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Revision as of 16:14, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 455795909 of page Xanthone for the Chem/Drugbox validation project (updated: '').  Latest revision as of 18:30, 2 April 2024 edit Marbletan (talk | contribs)Extended confirmed users5,415 editsm clearer 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed | Watchedfields = changed
| verifiedrevid = 419140516 | verifiedrevid = 470632897
| Name = Xanthone | Name = Xanthone
| ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Xanthone.svg | ImageFile = Xanthone.svg
| ImageAlt = Skeletal formula
| ImageSize = 200px
| ImageName = Xanthone | ImageFile1 = Xanthone-3D-balls.png
| ImageAlt1 = Ball-and-stick model
| IUPACName = ''9H''-xanthen-9-one | PIN = 9''H''-Xanthen-9-one
| OtherNames = 9-oxo-]<br />diphenyline ketone oxide | OtherNames = 9-Oxoxanthene<br />Diphenyline ketone oxide
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
⚫ | ChEBI_Ref = {{ebicite|changed|EBI}}
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo = 90-47-1
| Beilstein = 140443
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 37647 | ChEBI = 37647
⚫ | ChEMBL_Ref = {{ebicite|correct|EBI}}
| SMILES = O=C1c3c(Oc2c1cccc2)cccc3
⚫ | ChEMBL = 186784
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6753 | ChemSpiderID = 6753
| EINECS = 201-997-7
| Gmelin = 166003
| PubChem = 7020 | 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 | 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 | InChIKey = JNELGWHKGNBSMD-UHFFFAOYAA
⚫ | ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | ChEMBL = 186784
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | 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 | 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_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JNELGWHKGNBSMD-UHFFFAOYSA-N | StdInChIKey = JNELGWHKGNBSMD-UHFFFAOYSA-N
| SMILES = O=C1c2ccccc2Oc3ccccc31
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo = 90-47-1
| RTECS =
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=13 | H=8 | O=2
| Formula = C<sub>13</sub>H<sub>8</sub>O<sub>2</sub>
| MolarMass = 196.19 g/mol | Appearance = white solid
⚫ | Density =
| Appearance = off-white solid
⚫ | Solubility = Sl. sol. in hot water
⚫ | Density =
⚫ | MeltingPtC = 174
⚫ | Solubility = sl. sol. in hot water
⚫ | BoilingPtC =
⚫ | MeltingPtC = 174
| MagSus = -108.1·10<sup>−6</sup> cm<sup>3</sup>/mol
⚫ | BoilingPtC = 351
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| RPhrases = {{R36/37/38}} | GHSPictograms = {{GHS06}}
| GHSSignalWord = Danger
| SPhrases = {{S26}} {{S37}}<ref name="Alpha">] from AlphaAesar]</ref>
| 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 |Section8={{Chembox Related
| OtherCpds = ] | OtherCompounds = ]
}} }}
}} }}

'''Xanthone''' is an ] with the ] C<sub>13</sub>H<sub>8</sub>O<sub>2</sub>. It is a white solid.

In 1939, xanthone was introduced as an ] and it currently finds uses as ] for ] eggs and as a ].<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 ], which is used in the determination of ] 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 ].<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 ]:<ref>{{cite journal|journal=Org. Synth.|year=1927|volume=7|page=84|doi= 10.15227/orgsyn.007.0084|title=Xanthone|author=A. F. Holleman}}</ref>

]

Six methods have been reported for synthesizing xanthone derivatives:<ref name="Khan & Ather 2006"/>

*The Michael-Kostanecki method uses an ] mix of a ] and an ''O''-], which are heated with a ].
*The ] method has a ] intermediate.
*The Robinson-Nishikawa method is a variant of the ] synthesis but with low yields.
*The Asahina-Tanase method synthesizes some ]ated xanthones, and xanthones with acid-sensitive ]s.
*The Tanase method is used to synthesize polyhydroxyxanthones.
*The ] condenses a ] with an ''O''-] and ] the resulting ].

==Xanthone derivatives==
Xanthone forms the core of a variety of natural products, such as ] or ]. These compounds are sometimes referred to as ''xanthones'' or ]s. Over 200 natural xanthones have been identified. Many are phytochemicals found in plants in the families ], ], and ].<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 ].<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}}</ref> Some xanthones are found in the ] of the ] fruit (''] mangostana'') as well as in the bark and timber of '']''.<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==
* ]s
* ]
* ]

==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>

}}

]
]