Quinizarin

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of quinizarine
General
Surname Quinizarin
other names
  • 1,4-dihydroxy-9,10-anthraquinone
  • 1,4-dihydroxyanthracene-9,10-dione
  • CI 58050
  • Macrolex Orange GG
  • Smoke Orange R
  • Solvent Orange 86
Molecular formula C 14 H 8 O 4
Brief description

yellow-red leaflets or deep red needles

External identifiers / databases
CAS number 81-64-1
EC number 201-368-7
ECHA InfoCard 100.001.245
PubChem 6688
ChemSpider 6433
Wikidata Q906609
properties
Molar mass 240.20 g mol −1
Physical state

firmly

Melting point
  • 198-199 ° C
  • 200-202 ° C
solubility

soluble in water, ethanol , diethyl ether and benzene

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 317-319
P: 280-305 + 351 + 338
Toxicological data

> 5000 mg kg −1 ( LD 50 ,  mouse ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Quinizarin is an organic-chemical aromatic compound. It is an anthraquinone dye related to alizarin .

Occurrence

Madder madder ( Rubia tinctorum )

Like other anthraquinones, quinizarin occurs in the roots of the madder .

presentation

Chinizarin ( historical dye collection of the TU Dresden )

A number of synthesis options are described in the literature. Quinizarin can be obtained from the reaction between phthalic anhydride and hydroquinone . Aluminum chloride can be used as Lewis acid for this purpose . Another synthetic route is given by the reaction of 1,4-dihydroxynaphthalene with maleic anhydride and aluminum chloride. Quinizarin can also be produced by reducing the purpurine in a weakly alkaline, neutral or acidic solution, or with glacial acetic acid and zinc dust .

use

The dye is orange in its protonated form. When adding hydroxide ions, the dye turns violet. Thus it can be used as a pH indicator.

Individual evidence

  1. ↑ a b c Entry on quinizarin. In: Römpp Online . Georg Thieme Verlag, accessed on March 28, 2014.
  2. ↑ a b c Quinizarin data sheet from Sigma-Aldrich , accessed on May 25, 2011 ( PDF ).
  3. ^ Entry on quinizarin in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  4. ↑ Goverdina CH Derksen, Harm AG Niederländer and Teris A. van Beek: Analysis of anthraquinones in Rubia tinctorum L. by liquid chromatography coupled with diode-array UV and mass spectrometric detection , in: Journal of Chromatography A , 2002 , 978  (1- 2), pp. 119-127; doi : 10.1016 / S0021-9673 (02) 01412-7 .
  5. ↑ H. Raudnitz: About 5.8-Dioxy-alpha-anthrapyridinequinones , in: Chem. Ber. , 1929 , 62 , pp. 509-513; doi : 10.1002 / cber.19290620310 .
  6. ↑ K. Zahn, P. Ochwat: On the constitution and reaction of polynuclear polyoxyquinones. About naphtazarin and quinizarin , in: Liebigs Annalen , 1928 , 462 , pp. 82-97; doi : 10.1002 / jlac.19284620105 .
  7. ^ Rudolf Bauer, Heinrich Wieland: Reduction and hydrogenation of organic compounds . Springer-Verlag, 1918, ISBN 978-3-662-33872-8 , p. 56 ( limited preview in Google Book search).

Web links

Commons : Chinizarin  - collection of images, videos and audio files