Anthrone is a tricyclic

aromatic In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated system, conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugati ...

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

. It is used for a common

cellulose Cellulose is an organic compound with the chemical formula, formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of glycosidic bond, β(1→4) linked glucose, D-glucose units. Cellulose is an important s ...

assay An assay is an investigative (analytic) procedure in laboratory medicine, mining, pharmacology, environmental biology and molecular biology for qualitatively assessing or quantitatively measuring the presence, amount, or functional activity ...

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 medication ...

'', ''

Rheum officinale ''Rheum officinale'', the Chinese rhubarb, or Indian rhubarb is a Rheum (plant), rhubarb from the family Polygonaceae native to western China and Tibet. In Chinese language, Chinese it is called ''yào yòng dà huáng'' (), literally meaning ''m ...

'', and '' Cassia senna''.

Glycoside In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. ...

s of anthrone are also found in high amounts in

rhubarb Rhubarb is the fleshy, edible stalks ( petioles) of species and hybrids (culinary rhubarb) of ''Rheum'' in the family Polygonaceae, which are cooked and used for food. The plant is a herbaceous perennial that grows from short, thick rhizomes. ...

leaves, and alongside concentrated amounts of

oxalic acid Oxalic acid is an organic acid with the systematic name ethanedioic acid and chemical formula , also written as or or . It is the simplest dicarboxylic acid. It is a white crystalline solid that forms a colorless solution in water. Its name i ...

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 hydrocarbon, aromatic organic compound with formula . Several isomers exist but these terms usually refer to 9,10-anthraquinone (IUPAC: 9,10-dioxoanthracene) wherein th ...

by reduction with

tin Tin is a chemical element; it has symbol Sn () and atomic number 50. A silvery-colored 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, a bar of tin makes a sound, the ...

copper Copper is a chemical element; it has symbol Cu (from Latin ) and atomic number 29. It is a soft, malleable, and ductile metal with very high thermal and electrical conductivity. A freshly exposed surface of pure copper has a pinkish-orang ...

. 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 Hydrogen fluoride (fluorane) is an Inorganic chemistry, inorganic compound with chemical formula . It is a very poisonous, colorless gas or liquid that dissolves in water to yield hydrofluoric acid. It is the principal industrial source of fluori ...

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. 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