Xanthene: Difference between revisions

{{Short description|Chemical compound used to make dyes}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 412200450

| ImageSize =

| ImageAlt = Skeletal formula

| ImageFile1 = Xanthene-3D-balls.png

| ImageSize1 = 220

| ImageAlt1 = Ball-and-stick model

| PIN = 9''H''-Xanthene<ref>{{cite book |author=[[International Union of Pure and Applied Chemistry]] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=[[Royal Society of Chemistry|The Royal Society of Chemistry]] |pages=213 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref>

| OtherNames = Dibenzo[''a'',''e'']pyran<br>10''H''-9-Oxaanthracene

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| Beilstein = 133939

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 10057

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 486760

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 6840

| Gmelin = 83576

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C01464

| PubChem = 7107

| RTECS =

| MeSHName =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = A762Z8101Y

| InChI = 1/C13H10O/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-8H,9H2

| InChIKey = GJCOSYZMQJWQCA-UHFFFAOYAO

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C13H10O/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-8H,9H2

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = GJCOSYZMQJWQCA-UHFFFAOYSA-N

| SMILES = O1c2ccccc2Cc3ccccc31

}}

|Section2={{Chembox Properties

| C=13 | H=10 | O=1

| MeltingPtC = 101 to 102

| MeltingPt_ref = <ref name=Aldrich>[http://www.sigmaaldrich.com/catalog/product/aldrich/x201 Xanthene] at [[Sigma-Aldrich]]</ref>

| BoilingPtC = 310 to 312

| BoilingPt_ref = <ref name=Aldrich/>

|Section6={{Chembox Pharmacology

| ATCCode_prefix =

| ATCCode_suffix =

| ATC_Supplemental =

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|Section7={{Chembox Hazards

| NFPA-S =

| Hazards_ref=<ref>{{cite web |title=Xanthene 99% |url=https://www.sigmaaldrich.com/AU/en/product/aldrich/x201 |publisher=Sigma Aldrich}}</ref>

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|317}}

| PPhrases = {{P-phrases|280}}

| AutoignitionPt =

| PEL =

}}

'''Xanthene''' (9''H''-xanthene, 10''H''-9-oxaanthracene) is the [[organic compound]] with the formula CH₂[C₆H₄]₂O. 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>

==Xanthene dyes==

[[Image:Rhodamine skeleton.svg|thumb|left|[[Rhodamine]]s are commercial dyes with xanthene cores.]]

[[Dye]]s that contain a xanthene core include [[bikaverin]], [[fluorescein]], [[eosin]]s, and [[rhodamine]]s. Xanthene dyes tend to be [[fluorescent]], yellow to pink to bluish red, brilliant dyes. Many xanthene dyes can be prepared by condensation of derivates of [[phthalic anhydride]] with derivates of [[resorcinol]] or [[3-Aminophenol|3-aminophenol]].

{{Break|5}}

==Further reading==

*{{cite journal|title=Photochemistry of the Xanthene Dyes|author1=Neckers, Douglas C. |author2=Valdes-Aguilera Oscar M. |journal=Advances in Photochemistry|year=1993|volume=18|pages=315–94|doi=10.1002/9780470133491.ch4|isbn=9780470133491}}

==References==

{{Reflist}}

[[Category:Dyes]]