Xanthone

Xanthone

Names
Preferred IUPAC name 9H-Xanthen-9-one
Other names 9-Oxoxanthene Diphenyline ketone oxide
Identifiers
CAS Number	90-47-1 Y
3D model (JSmol)	Interactive image
Beilstein Reference	140443
ChEBI	CHEBI:37647 Y
ChEMBL	ChEMBL186784 Y
ChemSpider	6753 Y
ECHA InfoCard
EC Number	201-997-7
E number
Gmelin Reference	166003
PubChem CID	7020
UNII	9749WEV0CA Y
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C13H8O2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H Y Key: JNELGWHKGNBSMD-UHFFFAOYSA-N Y 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). Y verify (what is YN ?) Infobox references

Xanthone is an organic compound with the molecular formula C₁₃H₈O₂. It is a white solid.

In 1939, xanthone was introduced as an insecticide and it currently finds uses as ovicide for codling moth eggs and as a larvicide. Xanthone is also used in the preparation of xanthydrol, which is used in the determination of urea levels in the blood. It can also be used as a photocatalyst.

Synthesis

Xanthone can be prepared by the heating of phenyl salicylate:

Various other methods of synthesis given are:

• Heating a mixture of salicylic acid, phenol, and acetic anhydride.
• Warming o-phenoxybenzoic acid with sulfuric acid or phosphorous pentoxide.
• Distillation of o-phenoxybenzoyl chloride under vacuum.
• Heating of aspirin or o-hydroxybenzophenone.

Derivatives

Multiple methods have been reported for synthesizing xanthone derivatives:

• The Michael-Kostanecki method uses an equimolar mix of a polyphenol and a salicylic acid derivative, which are heated with a dehydrating agent in a condensation reaction.
• 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 Ullman method condenses a phenol with an O-chlorobenzene and cyclizes the resulting diphenylether.

Xanthone derivatives

Xanthone forms the core of a variety of natural products, such as mangostin or lichexanthone. These compounds are sometimes referred to as xanthones or xanthonoids. Over 200 natural xanthones have been identified. Many are phytochemicals found in plants in the families Bonnetiaceae, Clusiaceae, and Podostemaceae. They are also found in some species of the genus Iris. Some xanthones are found in the pericarp of the mangosteen fruit (Garcinia mangostana) as well as in the bark and timber of Mesua thwaitesii.

See also

• Tetrahydroxanthones
• Thioxanthone
• Xanthene