Rhodamine B
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Rhodamine B
structure -
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CAS No:
81-88-9
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Formula:
C28H31N2O3.Cl
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Chemical Name:
Rhodamine B
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Synonyms:
Xanthylium,9-(2-carboxyphenyl)-3,6-bis(diethylamino)-,chloride (1:1);[9-(o-Carboxyphenyl)-6-(diethylamino)-3H-xanthen-3-ylidene]diethylammonium chloride;Ammonium,[9-(o-carboxyphenyl)-6-(diethylamino)-3H-xanthen-3-ylidene]diethyl-,chloride;Xanthylium,9-(2-carboxyphenyl)-3,6-bis(diethylamino)-,chloride;11411 Red;C.I. 45170;ADC Rhodamine B;Aizen Rhodamine BH;Akiriku Rhodamine B;Calcozine Red BX;Calcozine Rhodamine BXP;Cerise Toner X 1127;Diabasic Rhodamine B;Edicol Supra Rose B;Eriosin Rhodamine B;Hexacol Rhodamine B Extra;Ikada Rhodamine B;Mitsui Rhodamine BX;Rheonine B;Rhodamine,tetraethyl-;Rhodamine B;Rhodamine BA;Rhodamine BA Export;Rhodamine BN;Rhodamine BS;Rhodamine BX;Rhodamine BXL;Rhodamine BXP;Rhodamine B Extra S;Rhodamine B Extra M 310;Rhodamine FB;Rhodamine Lake Red B;Sicilian Cerise Toner A 7127;Symulex Magenta F;Symulex Rhodamine B Toner F;Takaoka Rhodamine B;Tetraethylrhodamine;C.I. Food Red 15;Aizen Rhodamine BHC;Edicol Supra Rose BS;Rhodamine B Extra;D and C Red No. 19;C.I. Basic Violet 10;FD And C Red No. 19;Rhodamine B 500 hydrochloride;Basic Violet 10;Red No. 213;Rhodamine B 500;Rhodamine S (Russian);Rhodamine S;Rhodamine O;Japan Red 213;Japan Red No. 213;Flexo Red 540;Basonyl Red 540;D&C Red No. 19;Basonyl Red 545;Basazol Red 71P;Aizen Rhodamine B;Rhodamine 610 chloride;Sumiplast Pink B;Brilliant Pink B;OP 312;Basic Rose Red;D&C Red 19;Basic Rose Extract;3521-79-7;11111-29-8;17181-58-7;53664-59-8;69319-23-9;86513-49-7;86893-15-4;96119-80-1;105480-59-9;248928-56-5;408346-58-7;412909-17-2;433215-26-0;539821-35-7;850856-47-2;859039-47-7;875572-56-8;918962-66-0;925914-34-7;956491-27-3;1023342-65-5;1051370-49-0;1236042-79-7;1394971-11-9;1773488-62-2;1825993-87-0;2254248-91-2
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CAS No:
Description
Rhodamine B is a staining fluorescent dye, commonly used for dyeing textiles, paper, soap, leather, and drugs.
C.i. food red 15 appears as green crystals or reddish-violet powder. Used as a dye, especially for paper, as a metal chelating reagent, and in drugs and cosmetics.|Green crystals or reddish-violet powder.
C.i. food red 15 appears as green crystals or reddish-violet powder. Used as a dye, especially for paper, as a metal chelating reagent, and in drugs and cosmetics.|Rhodamine B is an organic chloride salt having N-[9-(2-carboxyphenyl)-6-(diethylamino)-3H-xanthen-3-ylidene]-N-ethylethanaminium as the counterion. An amphoteric dye commonly used as a fluorochrome. It has a role as a fluorochrome, a fluorescent probe and a histological dye. It is an organic chloride salt and a xanthene dye. It contains a rhodamine B(1+).
