Rhodamine B

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Rhodamine B
File:Rhodamine B.svg
File:Rhodamine B powder.jpg
Names
Preferred IUPAC name
9-(2-Carboxyphenyl)-6-(diethylamino)-N,N-diethyl-3H-xanthen-3-iminium chloride
Other names
Rhodamine 610, C.I. Pigment Violet 1, Basic Violet 10, C.I. 45170
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
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KEGG
UNII
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  • InChI=1S/C28H30N2O3.ClH/c1-5-29(6-2)19-13-15-23-25(17-19)33-26-18-20(30(7-3)8-4)14-16-24(26)27(23)21-11-9-10-12-22(21)28(31)32;/h9-18H,5-8H2,1-4H3;1H checkY
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Properties
C28H31ClN2O3
Molar mass 479.02
Appearance Green powder[1]
Melting point 210 to 211 °C (410 to 412 °F; 483 to 484 K) (Decomposes)
8 to 15 g/L (20 °C)[2][nt 1]
Hazards
Safety data sheet (SDS) 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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Rhodamine B /ˈroʊdəmiːn/ 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 fluorometers.

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 dyes are also used extensively in biotechnology applications such as fluorescence microscopy, flow cytometry, fluorescence correlation spectroscopy and ELISA.[citation needed]

Other uses

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Rhodamine B solution in water

Rhodamine B is often mixed with herbicides to show where they have been used.[3]

It is also 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.[4] Rhodamine B is an important hydrophilic xanthene dye well known for its stability and is widely used in the textile industry, leather, paper printing, paint, coloured glass and plastic industries.[5]

Rhodamine B (BV10) is mixed with quinacridone magenta (PR122) to make the bright pink watercolor known as Opera Rose.[6]

Properties

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A is the "open" form and B is the "closed" form
Rhodamine B closed form (A) and open form (B)

Rhodamine B can exist in equilibrium between two forms: an "open"/fluorescent form and a "closed"/nonfluorescent spirolactone form. The "open" form dominates in acidic condition while the "closed" form is colorless in basic condition.[7]

A small amount of aqueous Rhodamine B in a 250 mL bottle

The fluorescence intensity of rhodamine B will decrease as temperature increases.[8]

The solubility of rhodamine B in water varies by manufacturer, and has been reported as 8 g/L and ~15 g/L,[2] while solubility in alcohol (presumably ethanol) has been reported as 15 g/L.[nt 1] Chlorinated tap water decomposes rhodamine B. Rhodamine B solutions adsorb to plastics and should be kept in glass.[9] Rhodamine B is tunable around 610 nm when used as a laser dye.[10] Its luminescence quantum yield is 0.65 in basic ethanol,[11] 0.49 in ethanol,[12] 1.0,[13] and 0.68 in 94% ethanol.[14] The fluorescence yield is temperature dependent;[15] the compound is fluxional in that its excitability is in thermal equilibrium at room temperature.[16]


Safety and health

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In California, rhodamine B is suspected to be carcinogenic and thus products containing it must contain a warning on its label.[17] 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.[18]

See also

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References

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Notes

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  1. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). Note that most sources simply indicate that the compound is water soluble without providing a g/L value.
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