Acid Green
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Acid Green
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CAS No:
4680-78-8
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Formula:
C37H36N2O6S2.Na
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Chemical Name:
Acid Green
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Synonyms:
Benzenemethanaminium,N-ethyl-N-[4-[[4-[ethyl[(3-sulfophenyl)methyl]amino]phenyl]phenylmethylene]-2,5-cyclohexadien-1-ylidene]-3-sulfo-,inner salt,sodium salt (1:1);C.I. Acid Green 3;C.I. Acid Green 3,sodium salt;Benzenemethanaminium,N-ethyl-N-[4-[[4-[ethyl[(3-sulfophenyl)methyl]amino]phenyl]phenylmethylene]-2,5-cyclohexadien-1-ylidene]-3-sulfo-,hydroxide,inner salt,sodium salt;Benzenemethanaminium,N-ethyl-N-[4-[[4-[ethyl[(3-sulfophenyl)methyl]amino]phenyl]phenylmethylene]-2,5-cyclohexadien-1-ylidene]-3-sulfo-,inner salt,sodium salt;C.I. 42085;Acidal Green G;Acid Green B;Acid Green S;Acid Green 2G;Acid Leather Green F;Acid Leather Green 3G;Acilan Green B;Amacid Green B;Brilliant Green 3EMBL;Bucacid Guinea Green BA;Calcocid Green G;C.I. Food Green 1;4-[4-(N-Ethyl-p-sulfobenzylamino)diphenylmethylene]-[1-(N-ethyl-N-p-sulfoniumbenzyl)-Δ2,5-cyclohexadienimine] monosodium salt;FD and C Green No. 1;Fenazo Green L;A.F. Green No. 1;Guinea Green B;Guinea Green BA;Hidacid Emerald Green;Hispacid Green GB;Kiton Green F;Kiton Green FC;Leather Green B;Merantine Green G;Naphthalene Green G;Naphthalene Lake Green G;Naphthalene Leather Green G;Neran Brilliant Green G;Pontacyl Green BL;Sulpho Green 2B;Vondacid Green L;Guinea green;Acid Green;Acid green 3;Pontacyl Green B;Japan Green 1;Japan Green No. 1;Acid Green G (Polish);Acid Green G;Japan Green No. 402;Japan Green 402;NSC 5016;NSC 8684;260057-95-2
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CAS No:
Description
Green powder
C.i. acid green 3 appears as a dull dark green powder. Used as a dye for silk or wool and biological stains.
C.i. acid green 3 appears as a dull dark green powder. Used as a dye for silk or wool and biological stains.|Guinee green B is an organic sodium salt having 3-[(ethyl{4-[(4-{ethyl[(3-sulfonatophenyl)methyl]amino}phenyl)(phenyl)methylidene]cyclohexa-2,5-dien-1-ylidene}azaniumyl)methyl]benzene-1-sulfonate. Used as a substitute for Light green SF yellowish in Masson's trichrome, although it is prone to fade. Previously used as a food dye but is now no longer approved. It has a role as a fluorochrome, a food colouring and a histological dye. It contains a Guinee green B(1-).
Acid Green Basic Attributes
690.80300
690.18300
225-132-8
4L2574620F
DTXSID3020671
A dull, dark green powder or bright crystalline solid|Maroon-purple powder|A dull, dark green powder or a bright, crystalline solid
3204120000
Characteristics
137.41000
8.28440
C.i. acid green 3 appears as a dull dark green powder. Used as a dye for silk or wool and biological stains.
255ºC (dec.)(lit.)
In water, 30 mg/mL
7.2X10-39 mm Hg at 25 deg C (est)
LD50 orally in rats: >2 g/kg (Lu, Lavalle)
Henry's Law constant = 4.9X10-29 atm-cu m/mol at 25 °C (est)
Soluble in water to a green solution which becomes brownish-yellow on addition of hydrochloric acid and blackish-green with sodium hydroxide. An excess of sodium hydroxide decolorizes the solution.|Sparingly soluble in alcohol; it dissolves in concentrated sulfuric acid to a yellow solution which, when diluted with water, turns first yellowish-red, then green.|Hydroxyl radical reaction rate constant = 4.1X10-10 cu cm/molec-sec at 25 °C (est)
Very soluble in water. Forms a green solution, which becomes brownish-yellow by addition of HCl, and blackish-green with NaOH.
