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Thionine

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(Redirected from Lauth's violet) Chemical compound and histologic stain C12H10N3S For other uses, see Thionine (disambiguation).
Thionine
Names
Preferred IUPAC name 3,7-Diamino-5λ-phenothiazin-5-ylium
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.611 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=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+1Key: CBBMGBGDIPJEMI-UHFFFAOYSA-N
SMILES
  • C1=CC2=C(C=C1N)=C3C=C(C=CC3=N2)N
Properties
Chemical formula C12H10N3S
Molar mass 228.29 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. The dye's name is frequently misspelled with omission of the e, and is not to be confused with the plant protein thionin. The -ine ending indicates that the compound is an amine.

Dye properties and use

Thionine is a strongly staining metachromatic dye, which is widely used for biological staining. 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. Thionine is a pH-dependent redox indicator with E = 0.06 at pH 7.0. Its reduced form, leuco-thionine, is colorless.

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 a primary amine), and Azure B (Trimethyl thionine). When methylene blue is "polychromed" by ripening (oxidized in solution or metabolized by fungal contamination, as originally noted in the thesis of Dr D L Romanowski in 1890s), it forms thionine and all the Azure intermediates.

Notes and references

  1. Gérard Taurand, "Phenothiazine and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.doi:10.1002/14356007.a19_387
  2. Kiernan JA (2001). "Classification and naming of dyes, stains and fluorochromes". Biotech Histochem. 76 (5–6): 261–78. doi:10.1080/bih.76.5-6.261.278. PMID 11871748. S2CID 32479873.
  3. Webster's Third New International Dictionary. G & C Merriam Co. 1976, p.2377.
  4. "Stainsfile — Thionin". Archived from the original on 18 June 2024. Retrieved 30 October 2024.
  5. Eugenii Katz; Andrew N. Shipway; Itamar Willner (2003). "21". In Wolf Vielstich (ed.). Handbook of Fuel Cells: Fundamentals, Technology, Applications, 4-Volume Set (PDF). Wiley. p. 5. ISBN 978-0-471-49926-8.
  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 Archived 2012-05-13 at the Wayback Machine
  7. Wilson TM (1907). "On the Chemistry and Staining Properties of Certain Derivatives of the Methylene Blue Group when Combined with Eosin". J Exp Med. 9 (6): 645–70. doi:10.1084/jem.9.6.645. PMC 2124692. PMID 19867116.
  8. Marshall, PN (1978) Romanowsky-type stains in haematology. Histochemical Journal 10: 1-29.
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