Xanthone

Structural formula
General
Surname	Xanthone
other names	9 H -Xanthene-9-one ( IUPAC ) Dibenzo-γ-pyrone 9-oxo- xanthene
Molecular formula	C 13 H 8 O 2
Brief description	colorless needles
External identifiers / databases
CAS number 90-47-1 EC number 201-997-7 ECHA InfoCard 100.001.816 PubChem 7020 Wikidata Q421789
properties
Molar mass	196.19 g · mol -1
Physical state	firmly
Melting point	174-176 ° C
boiling point	351 ° C
solubility	almost insoluble in cold water slightly soluble in hot water and petroleum ether soluble in ethanol , diethyl ether , chloroform , benzene and in concentrated sulfuric acid
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 301 P: 301 + 310
Toxicological data	180 mg kg −1 ( LD 50 ,  mouse ,  iv ) > 500 mg kg −1 ( LD ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Xanthone (also xanthen-9-one or dibenzo-γ-pyrone ) is a heterocyclic chemical compound that belongs to the ethers and ketones and gives its name to the substance group of xanthones . The reduction product xanthene forms the basic body of the xanthene plant dyes . It is isomeric to fluorone ( xanthen-3-one ).

Occurrence and representation

Xanthone itself does not occur naturally, but about 200 of its derivatives such as euxanthone , corymbiferin and gentisin . Xanthone is produced by distillation of phenyl salicylate .

Properties and use

Xanthone forms colorless, easily sublimable needles that melt from 174 to 176 ° C and boil at around 351 ° C. It is slightly soluble in ethanol , ether , chloroform and benzene , but insoluble in water. In concentrated sulfuric acid , the compound with its yellow color dissolves to form a liquid with an intense light blue fluorescence. Under reductive conditions, xanthone can be converted into xanthene and xanthydrol ; the action of Grignard compounds produces xanthylium salts . The only known use of xanthone is as a specific insecticide , which acts primarily as a so-called larvicide on moth larvae .

Individual evidence

1. ↑ ^{a b c d} Entry on xanthone. In: Römpp Online . Georg Thieme Verlag, accessed on September 30, 2014.
2. ↑ ^{a b} Data sheet Xanthone at AlfaAesar, accessed on January 22, 2010 ( PDF )(JavaScript required) .
3. ↑ ^{a b} Xanthones data sheet from Sigma-Aldrich , accessed on November 3, 2016 ( PDF ).
4. ^ US Army Armament Research & Development Command. Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX # 01611.
5. ↑ ^{a b} Entry on xanthone in the ChemIDplus database of the United States National Library of Medicine (NLM) .
6. ^ National Academy of Sciences. National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, p. 25, 1953.
7. ↑ Steiner, LF and SA Summerland. 1943. Xanthones as an ovicide and larvicide for the codling moth. Journal of economic entomology 36, 435-439.