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Anthrone

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Through Aromaticity, Ketone and Copper

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.

Synthesis 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.

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