| Identification | Back Directory | [Name]
ACRIDINE ORANGE | [CAS]
494-38-2 | [Synonyms]
494-38-2
c.i.46005b
EUCHRYSINE
CI NO 46005
C.I.46005:1
c.i.no.46005:1
waxolineorangea
oranzakridinova
Euchrysine 3RXA
rhodulineorangen
RHODULINE ORANGE
SOLVENT ORANGE 15
acridrineorangebase
c.i.solventorange15
ACRIDINE ORANGE BASE
ACRIDINE ORANGE BASIC
oranzrozpoustedlova15
Acridine Orange Stain
acridineorangefreebase
LABOTEST-BB LT00452868
brilliantacridineorangee
Acridine Orange,Dye content
2,8-bisdimethylaminoacridine
3,6-di(dimethylamino)acridine
3,6-bis-(dimethylamino)akridin
3,6-bis(dimethylamino)-acridin
ACRIDINE ORANGE (C.I. 46005:1)
3,6-BIS(DIMETHYLAMINO)ACRIDINE
C.I.Solvent Orange 15:C.I.46005:1
n,n,n’,n’-tetramethyl-acridinediamin
n,n,n’,n’-tetramethylacridinediamine
3,6-Acridinediamine, N,N,N,N-tetramethyl-
n,n,n’,n’-tetramethyl-3,6-acridinediamine
N3,N3,N6,N6-TetraMethylacridine-3,6-diaMine
N,N,N,N-tetramethyl(acridine-3,6-diyldiamine
3,6-Acridinediamine, N3,N3,N6,N6-tetramethyl-
3-N,3-N,6-N,6-N-tetramethylacridine-3,6-diamine
N3,N3,N6,N6-tetramethyl-acridine-3,6-diyldiamine
compound with zinc-chloride and hydrogen chloride
3,6-Bis(dimethylamino)acridine, Solvent Orange15
Acridine Orange base,3,6-Bis(dimethylamino)acridine, Solvent Orange15
3,6-Bis(dimethylamino)acridine N,N,N',N'-Tetramethyl-3,6-acridinediamine | [EINECS(EC#)]
207-787-1 | [Molecular Formula]
C17H19N3 | [MDL Number]
MFCD00005029 | [MOL File]
494-38-2.mol | [Molecular Weight]
265.35 |
| Chemical Properties | Back Directory | [Melting point ]
165 °C (dec.)(lit.)
| [Boiling point ]
469℃ | [density ]
1.169 | [refractive index ]
1.6080 (estimate) | [Fp ]
237℃ | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMF: 2 mg/ml; DMSO: 20 mg/ml; Ethanol: 0.3 mg/ml; PBS (pH 7.2): 1 mg/ml | [Colour Index ]
46005 | [form ]
A crystalline solid | [pka]
9.97±0.30(Predicted) | [color ]
Yellow needles from EtOH | [ε(extinction coefficient)]
≥14000 at 227-233nm
≥20000 at 289-295nm
≥35000 at 486-492nm
≥40000 at 266-272nm | [λmax]
488 nm | [Stability:]
Light Sensitive | [IARC]
3 (Vol. 16, Sup 7) 1987 |
| Hazard Information | Back Directory | [Description]
Acridine orange is a cell-permeable, nucleic acid-selective fluorescent cationic dye useful for cell cycle determination and detection of cellular autophagy.1,2,3 It exhibits excitation/emission spectra of 502/525, 460/650, and 475/590 nm when bound to dsDNA, bound to ssDNA or RNA, and under acidic conditions, respectively.1,2 The ratio of acridine orange emission at 590 to emission at 525 nm can be used to quantify the increase in the number of acidic vesicular organelles observed during cellular autophagy. | [Uses]
A fluorescent nucleic acid binding dye which interacts with both DNA and RNA. | [Definition]
ChEBI: 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. | [Preparation]
4,4′-Bis(N,N-dimethyl)aminodiphenylmethane?dinitration, the resultant 4-(4-(Dimethylamino)-3-nitrobenzyl)-N,N-dimethyl-2-nitrobenzenamine?reduction, and acid heating will diamino compound cyclization, then will product oxidation and made free base. | [Safety Profile]
Poison by subcutaneous route.Questionable carcinogen with experimental tumorigenicand carcinogenic data. Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx. | [Properties and Applications]
brilliant yellow orange. Soluble in water and ethanol as orange, with green fluorescence. In concentrated sulfuric acid in almost colorless, with green fluorescent, dilution after orange. Dye aqueous solution to join sodium hydroxide have yellow precipitation.
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Standard
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Light Fastness
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Heat-resistant(℃)
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water
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Sodium Carbonate(5%)
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Hydrochloric acid(5%)
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Melting point
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Stable
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ISO
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Poor
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Poor
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| [Purification Methods]
The 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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