Anthrone
Chemical compound
Anthrone is a tricyclic aromatic ketone. It is used for a common cellulose assay and in the colorimetric determination of carbohydrates.
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. 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.
01Synthesis and reactions
Anthrone can be prepared from anthraquinone by reduction with tin or copper.
An alternative synthesis involves cyclization of o-benzylbenzoic acid induced with hydrogen fluoride.
Anthrone condenses with glyoxal to give, following dehydrogenation, acedianthrone, a useful octacyclic pigment.
Anthrone is the more commonly encountered tautomer of anthrol, as has been established also by X-ray crystallography. The tautomeric equilibrium constant is estimated at 100 in aqueous solution. For the two other isomeric anthrols, the tautomeric equilibrium is reversed: they are phenolic.
Anthrone undergoes nitration using conventional conditions for aromatic nitration, implying that it is the hydroxy tautomer that is the reactant.
02Applications
This is a list of some of the applications of anthrone: XE-991, DMP 543, maprotiline, 1-(9-Anthryloxy)-2-aminoethane (c.f. flunamine). In Lednicer's textbook it was said that melitracen was made from anthrone. However, since the time of publication it has now been discovered that there are other avenues to making the 10,10-dimethylanthrone [5447-86-9] precursor compound.
The Beckmann rearrangement or Schmidt reaction of anthrone would give 6-morphanthridinone [1211-06-9]. The relevance of this to drug chemistry is that it finds involvement in the synthesis of perlapine, epinastine, mianserin, prazepine & pitrazepin, for example.
Sources and credits
This article is adapted from the Wikipedia article “Anthrone”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.
Images, from Wikimedia Commons:
- Anthrone.png by Edgar181, Public domain
- Anthrone synthesis.svg by Nuklear, CC BY-SA 4.0
- Anthrol-AnthroneEq.svg by Smokefoot, Public domain
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