| Revision as of 16:18, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 469541539 of page Malachite_green for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 06:56, 28 June 2024 edit 2024asad12 (talk | contribs)2 edits →External linksTag: Visual edit |
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{{short description|Organic dye}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{about|the organic dye called "malachite green"|the use of malachite as a pigment|Malachite#Use|and|Basic copper carbonate#Uses}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 438218601 |
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| verifiedrevid = 470455842 |
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| ImageFile =Malachite green structure.svg |
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| ImageFile = Malachite green structure.svg |
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| ImageSize = |
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| ImageSize = |
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| ImageFile1 = Malachite green oxalate.jpg |
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| ImageFile1 = Malachite green oxalate.jpg |
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| IUPACName = 4--''N'',''N''-dimethylaniline |
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| PIN = 4-{(phenyl)methylidene}-''N'',''N''-dimethylcyclohexa-2,5-dien-1-iminium chloride |
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| OtherNames = Aniline green; Basic green 4; Diamond green B; Victoria green B |
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| OtherNames = Aniline green; Basic green 4; Diamond green B; Victoria green B |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 569-64-2 |
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| ChemSpiderID = 10820 |
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| CASNo_Comment = (chloride salt) |
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| CASNo2 = 2437-29-8 |
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| CASNo2_Ref = {{cascite|changed|??}} |
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| CASNo2_Comment = (oxalate salt) |
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| ChEBI = 72449 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 186357 |
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| ChEMBL = 186357 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10820 |
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| KEGG = C18367 |
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| PubChem = 11294 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 12058M7ORO |
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| UNII = 12058M7ORO |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = FDZZZRQASAIRJF-UHFFFAOYSA-M |
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| StdInChIKey = FDZZZRQASAIRJF-UHFFFAOYSA-M |
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| SMILES = CN(C)c1ccc(cc1)C(=C2C=CC(=(C)C)C=C2)c3ccccc3. |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 569-64-2 |
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| PubChem = 11294 |
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| SMILES = CN(C)c1ccc(cc1)C(=C2C=CC(=(C)C)C=C2)c3ccccc3. |
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| ATCvet = yes |
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| ATCCode_prefix = P53 |
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| ATCCode_suffix = AX16 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>23</sub>H<sub>25</sub>ClN<sub>2</sub> (chloride) |
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| Formula = C<sub>23</sub>H<sub>25</sub>ClN<sub>2</sub> (chloride) |
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| MolarMass = 364.911 g/mol (chloride) |
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| MolarMass = 364.911 g/mol (chloride) |
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| Appearance = |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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<!-- See data sheet from Fischer --> |
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|Section6={{Chembox Pharmacology |
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| ATCvet = yes |
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| ATCCode_prefix = P53 |
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| ATCCode_suffix = AX16 |
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}} |
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|Section7={{Chembox Hazards |
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| MainHazards = Moderately toxic, Extreme ] |
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| GHS_ref=<ref>{{cite web |title=C&L Inventory |url=https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/66706 |website=echa.europa.eu |access-date=27 December 2021}}</ref> |
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| GHSPictograms = {{GHS05}}{{GHS07}}{{GHS08}}{{GHS09}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|302|318|361d|410}} |
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| PPhrases = {{P-phrases|264|270|280|301+312|305+351+338|310|330|501}} |
