Grundinformationen
- Standard-SMILES
CCN(CC)c1ccc2c(-c3ccccc3C(=O)O)c3ccc(=[N+](CC)CC)cc-3oc2c1.[Cl-]- InChIKey
PYWVYCXTNDRMGF-UHFFFAOYSA-N- Summenformel
- C28H31N2O3.Cl
- Durchschnittliche Molmasse
- 479 g/mol
Überblick
D&C Red No. 19 can cause cancer according to The Food and Drug Administration (FDA).
Namen und Bezeichner
- Bevorzugter Name
- Rhodamine B
- IUPAC
- [9-(2-carboxyphenyl)-6-(diethylamino)xanthen-3-ylidene]-diethylazanium chloride
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
81-88-9- PubChem CID
- 6694
- DTXSID
DTXSID6042369- ChEMBL
CHEMBL428971、CHEMBL551133- ChEBI
CHEBI:52334- UNII
- K7G5SCF8IL
- EC Number
- 201-383-9
Eigenschaften
Berechnete Struktureigenschaften
- Polarare Oberfläche (TPSA)
- 52,8 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 7
- Schwere Atome
- 34
- Formalladung
- 0
- Komplexität
- 811
Experimentelle und physikochemische Eigenschaften
Color/Form
GREEN CRYSTALS OR REDDISH-VIOLET POWDER; WATER SOLN WITH BLUISH-RED COLOR, DIL SOLN STRONGLY FLUORESCENT
LEAFLETS FROM DILUTE HYDROCHLORIC ACID
Solubility
SOL IN WATER, ALCOHOL & ETHER, BENZENE /BASIC ANHYDROUS FORM/
INSOL IN ORG SOLVENTS /BASIC ANHYDROUS FORM/
SOL IN ... HOT XYLENE /BASIC ANHYDROUS FORM/
VERY SOL IN WATER & ALCOHOL
SLIGHTLY SOL IN HYDROCHLORIC ACID & SODIUM HYDROXIDE
SOL IN BENZENE
Physical Description
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 red-violet powder soluble in water; Dilute solutions are fluorescent. [CAMEO]
Green crystals or reddish-violet powder.
Other Experimental Properties
GREEN LEAFLETS FROM WATER WITH 4 MOL OF WATER OF CRYSTALLIZATION, COLORLESS PRISMS FROM ALCOHOL, XYLENE /BASIC ANHYDROUS FORM/
165 °C (anhydrous)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 0.9% (22 of 2557) of reports.
Danger
H302 (13.6%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P273, P280, P301+P317, P305+P354+P338, P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2557 reports by companies from 31 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
Gefahrenhinweise
Regulatory Information
Chemical: Ethanaminium, N-[9-(2-carboxyphenyl)-6-(diethylamino)-3H-xanthen-3-ylidene]-N-ethyl-, chloride
Hazard Traits - Carcinogenicity
Regulation (EC) No 178/2002 (amended)
Status: Active Update: 25-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26187
Xanthylium, 9-(2-carboxyphenyl)-3,6-bis(diethylamino)-, chloride: Does not have an individual approval but may be used under an appropriate group standard
FIFRA Requirements
Residues of Rhodamine B are exempted from the requirement of a tolerance when used as a dye in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest.
Rhodamine B is exempted from the requirement of a tolerance when used as a dye in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to animals.
Hazard Classes and Categories
Acute Tox. 4 (13.6%)
Acute toxicity (Oral) - Category 4
Sicherheit und Schutzausrüstung
Preventive Measures
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.
Allowable Tolerances
Residues of Rhodamine B are exempted from the requirement of a tolerance when used as a dye in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest.
Rhodamine B is exempted from the requirement of a tolerance when used as a dye in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to animals.
Toxikologische Informationen
TSCA Test Submissions
Male and female Charles River albino rats (60/sex/group) were exposed orally to rhodamine b (D&C red #19) in the diet at 0 and 0.075% for 2 months prior to mating. Following the reproductive phase, a maximum of 2 animals/sex/litter within each group were randomly selected for the long-term study of chronic toxicity and oncogenicity in which 280 rats (70/sex/group) were exposed to rhodamine b at the same dose levels for approximately 29 months. There were significant differences between treated animals and controls in the following: body weights (lower), and mean food consumption (higher). There were significant increases in the mean absolute and/or relative weights of: liver, kidneys and uterus (at 12-month sacrifice and end of experiment), testes (at 12-month sacrifice), and adrenals and thyroids (at end of experiment). A significant increase in thyroid follicular cell adenomas and carcinomas was observed in the treated males. There were no significant differences between treated animals and controls in the following: mortality, ophthalmology or laboratory parameters (including hematology, clinical chemistry and urinalysis).
Male and female Charles River albino rats (60/sex/group) were exposed orally to rhodamine b (D&C red #19) in the diet at 0 and 0.002, 0.005 and 0.02% for 2 months prior to mating. Following the reproductive phase, a maximum of 2 animals/sex/litter within each group were randomly selected for the long-term study of chronic toxicity and oncogenicity in which 700 rats (70/sex/group) were exposed to rhodamine b at the same dose levels for 27 or 29 months (males and females, respectively). There were significant differences between treated animals and controls in the following: body weights (lower for females at 0.002 and 0.02%), mortality (higher in high-dose males), and mean food consumption (higher for females at high-dose at all times). There were significant increases in the mean absolute and/or relative weights of: liver, kidneys, spleen and thyroid, (high-dose females), and adrenals (mid- and high-dose females). There was a slight increase in astrocytomas of the brain and/or spinal cord and granular cell tumors of the brain in the high-dose males. There were no significant differences between treated animals and controls in ophthalmology.
