Hydroxyanthraquinone
| Related molecular formulas | ||
|---|---|---|
| C14H10O3 | ||
| C13H6O3 | C14H8O3 | C15H10O3 |
| C14H6O3 | ||
| C14H8O2 | C14H8O4 | |
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
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
Hexahydroxyanthraquinones have the formula C12H2(OH)6(CO)2.1,2,3,5,6,7-hexahydroxy-9,10-anthraquinone (rufigallol) occurs in nature.
See also
- Hydroxybenzoquinone
- Hydroxynaphthoquinone
References
- ^ 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.
- ^ 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.