结构:CN(C)c1ccc(C(=C2C=CC(=[N+](C)C)C=C2)c2ccccc2)cc1.[Cl-]
HCID11294

Malachite Green

[4-[[4-(dimethylamino)phenyl]-phenylmethylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium chloride

C23H25ClN2364.9 g/molCAS 10309-95-2

IDENTITY

结构与身份

标准 SMILES
CN(C)c1ccc(C(=C2C=CC(=[N+](C)C)C=C2)c2ccccc2)cc1.[Cl-]
InChIKey
FDZZZRQASAIRJF-UHFFFAOYSA-M
分子式
C23H25ClN2
平均分子量
364.9 g/mol
单同位素质量
364.1706265

COMPUTED

结构计算性质

已同步
极性表面积
6.3 Ų
氢键供体
0
氢键受体
2
可旋转键
3
重原子
26
形式电荷
0
复杂度
516

PROPERTIES

实验与物化性质

来源:PubChem
pH

1% sol in water has a pH of 1.4

LogP

log Kow = 0.62

Color/Form

Green crystals with metallic luster

Solubility

Sol in alcohol, methanol, amyl alcohol

Sol 1 /part/ in 15 /parts/ of water and 1 /part/ in 15 /parts/ of alcohol.

Very soluble in ethanol

In water, 4.0X10+4 mg/L at 25 °C

Decomposition

When heated to decomposition it emits very toxic fumes of /nitrogen oxide and hydrogen chloride/.

Vapor Pressure

2.4X10-13 mm Hg at 25 °C /Estimated/

Physical Description

C.i. basic green 4 appears as green crystals with metallic luster. Water solutions are blue-green. Used in dyeing silk, wool, biological staining, etc.

Wet Solid; Liquid

Green metallic solid; [HSDB]

Ionization Efficiency

Positive

4.27

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Other Experimental Properties

Water soln are blue-green; yellow below pH 2; as acid-base indicator; ph: 0.0 yellow; 2.0 green; 11.6 blue-green; 14 colorless.

GHS

GHS 分类

来源:PubChem
GHS Classification

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral];H318: Causes serious eye damage [Danger Serious eye damage/eye irritation];H361d ***: Suspected of damaging the unborn child [Warning Reproductive toxicity];H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P203, P264, P264+P265, P270, P273, P280, P301+P317, P305+P354+P338, P317, P318, P330, P391, P405, and P501 (click each P-code to see the statement)

Danger

HAZARDS

危害信息

来源:PubChem
Regulatory Information

Chemical: Methanaminium, N-[4-[[4-(dimethylamino)phenyl]phenylmethylene]-2,5-cyclohexadien-1-ylidene]-N-methyl-, chloride

Commission Regulation (EC) No 470/2009

Methanaminium, N-[4-[[4-(dimethylamino)phenyl]phenylmethylene]-2,5-cyclohexadien-1-ylidene]-N-methyl-, chloride (1:1) is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methanaminium, N-[4-[[4-(dimethylamino)phenyl]phenylmethylene]-2,5-cyclohexadien-1-ylidene]-N-methyl-, chloride (1:1) are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Malachite green: Does not have an individual approval but may be used under an appropriate group standard

Other Safety Information

IMAP assessments - Malachite green and related chemicals: Human health tier II assessment

DOT Label

Poison

Fire Hazards

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:;Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Corrosives in contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For electric vehicles or equipment, ERG Guide 147 (lithium ion or sodium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2024)

Health Hazards

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:;TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause environmental contamination. (ERG, 2024)

Hazards Summary

Toxic by ingestion; [Hawley] Severe eye irritant; [ESIS] Toxic by ingestion; May damage eyes; Wear gloves and eye protection; Do not breathe dust; [MSDSonline]

Reactive Group

Amines, Phosphines, and Pyridines;Hydrocarbons, Aromatic;Hydrocarbons, Aliphatic Unsaturated;Conjugated Dienes;Quaternary Ammonium and Phosphonium Salts

FIFRA Requirements

Product registrations which once contained active ingredients /incl malachite green/ have previously been amended to remove the ingredient from the formula or have been cancelled for other reasons. ... These ingredients will be removed from Reregistration List D effective 90 days after publication of this notice ... and will not be considered further for reregistration.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Malachite green is found on List D. Case No: 4011; Case Status: No products containing the pesticide are actively registered. Therefore, we are characterizing the case as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): malachite green; AI Status: The active ingredient is no longer contained in any registered products ... "cancelled."

