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{{Short description|Chemical compound used to make dyes}} |
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{{Unreferenced stub|auto=yes|date=December 2009}} |
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{{Distinguish|xanthine}} |
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{{Distinguish|xanthine}} |
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{{Chembox |
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{{Chembox |
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| verifiedrevid = 384578048 |
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| verifiedrevid = 412200450 |
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| ImageFile = Xanthen.svg |
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| ImageFile = Xanthen.svg |
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| ImageSize = 200px |
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| ImageSize = |
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| ImageAlt = Skeletal formula |
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| IUPACName = ''9H''-Xanthene |
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| ImageFile1 = Xanthene-3D-balls.png |
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| OtherNames = Dibenzopyran<br>10''H''-9-oxaanthracene |
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| ImageSize1 = 220 |
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| Section1 = {{Chembox Identifiers |
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| ImageAlt1 = Ball-and-stick model |
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| PIN = 9''H''-Xanthene<ref>{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |pages=213 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref> |
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| OtherNames = Dibenzopyran<br>10''H''-9-Oxaanthracene |
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|Section1={{Chembox Identifiers |
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| Abbreviations = |
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| Abbreviations = |
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| CASNo = 92-83-1 |
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| CASNo = 92-83-1 |
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| CASNo_Ref = {{cascite}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| Beilstein = 133939 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 10057 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 486760 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 6840 |
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| EINECS = 202-194-4 |
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| EINECS = 202-194-4 |
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| PubChem = |
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| Gmelin = 83576 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| SMILES = c1(Oc2ccccc2C3)c3cccc1 |
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| InChI = |
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| KEGG = C01464 |
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| RTECS = |
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| PubChem = 7107 |
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| MeSHName = |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| KEGG = |
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| UNII = A762Z8101Y |
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| ATCCode_prefix = |
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| InChI = 1/C13H10O/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-8H,9H2 |
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| ATCCode_suffix = |
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| InChIKey = GJCOSYZMQJWQCA-UHFFFAOYAO |
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| ATC_Supplemental =}} |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| Section2 = {{Chembox Properties |
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| StdInChI = 1S/C13H10O/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-8H,9H2 |
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| Formula = {{Carbon}}<sub>13</sub>{{Hydrogen}}<sub>10</sub>{{Oxygen}} |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| MolarMass = 182.22 g/mol |
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| StdInChIKey = GJCOSYZMQJWQCA-UHFFFAOYSA-N |
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| SMILES = O1c2ccccc2Cc3ccccc31 |
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}} |
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|Section2={{Chembox Properties |
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| C=13 | H=10 | O=1 |
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| Appearance = Yellow solid |
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| Appearance = Yellow solid |
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| Density = |
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| Density = |
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| MeltingPt = 101-102 °C |
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| MeltingPtC = 101 to 102 |
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| MeltingPt_ref = <ref name=Aldrich> at ]</ref> |
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| Melting_notes = |
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| BoilingPt = 310-312 °C |
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| BoilingPtC = 310 to 312 |
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| BoilingPt_ref = <ref name=Aldrich/> |
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| pKa = |
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| pKb = }} |
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| pKb = }} |
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| Section7 = {{Chembox Hazards |
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|Section6={{Chembox Pharmacology |
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| ATC_Supplemental = |
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}} |
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|Section7={{Chembox Hazards |
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| Hazards_ref=<ref>{{cite web |title=Xanthene 99% |url=https://www.sigmaaldrich.com/AU/en/product/aldrich/x201 |publisher=Sigma Aldrich}}</ref> |
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| RPhrases = {{R42}} {{R43}} |
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| GHSPictograms = {{GHS07}} |
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| SPhrases = {{S22}} {{S36}} {{S37}} {{S45}} |
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| GHSSignalWord = Warning |
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| RSPhrases = |
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| HPhrases = {{H-phrases|317}} |
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| PPhrases = {{P-phrases|280}} |
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| FlashPt = |
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'''Xanthene''' (9''H''-xanthene, 10''H''-9-oxaanthracene) is the ] with the formula CH<sub>2</sub><sub>2</sub>O. It is a yellow solid that is soluble in common organic solvents. Xanthene itself is an obscure compound, but many of its derivatives are useful dyes.<ref name=Ull>{{Ullmann's | last1 = Gessner | first1 = Thomas | last2 = Mayer | first2 = Udo | title = Triarylmethane and Diarylmethane Dyes | year = 2000 | doi = 10.1002/14356007.a27_179}}</ref> |
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==Xanthene dyes== |
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'''Xanthene''' (9''H''-xanthene, 10''H''-9-oxaanthracene) is a yellow ] ]. Its chemical formula is {{Carbon}}<sub>13</sub>{{Hydrogen}}<sub>10</sub>{{Oxygen}}. It is soluble in ]. Its melting point is 101-102 °C and its boiling point is 310-312 °C. Xanthene is used as a ] and it is also a useful intermediate in ]. |
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]s are commercial dyes with xanthene cores.]] |
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]s that contain a xanthene core include ], ], ]s, and ]s. Xanthene dyes tend to be ], yellow to pink to bluish red, brilliant dyes. Many xanthene dyes can be prepared by condensation of derivates of ] with derivates of ] or ]. |
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{{Break|5}} |
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==Further reading== |
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Derivatives of xanthene are commonly referred to collectively as xanthenes, and among other uses are the basis of a class of ]s which includes ], ]s, and ]s. Xanthene dyes tend to be ], yellow to pink to bluish red, brilliant dyes. Many xanthene dyes can be prepared by condensation of derivates of ] with derivates of ] or ]. |
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*{{cite book|chapter=Photochemistry of the Xanthene Dyes|author1=Neckers, Douglas C. |author2=Valdes-Aguilera Oscar M. |title=Advances in Photochemistry|series=<!--Advances in Photochemistry-->|year=1993|volume=18|pages=315–94|doi=10.1002/9780470133491.ch4|isbn=9780470133491}} |
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==See also== |
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==See also== |
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==References== |
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{{Organic-compound-stub}} |
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{{Reflist}} |
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