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Rhodamine 6G

Rhodamine 6G structure

Rhodamine 6G 

structure
  • CAS No:

    989-38-8

  • Formula:

    C28H31N2O3.Cl

  • Chemical Name:

    Rhodamine 6G

  • Synonyms:

    Xanthylium,9-[2-(ethoxycarbonyl)phenyl]-3,6-bis(ethylamino)-2,7-dimethyl-,chloride (1:1);Rhodamine 6GCP;Benzoic acid,o-[6-(ethylamino)-3-(ethylimino)-2,7-dimethyl-3H-xanthen-9-yl]-,ethyl ester,monohydrochloride;Xanthylium,9-[2-(ethoxycarbonyl)phenyl]-3,6-bis(ethylamino)-2,7-dimethyl-,chloride;C.I. 45160;Calcozine Red 6G;Calcozine Rhodamine 6GX;Eljon Pink Toner;C.I. Basic Red 1;Fanal Pink GFK;Fanal Red 25532;Heliostable Brilliant Pink B extra;Mitsui Rhodamine 6GCP;Nyco Liquid Red GF;Rhodamine F 5G;Rhodamine Y 20-7425;Rhodamine 4GD;Rhodamine 4GH;Rhodamine 5GDN;Rhodamine 5GL;Rhodamine 6GB;Rhodamine 6GBN;Rhodamine 6GDN;Rhodamine 6GH;Rhodamine 6G Extra;Rhodamine 6GDN Extra;Rhodamine 6G Extra Base;Rhodamine 6GX;Rhodamine 6JH;Silosuper Pink B;Rhodamine 6G;Rhodamine Zh;Rhodamine 6GEx ethyl ester;Rhodamin 6G;Rhodamine GDN;Rhodamine 6GD;Rhodamine 6Zh-DN;Aizen Rhodamine 6GCP;Rhodamine 6GO;Rhodamine F 5GL;Fanal Pink B;Rhodamine 6G chloride;Vali Fast Red 1308;Flexo Red 482;Rhodamine 6JH-SA Extra 1150;Rhodamine 5GDN Extra;Rhodamine GDN Extra;Basonyl Red 483;Basonyl Red 482;Basic Red 1;Rh 6G;R 6G;Rhodamine 6JH-SA;NSC 36345;Exciton 590;R 634;6-Carboxyrhodamine;6GDN;23479-08-5;37317-74-1;66796-55-2;79818-96-5;82853-32-5;88491-15-0;102395-11-9;126371-14-0;136590-25-5;160336-35-6;162887-53-8;201799-71-5;226555-16-4;232598-90-2;539820-31-0;1021498-98-5;1173373-14-2;1228661-69-5;1239677-99-6

  • Categories:

    Cosmetic Ingredient  >  Hair Dyeing

Description

Rhodamine 6G is a rhodamine analog useful in Pgp efflux assays. It can be used in characterizing the kinetics of MRP1- mediated efflux, and as a laser dye and potential mitochondrial probe.


C.i. basic red 1 appears as bright bluish-pink crystals or reddish purple powder. (NTP, 1992)


C.i. basic red 1 appears as bright bluish-pink crystals or reddish purple powder. (NTP, 1992)|Rhodamine 6G is a rhodamine 6G(1+), an organic chloride salt and a xanthene dye. It has a role as a fluorochrome.

Rhodamine 6G Basic Attributes

479.01

478.202332

213-584-9

037VRW83CF

DTXSID1021243

2922199090

Characteristics

63.83000

7.22550

Red-brown to brown Powder

1.15g/cm3

290 °C

<200ºC

318.6ºC

1.593

H2O: soluble 1mg/mL, dark red

Store at +15°C to +30°C.

CATIONIC

Insoluble in water.

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

Safety Information

NONH for all modes of transport

3

22-36/37/38

36/37/39-26-36-24/25

DH0175000

Xn,Xi

Stable. Incompatible with strong oxidizing agents.

H302

Bottled water shall, when a composite of analytical units of equal volume from a sample is examined by the methods described in paragraph (d)(1)(ii) of this section, meet the standards of chemical quality and shall not contain chloride in excess of 250.0 mg/l. /Chloride/

DHHS/NTP; Toxicology and Carcinogenesis Studies of Rhodamine 6G (CI Basic Red 1) in F344/N Rats and B6C3F1 Mice (Feed Studies) 1989) Technical Rpt Series No.364 NIH Pub No.89-2819

Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)

|Danger|H301 (52.37%): Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P273, P280, P301+P310, P301+P312, P305+P351+P338, P310, P321, P330, P391, P405, and P501|Aggregated GHS information provided by 1308 companies from 26 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this compound can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicity

