| 词条 | Thionine |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424770911 | ImageFile = Thionine.png | ImageSize = | ImageAlt = | IUPACName = 3,7-Diaminophenothiazin-5-ium | OtherNames = |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|changed|??}} | CASNo = 26754-93-8 | PubChem = 65043 | PubChem_Comment = (chloride salt) | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 10554883 | SMILES = C1=CC2=C(C=C1N)[S+]=C3C=C(C=CC3=N2)N | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | 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 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = CBBMGBGDIPJEMI-UHFFFAOYSA-N }} |Section2={{Chembox Properties | C=12|H=10|N=3|S=1 | Formula_Charge = + | MolarMass = | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}Thionine, also known as Lauth's violet, is the salt of a heterocyclic compound. It was firstly synthesised by Charles Lauth. A variety of salts are known including the chloride and acetate, called respectively thionine chloride and thionine acetate. The dye is structurally related to methylene blue, which also features a phenothiazine core.[1] The dye's name is frequently misspelled, with omission of the e. The -ine ending indicates that the compound is an amine.[2][3] Dye properties and useThionine is a strongly staining metachromatic dye, which is widely used for biological staining.[4] Thionine can also be used in place of Schiff reagent in quantitative Feulgen staining of DNA. It can also be used to mediate electron transfer in microbial fuel cells.[5] When both the amines are dimethylated, the product tetramethyl thionine is the famous methylene blue, and the intermediates are Azure C (Monomethyl thionine), Azure A (when one of the amines is dimethylated and the other remains primary amine), and Azure B (Trimethyl thionine). When methylene blue is "polychromed" by ripening (Oxidized in solution or metabolized by fungal contamination,[6] as originally noted in the thesis of Dr D L Romanowski in 1890s), it forms thionine and all the Azure intermediates.[7][8] Notes and references1. ^Gérard Taurand, "Phenothiazine and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.{{DOI|10.1002/14356007.a19_387}} 2. ^{{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}} 3. ^Webster's Third New International Dictionary. G & C Merriam Co. 1976, p.2377. 4. ^{{cite web |url=http://stainsfile.info/StainsFile/dyes/52000.htm |title=Stainsfile — Thionin }} 5. ^{{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|editor=Wolf Vielstich|page=5|chapter=21}} 6. ^Dako Education Guide - Special Stains and H & E ” second edition Chapter 19: On Chemical Reactions and Staining Mechanisms by John A. Kiernan, Subsection What is Giemsa’s stain and how does it color blood cells, bacteria and chromosomes? p172 {{Webarchive|url=https://web.archive.org/web/20120513002342/http://www.dako.com/08066_12may10_webchapter19.pdf |date=2012-05-13 }} 7. ^{{cite journal | pmc = 2124692 | pmid=19867116 | volume=9 | title=ON THE CHEMISTRY AND STAINING PROPERTIES OF CERTAIN DERIVATIVES OF THE METHYLENE BLUE GROUP WHEN COMBINED WITH EOSIN | journal=J Exp Med | pages=645–70 | author=Wilson TM | doi=10.1084/jem.9.6.645}} 8. ^Marshall, PN (1978) Romanowsky-type stains in haematology. Histochemical Journal 10: 1-29. 2 : Staining|Phenothiazines |
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