Xanthone is an organic compound with the molecular formula C13H8O2. It is a white solid.
Names | |
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Preferred IUPAC name
9H-Xanthen-9-one | |
Other names
9-Oxoxanthene
Diphenyline ketone oxide | |
Identifiers | |
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3D model (JSmol)
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140443 | |
ChEBI |
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ChEMBL |
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ChemSpider |
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ECHA InfoCard | 100.001.816 |
EC Number |
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166003 | |
PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |
C13H8O2 | |
Molar mass | 196.205 g·mol−1 |
Appearance | white solid |
Melting point | 174 °C (345 °F; 447 K) |
Sl. sol. in hot water | |
-108.1·10−6 cm3/mol | |
Hazards | |
GHS labelling:[1] | |
Danger | |
H301 | |
P264, P270, P301+P310, P321, P330, P405, P501 | |
Related compounds | |
Related compounds
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xanthene |
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
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In 1939, xanthone was introduced as an insecticide and it currently finds uses as ovicide for codling moth eggs and as a larvicide.[2] Xanthone is also used in the preparation of xanthydrol, which is used in the determination of urea levels in the blood.[3] It can also be used as a photocatalyst.[4]
Xanthone can be prepared by the heating of phenyl salicylate:[5]
Six methods have been reported for synthesizing xanthone derivatives:[6]
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.[7] They are also found in some species of the genus Iris.[8] Some xanthones are found in the pericarp of the mangosteen fruit (Garcinia mangostana) as well as in the bark and timber of Mesua thwaitesii.[9]