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Auramine O

August 25, 2023

"Canary yellow" redirects here. For the color, see Yellow. For the bird, see Yellow canary.

Auramine O is a diarylmethane dye used as a fluorescent stain. In its pure form, Auramine O appears as yellow needle crystals. It is insoluble in water and soluble in ethanol and DMSO.

Auramine O
Solid Auramine O
Auramine O in aqueous solution
Names
IUPAC name
bis[4-(dimethylamino)phenyl]methaniminium chloride
Other names
auramine hydrochloride, basic yellow 2, pyocatanium aureum, aizen auramine, pyoktanin yellow, canary yellow, pyoktanin, or C.I. 41000
Identifiers
  • 2465-27-2 Y
3D model (JSmol)
  • Interactive image
  • Interactive image
ChemSpider
  • 16254 Y
ECHA InfoCard 100.017.789
EC Number
  • 219-567-2
  • 17170
UNII
  • DL992L7W39
  • DTXSID9020114
  • 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 Y
    Key: KSCQDDRPFHTIRL-UHFFFAOYSA-N Y
  • InChI=1/C17H21N3/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
    Key: JPIYZTWMUGTEHX-UHFFFAOYAY
  • InChI=1/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
    Key: KSCQDDRPFHTIRL-UHFFFAOYAK
  • [N@H]=C(c1ccc(N(C)C)cc1)c2ccc(N(C)C)cc2
  • Cl.[N@H]=C(c1ccc(N(C)C)cc1)c2ccc(N(C)C)cc2
Properties
C17H22ClN3
Molar mass 303.83 g·mol−1
Melting point 267 °C (513 °F; 540 K)
Hazards
GHS labelling:
Danger
H302, H311, H319, H351, H411
P201, P202, P264, P270, P273, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P312, P322, P330, P337+P313, P361, P363, P391, P405, P501
NFPA 704 (fire diamond)
Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

Auramine O can be used to stain acid-fast bacteria (e.g. Mycobacterium, where it binds to the mycolic acid in its cell wall) in a way similar to Ziehl–Neelsen stain.[1] It can also be used as a fluorescent version of the Schiff reagent.[2]

Auramine O can be used together with Rhodamine B as the Truant auramine-rhodamine stain for Mycobacterium tuberculosis.[3][4] It can be also used as an antiseptic agent.

References Edit

  1. ^ Kommareddi S, Abramowsky C, Swinehart G, Hrabak L (1984). "Nontuberculous mycobacterial infections: comparison of the fluorescent auramine-O and Ziehl–Neelsen techniques in tissue diagnosis". Hum Pathol. 15 (11): 1085–9. doi:10.1016/S0046-8177(84)80253-1. PMID 6208117.
  2. ^ Khavkin T, Kudryavtseva M, Dragunskaya E, et al. (1980). "Fluorescent PAS-reaction study of the epithelium of normal rabbit ileum and after challenge with enterotoxigenic Escherichia coli". Gastroenterology. 78 (4): 782–90. doi:10.1016/0016-5085(80)90684-8. PMID 6986320.
  3. ^ Truant J, Brett W, Thomas W (1962). "Fluorescence microscopy of tubercle bacilli stained with auramine and rhodamine". Henry Ford Hosp Med Bull. 10: 287–96. PMID 13922644.
  4. ^ Arrowood M, Sterling C (1989). "Comparison of conventional staining methods and monoclonal antibody-based methods for Cryptosporidium oocyst detection". J Clin Microbiol. 27 (7): 1490–5. doi:10.1128/JCM.27.7.1490-1495.1989. PMC 267601. PMID 2475523.

External links Edit

  • Auramine O spectra data

August 25, 2023
auramine, canary, yellow, redirects, here, color, yellow, bird, yellow, canary, diarylmethane, used, fluorescent, stain, pure, form, appears, yellow, needle, crystals, insoluble, water, soluble, ethanol, dmso, solid, aqueous, solutionnamesiupac, name, dimethyl. Canary yellow redirects here For the color see Yellow For the bird see Yellow canary Auramine O is a diarylmethane dye used as a fluorescent stain In its pure form Auramine O appears as yellow needle crystals It is insoluble in water and soluble in ethanol and DMSO Auramine O Solid Auramine O Auramine O in aqueous solutionNamesIUPAC name bis 4 dimethylamino phenyl methaniminium chlorideOther names auramine hydrochloride basic yellow 2 pyocatanium aureum aizen auramine pyoktanin yellow canary yellow pyoktanin or C I 41000IdentifiersCAS Number 2465 27 2 Y3D model JSmol Interactive imageInteractive imageChemSpider 16254 YECHA InfoCard 100 017 789EC Number 219 567 2PubChem CID 17170UNII DL992L7W39CompTox Dashboard EPA DTXSID9020114InChI 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 YKey KSCQDDRPFHTIRL UHFFFAOYSA N YInChI 1 C17H21N3 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 4H3Key JPIYZTWMUGTEHX UHFFFAOYAYInChI 1 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 1HKey KSCQDDRPFHTIRL UHFFFAOYAKSMILES N H C c1ccc N C C cc1 c2ccc N C C cc2Cl N H C c1ccc N C C cc1 c2ccc N C C cc2PropertiesChemical formula C 17H 22Cl N 3Molar mass 303 83 g mol 1Melting point 267 C 513 F 540 K HazardsGHS labelling PictogramsSignal word DangerHazard statements H302 H311 H319 H351 H411Precautionary statements P201 P202 P264 P270 P273 P280 P281 P301 P312 P302 P352 P305 P351 P338 P308 P313 P312 P322 P330 P337 P313 P361 P363 P391 P405 P501NFPA 704 fire diamond 310Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Auramine O can be used to stain acid fast bacteria e g Mycobacterium where it binds to the mycolic acid in its cell wall in a way similar to Ziehl Neelsen stain 1 It can also be used as a fluorescent version of the Schiff reagent 2 Auramine O can be used together with Rhodamine B as the Truant auramine rhodamine stain for Mycobacterium tuberculosis 3 4 It can be also used as an antiseptic agent References Edit Kommareddi S Abramowsky C Swinehart G Hrabak L 1984 Nontuberculous mycobacterial infections comparison of the fluorescent auramine O and Ziehl Neelsen techniques in tissue diagnosis Hum Pathol 15 11 1085 9 doi 10 1016 S0046 8177 84 80253 1 PMID 6208117 Khavkin T Kudryavtseva M Dragunskaya E et al 1980 Fluorescent PAS reaction study of the epithelium of normal rabbit ileum and after challenge with enterotoxigenic Escherichia coli Gastroenterology 78 4 782 90 doi 10 1016 0016 5085 80 90684 8 PMID 6986320 Truant J Brett W Thomas W 1962 Fluorescence microscopy of tubercle bacilli stained with auramine and rhodamine Henry Ford Hosp Med Bull 10 287 96 PMID 13922644 Arrowood M Sterling C 1989 Comparison of conventional staining methods and monoclonal antibody based methods for Cryptosporidium oocyst detection J Clin Microbiol 27 7 1490 5 doi 10 1128 JCM 27 7 1490 1495 1989 PMC 267601 PMID 2475523 External links EditAuramine O spectra data Retrieved from https en wikipedia org w index php title Auramine O amp oldid 1081651266, wikipedia, wiki, book, books, library,

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