ChemicalBook > CAS DataBase List > ACRIDINE ORANGE

ACRIDINE ORANGE

Product Name: ACRIDINE ORANGE
CAS No.: 494-38-2
Chemical Name: ACRIDINE ORANGE
Synonyms: ACRIDINE ORANGE BASE;N3,N3,N6,N6-TetraMethylacridine-3,6-diaMine;SOLVENT ORANGE 15;c.i.46005b;EUCHRYSINE;CI NO 46005;C.I.46005:1;c.i.no.46005:1;waxolineorangea;oranzakridinova
CBNumber: CB4378880
Molecular Formula: C17H19N3
Formula Weight: 265.35
MOL File: 494-38-2.mol

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ACRIDINE ORANGE Property

Melting point:: 165 °C (dec.)(lit.)
Boiling point:: 469℃
Density: 1.169
refractive index: 1.6080 (estimate)
Flash point:: 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
form: A crystalline solid
Colour Index: 46005
pka: 9.97±0.30(Predicted)
color: Yellow needles from EtOH
λmax: 488 nm
ε(extinction coefficient): ≥14000 at 227-233nm
≥20000 at 289-295nm
≥35000 at 486-492nm
≥40000 at 266-272nm
Stability:: Light Sensitive
IARC: 3 (Vol. 16, Sup 7) 1987

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Safety

Safety Statements: 22-24/25
WGK Germany: 3
RTECS: AR7600000
Toxicity: mmo-omi 10 mg/L MIBLAO 49,223,80

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 235474
Product name: Acridine Orange base
Purity: Dye content 75%
Packaging: 5g
Price: $71.5
Updated: 2025/07/31

Sigma-Aldrich

Product number: 235474
Product name: Acridine Orange base
Purity: Dye content 75%
Packaging: 25g
Price: $298
Updated: 2025/07/31

Cayman Chemical

Product number: 14338
Product name: Acridine Orange
Packaging: 5g
Price: $62
Updated: 2024/03/01

Cayman Chemical

Product number: 14338
Product name: Acridine Orange
Packaging: 10g
Price: $104
Updated: 2024/03/01

Cayman Chemical

Product number: 14338
Product name: Acridine Orange
Packaging: 25g
Price: $239
Updated: 2024/03/01

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ACRIDINE ORANGE Chemical Properties,Usage,Production

Description

Acridine orange is a cell-permeable, nucleic acid-selective fluorescent cationic dye useful for cell cycle determination and detection of cellular autophagy. 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. 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

Acridine Orange Stain is a fluorescent nucleic acid binding dye which interacts with both DNA and RNA. When bound to DNA, it emits green fluorescence (Em=525 nm) and when bound to RNA, it emits red fluorescence (Em=~650 nm).

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.

Standard	Light Fastness	Heat-resistant(℃)		water	Sodium Carbonate(5%)	Hydrochloric acid(5%)
		Melting point	Stable
ISO	Poor			Poor

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.]

References

[1] I. VIRANT-KLUN H M T Toma?evi?. Sperm Single-Stranded DNA, Detected by Acridine Orange Staining, Reduces Fertilization and Quality of ICSI-Derived Embryos[J]. Journal of Assisted Reproduction and Genetics, 2002, 19 1: 319-328. DOI: 10.1023/a:1016006509036
[2] JUNYAN HAN Kevin B. Fluorescent Indicators for Intracellular pH[J]. Chemical Reviews, 2009, 110 5: 2709-2728. DOI: 10.1021/cr900249z
[3] MARCOS P THOMé. Ratiometric analysis of Acridine Orange staining in the study of acidic organelles and autophagy.[J]. Journal of cell science, 2016: 4622-4632. DOI: 10.1242/jcs.195057

ACRIDINE ORANGE Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from ACRIDINE ORANGE manufacturers

Shaanxi Dideu New Materials Co. Ltd

Product: ACRIDINE ORANGE 494-38-2
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 98
Supply Ability: 10000KGS
Release date: 2025-11-24

Hebei Chuanghai Biotechnology Co., Ltd

Product: ACRIDINE ORANGE 494-38-2
Price: US $10.00/KG
Min. Order: 100KG
Purity: 99%
Supply Ability: 100 mt
Release date: 2024-11-22

Shaanxi Dideu Medichem Co. Ltd

Product: ACRIDINE ORANGE 494-38-2
Price: US $30.00-18.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 500KG
Release date: 2024-07-15

494-38-2, ACRIDINE ORANGERelated Search:

p-[[2-methyl-4-[(o-tolyl)azo]phenyl]azo]phenol 4',5',7-Tribromo-3',6'-dihydroxy-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthene]-2',7'-dicarboxylic acid SOLVENT ORANGE 22 Solvent Orange 14 4',5'-DINITROFLUORESCEIN D&CORANGENO.16 AZOSOL FAST ORANGE RA SOLVENT ORANGE 23 Solvent Orange 2 10-OCTADECYLACRIDINE ORANGE BROMIDE ACRIDINE ORANGE 2,8-BIS(DIMETHYLAMINO)-10-DODECYL-ACRIDINIUM BROMIDE NONYL ACRIDINE ORANGE Basic Orange 14 ACRIDINE ORANGE

N3,N3,N6,N6-TetraMethylacridine-3,6-diaMine

3,6-Bis(dimethylamino)acridine N,N,N',N'-Tetramethyl-3,6-acridinediamine

Acridine Orange Stain

brilliantacridineorangee

compound with zinc-chloride and hydrogen chloride

N3,N3,N6,N6-tetramethyl-acridine-3,6-diyldiamine

3,6-bis-(dimethylamino)akridin

3,6-di(dimethylamino)acridine

acridineorangefreebase

acridrineorangebase

oranzrozpoustedlova15

rhodulineorangen

waxolineorangea

Acridine Orange,Dye content

c.i.46005b

c.i.no.46005:1

c.i.solventorange15

n,n,n’,n’-tetramethyl-3,6-acridinediamine

n,n,n’,n’-tetramethyl-acridinediamin

n,n,n’,n’-tetramethylacridinediamine

oranzakridinova

3,6-bis(dimethylamino)-acridin

N,N,N,N-tetramethyl(acridine-3,6-diyldiamine

ACRIDINE ORANGE (C.I. 46005:1)

3,6-BIS(DIMETHYLAMINO)ACRIDINE

3,6-Acridinediamine, N,N,N,N-tetramethyl-

3,6-Bis(dimethylamino)acridine, Solvent Orange15

RHODULINE ORANGE

SOLVENT ORANGE 15

LABOTEST-BB LT00452868

EUCHRYSINE

CI NO 46005

3-N,3-N,6-N,6-N-tetramethylacridine-3,6-diamine

ACRIDINE ORANGE BASE

ACRIDINE ORANGE BASIC

2,8-bisdimethylaminoacridine

C.I.46005:1

Acridine Orange base,3,6-Bis(dimethylamino)acridine, Solvent Orange15

Euchrysine 3RXA

3,6-Acridinediamine, N3,N3,N6,N6-tetramethyl-

C.I.Solvent Orange 15:C.I.46005:1

494-38-2

C34H38ClN6Zn