Acridine orange

Structural formula
General
Surname	Acridine orange
other names	N , N , N ', N ' -tetramethylacridine-3,6-diamine 3,6-bis (dimethylamino) acridine
Molecular formula	C 17 H 19 N 3
Brief description	dark orange to brown solid
External identifiers / databases
CAS number 494-38-2 (free base) EC number 610-452-6 ECHA InfoCard 100.122.153 PubChem 62344 ChemSpider 56136 Wikidata Q342717
properties
Molar mass	265.35 g mol −1
Physical state	firmly
Melting point	165 ° C (decomposition)
safety instructions
GHS labeling of hazardous substances 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 .

Acridine orange is an acridine - dye , in the molecular biology for the detection of nucleic acids , DNA and RNA , is used. Acridine orange has an intercalating effect . It can also be used to detect acidic compartments in cells.

variants

Acridine orange is available as a free base, as a hydrochloride and as a zinc chloride double salt.

Acridine orange
Surname	Acridine orange, free base	Acridine orange, hydrochloride	Acridine orange zinc chloride double salt
Structural formula
other names	CI 46005 Solvent Orange 15	Basic orange 14 Rhodulinorange	CI 46005 Euchrysin
CAS number	494-38-2	65-61-2	10127-02-3
PubChem	62344	517204	159263
Molecular formula	C 17 H 19 N 3	C 17 H 20 ClN 3	C 17 H 20 Cl 3 N 3 Zn
Molar mass	265.35 g mol −1	301.81 g mol −1	438.11 g mol −1
Physical state	firmly
Melting point	165 ° C (decomposition)	284-287 ° C	165 ° C
solubility		soluble in water and ethanol
GHS labeling	no GHS pictograms	Caution	Caution
H and P phrases	no H-phrases	302-312-332-341	341
	no P-phrases	280-281-302 + 352-260-301 + 312-304 + 340	281-308 + 313

use

Acridine orange is used as a fluorescent dye to differentiate between DNA and RNA. The DNA-dye complex shows an absorption maximum at 502  nm and an emission maximum at 526 nm (green), while the RNA-dye complex shows an absorption maximum at 460 nm and an emission maximum at 650 nm (red).

Individual evidence

1. ↑ ^{a b c d} Entry on acridine orange. In: Römpp Online . Georg Thieme Verlag, accessed on November 11, 2014.
2. ↑ ^{a b c d e f g} Data sheet Acridine Orange base from Sigma-Aldrich , accessed on February 11, 2018 ( PDF ).
3. ^ ^{A b} F. WD Rost: Fluorescence Microscopy, Vol. II , p. 202, Cambridge University Press Cambridge, ISBN 0-521-41088-6 .
4. ↑ DJ Klinonsky: Autophagy in Disease and Clinical Applications, Part C, vol 453 , p 275, 1st Edition, Academic Press, Elsevier San Diego, ISBN 0-12-374936-0 .
5. ↑ Data sheet Acridine Orange, hydrochloride hydrate from Acros, accessed on February 11, 2018.
6. ↑ ^{a b c} Entry on N, N, N ′, N′-Tetramethylacridin-3,6-yldiamine hydrochloride in the GESTIS substance database of the IFA , accessed on February 8, 2018(JavaScript required) .
7. ↑ ^{a b c} data sheet Acridine orange zinc chloride double salt (CI46005) from Sigma-Aldrich , accessed on February 11, 2018 ( PDF ).