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861030

Sigma-Aldrich

Auramine O

Dye content 85 %, certified by the Biological Stain Commission

Synonym(s):

4,4′-(Imidocarbonyl)bis(N,N-dimethylaniline) monohydrochloride, Basic Yellow 2, Pyoctaninum aureum

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About This Item

Empirical Formula (Hill Notation):
C17H21N3 · HCl
CAS Number:
Molecular Weight:
303.83
Colour Index Number:
41000
Beilstein:
4030061
EC Number:
MDL number:
UNSPSC Code:
12171500
PubChem Substance ID:
NACRES:
NA.47

grade

certified by the Biological Stain Commission

Quality Level

form

powder or chunks

composition

Dye content, 85%

mp

>250 °C (dec.) (lit.)

solubility

95% ethanol: 1 mg/mL, clear to hazy, yellow to very deep yellow

λmax

370 nm
434 nm (2nd)

ε (extinction coefficient)

≥12000 at 249-255 nm in water at 0.005 g/L
≥15000 at 367-373 nm in water at 0.005 g/L
≥36000 at 429-435 nm in water at 0.005 g/L

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

Cl[H].CN(C)c1ccc(cc1)C(=N)c2ccc(cc2)N(C)C

InChI

1S/C17H21N3.ClH/c1-19(2)15-9-5-13(6-10-15)17(18)14-7-11-16(12-8-14)20(3)4;/h5-12,18H,1-4H3;1H

InChI key

KSCQDDRPFHTIRL-UHFFFAOYSA-N

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Application

Auramine O has been used to study the cuticle/cutin in the epidermis of the pollen presenter in Vangueria infausta.

Biochem/physiol Actions

Auramine O is used for the staining of acid-fast organisms, coccidia. Auramine O along with carbol generates brilliant yellow fluorochrome of tubercle bacilli. It is effective in detecting positive cases of tuberculosis. Auramine O binds to the mycolic acid in the bacterial cell wall.

Suitability

Certified for use by fluorescence microscopy in Churukian′s modification of Truant′s fluorescent method for acid fast bacilli on paraffin sections.

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Carc. 2 - Eye Irrit. 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3


Certificates of Analysis (COA)

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Jessica Minion et al.
Journal of clinical microbiology, 49(5), 2024-2026 (2011-03-25)
Light-emitting diode fluorescence microscopy is being scaled up for tuberculosis control, but fading of auramine-stained slides could compromise external quality assurance. We stored auramine-stained slides and reexamined them over time. Slides stored in all environments faded quickly, with significant changes
Ismael A Heisler et al.
The journal of physical chemistry. B, 113(6), 1623-1631 (2009-01-17)
The effects of confinement on the ultrafast torsional reaction of auramine O in aqueous solution are investigated through ultrafast fluorescence up-conversion with 50 fs time resolution. The aqueous solution is confined in nanoscale water droplets by an ionic surfactant. The

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