Xanthone

Xanthone
Names
	Preferred IUPAC name 9H-Xanthen-9-one
	Other names 9-Oxoxanthene; Diphenyline ketone oxide
Identifiers
CAS Number	90-47-1 ;
3D model ( JSmol)	Interactive image;
Beilstein Reference	140443
ChEBI	CHEBI:37647 ;
ChEMBL	ChEMBL186784 ;
ChemSpider	6753 ;
ECHA InfoCard	100.001.816
EC Number	201-997-7;
Gmelin Reference	166003
PubChem CID	7020;
UNII	9749WEV0CA ;
CompTox Dashboard (EPA)	DTXSID6021795 ;
	InChI InChI=1S/C13H8O2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H Key: JNELGWHKGNBSMD-UHFFFAOYSA-N ; InChI=1/C13H8O2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H Key: JNELGWHKGNBSMD-UHFFFAOYAA;
	SMILES O=C1c2ccccc2Oc3ccccc31;
Properties
Chemical formula	C13H8O2
Molar mass	196.205 g·mol−1
Appearance	white solid
Melting point	174 °C (345 °F; 447 K)
Solubility in water	Sl. sol. in hot water
Magnetic susceptibility (χ)	-108.1·10−6 cm3/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301
Precautionary statements	P264, P270, P301+P310, P321, P330, P405, P501
Related compounds
Related compounds	xanthene
	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

Xanthone is an

molecular formula

C₁₃H₈O₂. It is a white solid.

In 1939, xanthone was introduced as an

photocatalyst.^[4]

Synthesis

Xanthone can be prepared by the heating of phenyl salicylate:^[5]

Six methods have been reported for synthesizing xanthone derivatives:^[6]

The Michael-Kostanecki method uses an
equimolar mix of a polyphenol and an O-hydroxybenzoic acid, which are heated with a dehydrating agent
.

The Friedel-Crafts method has a benzophenone intermediate.
The Robinson-Nishikawa method is a variant of the Hoesch synthesis but with low yields.
The Asahina-Tanase method synthesizes some
methoxylated xanthones, and xanthones with acid-sensitive substituents
.

The Tanase method is used to synthesize polyhydroxyxanthones.

The

diphenylether

.

Xanthone derivatives

Xanthone forms the core of a variety of natural products, such as

pericarp of the mangosteen fruit (Garcinia mangostana) as well as in the bark and timber of Mesua thwaitesii.^[9]

References

^ "Xanthone". pubchem.ncbi.nlm.nih.gov.
^ Steiner, L. F. and S. A. Summerland. 1943. Xanthone as an ovicide and larvicide for the codling moth. Journal of Economic Entomology 36, 435-439.
doi:10.1111/j.1748-5827.1962.tb04191.x
.

PMID 27285582
.

doi:10.15227/orgsyn.007.0084
.

ISBN 978-0-08-045933-2
.

doi:10.1046/j.1095-8339.2003.t01-1-00158.x
.

^ Williams, C.A; Harborne, J.B.; Colasante, M. (2000). "The pathway of chemical evolution in bearded iris species based on flavonoid and xanthone patterns" (PDF). Annali di Botanica. 58: 51–54. Retrieved 28 October 2015.

doi:10.1016/0031-9422(75)85052-7
.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Xanthone&oldid=1216915041"

[1] "Xanthone". pubchem.ncbi.nlm.nih.gov.

[2] Steiner, L. F. and S. A. Summerland. 1943. Xanthone as an ovicide and larvicide for the codling moth. Journal of Economic Entomology 36, 435-439.

[3] :10.1111/j.1748-5827.1962.tb04191.x
.

[Nicewicz-4] PMID 27285582
.

[5] :10.15227/orgsyn.007.0084
.

[Khan_&_Ather_2006-6] ISBN 978-0-08-045933-2
.

[7] :10.1046/j.1095-8339.2003.t01-1-00158.x
.

[8] Williams, C.A; Harborne, J.B.; Colasante, M. (2000). "The pathway of chemical evolution in bearded iris species based on flavonoid and xanthone patterns" (PDF). Annali di Botanica. 58: 51–54. Retrieved 28 October 2015.

[9] :10.1016/0031-9422(75)85052-7
.

[1]

[4]

[5]

[6]

[9]

Synthesis

Xanthone derivatives

See also

References