9,10-anthraquinone
Molecular formula C 14 H 8 O 4
Brief description

yellow powder

External identifiers / databases
CAS number 84-60-6
EC number 201-544-3
ECHA InfoCard 100.001.404
PubChem 6776
Wikidata Q27115942
properties
Molar mass 240.21 g · mol -1
solubility
safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2,6-Dihydroxyanthraquinone , also known as anthraflavic acid , is a natural substance that occurs in madder . It is an organic compound from the substance group of the anthraquinones (more precisely the dihydroxyanthraquinones ).

Occurrence

Madder madder ( Rubia tinctorum )

2,6-Dihydroxyanthraquinone occurs glycosidically bound together with other anthraquinones in the roots of madder madder .

Extraction and presentation

The 2,6-dihydroxyanthraquinone can be extracted directly from the roots of the madder.

To make anthraflavic acid , methoxybenzoic acid is heated with benzoic acid , concentrated sulfuric acid, and water. This mixture is then boiled with water and then with barite water . By adding hydrochloric acid , the remaining components are precipitated, which are then washed with benzene . Only the anthraflavic acid remains undissolved.

Individual evidence

  1. ↑ a b c data sheet Anthraflavic Acid from Sigma-Aldrich , accessed on July 24, 2017 ( PDF ).
  2. ^ A b Carl Liebermann, STV Kostanecki: About the coloring properties and the syntheses of oxyanthraquinones. In: Justus Liebig's Annals of Chemistry . 240, 1887, pp. 245-304, doi : 10.1002 / jlac.18872400302 .
  3. ↑ a b E. Schunk, H. Roemer: Ueber Anthraflavinsäure und Isoanthraflavinsäure. In: Reports of the German Chemical Society . 9, 1876, pp. 379-383, doi : 10.1002 / cber.187600901119 .
  4. ↑ E. Schunck, H. Römer: Ueber Anthrarufin, a new Bioxyanthraquinone from metaoxybenzoic acid. In: Reports of the German Chemical Society . 11, 1878, pp. 1176-1179, doi : 10.1002 / cber.187801101314 .
  5. ↑ a b Goverdina CH Derksen, Harm AG Niederländer, Teris A. van Beek: Analysis of anthraquinones in Rubia tinctorum L. by liquid chromatography coupled with diode-array UV and mass spectrometric detection . Journal of Chromatography A , 978, 2002, pp. 119-127, doi : 10.1016 / S0021-9673 (02) 01412-7 .