Anthrone

Anthrone is a tricyclic aromatic ketone. It is used for a common cellulose assay and in the colorimetric determination of carbohydrates.[1]

Derivatives of anthrone are used in pharmacy as laxative. They stimulate the motion of the colon and reduce water reabsorption. Some anthrone derivatives can be extracted from a variety of plants, including Rhamnus frangula, Aloe ferox, Rheum officinale, and Cassia senna.[2] Glycosides of anthrone are also found in high amounts in rhubarb leaves, and alongside concentrated amounts of oxalic acid are the reason for the leaves being inedible.

## Synthesis and reactions

Anthrone can be prepared from anthraquinone by reduction with tin or copper.[3]

An alternative synthesis involves cyclization of o-benzylbenzoic acid induced with hydrogen fluoride.[4]

Anthrone syntheses

Anthrone condenses with glyoxal to give, following dehydrogenation, acedianthrone, a useful octacyclic pigment.[5]

Tautomeric equilibrium for anthrone.

Anthrone is the more stable tautomer relative to the anthrol as has been established also by X-ray crystallography.[6] The tautomeric equilibrium is estimated at 100 in aqueous solution. For the two other isomeric anthrols, the tautomeric equilibrium is reversed: they are phenolic.[7]

Anthrone undergoes nitration using conventional conditions for aromatic nitration, implying that it is the hydroxy tautomer that is the reactant.[8]

## References

1. ↑ Trevelyan, W. E.; Forrest, RS; Harrison, JS (1952). "Determination of Yeast Carbohydrates with the Anthrone Reagent". Nature 170 (4328): 626–627. doi:10.1038/170626a0. PMID 13002392. Bibcode: 1952Natur.170..626T.
2. ↑ Niaz, Kamal; Khan, Fazlullah (2020-01-01), Sanches Silva, Ana; Nabavi, Seyed Fazel; Saeedi, Mina et al., eds., "Chapter 3 - Analysis of polyphenolics", Recent Advances in Natural Products Analysis (Elsevier): pp. 39–197, doi:10.1016/b978-0-12-816455-6.00003-2, ISBN 978-0-12-816455-6, https://www.sciencedirect.com/science/article/pii/B9780128164556000032, retrieved 2024-06-01
3. ↑ Macleod, L. C.; Allen, C. F. H. (1934). "Benzanthrone". Organic Syntheses 14: 4. doi:10.15227/orgsyn.014.0004.
4. ↑ Fieser, Louis F.; Hershberg, E. B. (May 1939). "Inter- and Intramolecular Acylations with Hydrogen Fluoride". Journal of the American Chemical Society 61 (5): 1272–1281. doi:10.1021/ja01874a079. Bibcode: 1939JAChS..61.1272F.
5. ↑ Bien, H.-S.; Stawitz, J.; Wunderlich, K. (2005). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_355.
6. ↑ Lian, Jian-Jou; Lin, Chung-Chang; Chang, Hsu-Kai; Chen, Po-Chiang; Liu, Rai-Shung (2006). "Thermal and Metal-Catalyzed Cyclization of 1-Substituted 3,5-Dien-1-ynes via a [1,7]-Hydrogen Shift: Development of a Tandem Aldol Condensation−Dehydration and Aromatization Catalysis between 3-En-1-yn-5-al Units and Cyclic Ketones". Journal of the American Chemical Society 128 (30): 9661–9667. doi:10.1021/ja061203b. PMID 16866518. Bibcode: 2006JAChS.128.9661L.
7. ↑ Ośmiałowski, Borys; Raczyńska, Ewa D.; Krygowski, Tadeusz M. (2006). "Tautomeric Equilibria and Pi Electron Delocalization for Some Monohydroxyarenes Quantum Chemical Studies". The Journal of Organic Chemistry 71 (10): 3727–3736. doi:10.1021/jo052615q. PMID 16674042.
8. ↑ Kurt H. Meyer (1928). "Nitroanthrone". Organic Syntheses 8: 78. doi:10.15227/orgsyn.008.0078.

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