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A dihydroxyanthraquinone is any of several isomeric organic compounds with formula (C₁₂H₆(OH)₂)(CO)₂, 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.

Isomers

From 9,10-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, xanthopurpurin)
• 1,4-Dihydroxyanthraquinone (quinizarin)
• 1,5-Dihydroxyanthraquinone (anthrarufin)
• 1,6-Dihydroxyanthraquinone
• 1,7-Dihydroxyanthraquinone
• 1,8-Dihydroxyanthraquinone (dantron, chrysazin)
• 2,3-Dihydroxyanthraquinone (histazarin)
• 2,6-Dihydroxyanthraquinone (anthraflavic acid)
• 2,7-Dihydroxyanthraquinone (isoanthraflavic acid)

From other anthraquinones

There are also many dihydroxy derivatives of other anthraquinones, such as 1,2-anthraquinone, 1,4-anthraquinone, and 2,6-anthraquinone.

See also

• Hydroxyquinone
• Hydroxybenzoquinone
• Hydroxynaphthoquinone
• Hydroxyanthraquinone
• Trihydroxyanthraquinone
• Tetrahydroxyanthraquinone
• Pentahydroxyanthraquinone
• Hexahydroxyanthraquinone
• Heptahydroxyanthraquinone
• Octahydroxyanthraquinone

References

1. ^ Wahl, Andre; Atack, F. W. (1919). The Manufacture Of Organic Dyestuffs. London: G. Bell And Sons, Limited. pp. 202–212.
2. McGuigan, Hugh Alister (1921). An introduction to chemical pharmacology; pharmacodynamics in relation to chemistry. Philadelphia: P. Blakiston's son & Co. p. 132.
3. Khalafy, Jabbar; Bruce, J.M. (2002-06-01). "Oxidative dehydrogenation of 1-tetralones: Synthesis of juglone, naphthazarin, and α-hydroxyanthraquinones". Journal of Sciences, Islamic Republic of Iran. 13 (2). ISSN 1016-1104. 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.
4. Thomson, Ronald Hunter (1971). Naturally Occurring Quinones. Academic Press. p. 66. ISBN 978-0-12-689650-3.
5. Thomson, Ronald Hunter (1987). Naturally Occurring Quinones III: Recent Advances. Springer Netherlands. p. 358. ISBN 978-0-412-26730-7.
6. Arcamone, Federico (1981). Doxorubicin: Anticancer Antibiotics. Academic Press. ISBN 978-0-12-059280-7.
7. Ross Kelly, T. (1984). "Preface". Tetrahedron. 40 (22): 4537. doi:10.1016/S0040-4020(01)91512-1.
8. Ashton, Richard E.; Andre, Pierre; Lowe, Nicholas J.; Whitefield, Martin (1983). "Anthralin: Historical and current perspectives". Journal of the American Academy of Dermatology. 9 (2): 173–192. doi:10.1016/s0190-9622(83)70125-8. PMID 6309924.
9. Kemény, L.; Ruzicka, T.; Braun-Falco, O. (1990). "Dithranol: a review of the mechanism of action in the treatment of psoriasis vulgaris". Skin Pharmacology. 3 (1): 1–20. ISSN 1011-0283. PMID 2202336.
10. ^ Buckingham, John B. (1996). Dictionary of Organic Compounds. Vol. 1. Chapman & Hall. ISBN 978-0-412-54090-5.

• Dihydroxyanthraquinones