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Latest revision as of 17:50, 30 October 2024 edit undoBlubberdorf (talk | contribs)1 editm Fixed a dead link for the 4th footnote.Tag: Visual edit |
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{{Short description|Chemical compound and histologic stain C12H10N3S}} |
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{{Other uses}} |
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{{Chembox |
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{{Chembox |
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| verifiedrevid = 369902717 |
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| ImageFile = Thionine.png |
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| verifiedrevid = 424770911 |
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| ImageSize = 200px |
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| ImageFile = Thionine.svg |
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| Section1 = {{Chembox Identifiers |
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| CASNo = 135-59-1 |
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| PIN = 3,7-Diamino-5λ<sup>4</sup>-phenothiazin-5-ylium |
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| OtherNames = |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 26754-93-8 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 8CFV7T4334 |
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| PubChem = 65043 |
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| PubChem_Comment = (chloride salt) |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 10554883 |
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| SMILES = C1=CC2=C(C=C1N)=C3C=C(C=CC3=N2)N |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C12H10N3S/c13-7-1-3-9-11(5-7)16-12-6-8(14)2-4-10(12)15-9/h1-6H,13-14H2/q+1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = CBBMGBGDIPJEMI-UHFFFAOYSA-N }} |
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|Section2={{Chembox Properties |
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| C=12|H=10|N=3|S=1 |
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| Formula_Charge = + |
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|Section3={{Chembox Hazards |
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'''Thionine''', also known as '''thionine acetate''' or '''Lauth's violet''', is a strongly staining metachromatic dye that are widely used for biological staining.<ref>{{cite web |url=http://stainsfile.info/StainsFile/dyes/52000.htm |title=Stainsfile — Thionin }}</ref> Thionine can also be used in place of ] in quantitative ]ing of DNA. It can also be used to mediate electron transfer in ]s.{{Fact|date=April 2008}} The dye's name is frequently mis-spelled, with omission of the e. The -ine ending indicates that the compound is an ]<ref>{{cite journal |author=Kiernan JA |title=Classification and naming of dyes, stains and fluorochromes |journal=Biotech Histochem |volume=76 |issue=5-6 |pages=261–78 |year=2001 |pmid=11871748 }}</ref><ref>Webster's Third New International Dictionary. G & C Merriam Co. 1976, p.2377.</ref>. |
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'''Thionine''', also known as '''Lauth's violet''', is the salt of a ]. It was firstly synthesised by ]. A variety of salts are known including the chloride and acetate, called respectively '''thionine chloride''' and '''thionine acetate'''. The dye is structurally related to ], which also features a ] core.<ref>Gérard Taurand, "Phenothiazine and Derivatives" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2005.{{doi|10.1002/14356007.a19_387}}</ref> The dye's name is frequently misspelled with omission of the e, and is not to be confused with the plant protein ]. The -ine ending indicates that the compound is an ].<ref>{{cite journal |author=Kiernan JA |title=Classification and naming of dyes, stains and fluorochromes |journal=Biotech Histochem |volume=76 |issue=5–6 |pages=261–78 |year=2001 |pmid=11871748 |doi=10.1080/bih.76.5-6.261.278|s2cid=32479873 }}</ref><ref>Webster's Third New International Dictionary. G & C Merriam Co. 1976, p.2377.</ref> |
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==Dye properties and use== |
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Thionine is a strongly staining metachromatic dye, which is widely used for ].<ref>{{cite web |title=Stainsfile — Thionin |url=https://www.stainsfile.com/dyes/thionin/ |archive-url=https://web.archive.org/web/20240618153719/https://www.stainsfile.com/dyes/thionin/ |archive-date=18 June 2024 |access-date=30 October 2024}}</ref> Thionine can also be used in place of ] in quantitative ]ing of DNA. It can also be used to mediate electron transfer in ]s.<ref>{{cite book|title=Handbook of Fuel Cells: Fundamentals, Technology, Applications, 4-Volume Set|year=2003|publisher=Wiley|isbn=978-0-471-49926-8|url=http://www.cbs.umn.edu/sites/default/files/public/downloads/0471499269.pdf|author=Eugenii Katz |author2=Andrew N. Shipway |author3=Itamar Willner |author3-link=Itamar Willner |editor=Wolf Vielstich|page=5|chapter=21}}</ref> Thionine is a pH-dependent ] with E<sup>0</sup> = 0.06 at pH 7.0. Its reduced form, leuco-thionine, is colorless. |
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When both the amines are dimethylated, the product tetramethyl thionine is the famous ], and the intermediates are ] (Monomethyl thionine), ] (when one of the amines is dimethylated and the other remains a primary amine), and ] (Trimethyl thionine). When ] is "polychromed" by ripening (oxidized in solution or metabolized by fungal contamination,<ref> {{Webarchive|url=https://web.archive.org/web/20120513002342/http://www.dako.com/08066_12may10_webchapter19.pdf |date=2012-05-13 }}</ref> as originally noted in the thesis of Dr D L Romanowski in 1890s), it forms thionine and all the Azure intermediates.<ref>{{cite journal | pmc = 2124692 | pmid=19867116 | volume=9 | journal=J Exp Med | pages=645–70 | author=Wilson TM | title=On the Chemistry and Staining Properties of Certain Derivatives of the Methylene Blue Group when Combined with Eosin | year=1907 | issue=6 | doi=10.1084/jem.9.6.645}}</ref><ref>Marshall, PN (1978) Romanowsky-type stains in haematology. Histochemical Journal 10: 1-29.</ref> |
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==Notes and references== |
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==Notes and references== |
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{{Reflist}} |
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