Toxicology and carcinogenesis studies of rhodamine 6G were conducted ... by administering rhodamine 6G (greater than 95% pure) in feed to groups of F344/N rats and B6C3F1 mice of each sex for 2 years. Dietary concentrations selected for the 2 year studies were 0, 120, or 250 ppm rhodamine 6G for rats, 0, 1,000, or 2,000 ppm for male mice, and 0, 500, or 1,000 ppm for female mice. Under the conditions of these 2 year feed studies, there was equivocal evidence of carcinogenic activity for male F344/N rats administered rhodamine 6G, as indicated by a marginally increased incidence of integumentary keratoacanthomas. There was equivocal evidence of carcinogenic activity for female F344/N rats administered rhodamine 6G, as indicated by a marginal increase in pheochromocytomas or malignant pheochromocytomas (combined) of the adrenal gland. There was no evidence of carcinogenic activity for male B6C3F1 mice administered, 1,000 or 2,000 ppm rhodamine 6G in the diet. There was no evidence of carcinogenic activity for female B6C3D1 mice adminsitered 500 or 1,000 ppm rhodamine 6G in the diet. There were no significant nonneoplastic lesions attributed to rhodamine 6G administration to male or female rats or male or female mice. Male and female rats might have been able to tolerate a higher concentration of rhodamine 6G in the feed.

Some important causes of occupational phototoxic or photoallergic reactions /are rhodamine dyes/. /Rhodaminedyes/

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.)|Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

RHODAMINE 6G EXHIBITS HIGH PLASMA PROTEIN BINDING.|Rhodamine 6G and rhodamine B were reported to be excreted in the pancreatic juice in situ after intravenous infusion of 1 mg dye per minute to dogs (strain, age, and sex not specified) followed by the administration of secretin or cholecystokinin-pancreozymin stimulation. The rate of excretion was not reported.

ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits very toxic fumes. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

In treatment of eyes contaminated with cationic dyes, first aid measures are aimed at getting rid of dye which has not yet 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/

Some important causes of occupational phototoxic or photoallergic reactions /are rhodamine dyes/. /Rhodamine dyes/|Two variants have been isolated from the cultured human cell line VA2-B which are resistant in vivo to the mitochondrial specific fluorescent dyes rhodamine 6G and rhodamine 123. Both mutants are cross-resistant to ethidium bromide but are sensitive to both colchicine and chloramphenicol. When either mutant is treated with low levels of rhodamine 6G, mitochondrial associated fluorescence is significantly lower than in wild type cells. Furthermore, when cell cultures are treated with high concentrations of either rhodamine 123 or 6G, and then washed free of the dye, mitochondrial associated rhodamine fluorescence rapidly diminishes in the parental cell line. In hybrid cell fusions between resistant and sensitive cell lines, rhodamine resistance is gradually expressed, reaching maximal expression approximately 11 days after fusion. Cytoplasmic transmission of rhodamine resistance has not been clearly demonstrated in cytoplast-cell fusions, and thus resistance is probably due to a mutation of a nuclear, rather than mitochondrial DNA gene(s). These observations indicate that mitochondria of both rhodamine resistant variants, unlike wild type, have a significantly decreased ability to bind and retain rhodamine, and thus their mitochondrial tramsmembrane electrical potential may be significantly reduced.

basic red 1

Rhodamine 6G Use and Manufacturing

Methods of Manufacturing

Using 3-ethylamino-p-cresol (3-ethylamino) and phthalic anhydride as raw materials, first condense the two, and then esterify with ethanol to obtain the product.

Uses

Using generated ion associations, fluorescence and photometric determination of metal ions; adsorption indicator; biological stain.

Production

(1977) PROBABLY GREATER THAN 6.81X10+6 G|(1979) PROBABLY GREATER THAN 4.54X10+6 G

ESSENTIALLY 100% AS A DYE

Xanthylium, 9-[2-(ethoxycarbonyl)phenyl]-3,6-bis(ethylamino)-2,7-dimethyl-, chloride (1:1): ACTIVE|IN WESTERN EUROPE ... MAY PROVISIONALLY BE USED IN COSMETICS WHICH MAY COME INTO CONTACT WITH MUCOUS MEMBRANES. IN JAPAN, RHODAMINE 6G IS USED AS DYE.

Dyes used in lipsticks, including rhodamine 6G, have been separated by thin-layer chromatography and identified by their absorption and fluorescene spectra or determined fluorimetrically. Thin layer chromatography on unactivated, precoated silica, using one solvent system, has been used to separate biological stains, including rhodamine 6G. The separated dyes were then identified by their nuclear magnetic resonance or visible spectra. Also gel permeation chromatography on Sephadex LH-20 resin has been used to separate and identify biological stains, including rhodamine 6G.|ANALYTICAL SEPARATION OF ROSE BENGAL (I) WAS CARRIED OUT BY HIGH PERFORMANCE LIQ CHROMATOGRAPHY. PREPARATIVE SEPN OF ROSE BENGAL WAS CARRIED OUT WITH PREPAK-500/C18 REVERSE PHASE COLUMN. SIMILARLY RHODAMINE 6G WAS SEPARATED.

Computed Properties

Molecular Weight:479.0
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:7
Exact Mass:478.2023205
Monoisotopic Mass:478.2023205
Topological Polar Surface Area:61.5
Heavy Atom Count:34
Complexity:823
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

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