Amines, Phosphines, and Pyridines
C.I. ACID GREEN 3 neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides.
Safety Information
NONH for all modes of transport
3
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.
Combes RD, Haveland-Smith RB; Mutat Res 98 (2): 101-248 (1982). A review of the genotoxicity of food drug and cosmetic colors and other azotriphenylmethane and xanthene dyes.
Toxicity
LD50 Rat oral >3000 mg/kg
C.I. Green 3 is not known to occur as a natural product(1).
C.I. Acid Green 3's production and use as a dye(1) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Acid dyes, such as C.I. Acid Green 3, typically exhibit very low solubilities in octanol and have water solubilities that exceed 100 g/L. Therefore, these compounds would be expected to remain in the water column in the aquatic environment and show little affinity for organic matter(1) which suggests a potential to leach in soil(SRC). Volatilization of C.I. Acid Green 3 from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.9X10-29 atm-cu m/mole(SRC), using a fragment constant estimation method(2). C.I. Acid Green 3 not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.2X10-39 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2011).|AQUATIC FATE: Acid dyes, such as C.I. Acid Green 3, typically exhibit very low solubilities in octanol and have water solubilities that exceed 100 g/L. Therefore, these compounds would be expected to remain in the water column in the aquatic environment and show little affinity for organic matter(1). Volatilization from water surfaces is not expected(2) based upon an estimated Henry's Law constant of 4.9X10-29 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). According to a classification scheme(4), an estimated BCF of 3(SRC), from an estimated log Kow of -3.20(3) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2011).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), C.I. Acid Green 3, which has an estimated vapor pressure of 7.2X10-39 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase C.I. Acid Green 3 may be removed from the air by wet or dry deposition(SRC). C.I. Acid Green 3 absorbs light at wavelengths of 618 nm(4), and therefore may be susceptible to direct photolysis by sunlight(SRC).
Acid dyes, such as C.I. Acid Green 3, readily dissociate in water(1). C.I. Acid Green 3 absorbs light at wavelengths of 618 nm(2), and therefore may be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 3 was calculated in fish for C.I. Acid Green 3(SRC), using an estimated log Kow of -3.20(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Acid dyes, such as C.I. Acid Green 3, typically exhibit very low solubilities in octanol and have water solubilities that exceed 100 g/L. Therefore, these compounds would be expected to remain in the water column in the aquatic environment and show little affinity for organic matter(1).
The Henry's Law constant for C.I. Acid Green 3 is estimated as 4.9X10-29 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that C.I. Acid Green 3 is expected to be essentially nonvolatile from water surfaces(2). C.I. Acid Green 3's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected occur(SRC). C.I. Acid Green 3 is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.2X10-39 mm Hg(SRC), determined from a fragment constant method(1).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 5,996 workers (3,818 of these were female) were potentially exposed to C.I. Acid Green 3 in the US(1). Occupational exposure to C.I. Acid Green 3 may occur through dermal contact with this compound at workplaces where C.I. Acid Green 3 is produced or used(SRC).|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. /Organic dyes/|Textile dye allergy is frequently caused by azo dyes, which can cross-react with structurally similar compounds, including paraphenylenediamine. A case of allergic contact dermatitis to azo textile dyes, presenting principally as a sock dermatitis, is presented. The patient also gave a history of an episode of scalp dermatitis consistent with contact allergy to paraphenylenediamine in hair dye. It is proposed that paraphenylenediamine sensitization from a temporary skin tattoo may have been the primary sensitizing event for these reactions. /Paraphenylenediamine/
Drug Information
Studies in rats involving oral administration showed that only small amounts of the dye (< 5%) are absorbed and excreted unchanged in the bile. Following its iv injection in rats, about 75% of the dye was excreted in the bile within 4 hr.
