A dihydroxyanthraquinone is any of several isomeric organic compounds with formula C
4, formally derived from 9,10-anthraquinone by replacing two hydrogen atoms by hydroxyl groups. Dihyroxyantraquinones have been studied since the early 1900s, and include some compounds of historical and current importance. The isomers differ in the position of the hydroxyl groups, and of the carbonyl oxygens (=O) of the underlying anthraquinone.
The unqualified term "dihydroxyanthraquinone" usually means a hydroxy derivative of 9,10-anthraquinone. The dihydroxy-9,10-anthraquinone functional group occurs widely in natural products, and is an important feature of the anthracycline antitumour antibiotics. In particular, 1,8-Dihydroxy-9,10-anthraquinone is the precursor for the important topical antipsoriatic drug anthralin, 1,8-dihydroxy-9-anthrone,
There are 28 ways of choosing two of the 8 possible hydrogens, but because of the four-fold symmetry of the 9,10-anthraquinone core there are only 10 distinct isomers.
- 1,2-Dihydroxyanthraquinone (alizarin)
- 1,3-Dihydroxyanthraquinone (purpuroxanthin, xantopurpurin)
- 1,4-Dihydroxyanthraquinone (quinizarin)
- 1,5-Dihydroxyanthraquinone (anthrarufin)
- 1,8-Dihydroxyanthraquinone (dantron, chrysazin)
- 2,6-Dihydroxyanthraquinone (anthraflavic acid)
From other anthraquinones
- Wahl, Andre; Atack, F. W (1919) The Manufacture Of Organic Dyestuffs. G. Bell And Sons, Limited. Online version accessed on 2010-01-22.
- Hugh Alister McGuigan (1921), An introduction to chemical pharmacology; pharmacodynamics in relation to chemistry. P. Blakiston's son, Philadelphia. Online version at archive.org, accessed on 2010-01-30.
- J. Khalafy and J.M. Bruce (2002), Oxidative dehydrogenation of 1-tetralones: Synthesis of juglone, naphthazarin, and [alpha]-hydroxyanthraquinones. Journal of Sciences, Islamic Republic of Iran, volume 13 issue 2, pages 131-139. "Silver(I) oxide in 1,4-dioxane converted 9,10-dihydroxy-1-oxo, 9,10-dihydroxy-1,5-dioxo, and 1,8-dioxo-1,2,3,4,5,6,7,8-octahydro anthracene into, respectively, 1-hydroxy-5,6,7,8-tetrahydro-, 1,5-dihydroxy-, and 1,8-dihydroxy-9,10-anthraquinone, in high yield."
- Thomson R.H. Naturally Occurring Quinones. Academic Press, London (1971). Quoted by Khalafy and Bruce.
- Thomson R.H. Naturally Occurring Quinones III. Chapman and Hall, London (1987). Quoted by Khalafy and Bruce.
- Arcamone F. (1981). Doxorubicin Anticancer Antibiotics. Academic Press, New York. Quoted by Khalafy and Bruce.
- Kelly T.R. (1984). Tetrahedron, 40: 22. Quoted by Khalafy and Bruce.
- Ashton R.E., Andre P., Lowe N.J. and Whitefield M. J. (1983). Am. Acad. Dermatol., 9: 173. Quoted by Khalafy and Bruce.
- Kemeny L., Ruzicka T. and Braun-Falco O. (1990). Skin Pharmacol., 3: 1. Quoted by Khalafy and Bruce.
- CRC (1996), Dictionary of organic compounds, Volume 1 CRC Press Online version at books.google.com, accessed on 2010-01-22.