{{chembox | Watchedfields = changed | verifiedrevid = 470632897 | Name = Xanthone | ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile = Xanthone.svg | ImageAlt = Skeletal formula | ImageFile1 = Xanthone-3D-balls.png | ImageAlt1 = Ball-and-stick model | PIN = 9''H''-Xanthen-9-one | OtherNames = 9-Oxoxanthene<br />Diphenyline ketone oxide |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 90-47-1 | Beilstein = 140443 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 37647 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 186784 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 6753 | EINECS = 201-997-7 | Gmelin = 166003 | PubChem = 7020 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 9749WEV0CA | InChI = 1/C13H8O2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H | InChIKey = JNELGWHKGNBSMD-UHFFFAOYAA | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C13H8O2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = JNELGWHKGNBSMD-UHFFFAOYSA-N | SMILES = O=C1c2ccccc2Oc3ccccc31 }} |Section2={{Chembox Properties | C=13 | H=8 | O=2 | Appearance = white solid | Density = | Solubility = Sl. sol. in hot water | MeltingPtC = 174 | BoilingPtC = | MagSus = -108.1·10<sup>−6</sup> cm<sup>3</sup>/mol }} |Section7={{Chembox Hazards | ExternalSDS = | MainHazards = | FlashPt = | GHSPictograms = {{GHS06}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|301}} | PPhrases = {{P-phrases|264|270|301+310|321|330|405|501}} | GHS_ref = <ref>{{cite web |title=Xanthone |url=https://pubchem.ncbi.nlm.nih.gov/compound/7020#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> }} |Section8={{Chembox Related | OtherCompounds = xanthene }} }}

'''Xanthone''' is an organic compound with the molecular formula C<sub>13</sub>H<sub>8</sub>O<sub>2</sub>. 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.<ref>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.</ref> Xanthone is also used in the preparation of xanthydrol, which is used in the determination of urea levels in the blood.<ref>{{cite journal | doi = 10.1111/j.1748-5827.1962.tb04191.x| title = The Estimation of Blood Urea by the Xanthydrol Reaction| journal = Journal of Small Animal Practice| volume = 3| issue = 4| pages = 217–218| year = 1962| last1 = Bowden| first1 = R. S. T.}}</ref> It can also be used as a photocatalyst.<ref name="Nicewicz">{{cite journal |last1=Romero |first1=Nathan A. |last2=Nicewicz |first2=David A. |title=Organic Photoredox Catalysis |journal=Chemical Reviews |date=10 June 2016 |volume=116 |issue=17 |pages=10075–10166 |doi=10.1021/acs.chemrev.6b00057|pmid=27285582 }}</ref>

== Synthesis == Xanthone can be prepared by the heating of phenyl salicylate:<ref name=OrgSyn>{{cite journal|journal=Org. Synth.|year=1927|volume=7|page=84|doi= 10.15227/orgsyn.007.0084|title=Xanthone|author=A. F. Holleman}}</ref>

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Various other methods of synthesis given are:<ref name=OrgSyn/> *Heating a mixture of salicylic acid, phenol, and acetic anhydride. *Warming ''o''-phenoxybenzoic acid with sulfuric acid or phosphorous pentoxide. *Distillation of ''o''-phenoxybenzoyl chloride under vacuum. *Heating of aspirin or ''o''-hydroxybenzophenone.

===Derivatives=== Multiple methods have been reported for synthesizing xanthone derivatives:<ref name="Khan & Ather 2006"/> *The Michael-Kostanecki method uses an equimolar mix of a polyphenol and a salicylic acid derivative, which are heated with a dehydrating agent in a condensation reaction. *The Friedel-Crafts method has a benzophenone intermediate. *The Robinson-Nishikawa method is a variant of the Hoesch synthesis but with low yields. *The Asahina-Tanase method synthesizes some methoxylated xanthones, and xanthones with acid-sensitive substituents. *The Tanase method is used to synthesize polyhydroxyxanthones. *The Ullman method condenses a phenol with an ''O''-chlorobenzene and cyclizes the resulting diphenylether.

==Xanthone derivatives== 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.<ref>{{cite journal | doi = 10.1046/j.1095-8339.2003.t01-1-00158.x| title = An update of the Angiosperm Phylogeny Group classification for the orders and families of flowering plants: APG II| journal = Botanical Journal of the Linnean Society| volume = 141| issue = 4| pages = 399–436| year = 2003| doi-access = }}</ref> They are also found in some species of the genus ''Iris''.<ref>{{cite journal |last1=Williams |first1=C.A |last2=Harborne |first2=J.B. |last3=Colasante |first3=M. |date=2000 |title=The pathway of chemical evolution in bearded iris species based on flavonoid and xanthone patterns |url=http://ojs.uniroma1.it/index.php/Annalidibotanica/article/download/9062-9611-1-PB%20(3).pdf |journal=Annali di Botanica |volume=58 |pages=51–54 |access-date=28 October 2015 |archive-date=23 August 2016 |archive-url=https://web.archive.org/web/20160823015841/http://ojs.uniroma1.it/index.php/Annalidibotanica/article/download/9062-9611-1-PB%20(3).pdf |url-status=dead }}</ref> Some xanthones are found in the pericarp of the mangosteen fruit (''Garcinia mangostana'') as well as in the bark and timber of ''Mesua thwaitesii''.<ref>{{cite journal | doi = 10.1016/0031-9422(75)85052-7| title = Xanthones and 4-phenylcoumarins of Mesua thwaitesii| journal = Phytochemistry| volume = 14| pages = 265–269| year = 1975| last1 = Bandaranayake| first1 = Wickramasinghe M.| last2 = Selliah| first2 = Sathiaderan S.| last3 = Sultanbawa| first3 = M.Uvais S.| last4 = Games| first4 = D.E.| issue = 1| bibcode = 1975PChem..14..265B}}</ref>

==See also== * Tetrahydroxanthones * Thioxanthone * Xanthene

==References== {{Reflist|refs=

<ref name="Khan & Ather 2006">{{cite book |editor-last1=Khan |editor-first1=M.T.H. |editor-last2=Ather |editor-first2=A. |title=Lead Molecules from Natural Products: Discovery and New Trends |chapter=Xanthones as therapeutic agents: chemistry and pharmacology |last1=Diderot |first1=Noungoue Tchamo |last2=Silvere |first2=Ngouela |last3=Etienne |first3=Tsamo |publisher=Elsevier Science |series=Advances in Phytomedicine |year=2006 |isbn=978-0-08-045933-2 |chapter-url=https://books.google.com/books?id=CvfvjJ9TZs0C&pg=PA285 |pages=284–285}}</ref>

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Category:Insecticides Category:Xanthones