In Japan, guinea green B has the following specifications: purity, 85% min; inorganic salt, 4% max; and water content, 10% max.
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
/OTHER TOXICITY INFORMATION/ Most organic azo dyes are potential skin sensitizers, the most important of which are paraphenylenediamine and its analogs. Water soluble azo dyes are more likely to cause clinical sensitization than insoluble dyes. ... In addition to allergic eczematous contact dermatitis, color developing solutions have caused lichen planus like eruptions. /Organic dyes/
C.I. 42085
Acid Green Use and Manufacturing
/Guinea Green B/ may be prepared commercially by condensing benzaldehyde with alpha-(N-ethylanilino)-meta-toluenesulfonic acid, followed by oxidation and conversion to the sodium salt.
Limited use as a dye for silk and wool fabrics; as biological stain.
(1973) approx 93,500 kg
Benzenemethanaminium, N-ethyl-N-[4-[[4-[ethyl[(3-sulfophenyl)methyl]amino]phenyl]phenylmethylene]-2,5-cyclohexadien-1-ylidene]-3-sulfo-, inner salt, sodium salt (1:1): ACTIVE|Guinea Green B has been produced commercially in the USA for over fifty years. Guinea green B was first produced commercially in Japan in 1940. It is believed that there is one producer currently; however, no production has been reported since 1973, when 200 kg were manufactured. There are no Japanese exports or imports of this chemical.|Color additives were initially regulated in the United States under the U.S. Department of Agriculture's (USDA) Bureau of Chemistry. In 1906, the Food and Drugs Act was passed by Congress, which prohibited the use of poisonous or deleterious colors in confectionery and the coloring or staining of food to conceal damage or inferiority. In 1927, responsibility of the Food and Drugs Act was transferred to FDA. Increasing government oversight, the Federal Food, Drug, and Cosmetic Act (FFDCA) was passed in 1938 and established the three following categories for colors: FD&C: colors used in foods, drugs and cosmetics; D&C: colors used in drugs and cosmetics when in contact with mucous membranes or ingested; and Ext. D&C: colors used in products applied externally.
Chromatographic and spectrophotometric methods for the identification of food dyes, including guinea green B, have been reviewed. Prior to its cancellation for use in foods, drugs and cosmetics, the Association of Official Analytical Chemists published recommended methods for use in batch certifications of guinea green B so that it met specifications defined by the FDA. It has similarly published Official First Actions for dyes, including guinea green B, in foods by selective solvent extraction or by column chromatography and spectrophotometric identification. A titration method for determining the dye content in a sample of guinea green B has been published. Nuclear magnetic resonance spectroscopy has been evaluated as a means of identifying and differentiating food colors. Paper chromatography has been used to separate and identify dyes, including guinea green B, used to dye paper and foods using spectrodensitometric quantitation. Dyes used in foods, including guinea green B, have been separated and identified by thin-layer chromatography on polyamide-silica gel and polyamide-diatomaceous earth, on polyamide plates and on cellulose manganese after isolation of the dyes from the food sample by adsorption on wool. Adsorption on diethylaminoethyl-Sephadex has also been used to isolate dyes.|HPLC with detection was used for the determination of organic dyes in cosmetics. One hundred and twenty six colorants were characterized by their retention times in an ion pair reversed-phase HPLC system with gradient elution, and by their UV spectra, recorded with a diode array detector. The method is rapid and efficient, as was demonstrated by the analysis of 45 cosmetic samples. /Organic dyes in cosmetics/
Food Additives -> COLOUR;
Computed Properties
Molecular Weight:690.8
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:9
Exact Mass:690.18342347
Monoisotopic Mass:690.18342347
Topological Polar Surface Area:137
Heavy Atom Count:48
Complexity:1250
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes
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