2,3-dihydroxyanthraquinone

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Structural formula
Structure of 2,3-dihydroxyanthraquinone
General
Surname 2,3-dihydroxyanthraquinone
other names
  • Hystazarin
  • Hystazine
  • 2,3-dihydroxy-9,10-anthracenedione
  • 2,3-dihydroxy-9,10-anthraquinone
Molecular formula C 14 H 8 O 4
Brief description

Yellow-brown needles

External identifiers / databases
CAS number 483-35-2
PubChem 11031986
ChemSpider 9207160
Wikidata Q43685794
properties
Molar mass 240.21 g · mol -1
Physical state

Firmly

solubility
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2,3-Dihydroxyanthraquinone , also known as hystazarin , is an organic compound from the group of anthraquinones (more precisely the dihydroxyanthraquinones ).

history

2,3-Dihydroxyanthraquinone was discovered by Carl Liebermann in 1888 . He called it hystazarin.

Occurrence

Indian madder ( Rubia cordifolia )

Hystazarin occurs as 2-hydroxy-3-methoxyanthraquinone in Indian madder (Latin Rubia cordifolia ).

Extraction and presentation

The derivative from the Indian madder can be prepared by heating with conc. Convert hydrochloric acid to hystazarin with elimination of chloromethyl .

If pyrocatechol and phthalic anhydride are heated together with sulfuric acid , next to alizarin mainly hystazarin is formed. If, however, catechol and phthalic anhydride are condensed beforehand in a sodium-aluminum chloride melt , a keto acid can be obtained which, when heated with sulfuric acid , gives almost pure hystazarine (90% yield).

Synthesis of 2,3-dihydroxyanthraquinone

If hystazarine dimethyl ether is mixed with hydrobromic acid , pure hystazarine is formed with elimination of bromomethane after prolonged heating .

Individual evidence

  1. ↑ a b entry on hystazarin. In: Römpp Online . Georg Thieme Verlag, accessed on August 4, 2018.
  2. ↑ P. Pfeiffer, Ph. Fischer, J. Kuntner, P. Monti, Z. Pros: On the theory of color lacquers, II. In: Justus Liebigs Annalen der Chemie . 398, 1913, pp. 137-196, doi : 10.1002 / jlac.19133980203 .
  3. ↑ a b c Carl Liebermann: About a new dioxyanthraquinone, the hystazarin , In: Reports of the German Chemical Society , Volume 21, No. 2, July 1888, pp. 2501-2502, doi : 10.1002 / cber.18880210252 .
  4. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  5. ↑ a b Emil Abderhalden (Ed.): Biochemisches Handlexikon: VI. Volume dyes of the flora and fauna . tape 4 . Springer Berlin Heidelberg, 1911, ISBN 3-642-90816-0 , p. 97-98 . doi : 10.1007 / 978-3-642-90816-3 .
  6. ↑ Hans Waldmann: Synthesis of Hystazarins. In: Journal for Practical Chemistry . 150, 1938, pp. 99-106, doi : 10.1002 / prac.19381500403 .
  7. ↑ K. Lagodzinski: About 2,3-Dioxyanthracen. In: Justus Liebig's Annals of Chemistry . 342, 1905, pp. 90-111, doi : 10.1002 / jlac.19053420106 .