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Revision as of 04:30, 16 October 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to verified fields - updated 'DrugBank_Ref', 'UNII_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or bugs)← Previous edit Revision as of 18:05, 13 January 2012 edit undoCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or bugs)Next edit →
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{{chembox {{chembox
⚫ | verifiedrevid = 470632897
| Verifiedfields = changed
⚫ | verifiedrevid = 419140516
| Name = Xanthone | Name = Xanthone
| ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile_Ref = {{chemboximage|correct|??}}
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| OtherNames = 9-oxo-]<br />diphenyline ketone oxide | OtherNames = 9-oxo-]<br />diphenyline ketone oxide
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 37647 | ChEBI = 37647
| SMILES = O=C1c3c(Oc2c1cccc2)cccc3 | SMILES = O=C1c3c(Oc2c1cccc2)cccc3

Revision as of 18:05, 13 January 2012

Xanthone
Xanthone
Names
IUPAC name 9H-xanthen-9-one
Other names 9-oxo-xanthene
diphenyline ketone oxide
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.816 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C13H8O2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8HKey: JNELGWHKGNBSMD-UHFFFAOYSA-N
  • InChI=1/C13H8O2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8HKey: JNELGWHKGNBSMD-UHFFFAOYAA
SMILES
  • O=C1c3c(Oc2c1cccc2)cccc3
Properties
Chemical formula C13H8O2
Molar mass 196.19 g/mol
Appearance off-white solid
Melting point 174 °C (345 °F; 447 K)
Boiling point 351 °C (664 °F; 624 K)
Solubility in water sl. sol. in hot water
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Xanthone is an organic compound with the molecular formula C13H8O2. It can be prepared by the heating of phenyl salicylate. 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.

Xanthone derivatives

The chemical structure of xanthone forms the central core of a variety of naturally occurring organic compounds, such as mangostin, which are sometimes collectively referred to as xanthones or xanthonoids. Over 200 xanthones have been identified. Xanthones are natural constituents of plants in the families Bonnetiaceae and Clusiaceae and are found in some species in the family Podostemaceae. Many of these xanthones are found in the pericarp of the mangosteen fruit (Garcinia mangostana), which can be found in the region of Southeast Asia.

Synthetic derivatives of xanthone can be added during the polymerization of polyester, to form a plastic that has a greater resistance to degradation by ultraviolet light. The most useful derivative is tetrahydroxyxanthone. Polyester film can be used for the production of third generation printed solar cells, to make them a cost effective alternative to silica-based solar energy generation. It was originally intended that the additive be used for polyester greenhouses in hot climates, where the plastic would degrade after a few years from UV exposure. The xanthone-treated product has an extended useful lifetime of ten years instead of three.

See also

References

  1. Organic Syntheses, Coll. Vol. 1, p.552 (1941) - preparation of xanthone
  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. PubMed.gov - journal articles on xanthones
  4. *Angiosperm Phylogeny Group (2003). An update of the Angiosperm Phylogeny Group classification for the orders and families of flowering plants: APG II. Botanical Journal of the Linnean Society 141: 399-436 (Available online: Abstract | Full text (HTML) | Full text (PDF))
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