Anthrone is a tricyclic

aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...

ketone. It is used for a common

cellulose Cellulose is an organic compound with the formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of β(1→4) linked D-glucose units. Cellulose is an important structural component of the primary cell w ...

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 ''Frangula alnus'', commonly known as alder buckthorn, glossy buckthorn, or breaking buckthorn, is a tall deciduous shrub in the family Rhamnaceae. Unlike other "buckthorns", alder buckthorn does not have thorns. It is native to Europe, northern ...

'', ''

Aloe ferox ''Aloe ferox'', commonly known as bitter aloe, is a species of flowering plant in the family Asphodelaceae. This woody aloe is indigenous to southern Africa. It is one of several ''Aloe'' species used to make bitter aloes, a purgative medicatio ...

'', '' Rheum officinale'', and ''

Cassia senna ''Senna alexandrina'' (Alexandrian senna, in Arabic عشرج or عشرق or سنامكي and see below) is an ornamental plant in the genus '' Senna''. It is used in herbalism. It grows natively in upper Egypt, especially in the Nubian region, a ...

''. 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 Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula . Isomers include various quinone derivatives. The term anthraquinone however refers to the isomer, 9,10-anthraquinone (IUPAC: 9,10-dioxoan ...

by reduction with

tin Tin is a chemical element with the symbol Sn (from la, stannum) and atomic number 50. Tin is a silvery-coloured metal. Tin is soft enough to be cut with little force and a bar of tin can be bent by hand with little effort. When bent, t ...

or copper. An alternative synthesis involves

cyclization A cyclic compound (or ring compound) is a term for a compound in the field of chemistry in which one or more series of atoms in the compound is connected to form a ring. Rings may vary in size from three to many atoms, and include examples where ...

of ''o''-benzylbenzoic acid induced with hydrogen fluoride. Anthrone synthesis

Anthrone condenses with

glyoxal Glyoxal is an organic compound with the chemical formula OCHCHO. It is the smallest dialdehyde (a compound with two aldehyde groups). It is a crystalline solid, white at low temperatures and yellow near the melting point (15 °C). The liquid ...

to give, following dehydrogenation, acedianthrone, a useful octacyclic pigment.

Tautomer

center, 314px, Tautomeric equilibrium for anthrone. Anthrone is the more stable tautomer relative to the

anthrol Anthrols (sometimes called anthranols) are the hydroxylated derivatives of anthracene. For the monohydroxo derivatives, three isomers are possible: 1-anthrol, 2-anthrol, and 9-anthrol. The latter exists as a minor tautomer of 9-anthrone. Despite ...

. The tautomeric equilibrium is estimated at 100 in aqueous solution. For the two other isomeric anthrols, the tautomeric equilibrium is reversed.

References

{{reflist Aromatic ketones Anthracenes