Xanthone

Xanthone
Xanthone
Identifiers
CAS number 90-47-1 YesY
PubChem 7020
ChemSpider 6753 YesY
ChEBI CHEBI:37647 N
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, 447 K, 345 °F

Boiling point

351 °C, 624 K, 664 °F

Solubility in water sl. sol. in hot water
Hazards
R-phrases R36/37/38
S-phrases S26 S37[1]
Related compounds
Related compounds xanthene
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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

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.

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.[citation needed] 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. ^ 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))

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Look at other dictionaries:

  • Xanthone — Structure de la xanthone, un composé aromatique. Général No CAS …   Wikipédia en Français

  • xanthone — [zan′thōn΄] n. 〚 XANTH(O) + ONE〛 a ring ketone, C6H4 (CO)OC6H4, occurring in some plant pigments and dyes * * * …   Universalium

  • xanthone — ● xanthone nom féminin Dibenzopyrone C13H8O2, dont certains dérivés hydroxylés sont des colorants jaunes …   Encyclopédie Universelle

  • xanthone — [zan′thōn΄] n. [ XANTH(O) + ONE] a ring ketone, C6H4 (CO)OC6H4, occurring in some plant pigments and dyes …   English World dictionary

  • Xanthone — Strukturformel von 9H Xanthon. Xanthone sind aromatische Oxoverbindungen, die sich vom Ringsystem des Xanthens ableiten und in der Natur die farbgebenden Substanzen einiger Pflanzen stellen. Sie sind damit sekundäre Pflanzenstoffe, die als Farb …   Deutsch Wikipedia

  • xanthone — ksantonas statusas T sritis chemija apibrėžtis Heterociklinis junginys. formulė C₆H₄:(O)(CO):C₆H₄ atitikmenys: angl. xanthone rus. ксантон ryšiai: sinonimas – 9(9H) ksantenonas …   Chemijos terminų aiškinamasis žodynas

  • xanthone — noun Etymology: International Scientific Vocabulary Date: circa 1894 a ketone C13H8O2 that is the parent of several natural yellow pigments …   New Collegiate Dictionary

  • xanthone — noun An organic compound, CHO, used as an insecticide …   Wiktionary

  • xanthone — xan·thone zan .thōn n a ketone C13H8O2 that is the parent of several natural yellow pigments …   Medical dictionary

  • xanthone — xan·thone …   English syllables

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