Anthrone

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Anthrone
Skeletal formula
Ball-and-stick model
Names
IUPAC name
10H-Anthracen-9-one
Other names
Carbothrone; anthranone; 9-oxoanthracene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.813
Properties
C14H10O
Molar mass 194.23 g·mol−1
Appearance White to light yellow needles
Density Solid
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).
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Infobox references

Anthrone is a tricyclic aromatic ketone. It is used for a popular cellulose assay and in the colorometric determination of carbohydrates.[1] The anthrones are used in pharmacy as laxative. They stimulate the motion of the colon and are reduce water reabsorption. Anthrones can be extracted from a number of plant species, including Rhamnus frangula, Aloe ferox, Rheum officinale and Cassia senna.[citation needed]

Synthesis[edit]

Anthrone synthesis:[2][3]

Anthrone can be prepared from anthraquinone by reduction with tin, glacial acetic acid and hydrochloric acid, or cyclization of o-benzylbenzoic acid with liquid Hydrogen fluoride.

References[edit]

  1. ^ Trevelyan, W. E.; Forrest, RS; Harrison, JS (1952). "Determination of Yeast Carbohydrates with the Anthrone Reagent". Nature. 170 (4328): 626–627. doi:10.1038/170626a0. PMID 13002392. 
  2. ^ "ANTHRONE". Organic Syntheses. 8: 8. 1928. doi:10.15227/orgsyn.008.0008. 
  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.