Rhodamine B Basic Attributes
479.01000
478.20200
201-383-9
K7G5SCF8IL
41837|10475
DTXSID6042369
GREEN CRYSTALS OR REDDISH-VIOLET POWDER; WATER SOLN WITH BLUISH-RED COLOR, DIL SOLN STRONGLY FLUORESCENT|LEAFLETS FROM DILUTE HYDROCHLORIC ACID
32041300
Characteristics
56.69000
2.56500
C.i. food red 15 appears as green crystals or reddish-violet powder. Used as a dye, especially for paper, as a metal chelating reagent, and in drugs and cosmetics.
1.31
165 °C
12ºC
H2O: soluble ;SOL IN BENZENE
Store at RT.
LD50 i.v. in rats: 89.5 mg/kg (Webb)
GREEN LEAFLETS FROM WATER WITH 4 MOL OF WATER OF CRYSTALLIZATION, COLORLESS PRISMS FROM ALCOHOL, XYLENE /BASIC ANHYDROUS FORM/|165 °C (anhydrous)
Very soluble in water. Solution is bluish-red. Dilute solutions are strongly fluorescent.
Acids, Carboxylic
C.I. FOOD RED 15 is a quaternary ammonium salt and contains conjugated carbon-carbon double bonds. Many compounds with extended conjugated double bond systems are highly colored and used as dyes. Quaternary ammonium salts often serve as catalysts in reactions. They are incompatible with many strong oxidizers and reducing agents, such as metal hydrides, alkali/active metals, and organometallics.
Safety Information
UN 1219 3/PG 2
2
R22; R41; R68
S26-S36/37/39
BP3675000
Xn
Stable. Incompatible with strong oxidizing agents.
P273-P280-P305 + P351 + P338
H302-H318-H412
|Danger|H302 (11.76%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P305+P351+P338, P310, P330, and P501|Aggregated GHS information provided by 2538 companies from 31 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P301+P312, P304+P340, P312, P330, P403+P233, P405, and P501
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
... INJURIOUS TO ... HUMAN EYE.
Toxicity
1.70
Most organic azo dyes are potential skin sensitizers, the most important of which are paraphenylenediamine and its analogues. Water soluble azo dyes are more likely to cause clinical sensitization than insoluble dyes. Beauticians exposed to paraphenylenediamine derivatives in hair dyes, workers dyeing textile resins, and photographic film developers exposed to color developing solutions not infrequently become sensitized to azo dyes. In addition to allergic eczematous contact dermatitis, color developing solutions have caused lichen planus like eruptions. /Organic dyes/|Some important causes of occupational phototoxic or photoallergic reactions /are rhodamine dyes/. /Rhodamine dyes/
Drug Information
Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags. (See all compounds classified as Fluorescent Dyes.)
... WAS METABOLIZED SIMILARLY IN DOGS, RATS & RABBITS, AS EVIDENCED BY CHROMATOGRAPHIC ANALYSIS OF THEIR URINE & FECAL EXTRACTS. CMPD WAS EXTENSIVELY ABSORBED FROM GI TRACT: OF 1% GIVEN IN DIET, ONLY 3-5% WAS RECOVERED UNCHANGED IN URINE & FECES.|RHODAMINE B EXHIBITS HIGH PLASMA PROTEIN BINDING.|INTENSITY OF DYE COLOR IN PANCREATIC JUICE OF DOGS DECR IN ORDER: BASIC FUCHSINE, ACRIDINE RED, NEW FUCHSINE, RHODAMINE B, PHENOL RED, RHODAMINE 6G.|The adsorption equilibrium (as determined by Langmuir's or Freundlich's equations) of microbial suspensions containing Rhodamine B, and melting temperature of Rhodamine B-calf thymus DNA solution were determined. The adsorption constant of dye to cells for Rhodamine B was 6.86 cal/mol (adsorptive affinity in Langmuir's equation) and 2.86 (for the constant K in Freundlich's equation). Melting temperature values for Rhodamine B calf thymus DNA solution increased with dye concentration.
