Hydroxyanthraquinone
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.[3][4][5]
Isomers
[edit]One peculiarity of the hydroxyanthraquinones is the relative obscurity of the monohydroxy derivatives. Most hydroxyanthraquinones have two or more hydroxy groups.
Dihydroxy
[edit]Dihydroxyanthraquinones have the formula C12H6(OH)2(CO)2. The dyes alizarin (1,2-Dihydroxyanthraquinone) and quinizarin are prominent examples.
Trihydroxy
[edit]Trihydroxyanthraquinones have the formula C12H5(OH)3(CO)2. 1,2,4-Trihydroxyanthraquinone, commonly called purpurin, is a naturally occurring red/yellow dye.
Tetrahydroxy
[edit]Tetrahydroxyanthraquinones have the formula C12H4(OH)4(CO)2. The dye quinalizarin (1,2,5,8-tetrahydroxyanthraquinone is one example.
Hexahydroxy
[edit]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
[edit]References
[edit]- ^ 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.
- ^ Bigelow, L. A.; Reynolds, H. H. (1926). "Quinizarin". Org. Synth. 6: 78. doi:10.15227/orgsyn.006.0078.
- ^ 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.
- ^ Thomson, R. H. (1971). Naturally Occurring Quinones. London: Academic Press. Quoted by Khalafy and Bruce.
- ^ Thomson, R. H. (1987). Naturally Occurring Quinones III. London: Chapman and Hall. Quoted by Khalafy and Bruce.