Anthrone

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

Anthrone
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Anthracen-9(10H)-one
Other names
  • Carbothrone
  • 9-Oxoanthracene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.813
UNII
  • InChI=1S/C14H10O/c15-14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-8H,9H2 checkY
    Key: RJGDLRCDCYRQOQ-UHFFFAOYSA-N checkY
  • 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
  • O=C2c1c(cccc1)Cc3c2cccc3
Properties
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)
Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

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.[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
  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.
  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.
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