Chronic toxicity and oncogenicity were evaluated in male and female Charles River CD-1 mice (60/sex/group) exposed orally to rhodamine b in the diet at 0, 0.005, 0.02, and 0.10% for approximately 22 and 25 months for the males and females respectively. There was a significant increase in treated animals as compared to controls in the total number of hepatocellular carcinomas in high-dose females. There were no significant differences between treated and control animals in the following: mortality, body weight, food consumption, and hematology.
Human Toxicity Excerpts
... 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.
Carcinogen Classification
Rhodamine B
Group 3: Not classifiable as to its carcinogenicity to humans
Volume 16: (1978) Some Aromatic Amines and Related Nitro Compounds – Hair Dyes, Colouring Agents and Miscellaneous Industrial Chemicals
1987
1987
3, not classifiable as to its carcinogenicity to humans. (L135)
Non-Human Toxicity Excerpts
15 MALE & 15 FEMALE STOCK MICE ... GIVEN 0.05% ... IN DRINKING WATER FOR 52 WK; WEEKLY INTAKE/MOUSE WAS 17 MG, & TOTAL DOSE WAS 884 MG/ANIMAL. ... 2 OF MALE MICE THAT DIED BETWEEN 50 & 69 WK HAD INTESTINAL TUMORS. 1 ... WAS MALIGNANT; 3 MICE HAD POLYPOSIS OF STOMACH, & 7 HAD LYMPHOMAS. /NO CONTROLS WERE USED/
25 MICE OF BOTH SEXES OF MIXED SAITAMA STRAIN, WEIGHING APPROX 20 G, WERE GIVEN TWICE WEEKLY SC INJECTIONS OF 0.1 ML OF 0.5% AQ SOLN ... CONCN ... WAS REDUCED TO 0.25% AFTER 1.5 WK & INCR TO ORIGINAL CONCN AFTER 4 MO; 6 ... ALIVE @ 150 DAYS, & 1 SURVIVED FOR 260 DAYS. ... NONE ... DEVELOPED TUMORS @ SITE OF INJECTION.
21 RATS OF BOTH SEXES OF MIXED SAITAMA STRAIN, WEIGHING APPROX 150 G, WERE FED RICE DIET THAT INITIALLY CONTAINED 0.13% ... INCR TO 0.2% AFTER 7 MO. 18 RATS WERE ALIVE @ 300 DAYS, & 1 SURVIVED FOR 661 DAYS. NONE ... DEVELOPED TUMORS.
... 120 MALE & 180 FEMALE MICE ... GIVEN 0.1 ML OF 0.5% SOLN 2 OR 3 TIMES/WK FOR 4 WK ... INCR TO 0.7% FOR 1 MO & THEN REDUCED TO ORIGINAL CONCN. AFTER 6 MO ... CONCN ... WAS GRADUALLY DECR. SUBSEQUENTLY, INJECTIONS WERE DISCONTINUED FOR 2 MO. ... NONE OF MICE ... DEVELOPED TUMORS @ SITE OF INJECTION.
For more Non-Human Toxicity Excerpts (Complete) data for RHODAMINE B (15 total), please visit the HSDB record page.
Probable Routes of Human Exposure
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/
Antidote and Emergency Treatment
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/
Regulatorische Informationen
FIFRA Requirements
Residues of Rhodamine B are exempted from the requirement of a tolerance when used as a dye in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest.
Rhodamine B is exempted from the requirement of a tolerance when used as a dye in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to animals.
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological Classification
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.
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)
Absorption, Distribution and Excretion
... 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.
Verwendung und Herstellung
Uses
Used as a paper dye, a metal chelating agent, and an additive to drugs and cosmetics; [CAMEO] Rhodamine dyes (aminoxanthenes) are xanthene dyes that are very important commercially. They are brilliant, blue-red, fluorescent dyes used as colorants in inks, paper, and plastics. Sulfonated derivatives are used as wool and polyamide dyes. Red fluorescent pigments are produced from Rhodamine dyes, and some of these are used as laser dyes. Rhodamine B is used to make pink fluorescent pigments. [Ullmann]
Pulp and Paper Processing [Category: Industry]
AS DYE, ESP FOR PAPER; AS REAGENT FOR ANTIMONY, BISMUTH, COBALT, NIOBIUM, GOLD, MANGANESE, MERCURY, MOLYBDENUM, TANTALUM, THALLIUM, TUNGSTEN; AS BIOLOGICAL STAIN.
RED DYE FOR WOOL & SILK WHERE BRILLIANT FLUORESCENT EFFECTS ARE DESIRED.
Colorant for plastics.
Methods of 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.
Use Classification
Food Additives -> COLOUR -> JECFA Functional Classes
Food Additives -> COLOUR -> JECFA Functional Classes
Food Additives -> COLOUR -> JECFA Functional Classes
General Manufacturing Information
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.
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