Xanthone

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Xanthone
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
9H-Xanthen-9-one
Other names
9-Oxoxanthene
Diphenyline ketone oxide
Identifiers
3D model (JSmol)
140443
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.816 Edit this at Wikidata
EC Number
  • 201-997-7
166003
UNII
  • InChI=1S/C13H8O2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H checkY
    Key: JNELGWHKGNBSMD-UHFFFAOYSA-N checkY
  • 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
  • O=C1c2ccccc2Oc3ccccc31
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]
GHS06: Toxic
Danger
H301
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).
checkY verify (what is checkY☒N ?)

Xanthone is an organic compound with the molecular formula O[C6H4]2CO. 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.[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]

Synthesis[edit]

Xanthone can be prepared by the heating of phenyl salicylate:[5]

Xanthone synthesis.svg

Six methods have been reported for synthesizing xanthone derivatives:[6]

Xanthone derivatives[edit]

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]

  1. Bone fide agents include AH 7614 & TUG-1387.[10]

See also[edit]

References[edit]

  1. ^ "Xanthone". pubchem.ncbi.nlm.nih.gov.
  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. ^ Bowden, R. S. T. (1962). "The Estimation of Blood Urea by the Xanthydrol Reaction". Journal of Small Animal Practice. 3 (4): 217–218. doi:10.1111/j.1748-5827.1962.tb04191.x.
  4. ^ Romero, Nathan A.; Nicewicz, David A. (10 June 2016). "Organic Photoredox Catalysis". Chemical Reviews. 116 (17): 10075–10166. doi:10.1021/acs.chemrev.6b00057. PMID 27285582.
  5. ^ A. F. Holleman (1927). "Xanthone". Org. Synth. 7: 84. doi:10.15227/orgsyn.007.0084.
  6. ^ Diderot, Noungoue Tchamo; Silvere, Ngouela; Etienne, Tsamo (2006). "Xanthones as therapeutic agents: chemistry and pharmacology". In Khan, M.T.H.; Ather, A. (eds.). Lead Molecules from Natural Products: Discovery and New Trends. Advances in Phytomedicine. Elsevier Science. pp. 284–285. ISBN 978-0-08-045933-2.
  7. ^ "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 (4): 399–436. 2003. doi:10.1046/j.1095-8339.2003.t01-1-00158.x.
  8. ^ Williams, C.A; Harborne, J.B.; Colasante, M. (2000). "The pathway of chemical evolution in bearded iris species based on flavonoid and xanthone patterns" (PDF). Annali di Botanica. 58: 51–54. Retrieved 28 October 2015.
  9. ^ Bandaranayake, Wickramasinghe M.; Selliah, Sathiaderan S.; Sultanbawa, M.Uvais S.; Games, D.E. (1975). "Xanthones and 4-phenylcoumarins of Mesua thwaitesii". Phytochemistry. 14: 265–269. doi:10.1016/0031-9422(75)85052-7.
  10. ^ Watterson, Kenneth R.; Hansen, Steffen V. F.; Hudson, Brian D.; Alvarez-Curto, Elisa; Raihan, Sheikh Zahir; Azevedo, Carlos M. G.; Martin, Gabriel; Dunlop, Julia; Yarwood, Stephen J.; Ulven, Trond; Milligan, Graeme (2017). "Probe-Dependent Negative Allosteric Modulators of the Long-Chain Free Fatty Acid Receptor FFA4". Molecular Pharmacology. 91 (6): 630–641. doi:10.1124/mol.116.107821. ISSN 0026-895X. PMC 5438128. PMID 28385906.