Reactivity Profile

C.I. BASIC GREEN 4 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. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Air and Water Reactions

Very soluble in water.

Hazard Classes and Categories

Acute Tox. 4 (100%);Eye Dam. 1 (100%)

Acute Tox. 3 (21.4%);Acute Tox. 4 (78.6%);Eye Dam. 1 (100%);Repr. 2 (99.5%);Aquatic Acute 1 (98.6%);Aquatic Chronic 1 (100%)

Germ cell mutagenicity - category 2;Eye damage - category 1;Reproductive toxicity - category 2;Hazardous to the aquatic environment (acute) - category 1;Hazardous to the aquatic environment (chronic) - category 1;Acute toxicity - category 4

Acute toxicity (Oral) - Category 3;Serious eye damage/eye irritation - Category 1;Specific target organ toxicity - Repeated exposure - Category 2 (blood);Hazardous to the aquatic environment (Acute) - Category 1;Hazardous to the aquatic environment (Long-term) - Category 1

Acute toxicity (Oral) - Category 3;Serious eye damage/eye irritation - Category 1;Germ cell mutagenicity - Category 1B;Carcinogenicity - Category 2;Specific target organ toxicity - Repeated exposure - Category 1 (thyroid), Category 2 (haemal system, liver);Hazardous to the aquatic environment (Acute) - Category 1;Hazardous to the aquatic environment (Long-term) - Category 1

Repr. 2;Acute Tox. 4 *;Eye Dam. 1;Aquatic Acute 1;Aquatic Chronic 1

SAFETY

安全与防护

来源:PubChem
Fire Fighting

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:;SMALL FIRE: Dry chemical, CO2 or water spray.;LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. If it can be done safely, move undamaged containers away from the area around the fire. Dike runoff from fire control for later disposal.;FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. (ERG, 2024)

First Aid

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:;Refer to the "General First Aid" section. Specific First Aid: For corrosives, in case of contact, immediately flush skin or eyes with running water for at least 30 minutes. Additional flushing may be required. (ERG, 2024)

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 °C; the solution was completed decolorized in 22 hrs when incubated at 32 °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.

Nonfire Spill Response

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:;ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2024)

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.

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.

Isolation and Evacuation

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:;IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.;SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.;FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

Protective Action Criteria (PAC)

0.13 [mg/m3]

1.4 [mg/m3]

8.7 [mg/m3]

Personal Protective Equipment (PPE)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:;Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer when there is NO RISK OF FIRE. Structural firefighters' protective clothing provides thermal protection but only limited chemical protection. (ERG, 2024)

TOXICITY

毒理信息

来源:PubChem
Ecotoxicity Values

LC50 Lepomis macrochirus (Bluegill) 0.0305 mg/L/96 hr. /Conditions of bioassay not specified in source examined/

LC50 Salmon 0.338 mg/L/96 hr. /Conditions of bioassay not specified in source examined/

LC50 Rainbow trout (Oncorhynchus mykiss) 0.0998 mg/L/96 hr. /Conditions of bioassay not specified in source examined/

LC50 Frog 0.173 mg/L/96 hr. /Conditions of bioassay not specified in source examined/

For more Ecotoxicity Values (Complete) data for MALACHITE GREEN (13 total), please visit the HSDB record page.

Environmental Fate

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 °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.

Food Survey Values

Malachite green was not detected in 92 of 92 samples of farmed fish analyzed between October 1987 through February 1989, as part of the United Kingdom National Surveillance Scheme of home-produced and imported meat, meat products, and fish(1).

Ecotoxicity Excerpts

/AQUATIC SPECIES/ Fingerling channel catfish were exposed to 0.1 mg/L, neutrophilia at 1 & 3 days after treatment was observed. Increases in erythrocyte counts, hemoglobin concentration & hemoblast percentages 3 days after treatment; erythrocytosis after 7 days; hematocrit increases, 14 days; & leukopenia after 21 days.

/AQUATIC SPECIES/ Prophylactic dip treatments using formalin and malachite green were applied to 4-day old larvae and 12- and 20-day old juveniles of the European common carp, Cyprinus carpio and the African sharptooth catfish, Clarias gariepinus. Treatments consisted of 100 mg/L malachite green for exposure periods of 10, 30 or 90 s and 200 mg/L formalin administered for 30, 60 or 90 min. Larvae and juveniles of Clarias gariepinus could be treated with 100 mg/L malachite green for 10 s, or with 200 mg/L formalin for 30 min, with minimum mortalities. Both chemicals affected the survival of the Clarias gariepinus juveniles, especially the 90 min exposure to formalin. Juveniles of both species were sensitive to 100 mg/L malachite green concentrations.

