Anthrone

Anthrone

Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name Anthracen-9(10H)-one
Other names Carbothrone 9-Oxoanthracene
Identifiers
CAS Number	90-44-8 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:33835 Y
ChEMBL	ChEMBL124440 Y
ChemSpider	6751 Y
ECHA InfoCard
E number
PubChem CID	7018
UNII	FP0FJ7K744 Y
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C14H10O/c15-14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-8H,9H2 Y Key: RJGDLRCDCYRQOQ-UHFFFAOYSA-N Y InChI=1/C14H10O/c15-14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-8H,9H2 Key: RJGDLRCDCYRQOQ-UHFFFAOYAA
SMILES O=C2c1c(cccc1)Cc3c2cccc3
Properties
Chemical formula	C14H10O
Molar mass	194.233 g·mol−1
Appearance	White to light yellow needles
Melting point	155 to 158 °C (311 to 316 °F; 428 to 431 K)
Solubility in water	Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

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.

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 syntheses

Anthrone condenses with glyoxal to give, following dehydrogenation, acedianthrone, a useful octacyclic pigment.

Tautomeric equilibrium for anthrone.

Anthrone is the more stable tautomer relative to the anthrol as has been established also by X-ray crystallography. The tautomeric equilibrium 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.