1,4-Dihydroxyanthraquinone

1,4-Dihydroxyanthraquinone
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
1,4-Dihydroxyanthracene-9,10-dione
Other names
Quinizarin; Solvent Orange 86
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.245 Edit this at Wikidata
UNII
  • InChI=1S/C14H8O4/c15-9-5-6-10(16)12-11(9)13(17)7-3-1-2-4-8(7)14(12)18/h1-6,15-16H checkY
    Key: GUEIZVNYDFNHJU-UHFFFAOYSA-N checkY
  • InChI=1/C14H8O4/c15-9-5-6-10(16)12-11(9)13(17)7-3-1-2-4-8(7)14(12)18/h1-6,15-16H
    Key: GUEIZVNYDFNHJU-UHFFFAOYAX
  • O=C2c1ccccc1C(=O)c3c2c(O)ccc3O
Properties
C14H8O4
Molar mass 240.21 g/mol
Appearance Orange or red-brown crystalline powder
Melting point 198 to 199 °C (388 to 390 °F; 471 to 472 K)
Boiling point 450 °C (842 °F; 723 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkYX markN ?)

1,4-Dihydroxyanthraquinone, also called quinizarin or Solvent Orange 86, is a chromogenic organic compound derived from anthroquinone. Quinizarin is an orange or red-brown crystalline powder. It is formally derived from anthraquinone by replacement of two hydrogen atoms by hydroxyl (OH) groups. It is one of ten dihydroxyanthraquinone isomers and occurs in small amounts (as a glycoside) in the root of the madder plant, Rubia tinctorum.

Production

Quinizarin is produced by the reaction of phthalic anhydride and 4-chlorophenol followed by hydrolysis of the chloride:

Summary equation for one synthesis of alizarin.[sic.]

It can also be prepared less efficiently from phthalic anhydride and hydroquinone.[citation needed]

Uses

Industrial

Quinizarin is an inexpensive dye that is used to color gasoline and some heating oils. It is used as an intermediate for the synthesis of indanthrene- and alizarin-derived dyes. The OH groups can be replaced by chloride. Chlorination and bromination afford other dyes. Amination (replacement of one OH by ArNH) with aniline derivatives followed by sulfonation affords other dyes such as Acid Violet 43. It is also used to form lake pigments with calcium, barium, and lead.

Analytical Chemistry

In a dimethyl sulfoxide medium with the presence of sodium hydroxide and sodium carbonate, quinizarin reacts with lithium cations to produce a blue-violet color. This has been proposed as a method for the spectrophotometric determination of lithium in blood and human serum, as an alternative to the highly toxic organoarsenic reagent thorin.

Quinizarin sample (Historic Dye Collection of TU Dresden).

See also

References

  1. ↑ Derksen, G. C. H.; Niederländer, H. A. G.; van Beek, T. A. (2002). "Analysis of Anthraquinones in Rubia tinctorum L. by Liquid Chromatography Coupled with Diode-Array UV and Mass Spectrometric Detection". Journal of Chromatography A. 978 (1–2): 119–127. Bibcode:2002JChA..978..119D. doi:10.1016/S0021-9673(02)01412-7. PMID 12458949.
  2. 1 2 Bien, H.-S.; Stawitz, J.; Wunderlich, K. "Anthraquinone Dyes and Intermediates". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_355. ISBN 978-3-527-30673-2.
  3. ↑ Bigelow, L. A.; Reynolds, H. H. (1926). "Quinizarin". Org. Synth. 6: 78. doi:10.15227/orgsyn.006.0078.
  4. ↑ Gracia, L (January 1997). "Spectrophotometric determination of lithium with Quinizarin in drugs and serum". Talanta. 44 (1): 75–83. doi:10.1016/S0039-9140(96)02018-8. ISSN 0039-9140. PMID 18966719.