/AQUATIC SPECIES/ ...Rainbow trout eggs were treated during incubation with 5 mg/L of malachite green oxalate either every two days, or weekly. Mortality was minimal in the group treated with malachite green/formalin mixture. Residuesof malachite green in fish tissue were significantly greater in the fish treated with 5 mg/L of malachite green (both regimes) than in the fish treated with malachite green/formalin mixture. The residue levels in fry were directly related to the treatment concentration and frequency of treatments during egg incubation.

/AQUATIC SPECIES/ Exposure of the freshwater catfish H. fossilis to an acute concentration of 0.20 mg dm-3 (1/5th of 4 days LC50) of malachite green for 4 days evoked hepatic and muscle glycogenolysis with concomitant hyperglycemia and chloremia. Exposure of fish to sub-acute 0.10 mg dm-3 (1/10th of 4 days LC50) and sub-lethal 0.05 mg dm-3 (1/20th of 4 days LC50) concentrations of the dye also evoked a significant increase in blood glucose and chloride levels at short (10-20 days) and long (30-60 days) term as well as liver and muscle glycogenolysis at short term.

For more Ecotoxicity Excerpts (Complete) data for MALACHITE GREEN (7 total), please visit the HSDB record page.

Ongoing Test Status

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=569-64-2]

Soil Adsorption/Mobility

Malachite green is a cationic dye(1) and cations adsorb more strongly to organic carbon and clay than their neutral counterparts(2).

Human Toxicity Excerpts

/SIGNS AND SYMPTOMS/ Ingestion causes diarrhea and abdominal pain.

/CASE REPORTS/ ...Injurious to... eye. In one patient an attempt to treat conjunctivitis with 1% solution of this dye resulted in destructive keratitis with hypopyon and terminated in bilateral blindness due to corneal opacification.

Artificial Pollution Sources

Malachite green's production and use for directly dyeing silk, wool, jute and leather, in dyeing cotton after mordanting, as a biological stain, clinical reagent (inorganic phosphate assay), as a spot test reagent for detecting sulfurous acid and cerium, as an acid-base indicator(1), and as a dye for paper(2) may result in its release to the environment through various waste streams(SRC). It also has veterinary applications as a fungicide and parasiticide in fish(1).

Environmental Biodegradation

AEROBIC: 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 °C; the solution was completed decolorized in 22 hrs when incubated at 32 °C(4). The pH remained at 6.8 and the number of cells did not increase(3).

Carcinogen Classification

Malachite green

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 129: (2022) Gentian Violet, Leucogentian Violet, Malachite Green, Leucomalachite Green, and CI Direct Blue 218

2022 online

2021

Malachite Green

Environmental Bioconcentration

An estimated BCF of 3 was calculated for malachite green(SRC), using a log Kow of 0.62(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil

The Henry's Law constant for malachite green is estimated as 1.9X10-14 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that malachite green is expected to be essentially nonvolatile from water surfaces(2). Malachite green's Henry's Law constant indicates that volatilization from moist soil surfaces is unlikely to occur(SRC). 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).

REGULATORY

法规信息

来源:PubChem
Regulatory Information

Chemical: Methanaminium, N-[4-[[4-(dimethylamino)phenyl]phenylmethylene]-2,5-cyclohexadien-1-ylidene]-N-methyl-, chloride

Commission Regulation (EC) No 470/2009

Methanaminium, N-[4-[[4-(dimethylamino)phenyl]phenylmethylene]-2,5-cyclohexadien-1-ylidene]-N-methyl-, chloride (1:1) is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methanaminium, N-[4-[[4-(dimethylamino)phenyl]phenylmethylene]-2,5-cyclohexadien-1-ylidene]-N-methyl-, chloride (1:1) are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Malachite green: Does not have an individual approval but may be used under an appropriate group standard

FIFRA Requirements

Product registrations which once contained active ingredients /incl malachite green/ have previously been amended to remove the ingredient from the formula or have been cancelled for other reasons. ... These ingredients will be removed from Reregistration List D effective 90 days after publication of this notice ... and will not be considered further for reregistration.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Malachite green is found on List D. Case No: 4011; Case Status: No products containing the pesticide are actively registered. Therefore, we are characterizing the case as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): malachite green; AI Status: The active ingredient is no longer contained in any registered products ... "cancelled."

