3D model (JSmol)
|Molar mass||228.29 g·mol−1|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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. 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.
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, as originally noted in the thesis of Dr D L Romanowski in 1890s), it forms thionine and all the Azure intermediates.
Notes and references
- Gérard Taurand, "Phenothiazine and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.doi:10.1002/14356007.a19_387
- 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.
- Webster's Third New International Dictionary. G & C Merriam Co. 1976, p.2377.
- "Stainsfile — Thionin".
- 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.
- 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
- Wilson TM. "ON THE CHEMISTRY AND STAINING PROPERTIES OF CERTAIN DERIVATIVES OF THE METHYLENE BLUE GROUP WHEN COMBINED WITH EOSIN". J Exp Med. 9: 645–70. doi:10.1084/jem.9.6.645. PMC 2124692. PMID 19867116.
- Marshall, PN (1978) Romanowsky-type stains in haematology. Histochemical Journal 10: 1-29.