Acridine orange

Base Information

• Chemical Name: Acridine orange
• CAS No.: 494-38-2
• Molecular Formula: C17H19 N3
• Molecular Weight: 265.358
• European Community (EC) Number: 233-353-6,610-452-6
• NSC Number: 194350
• UNII: F30N4O6XVV
• DSSTox Substance ID: DTXSID60197783
• Nikkaji Number: J1.559H
• Wikipedia: Acridine_orange
• Wikidata: Q342717
• Pharos Ligand ID: R5G6W5NQPU9N
• Metabolomics Workbench ID: 67050
• ChEMBL ID: CHEMBL81880
• Mol file: 494-38-2.mol

Synonyms:3,6-Bis(dimethylamino)acridine;Acridine Diamine, Tetramethyl;Acridine Orange;Acridine Orange Base;Base, Acridine Orange;Basic Orange 3RN;C.I. 46005;C.I. Basic Orange 14;Diamine, Tetramethyl Acridine;euchrysine;N,N,N',N'-Tetramethyl-3,6-Acridinediamine Hydrochloride;Orange 3RN, Basic;Orange Base, Acridine;Orange, Acridine;Orange, Rhoduline;Rhoduline Orange;Tetramethyl Acridine Diamine

Chemical Property of Acridine orange

Chemical Property:

• Appearance/Colour: BROWN POWDER
• Melting Point: 165 °C (dec.)(lit.)
• Refractive Index: 1.6080 (estimate)
• Boiling Point: 468.6 °C at 760 mmHg
• PKA: 9.97±0.30(Predicted)
• Flash Point: 237.2 °C
• PSA: 19.37000
• Density: 1.169 g/cm³
• LogP: 3.52000
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 265.157897619
• Heavy Atom Count: 20
• Complexity: 298

Purity/Quality:

99%, ^*data from raw suppliers

Acridine Orange ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Dyes -> Acridine Dyes
• Canonical SMILES: CN(C)C1=CC2=C(C=C1)C=C3C=CC(=CC3=N2)N(C)C
• 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). A fluorescent nucleic acid binding dye which interacts with both DNA and RNA.

Technology Process of Acridine orange

There total 24 articles about Acridine orange which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 53.0%

3,6-dibromoacridine + dimethyl amine (124-40-3) → acridine orange (494-38-2)

Guidance literature:

With potassium tert-butylate; Tri(p-tolyl)phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In 1,4-dioxane; tert-butyl alcohol; at 110 ℃; for 12h; Schlenk technique; Inert atmosphere;

Reference yield:

N,N,N',N'-Tetramethyl-acridine-3,6-diamine; compound with 4-nitro-phenol → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + acridine orange (494-38-2) + N,N,N',N'-Tetramethyl-acridine-3,6-diamine; compound with 4-nitro-phenol

Guidance literature:

In benzonitrile; at 25 ℃; Equilibrium constant; ionic strength 0.1 M;

Reference yield:

2,2'-methylenebis(5-dimethylamino)aniline (200195-68-2) → acridine orange (494-38-2)

Guidance literature:

With hydrogenchloride; at 140 ℃; Oxydation mit Eisenchlorid oder Luft;

upstream raw materials:

2,2'-methylenebis(5-dimethylamino)aniline

oxalic acid

(E)-3-Ureido-but-2-enoic acid ethyl ester

glycerol

Downstream raw materials:

2,4,6-tri-tert-butylphenoxyl

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

acridine orange

Refernces

• 1、 Arsenyan, Pavel,Dimitrijevs, Pavels,Domracheva, Ilona. "Improved method for the preparation of nonyl acridine orange analogues and utilization in detection of cardiolipin". . p. 9626 - 9633. Retrieved 2020/07/03.
• 2、 Eisenhart, Thomas T.,Dempsey, Jillian L.. "Photo-induced proton-coupled electron transfer reactions of acridine orange: Comprehensive spectral and kinetics analysis". . p. 12221 - 12224. Retrieved 2014/11/08.