... DE-ETHYLATED ENZYMATICALLY; 2 OF 3 OBSERVED METABOLITES WERE IDENTIFIED AS N,N'-DIETHYL-3,6-DIAMINOFLUORAN & 3,6-DIAMINOFLUORAN.
In treatment of eyes contaminated with cationic dyes, first aid measures are aimed at getting rid of dye which has not reacted with the tissues. This includes copious irrigation, mechanical removal of particles, and in the case of imbedded colored pencil may necessitate surgical exploration and careful removal of the particles. Solutions of tannin or tannic acid precipitate cationic dyes and render them essentially noninjurious, but this disposes of only that portion of the dye which has not already reacted with the tissues. /It was/ determined experimentally that a 5% to 10% solution of tannin was effective essentially in a prophylactic sense if applied within three minutes following application of powdered basic dyes to the eyes of rabbits, but that the effectiveness of this treatment rapidly diminished after three minutes. Other forms of chemical treatment have been aimed at removing both combined and excess dye. However, studies of the reaction of cationic dyes with cornea in vitro have shown these dyes to bind very tenaciously and to be very difficult to remove from combination with the tissue. ... /Cationic dyes/
... INJURIOUS TO ... HUMAN EYE.|Some important causes of occupational phototoxic or photoallergic reactions /are rhodamine dyes/. /Rhodamine dyes/|This communication reports of two cases of digital clubbing in a factory manufacturing matches in Vitilevu, Fiji Islands. Both these cases were occupationally exposed to chemicals used in the manufacture of matches. They had physical contact with these chemicals including rhodamine B dye. Subjects who worked in the same factory area, including one worker who had FEV1.0 and FVC values below the predicted normal, but who did not handle chemicals showed no evidence of finger clubbing.|The effects of acute exposure to rhodamine-B were described in 17 patients who were exposed to the aerosolized dye in a maintenance shop. Approximately 10 pounds of rhodamine-B powder was spilled onto the floor of a vehicle maintenance shop; the aerosol resulted from the sweeping of the powder during cleanup. The mean duration of exposure to the dispersed dust was 26 minutes. Sixteen of the patients complained of acute symptoms including: burning of the eyes, excessive tearing of the eyes, nasal burning, nasal itching, chest pain and/or tightness, rhinorrhea, cough, dyspnea, burning of the throat, burning pruritic skin, chest burning, headache, and nausea. Chest x-rays demonstrated no acute pulmonary pathology. All of the patients had resolution of their symptoms within 24 hours of exposure, with 63 percent reporting resolution within 4 hours. Acute exposure to rhodamine-B may result in transient mucous membrane and skin irritation without evidence of serious sequelae.|For more Human Toxicity Excerpts (Complete) data for RHODAMINE B (7 total), please visit the HSDB record page.
rhodamine B
Rhodamine B Use and Manufacturing
... IS PRODUCED COMMERCIALLY BY CONDENSING N,N-DIETHYL-3-AMINOPHENOL WITH PHTHALIC ANHYDRIDE, FOLLOWED BY TREATMENT WITH DILUTE HYDROCHLORIC ACID.|Reaction of diethylamine with fluorescin dichloride (3,6-dichlorofluoran) under pressure.