PHARMACOLOGY

药理信息

来源:PubChem
ATC Code

QP - Antiparasitic products, insecticides and repellents;QP53 - Ectoparasiticides, insecticides and repellents;QP53A - Ectoparasiticides for topical use, incl. insecticides;QP53AX - Other ectoparasiticides for topical use;QP53AX16 - Malachite green

Mechanism of Action

... The mitogen activated protein (MAP) kinase signal transduction pathway in preneoplastic cells induced by MG /was studied/. Western blots of MG /Malachite Green/ induced preneoplastic cells showed no phosphorylation of ERK1, an increased phosphoactive ERK2 associated with a decreased expression of phosphoactive JNK2. However, total forms of ERKs, JNKs and p38 Kinases showed similar levels of expression in control and preneoplastic SHE /Syrian hamster embryo/ cells. Indirect immunofluorescence studies have shown a distinct nuclear localisation of phosphoactive ERKs in MG induced preneoplastic cells. Flow cytometric analysis showed an increase of S-phase cells in preneoplastic cells compared to control SHE cells.

... In order to understand the mechanism(s) of tumor promotion by MY /Metanil yellow/ and MG /malachite green/, we have studied the levels of PCNA, a marker of cell proliferation and cell cycle regulatory proteins, cyclin D1, and its associated kinase, cdk4, cyclin B1, and associated kinase, cdc2. Immunohistochemical staining showed an elevated level of PCNA in animals administered MY and MG subsequent to DEN /N-nitrosodiethylamine/ treatment. Western and Northern blot hybridization showed an increased expression of both cyclin D1 and its associated kinase cdk4, and cyclin B1 and its associated kinase cdc2, in livers of rats administered MY and MG after administration of DEN as compared to untreated or DEN controls. The increased level of mRNA was due to the increased rate of transcription of these genes as studied by run-on transcription assay.

MeSH Pharmacological Classification

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 that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc.

Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS.

Absorption, Distribution and Excretion

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.

USES

用途与制造

来源:PubChem
Uses

Used as a fungicide, textile dye (silk, wool, jute, leather, and cotton) biological stain, reagent, and pH indicator; [HSDB]

Textiles (Printing, Dyeing, or Finishing) [Category: Industry]

The active ingredient is no longer contained in any registered products ... "cancelled."

For malachite green (USEPA/OPP Pesticide Code: 039504) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

For directly dyeing silk, wool, jute and leather; dyeing cotton after mordanting. Biological stain, clinical reagent (inorganic phosphate assay). As spot test reagent for detecting sulfurous acid and cerium. As acid-base indicator ...

THERAP CAT (VET): Fungicide and parasiticide in fish. /SRP: Prohibited for use in aqua-culture in many parts of the world/.

U.S. Exports

(1972) No Data

(1975) No Data

U.S. Imports

(1972) 9.6X10+7 G (PRINCPL CUSTOMS DISTS)

(1975) 3.03X10+7 G (PRINCPL CUSTOMS DISTS)

U.S. Production

2023: 75,000 - <500,000 lb;2022: 75,000 - <500,000 lb;2021: 75,000 - <500,000 lb;2020: 75,000 - <500,000 lb

(1972) GREATER THAN 4.54X10+5 G

(1975) 1.45X10+8 G

Consumption Patterns

100% AS A DYE (1976)

Consumer Uses

Dye

Industry Uses

Dye

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.

Household Products

Information on 7 consumer products that contain Malachite green in the following categories is provided:;• Personal Care;• Pet Care

Use Classification

Food Contaminant -> -> JECFA Functional Classes;CONTAMINANTVeterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes

General Manufacturing Information

Synthetic Dye and Pigment Manufacturing

Methanaminium, N-[4-[[4-(dimethylamino)phenyl]phenylmethylene]-2,5-cyclohexadien-1-ylidene]-N-methyl-, chloride (1:1): ACTIVE

IT HAS ALSO FOUND USE AS AN AGRICULTURAL FUNGICIDE. CHEMICALLY RELATED TO GENTIAN VIOLET ... .

ALIASES

名称与别名

166
MALACHITE GREEN569-64-2Basic Green 4Malachite green chlorideAniline GreenChina GreenVictoria Green BGrenoble GreenDiamond Green BBenzaldehyde GreenVictoria GreenBenzal GreenBurma Green BDiamond Green BxLight Green NSolid Green OVictoria Green SFast Green OGreen MXCalcozine Green V

REACTIONS

参与反应

3