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| LD50 = 80mg/kg (oral, ]) |
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'''Malachite green''' is an ] that is used as a ] and controversially as an antimicrobial in ]. Malachite green is traditionally used as a dye for materials such as ], ], and ]. Despite its name the dye is not prepared from the ] ]; the name just comes from the similarity of color. |
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==Structures and properties== |
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Malachite green is classified in the dyestuff industry as a ] and also using in pigment industry. Formally, malachite green refers to the chloride salt {{chem2|Cl}}, although the term malachite green is used loosely and often just refers to the colored ]. The ] salt is also marketed. The ]s have no effect on the color. The intense green color of the cation results from a strong absorption band at 621 nm (] of {{nobr|10<sup>5</sup> M<sup>−1</sup> cm<sup>−1</sup>}}). |
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{{pH indicator template|indicator_name=Malachite green (second transition)|low_pH=11.5 |high_pH=13.2 |low_pH_color=#00bb88|low_pH_text=white |high_pH_color=white}} |
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{{pH indicator template|indicator_name=Malachite green (first transition)|low_pH=0.2 |high_pH=1.8 |low_pH_color=yellow |high_pH_color=#00bb88|high_pH_text=white}} |
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Malachite green is prepared by the condensation of ] and ] to give ] malachite green (LMG): |
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:<chem>C6H5CHO + C6H5N(CH3)2 -> (C6H5N(CH3)2)2C6H5 + H2O</chem> |
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Second, this colorless leuco compound, a relative of ], is oxidized to the cation that is MG: |
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:{{chem2|C6H5CH(C6H4N(CH3)2)2 + HCl + ½ O2 → Cl + H2O}} |
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A typical oxidizing agent is ]. |
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Hydrolysis of MG gives an ]:<ref>{{cite journal | last=Raducan | first=Adina | last2=Olteanu | first2=Alexandra | last3=Puiu | first3=Mihaela | last4=Oancea | first4=Dumitru | title=Influence of surfactants on the fading of malachite green | journal=Open Chemistry | volume=6 | issue=1 | date=2008-03-01 | issn=2391-5420 | doi=10.2478/s11532-007-0066-0 | pages=89–92| doi-access=free }}</ref> |
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:{{chem2|Cl + H2O → C6H5C(OH)(C6H4N(CH3)2)2 + HCl}} |
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This alcohol is important because it, not MG, traverses cell membranes. Once inside the cell, it is metabolized into LMG. Only the cation MG is deeply colored, whereas the leuco and alcohol derivatives are not. This difference arises because only the cationic form has extended pi-delocalization, which allows the molecule to absorb visible light. |
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]s of the MG cation. The alcohol derivative of MG is derived from LMG by replacement of the unique C–H by C–OH.]] |
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{{Clear}} <!-- DO NOT REMOVE; while this appears unnecessary under the Vector 2010 skin, it is necessary for proper layout with the Vector 2022 skin --> |
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==Preparation== |
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The ] form of malachite green was first prepared by ] in 1877 by condensing ] and ] in the molecular ratio 1:2 in the presence of ].<ref>{{cite book | title=Principles of organic chemistry | publisher=Jai Sai Publications | author=Dr. M Vishwanathan | pages=2/37}}</ref> |
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] |
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{{Clear}} |
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==Uses== |
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Malachite green is traditionally used as a dye. Kilotonnes of MG and related triarylmethane dyes are produced annually for this purpose.<ref>Thomas Gessner and Udo Mayer "Triarylmethane and Diarylmethane Dyes" in '']'' 2002, Wiley-VCH, Weinheim.{{doi|10.1002/14356007.a27_179}}</ref> |
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MG is active against the ] '']'', which infects fish eggs in commercial ], MG has been used to treat '']'' and is used as an ].<ref>{{cite journal|title=Toxicological effects of malachite green|journal=]|date=2004|volume=66|issue=3|pages=319–29|pmid=15129773|last1=Srivastava |first1=S |last2=Sinha |first2=R |last3=Roy |first3=D |doi=10.1016/j.aquatox.2003.09.008|bibcode=2004AqTox..66..319S }}</ref> It is a very popular treatment against '']'' in ] ]. The principal ], leuco-malachite green (LMG), is found in fish treated with malachite green, and this finding is the basis of controversy and government regulation. See also ]. |
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MG has frequently been used to catch thieves and pilferers. The bait, usually money, is sprinkled with the anhydrous powder. Anyone handling the contaminated money will find that on upon washing the hands, a green stain on the skin that lasts for several days will result.{{Citation needed|date=September 2020}} |
