ACRIDINE ORANGE Chemical Properties
- Melting point:165 °C (dec.)(lit.)
- Boiling point:469℃
- Density 1.169
- refractive index 1.6080 (estimate)
- Flash point:237℃
- Colour Index 46005
- color Yellow needles from EtOH
- IARC3 (Vol. 16, Sup 7) 1987
- Safety Statements 22-24/25
- WGK Germany 3
- RTECS AR7600000
- Toxicitymmo-omi 10 mg/L MIBLAO 49,223,80
ACRIDINE ORANGE Usage And Synthesis
- UsesA fluorescent nucleic acid binding dye which interacts with both DNA and RNA.
- DefinitionChEBI: A member of the class of aminoacridines that is acridine carrying two dimethylamino substituents at positions 3 and 6. The hydrochloride salt is the fluorescent dye 'acridine orange', used for cell cycle determination.
- Safety ProfilePoison by subcutaneous route.Questionable carcinogen with experimental tumorigenicand carcinogenic data. Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx.
- Purification MethodsThe double salt with ZnCl2 (6g) is dissolved in water (200mL) and stirred with four successive portions (12g each) of Dowex-50 ion-exchange resin (K+ form) to remove the zinc. The solution is then concentrated in vacuum to 20mL, and 100mL of ethanol is added to precipitate KCl which is removed. Ether (160mL) is added to the solution from which, on chilling, the dye crystallises as its chloride. It is separated by centrifugation, washed with chilled ethanol and ether, and dried under vacuum, before being recrystallised from ethanol (100mL) by adding ether (50mL), and chilling. Yield 1g. [Pal & Schubert J Am Chem Soc 84 4384 1962]. It was recrystallised twice as the free base from ethanol or methanol/water by dropwise addition of NaOH (less than 0.1M). The precipitate was washed with water and dried under vacuum. It was dissolved in CHCl3 and chromatographed on alumina: the main sharp band was collected, concentrated and cooled to -20o. The precipitate was filtered off, dried in air, then dried for 2hours under vacuum at 70o. [Stone & Bradley J Am Chem Soc 83 3627 1961, Blauer & Linschitz J Phys Chem 66 453 1962, Albert J Chem Soc 244 1947, Beilstein 22 III/IV 5490, 22/11 V 326.]
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