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Hydroxyanthraquinone

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(Redirected from 1-Hydroxyanthraquinone) Class of chemical compounds
1,4-Dihydroxyanthraquinone, commonly called quinizarin is a common hydroxyanthroquinone.

In organic chemistry hydroxyanthraquinones refers to compounds with the formula C12H8-n(OH)n(CO)2 where n ≥ 1. Almost all hydroxyanthraquinones are derivative of 9,10-anthraquinone.

Isomers

One peculiarity of the hydroxyanthraquinones is the relative obscurity of the monohydroxy derivatives. Most hydroxyanthraquinones have two or more hydroxy groups.

Dihydroxy

Dihydroxyanthraquinones have the formula C12H6(OH)2(CO)2. The dyes alizarin (1,2-Dihydroxyanthraquinone) and quinizarin are prominent examples.

Trihydroxy

Trihydroxyanthraquinones have the formula C12H5(OH)3(CO)2. 1,2,4-Trihydroxyanthraquinone, commonly called purpurin, is a naturally occurring red/yellow dye.

Tetrahydroxy

Tetrahydroxyanthraquinones have the formula C12H4(OH)4(CO)2. The dye quinalizarin (1,2,5,8-tetrahydroxyanthraquinone is one example.

Hexahydroxy

Dihydroxyanthraquinones have the formula C12H2(OH)6(CO)2.1,2,3,5,6,7-hexahydroxy-9,10-anthraquinone (rufigallol) occurs in nature.

See also

References

  1. 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 978-3527306732.
  2. Bigelow, L. A.; Reynolds, H. H. (1926). "Quinizarin". Org. Synth. 6: 78. doi:10.15227/orgsyn.006.0078.
  3. Khalafy, J.; Bruce, J. M. (2002). "Oxidative Dehydrogenation of 1-Tetralones: Synthesis of Juglone, Naphthazarin, and α-Hydroxyanthraquinones" (pdf). Journal of Sciences, Islamic Republic of Iran. 13 (2): 131–139.
  4. Thomson, R. H. (1971). Naturally Occurring Quinones. London: Academic Press. Quoted by Khalafy and Bruce.
  5. Thomson, R. H. (1987). Naturally Occurring Quinones III. London: Chapman and Hall. Quoted by Khalafy and Bruce.
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