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Sigma-Aldrich

Acridine Orange hydrochloride hydrate

≥98% (HPLC)

Synonym(s):

3,6-Bis(dimethylamino)acridine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C17H19N3 · HCl · xH2O
CAS Number:
65-61-2
Molecular Weight:
301.81 (anhydrous basis)
Colour Index Number:
46005
Beilstein:
3734978
EC Number:
200-614-0
MDL number:
MFCD00150070
UNSPSC Code:
12171500
PubChem Substance ID:
24859123
NACRES:
NA.47

Quality Level

200

Assay

≥98% (HPLC)

form

powder

color

orange

mp

284-287 °C (lit.)

solubility

H2O: 0.1%, clear, orange to red

λmax

492 nm

ε (extinction coefficient)

≥14,000 at 227-233 nm in water at 0.005 g/L
≥35000 at 265-271 nm in water at 0.005 g/L

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

Cl[H].[H]O[H].CN(C)c1ccc2cc3ccc(cc3nc2c1)N(C)C

InChI

1S/C17H19N3.ClH.H2O/c1-19(2)14-7-5-12-9-13-6-8-15(20(3)4)11-17(13)18-16(12)10-14;;/h5-11H,1-4H3;1H;1H2

InChI key

JUAAUEXLEKAEQC-UHFFFAOYSA-N

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Application

A rigorously purified zinc-free material suitable for use in flow cytometry.
Acridine Orange hydrochloride hydrate dye has been used:
  • to stain intracellular acidic vesicles.
  • to measure lysosomal membrane permeability (LMP).
  • or autophagy detection.
Fluorescent stain for nucleic acids in agarose and polyacrylamide gels. Has been used to study apoptosis in various cell culture and tissue models.

Biochem/physiol Actions

Acridine Orange is a metachromatic dye which can stain DNA, RNA and acid glycosaminoglycans. At low concentrations, it intercalates into DNA and precipitates RNA. However, at high concentrations it denatures and precipitates both RNA and DNA. Acridine Orange is also used to analyze autophagy. It enters into acidic organelles in a pH-dependent manner. At neutral pH, acridine orange gives a green fluorescence and in acidic conditions, it accumulates in acidic organelles giving a bright red fluorescence.

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Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H341

Hazard Classifications

Muta. 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Fluorescence Microscopy, 2 (1992)
Michael M Fisher et al.
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