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===Niche uses=== |
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]'' showing ] stained with malachite green (vegetative cells stained pink with safranin counterstain)]] Numerous niche applications exploit the intense color of MG. It is used as a ] for ] analysis of ] and ]. In the ], basic ] stains bacteria red or magenta, and malachite green is used as a blue-green ]. Malachite green is also used in ], since it can directly stain ]s within bacterial cells; here a ] counterstain is often used. Malachite green is a part of Alexander's ]. Malachite green can also be used as a ] in ]s, or as a ] between pH 0.2–1.8. However, this use is relatively rare.<!-- then why describe it--> Leuco-malachite green (LMG) is used as a detection method for latent blood in ]. ] catalyzes the reaction between LMG and ], converting the colorless LMG into malachite green. Therefore, the appearance of a green color indicates the presence of ].<ref>{{cite web|title=DNA Analyst Training Laboratory Training Manual Protocol 2.18 Leucomalachite Green Presumptive Test for Blood|url=https://static.training.nij.gov/lab-manual/Linked%20Documents/Protocols/pdi_lab_pro_2.18.pdf|publisher=National Forensic Science Technology Center|access-date=8 January 2018|ref=malachite green blood}}</ref> |
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A set of malachite green derivatives is also a key component in a fluorescence microscopy tool called the fluorogen activating protein/fluorogen system. Malachite green is in a class of molecules called fluorophores. When malachite green's rotational freedom is restricted, it transforms from a non fluorescent molecule to a highly fluorescent molecule.<ref>{{Cite journal|last=Szent-Gyorgyi|first=Christopher|date=2007|title=Fluorogen-activating single-chain antibodies for imaging cell surface proteins|url=https://www.nature.com/articles/nbt1368|journal=Nature Biotechnology|volume=26|issue=2|pages=235–240|doi=10.1038/nbt1368|pmid=18157118|s2cid=21815631}}</ref> In the fluorogen activating protein tool, established by a group at Carnegie Mellon University, Malachite green binds a specific fluorogen activating protein to become highly fluorescent. Expression of the fluorogen activating protein as fusions of targeting domains can impart subcellular localization. Its use is similar to that of ] but has the added benefit of having a 'dark state' before the malachite green fluorophore is added. This is especially useful for ] studies. |
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== Regulation == |
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In 1992, Canadian authorities determined that eating fish contaminated with malachite green posed a significant health risk.<ref>Wendy C. Andersen, Sherri B. Turnipseed, and José E. Roybal "Quantitative and Confirmatory Analyses of Malachite Green and Leucomalachite Green Residues in Fish and Shrimp" ''J. Agric. Food Chem.'' 2006, volume 54, pp. 4517–4523.{{doi|10.1021/jf0532258}} and references therein <!--delete and update this leading ref in future--></ref> Malachite green was classified a Class II Health Hazard. Due to its low manufacturing cost, malachite green is still used in certain countries with less restrictive laws for non ] purposes. In 2005, analysts in ] found traces of malachite green in ]s and fish imported from ]. In 2006, the United States ] (FDA) detected malachite green in seafood from China, ], where the substance is also banned for use in aquaculture.<ref>{{Cite journal |last1=Poopal |first1=Rama-Krishnan |last2=Ashwini |first2=Rajan |last3=Ramesh |first3=Mathan |last4=Li |first4=Bin |last5=Ren |first5=Zongming |date=2023-03-01 |title=Triphenylmethane dye (C52H54N4O12) is potentially a hazardous substance in edible freshwater fish at trace level: toxicity, hematology, biochemistry, antioxidants, and molecular docking evaluation study |url=https://doi.org/10.1007/s11356-022-24206-y |journal=Environmental Science and Pollution Research |language=en |volume=30 |issue=11 |pages=28759–28779 |doi=10.1007/s11356-022-24206-y |pmid=36401692 |s2cid=253671609 |issn=1614-7499}}</ref> In June 2007, the FDA blocked the importation of several varieties of seafood due to continued malachite green contamination.<ref>, ''USA Today'', 7/1/2007</ref> |
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Malachite green has been banned in the United States since 1983 in food-related applications. The substance is also banned in the United Kingdom.<ref>Veterinary Residues Committee. {{webarchive|url=https://web.archive.org/web/20120211234825/http://www.vmd.defra.gov.uk/vrc/Reports/annual.htm |date=2012-02-11 }}.</ref> It is prohibited from the use in food in Macao.<ref>{{Cite web | url=https://www.foodsafety.gov.mo/e/senseinspec/detail/c0f78a95-0827-4394-873c-8db1b8bcc21b | title=Food Safety Information - Prohibited Substances in Food }}</ref> |
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<!-- LogP of metabolite 4,4'-Benzylidenebis(N,N-dimethylaniline) was calculated using ] --> |
