Anthrone is a tricyclic
aromaticketone. It is used for a common
celluloseassay 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.
Anthrone condenses with
glyoxal to give, following dehydrogenation,
acedianthrone, a useful octacyclic pigment.[5]
Tautomer
Anthrone is the more stable tautomer relative to the
anthrol. The tautomeric equilibrium is estimated at 100 in aqueous solution. For the two other isomeric anthrols, the tautomeric equilibrium is reversed.[6]
^Macleod, L. C.; Allen, C. F. H. (1934). "Benzanthrone". Organic Syntheses. 14: 4.
doi:
10.15227/orgsyn.014.0004.
^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.
^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.
PMID16674042.