Anthrone

Anthrone
Names
	IUPAC name 10H-Anthracen-9-one
	Other names Carbothrone; 9-Oxoanthracene;
Identifiers
CAS Number	90-44-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:33835 ;
ChEMBL	ChEMBL124440 ;
ChemSpider	6751 ;
ECHA InfoCard	100.001.813
PubChem CID	7018;
UNII	FP0FJ7K744 ;
CompTox Dashboard (EPA)	DTXSID1049431 ;
	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 Key: RJGDLRCDCYRQOQ-UHFFFAOYSA-N ; 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)
Boiling point	721 °C (1,330 °F; 994 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).
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	Infobox references

Anthrone is a tricyclic aromatic ketone. It is used for a common cellulose assay and in the colorometric determination of carbohydrates.[1]

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.

Synthesis and reactions

Anthrone can be prepared from anthraquinone by reduction with tin or copper.[2]

An alternative synthesis involves cyclization of o-benzylbenzoic acid induced with hydrogen fluoride.[3]

Anthrone syntheses

Anthrone condenses with glyoxal to give, following dehydrogenation, acedianthrone, a useful octacyclic pigment.[4]

Tautomer

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.[5]

References

Trevelyan, W. E.; Forrest, RS; Harrison, JS (1952). "Determination of Yeast Carbohydrates with the Anthrone Reagent". Nature. 170 (4328): 626–627. Bibcode:1952Natur.170..626T. doi:10.1038/170626a0. PMID 13002392.
Macleod, L. C.; Allen, C. F. H. (1934). "Benzanthrone". Organic Syntheses. 14: 4. doi:10.15227/orgsyn.014.0004.
Fieser, Louis F.; Hershberg, E. B. (May 1939). "Inter- and Intramolecular Acylations with Hydrogen Fluoride". Journal of the American Chemical Society. 61 (5): 1272–1281. doi:10.1021/ja01874a079.
Bien, H.-S.; Stawitz, J.; Wunderlich, K. (2005). "Anthraquinone Dyes and Intermediates". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_355.
Ośmiałowski, Borys; Raczyńska, Ewa D.; Krygowski, Tadeusz M. (2006). "Tautomeric Equilibria and Pi Electron Delocalization for Some Monohydroxyarenes Quantum Chemical Studies". The Journal of Organic Chemistry. 71 (10): 3727–3736. doi:10.1021/jo052615q. PMID 16674042.

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[1] Trevelyan, W. E.; Forrest, RS; Harrison, JS (1952). "Determination of Yeast Carbohydrates with the Anthrone Reagent". Nature. 170 (4328): 626–627. Bibcode:1952Natur.170..626T. doi:10.1038/170626a0. PMID 13002392.

[2] Macleod, L. C.; Allen, C. F. H. (1934). "Benzanthrone". Organic Syntheses. 14: 4. doi:10.15227/orgsyn.014.0004.

[3] Fieser, Louis F.; Hershberg, E. B. (May 1939). "Inter- and Intramolecular Acylations with Hydrogen Fluoride". Journal of the American Chemical Society. 61 (5): 1272–1281. doi:10.1021/ja01874a079.

[UllmannDye-4] Bien, H.-S.; Stawitz, J.; Wunderlich, K. (2005). "Anthraquinone Dyes and Intermediates". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_355.

[5] Ośmiałowski, Borys; Raczyńska, Ewa D.; Krygowski, Tadeusz M. (2006). "Tautomeric Equilibria and Pi Electron Delocalization for Some Monohydroxyarenes Quantum Chemical Studies". The Journal of Organic Chemistry. 71 (10): 3727–3736. doi:10.1021/jo052615q. PMID 16674042.