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Malachite green ( CASNO:569-64-2;10309-95-2 )

Identification and Related Records
Name:
Malachite green
CAS Registry number:
569-64-2;10309-95-2
Synonyms:
C.I. 42000
C.I. Basic Green 4
C.I. Basic Green 4 (8CI)
Malachite green
Basic Green 4
N-(4-{[4-(dimethylamino)phenyl](phenyl)methylidene}cyclohexa-2,5-dien-1-ylidene)-N-methylmethanaminium chloride
N-(4-{[4-(dimethylamino)phenyl](phenyl)methylidene}cyclohexa-2,5-dien-1-ylidene)-N-methylmethanaminium
[4-[(4-dimethylaminophenyl)-phenyl-methylene]-1-cyclohexa-2,5-dienylidene]-dimethyl-ammonium
2-hydroxy-2-oxo-acetate
oxalic acid
N-(4-{[4-(dimethylamino)phenyl](phenyl)methylidene}cyclohexa-2,5-dien-1-ylidene)-N-methylmethanaminium hydrogen sulfate
N-(4-{[4-(dimethylamino)phenyl](phenyl)methylidene}cyclohexa-2,5-dien-1-ylidene)-N-methylmethanaminium benzoate
N-(4-{[4-(dimethylamino)phenyl](phenyl)methylidene}cyclohexa-2,5-dien-1-ylidene)-N-methylmethanaminium acetate
EINECS(EC#):
209-322-8
Molecular Formula:
C23H25Cl2N2
Molecular Weight:
400.3645
Inchi:
InChI=1/C23H25N2.2ClH/c1-24(2)21-14-10-19(11-15-21)23(18-8-6-5-7-9-18)20-12-16-22(17-13-20)25(3)4;;/h5-17H,1-4H3;2*1H/q+1;;/p-2
Canonical SMILES:
CN(C)C1=CC=C(C=C1)C(=C2C=CC(=[N+](C)C)C=C2)C3=CC=CC=C3.[Cl-]
Chemical and Physical Properties
Appearance:
green crystals
Melting Point:
158-160°C
Water:
1486 mg l-1 (e)
Storage temp:
Refrigerator
Spectral properties:
Max absorption: 616.9 nm
MASS: 7774 (NIST/EPA/MSDC Mass Spectra Database, 1990 version)
Computed Properties:
Molecular Weight:364.911 [g/mol]
Molecular Formula:C23H25ClN2
H-Bond Donor:0
H-Bond Acceptor:2
Rotatable Bond Count:3
Exact Mass:364.170627
MonoIsotopic Mass:364.170627
Topological Polar Surface Area:6.2
Heavy Atom Count:26
Formal Charge:0
Complexity:516
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:2
Safety and Handling
Hazard Codes:
Xn,N
Risk Statements:
22-41-50/53-63
Safety Statements:
S24/25
Cleanup Methods:
Malachite green had 0% biodegradation after 5 days using a sewage inoculum and the BOD5 test(1). However, ready biodegradability tests, i.e. static flask screening test, Warburg respirometer, and a semicontinuous flow activated sludge system, using acclimated wastewater from a malachite green-producing workshop resulted in a removal rate of greater than 70%, indicating ready biodegradability(2). A Mycobacterium sp has been shown to decolorize a 20 mg/ml solution of malachite green 53% in 2 hrs at 24 deg C; the solution was completed decolorized in 22 hrs when incubated at 32 deg C(4). The pH remained at 6.8 and the number of cells did not increase(3).
Coagulation with ferrous sulfate, ferric sulfate, and ferric chloride and treatment with ozone were tested for CI Basic Green 4 in wastewater. Effect of coagulation depended largely on pH of solution.
Transport:
UN 2811 6.1/PG 3
Other Preventative 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.
Octanol/Water Partition Coefficient:
log Kow = 0.62
Disposal Methods:
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.
A study was designed to (1) determine the type of filter and kind of carbon that was most efficient for removal of malachite green and (2) demonstrate that carbon filters can be used to remove malachite green from water used for egg incubation or to hold adult salmon before spawning. Minicolumn simulation studies showed that removing malachite green from water for 230 days at a flow rate of 500 gal/min for only 62 days at a flow rate of 1,000 gal/min. The removal capacity at the slower flow rate was 1.1 oz of malachite green per pound of carbon. A filter system that contained 20,000 lb of activated carbon in each of two chambers was effective for removal of malachite green from treated water in adult salmon holding ponds at flows of 500 gal/min (6.4 gal/min per sq ft) and greater. The removal efficiency was 99.8% after 105 hr of operation, and the adsorption capacity of the system was projected to be sufficient for 20 or more years of routine hatchery operation. A filter system that contained 2,000 lb of activated carbon in each of two chambers was effective for removal of malachite green from treated water in salmon egg incubation units at the designated flow rate of 50 gal/min (4.0 gal/min per sq ft) and also at faster flow rates. Removal efficiency decreased only slightly for faster flows in both filter systems, and the efficiency improved when treated water was passed through two filter chambers in series.
Use and Manufacturing
Use and Manufacturing:
Methods of Manufacturing

