Pyronine G.

Structural formula
General
Surname	Pyronine G.
other names	6- (Dimethylamino) - N , N -dimethyl-3 H -xanthene-3-iminium chloride ( IUPAC ) ; CI 45005;
Molecular formula	C 17 H 19 ClN 2 O
External identifiers / databases
EC number	202-147-8
ECHA InfoCard	100.001.953
PubChem	7085
ChemSpider	6818
Wikidata	Q2120020
properties
Molar mass	302.80 g mol −1
Physical state	firmly
Melting point	250-260 ° C
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pyronin G (also Pyronin Y) is a dye from the group of Pyronine . It is a cationic xanthene dye .

Surname

The G is an abbreviation for yellow, so that the substance in the English-speaking world contains a Y for yellow. Yellow describes the absorption maximum of the substance in the yellow-green area of the light spectrum .

description

The quaternary nitrogen is methylated. If there are ethyl groups instead, the substance is called pyronine B (bluish):

Pyronine B

Like pyronine G, it is cationic.

Manufacturing

Pyronine G can be synthesized by condensation of N , N -dimethyl- m -aminophenol with formaldehyde to give tetramethyldiaminodioxydiphenylmethane, which cyclizes to tetramethyldiaminoxanthene by means of sulfuric acid with elimination of water .

use

For blood tests, Artur Pappenheim introduced the fabric for dyeing purposes in 1899, which became known as Pappenheim dye . The method was modified in 1902 by Paul Gerson Unna for tissue studies so that it was called Pappenheim-Unna staining.

Histology uses the substance in combination with methyl green to stain nucleic acids in the specimen. In this intercalated pyronine G with RNA while Methyl Green binds to DNA. In flow cytometry, it is therefore an alternative to acridine orange for differential diagnosis .

The binding behavior depends on the dye concentration as well as on the conformation of the nucleic acids, which in turn varies depending on the phase of mitosis . The toxic effect on live samples is due to the binding.

Derivatives that are formed by reacting with cyanides to form nitrile at the 9'-C with subsequent oxidation are used as textile dyes.

literature

FWD Rost: Fluorescence microscopy , 1995, p. 357 ( limited preview in the Google book search).
Howard Maurice Shapiro: Practical flow cytometry , 2003, pp. 323-324 ( limited preview in Google book search).
James Sheridan Muspratt, Ernst Otto Beckmann, Hans Bunte, Bernhard Neumann, Arthur Heinrich Binz, Fritz Hayduch, Friedrich Karl Adolf Stohmann: Encyklopädisches Handbuch der technischen Chemie , Volume 3, Part 1, 1915, p. 448.
Fritz Ullmann, Matthias Bohnet: Ullmann's encyclopedia of industrial chemistry , Volume 37, 2003, p. 479.

Web links

AppliChem: Pyronin Y (CI 45005)
ihcworld.com: ABC of Safety in the Biological Sciences - Pyronin G

Individual evidence

↑ ^a ^b ^c ^d sheet pyronine Y, for microscopy (Bot., Fl., Hist.) At Sigma-Aldrich , accessed 30 January 2012 ( PDF ).

[Sigma-1] sheet pyronine Y, for microscopy (Bot., Fl., Hist.) At Sigma-Aldrich , accessed 30 January 2012 ( PDF ).