Anthrone

Anthrone
Names
	IUPAC name 10H-Anthracen-9-one
	Other names Carbothrone; anthranone; 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;
	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	194.23 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)
Solubility in water	Insoluble
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	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.

Synthesis

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.

Use: Perlapine by Beckmann rearrangement.

References

↑ 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.
↑ "ANTHRONE". Organic Syntheses. 8: 8. 1928. doi:10.15227/orgsyn.008.0008.
↑ 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.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[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.