Rhodamine B

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Rhodamine B
Rhodamine B.svg
Names
IUPAC name
[9-(2-carboxyphenyl)-6-diethylamino-3-xanthenylidene]-diethylammonium chloride
Other names
Rhodamine 610, C.I. Pigment Violet 1, Basic Violet 10, C.I. 45170
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.259
KEGG
Properties
C28H31ClN2O3
Molar mass 479.02
Appearance red to violet powder
Melting point 210 to 211 °C (410 to 412 °F; 483 to 484 K) (Decomposes)
~15 g/L (20 °C) [1]
Hazards
Safety data sheet MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Rhodamine B /ˈrdəmn/ is a chemical compound and a dye. It is often used as a tracer dye within water to determine the rate and direction of flow and transport. Rhodamine dyes fluoresce and can thus be detected easily and inexpensively with instruments called fluorometers. Rhodamine dyes are used extensively in biotechnology applications such as fluorescence microscopy, flow cytometry, fluorescence correlation spectroscopy and ELISA.

Rhodamine B is used in biology as a staining fluorescent dye, sometimes in combination with auramine O, as the auramine-rhodamine stain to demonstrate acid-fast organisms, notably Mycobacterium.

Rhodamine B is tunable around 610 nm when used as a laser dye.[2] Its luminescence quantum yield is 0.65 in basic ethanol,[3] 0.49 in ethanol,[4] 1.0,[5] and 0.68 in 94% ethanol.[6] The fluorescence yield is temperature dependent.[7]

Solubility[edit]

Rhodamine B solution in water

The solubility of rhodamine B in water is ~15 g/L.[8] However, the solubility in acetic acid solution (30 vol.%) is ~400 g/L. Chlorinated tap water decomposes rhodamine B. Rhodamine B solutions adsorb to plastics and should be kept in glass.[9]

Synthesis[edit]

Rhodamine B synthesis

Other uses[edit]

Rhodamine B is being tested for use as a biomarker in oral rabies vaccines for wildlife, such as raccoons, to identify animals that have eaten a vaccine bait. The rhodamine is incorporated into the animal's whiskers and teeth.[10]

It is also often mixed with herbicides to show where they have been used.

Rhodamine B (BV10) is mixed with Quinacridone Magenta (PR122) to make the bright pink watercolor known as Opera Rose.[11]

Safety and health[edit]

In California, rhodamine B is suspected to be carcinogenic and thus products containing it must contain a warning on its label.[12] Cases of economically motivated adulteration, where it has been illegally used to impart a red color to chili powder, have come to the attention of food safety regulators.[citation needed]

References[edit]

  1. ^ Sicherheitsdatenblatt Rhodamin B by Roth, 2013
  2. ^ Rhodamine B
  3. ^ Kubin, R (1983). "Fluorescence quantum yields of some rhodamine dyes". Journal of Luminescence. 27 (4): 455–462. doi:10.1016/0022-2313(82)90045-X. 
  4. ^ Casey, Kelly G.; Quitevis, Edward L. (1988). "Effect of solvent polarity on nonradiative processes in xanthene dyes: Rhodamine B in normal alcohols". The Journal of Physical Chemistry. 92 (23): 6590–6594. doi:10.1021/j100334a023. 
  5. ^ Kellogg, R. E.; Bennett, R. G. (1964). "Radiationless Intermolecular Energy Transfer. III. Determination of Phosphorescence Efficiencies". The Journal of Chemical Physics. 41 (10): 3042. doi:10.1063/1.1725672. 
  6. ^ Snare, M (1982). "The photophysics of rhodamine B". Journal of Photochemistry. 18 (4): 335–346. doi:10.1016/0047-2670(82)87023-8. 
  7. ^ Karstens, T.; Kobs, K. (1980). "Rhodamine B and rhodamine 101 as reference substances for fluorescence quantum yield measurements". The Journal of Physical Chemistry. 84 (14): 1871–1872. doi:10.1021/j100451a030. 
  8. ^ Sicherheitsdatenblatt Rhodamin B by Roth, 2013
  9. ^ Detection and prevention of leaks from dams By Antonio Plata Bedmar and Luís Araguás Araguás, Taylor & Francis, 2002, ISBN 90-5809-355-7
  10. ^ Slate, Dennis; Algeo, Timothy P.; Nelson, Kathleen M.; Chipman, Richard B.; Donovan, Dennis; Blanton, Jesse D.; Niezgoda, Michael; Rupprecht, Charles E. (2009). Bethony, Jeffrey M., ed. "Oral Rabies Vaccination in North America: Opportunities, Complexities, and Challenges". PLoS Neglected Tropical Diseases. 3 (12): e549. PMC 2791170Freely accessible. PMID 20027214. doi:10.1371/journal.pntd.0000549. 
  11. ^ http://www.handprint.com/HP/WCL/waterc.html
  12. ^ Naval Jelly msds with Rhodamine B

See also[edit]