Xanthone

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Xanthone
Skeletal formula
Ball-and-stick model
Identifiers
CAS number 90-47-1 YesY
PubChem 7020
ChemSpider 6753 YesY
ChEBI CHEBI:37647 YesY
ChEMBL CHEMBL186784 YesY
Jmol-3D images Image 1
Properties
Molecular 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
Hazards
R-phrases R36/37/38
S-phrases S26 S37[1]
Related compounds
Related compounds xanthene
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Xanthone is an organic compound with the molecular formula C13H8O2. It can be prepared by the heating of phenyl salicylate.[2] In 1939, xanthone was introduced as an insecticide and it currently finds uses as ovicide for codling moth eggs and as a larvicide.[3] Xanthone is also used in the preparation of xanthydrol, which is used in the determination of urea levels in the blood.

Xanthone derivatives[edit]

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.[4] 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.[5] 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.

See also[edit]

References[edit]

  1. ^ MSDS from AlphaAesar
  2. ^ Organic Syntheses, Coll. Vol. 1, p.552 (1941) - preparation of xanthone
  3. ^ 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.
  4. ^ PubMed.gov - journal articles on xanthones
  5. ^ *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))