This product is used for dyeing paper, acrylic, silk, leather, feathers, and can be used for food and certain metal analysis reagents. It can be used as an adsorption indicator and biological dyeing agent. It can be used for dyeing paper, paint, acrylic and wood products. the study
Xanthylium, 9-(2-carboxyphenyl)-3,6-bis(diethylamino)-, chloride (1:1): ACTIVE|... CERTIFIED FOR USE AS COLOR ADDITIVE IN DRUGS & COSMETICS IN USA BY USA FOOD & DRUG ADMIN, CONTAINS @ LEAST 92.0% PURE DYE ... & NOT MORE THAN: 5.0% VOLATILE MATTER, 2.0% SODIUM CHLORIDE & SODIUM SULFATE, 1.0% MIXED OXIDES, 1.0% WATER INSOL MATTER, 0.5% ETHER EXTRACTS, 0.2% DIETHYL-3-AMINOPHENOL ... .|/FOR USE AS COLOR ADDITIVE IN DRUGS & COSMETICS IN USA CONTAINS NOT MORE THAN:/ ... 30 MG/KG HEAVY METALS OTHER THAN LEAD & ARSENIC, 20 MG/KG LEAD & 2 MG/KG ARSENIC.|... MUST MEET PRODUCT SPECIFICATIONS AS PROMULGATED BY LAW. ITS USE IN DRUG PRODUCTS FOR INTERNAL USE & IN MOUTHWASHES, DENTIFRICES & PROPRIETARY PRODUCTS IS LIMITED TO MAX TOLERANCE LEVEL OF 0.75 MG IN AMT OF PRODUCT REASONABLY EXPECTED TO BE INGESTED IN ONE DAY.|IN LIPSTICKS, MAX AMT OF ALL COLORS USED, INCL RHODAMINE B, IS LIMITED TO MAX OF 6% PURE DYE BY WT OF EACH LIPSTICK. IT MAY BE USED WITHOUT TOLERANCE LEVELS IN OTHER EXTERNALLY APPLIED COSMETICS & DRUGS.|For more General Manufacturing Information (Complete) data for RHODAMINE B (7 total), please visit the HSDB record page.
RHODAMINE B WAS ISOLATED FROM SHAMPOOS & IDENTIFIED BY 2-DIMENSIONAL THIN-LAYER CHROMATOGRAPHY & COLUMN CHROMATOGRAPHY ON MICROCRYST CELLULOSE.|Thin-layer chromatography has been used to separate and identify rhodamine B as follows: (1) in the presence of other water soluble fluorescent compounds on silica gel and unmodified cellulose layers with two solvent systems, (2) in the presence of other low polarity dyes using a zigzag development path on silica gel plate, and (3) in the presence of other red food dyes on a polyamide silica gel mixed layer using five solvent systems, with a detection limit of approximately 2 ug. Thin-layer chromatography has also been used to separate rhodamine B and other dyes as part of a method of analysis in which the separated dyes have been: (1) identified by their nuclear magnetic resonance or visible spectra, (2) identified by their absorption or fluorescence spectra and determined fluorimetrically, and (3) identified by color under ultraviolet or ordinary light and determined with a spectrodensitometer.|Paper chromatography has been used to separate and identify basic dyes, including rhodamine B, using two solvent systems.|A simple HPLC method is described for the detn of Rhodamine B, Erio Acid Red and Automate Red B dyes which are used as tracers in forestry spray formulations. The dye soln were analyzed at 30 deg by reversed phase chromatography on an HP:RP-8, 10 um MOS Hypersil column using a mobile phase of MeOH-H2O at a flow rate of 1.0 ml/min with UV detection. Responses were linear for 0.1-10 ug/ml Rhodamine B and Erio Acid Red, whereas the range was 1.0-10 ug/ml for Automate Red B. The limits of detection were 0.1 ug/ml for Rhodamine B and Erio Acid Red, and 1 ug/ml for Automate Red B. The method was successfully used to quantify Rhodamine B and Erio Acid Red present in two aq formulations of fenitrothion insecticide. However, interference peaks were observed with the oil-based formulation and prevented the quantification of Automate Red B present.
Food Additives -> COLOUR; -> JECFA Functional Classes
Food Additives -> COLOUR;
Computed Properties
Molecular Weight:479.0
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:7
Exact Mass:478.2023205
Monoisotopic Mass:478.2023205
Topological Polar Surface Area:52.8
Heavy Atom Count:34
Complexity:811
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes
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