Malachite green is synthesized by condensation of benzaldehyde with dimethylaniline in sulfuric acid and oxidation of the leuco compound in hydrochloric acid solution with lead dioxide or manganese dioxide. ... For production of liquid dyes, benzaldehyde is condensed with dimethylaniline in acetic acid to give a leuco base, which is then oxidized catalytically with atmospheric oxygen in the presence of (dihydrodibenzotetraaza[14]-annulene)iron and chloranil.
CONDENSATION OF BENZALDEHYDE WITH N,N-DIMETHYLANILINE IN THE PRESENCE OF AN ACID, FOLLOWED BY OXIDATION OF THE RESULTING PRODUCT WITH LEAD PEROXIDE AND AN ACID; HEATING N,N-DIMETHYLANILINE WITH BENZOTRICHLORIDE
For dyeing it is prepared as a double salt with zinc chloride.
U.S. Exports

(1972) ND
(1975) ND
U.S. Imports

(1972) 9.6X10+7 G (PRINCPL CUSTOMS DISTS)
(1975) 3.03X10+7 G (PRINCPL CUSTOMS DISTS)
U.S. Production

(1972) GREATER THAN 4.54X10+5 G
(1975) 1.45X10+8 G
Consumption Patterns

100% AS A DYE (1976)
Biomedical Effects and Toxicity
Pharmacological Action:
- Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects.
- Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS.
- Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc.
Therapeutic Uses:
Anti-Infective Agents, Local; Fungicides, Industrial
MEDICATION (VET): Antiseptic. Internally, in calf scours and canine dysentery (Escherichia coli). Externally (0.5-10%), on infected wounds and abrasions- often as triple dye, containing brilliant green, gentian violet, and rivanol. Bacteriostatic effectiveness decreased by increased concentration of bile salts.
MEDICATION (VET): Approximately 10 times more effective against gram-positive than gram-negative organisms.
MEDICATION (VET): ... (medical grade, zinc-free) has been used for treatment of mycotic infect in fish.
MEDICATION (VET): Fungicide and parasiticide in fish
MEDICATION (VET): The arylmethane dye malachite green oxalate is used as an antimycotic and antiparasitic substance for treatment of fish diseases. ... [Kietzmann M et al; DTW Dtsch Tierarztl Wochenschr 97 (7): 290-3 (1990)]
Biomedical Effects and Toxicity:
The disposition of malachite green was determined in channel catfish (Ictalurus punctatus) after intravascular dosing (0.8 mg/kg) or waterborne exposure (0.8 mg/L for 1 hr). After intravascular dosing, mean plasma concentrations of the parent compound exhibited a triphasic decline with a terminal elimination half-life of 6.2 hr. Malachite green was rapidly absorbed and concentrated in the tissues during waterborne exposure. The rate of accumulation was directly related to pH of the exposure water. After waterborne exposure, elimination of the parent compound from plasma also was triphasic with a terminal half-life of 4.7 hr. In muscle, the half-life of the parent compound was approximately 67 hr. Malachite green and its metabolites were widely distributed in all tissues. In fish exposed to 14C-labeled malachite green, total drug equivalent concentrations were highest in abdominal fat and lowest in plasma. Malachite green was rapidly and extensively metabolized to its reduced form, leucomalachite green, which was slowly eliminated from the tissues. Leucomalachite green is an appropriate target analyte for monitoring exposure of channel catfish to this drug.
... A 6-day-lasting therapeutic bath of rainbow trout was performed in malachite green of 0.2 mg/L concentration. Its residues were then observed in muscle, liver and skin of treated fish. Immediately after the bath, malachite green was detected in muscle, liver and skin at the levels of 0.383, 0.834 and 0.649 mg/kg, respectively, as a sum of both coloured form and leukoform. Eight weeks after the bath, an expressive decrease of the coloured form of malachite green was found while its leukoform was detected in fish as late as after 10 months. Results of analyses were found negative twelve months after the bath.
Environmental Fate and Exposure Potential
Environmental Fate/Exposure Summary:
TERRESTRIAL FATE: Malachite green is a cationic dye(1) and cations generally adsorb more strongly to organic carbon and clay than their neutral counterparts Volatilization of malachite green from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.9X10-14 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Malachite green is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.4X10-13 mm Hg(SRC), determined from a fragment constant method(3). A 0% degradation in 5 days using a sewage inoculum and the BOD5 test indicates(4) that biodegradation is not expected to be an important fate process in soil(SRC).
AQUATIC FATE: Malachite green is a cationic dye(1) and cations adsorb more strongly to organic carbon and clay than their neutral counterparts(2). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.9X10-14 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 0% degradation in 5 days using a sewage inoculum and the BOD5 test indicates(8) that biodegradation is not expected to be an important fate process in water(SRC). [
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), malachite green, which has an estimated vapor pressure of 2.4X10-13 mm Hg at 25 deg C(SRC), as determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase malachite green may be removed from the air by wet and dry deposition(SRC). Since malachite green absorbs light at 617 nm)(3), it has the potential for direct photolysis.
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