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Animals ] malachite green to its ] form. Being ] (the leuco form has a ] of 5.70), the ] is retained in ] muscle longer (] = 10 days) than is the parent molecule (HL = 2.8 days). |
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==Toxicity== |
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The {{LD50}} (oral, mouse) is 80 mg/kg.{{citation needed|date=March 2017}} Rats fed malachite green experience "a dose-related increase in liver ]" along with lung ]s. Leucomalachite green causes an "increase in the number and severity of changes". As leucomalachite green is the primary metabolite of malachite green and is retained in fish muscle much longer, most human dietary intake of malachite green from eating fish would be in the leuco form. During the experiment, rats were fed up to 543 ppm of leucomalachite green, an extreme amount compared to the average 5 ppb discovered in fish. After a period of two years, an increase in lung adenomas in male rats was discovered but no incidences of liver tumors. Therefore, it could be concluded that malachite green caused carcinogenic symptoms, but a direct link between malachite green and ] was not established.<ref>{{cite journal |first1= S J |last1= Culp |first2= FA |last2= Beland |first3= R H |last3= Heflich |first4= R W |last4= Benson |first5= L R |last5= Blankenship |first6= P J |last6= Webb |display-authors= 3 |journal= ] |date= 2002 |pages= 55–63 |doi= 10.1016/S0027-5107(02)00152-5 |title= Mutagenicity and carcinogenicity in relation to DNA adduct formation in rats fed leucomalachite green |volume= 506–507 |pmid= 12351145|url= https://zenodo.org/record/1259663 }}</ref> |
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==Detection== |
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Although malachite green has almost no fluorescence in aqueous solution (] 7.9x10<sup>−5</sup>),<ref name="Babendure Adams Tsien 2003 pp. 14716–14717">{{cite journal | last1=Babendure | first1=Jeremy R. | last2=Adams | first2=Stephen R. | last3=Tsien | first3=Roger Y. | title=Aptamers Switch on Fluorescence of Triphenylmethane Dyes | journal=Journal of the American Chemical Society | publisher=American Chemical Society (ACS) | volume=125 | issue=48 | year=2003 | issn=0002-7863 | doi=10.1021/ja037994o | pages=14716–14717| pmid=14640641 }}</ref> several research groups have developed technologies to detect malachite green. For example, Zhao et al., demonstrated the use of malachite green aptamer in microcantilever based sensors to detect low concentration of malachite green.<ref>Effect of Receptor Attachment on Sensitivity of Label Free Microcantilever Based Biosensor Using Malachite Green Aptamer https://doi.org/10.1016/j.snb.2019.126963</ref> |
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==References== |
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{{reflist}} |
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==Further reading== |
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* {{cite journal |first1= Bongsup P. |last1= Cho |first2= Tianle |last2= Yang |first3= Lonnie R. |last3= Blankenship |first4= Joanna D. |last4= Moody |first5= Mona |last5= Churchwell |first6= Frederick A. |last6= Beland |first7= Sandra J. |last7= Culp |display-authors= 3 |journal= Chem. Res. Toxicol. |volume= 16 |issue= 3 |pages= 285–294 |date= 2003 |title= Synthesis and Characterization of N-Demethylated Metabolites of Malachite Green and Leucomalachite Green |doi= 10.1021/tx0256679 |pmid= 12641428}} |
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* {{cite journal |first1= S. M. |last1= Plakas |first2= K. R. |last2= El Said |first3= G. R. |last3= Stehly |first4= W. H. |last4= Gingerich |first5= J. H. |last5= Allen |display-authors= 3 |journal= Can. J. Fish. Aquat. Sci. |volume= 53 |pages= 1427–1433 |date= 1996 |doi= 10.1139/cjfas-53-6-1427 |title= Uptake, tissue distribution, and metabolism of malachite green in the channel catfish (''Ictalurus punctatus'') |issue= 6}} |
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* Schoettger, 1970; Smith and Heath, 1979; Gluth and Hanke, 1983. Bills ''et al.'' (1977) |
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* {{cite journal |first1= Steven C. |last1= DeFina |first2= Thorsten |last2= Dieckmann |doi= 10.1002/jlcr.554 |title= Synthesis of selectively <sup>15</sup>N- or <sup>13</sup>C-labelled malachite green |date= 2002 |journal= Journal of Labelled Compounds and Radiopharmaceuticals |volume= 45 |pages= 241–248 |issue= 3}} |
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* {{cite journal |last1= Dhamgaye |first1= S |last2= Devaux |first2= F |last3= Manoharlal |first3= R |last4= Vandeputte |first4= P |last5= Shah |first5= AH |last6= Singh |first6= A |last7= Blugeon |first7= C |last8= Sanglard |first8= D |last9= Prasad |first9= R |display-authors= 3 |date= Jan 2012 |title= In vitro effect of malachite green on Candida albicans involves multiple pathways and transcriptional regulators UPC2 and STP2 |journal= Antimicrob Agents Chemother |volume= 56 |issue= 1 |pages= 495–506 |doi= 10.1128/AAC.00574-11 |pmc= 3256066 |pmid=22006003}} |
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==External links== |
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{{Commons category|Malachite green}} |
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