View source for Chemistry:Brilliant green (dye)

{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 434149900
| ImageFile = Brilliant green (dye) Structural Formula V1.svg
| ImageSize = 150px
| Name = Brilliant green
| IUPACName =
| OtherNames = Malachite green G, Emerald green, Solid green JJO, Diamond green G, Aniline green, Benzaldehyde green, Fast green J
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 11941
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1181633
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 88173
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = G0L543D370
| InChI = 1/C27H33N2.H2O4S/c1-5-28(6-2)25-18-14-23(15-19-25)27(22-12-10-9-11-13-22)24-16-20-26(21-17-24)29(7-3)8-4;1-5(2,3)4/h9-21H,5-8H2,1-4H3;(H2,1,2,3,4)/q+1;/p-1
| InChIKey = NNBFNNNWANBMTI-REWHXWOFAJ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C27H33N2.H2O4S/c1-5-28(6-2)25-18-14-23(15-19-25)27(22-12-10-9-11-13-22)24-16-20-26(21-17-24)29(7-3)8-4;1-5(2,3)4/h9-21H,5-8H2,1-4H3;(H2,1,2,3,4)/q+1;/p-1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NNBFNNNWANBMTI-UHFFFAOYSA-M
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 633-03-4
| PubChem = 12449
| SMILES = [O-]S(=O)(=O)O.[N+](=C/1\C=C/C(C=C\1)=C(/c2ccccc2)c3ccc(N(CC)CC)cc3)(\CC)CC
}}
|Section2={{Chembox Properties
| Formula = [[Chemistry:Carbon|C]]<sub>27</sub>[[Chemistry:Hydrogen|H]]<sub>33</sub>[[Chemistry:Nitrogen|N]]<sub>2</sub>.H[[Chemistry:Oxygen|O]]<sub>4</sub>[[Chemistry:Sulfur|S]]
| MolarMass = 482.64 g/mol
| Appearance =
| Density =
| MeltingPtC = 210
| MeltingPt_notes = (decomposes)
| BoilingPt =
| Solubility = 100 g/L a 20 °C
  }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
 }}
}}

'''Brilliant green''' (also known as {{transl|ru|zelyonka}} or {{transl|uk|zelenka}}) is one of the [[Chemistry:Triarylmethane dye|triarylmethane dye]]s.  It is closely related to [[Chemistry:Malachite green|malachite green]].<ref name=gessner2002>{{citation | last1=Gessner | first1=T. | last2=Mayer | first2=U. | year=2002 | contribution= Triarylmethane and Diarylmethane Dyes | title= Ullmann's Encyclopedia of Industrial Chemistry 6th Edition | publisher=Wiley-VCH | place=Weinheim | doi=10.1002/14356007.a27_179 | isbn=3527306730 }}</ref>

==Uses==
[[File:Brilliant green 1a.jpg|thumb|left|150 px| {{transl|ru|Zelyonka}}]]
Brilliant green has been used to color [[Chemistry:Silk|silk]] and wool.

It is indicated for disinfection of fresh postoperative and post-traumatic scars, [[Biology:Umbilical cord|umbilical cord]] of newborns, abrasions, cuts, and other violations of the integrity of the skin, in the treatment of purulent-inflammatory processes of the skin - hordeolum ("barley"), meibomite, [[Medicine:Blepharitis|blepharitis]], pyoderma, local furunculosis, carbunculosis, [[Medicine:Staphylococcal infection|staphylococcal infection]].{{Citation needed|date=August 2020}} It is applied externally, the drug is applied to the damaged surface, capturing the surrounding healthy tissue.{{Citation needed|date=August 2020}}

In {{wipe|Russia}} and {{wipe|Ukraine}} (and much of the rest of the former Soviet Union), the dilute alcoholic solution of brilliant green is sold as a topical [[Chemistry:Antiseptic|antiseptic]], also known under a Latin name {{lang|la|solutio viridis nitentis spirituosa}} and the colloquial Russian name of {{transl|ru|zelyonka}} ({{wikt-lang|ru|зелёнка}}, {{literally|green thing}} in Russian),<ref>{{cite journal | doi = 10.1016/j.disamonth.2004.05.002| title = Dyes in dermatology| journal = Disease-a-Month| volume = 50| issue = 6| pages = 270| year = 2004| last1 = Balabanova| first1 = Maria| last2 = Popova| first2 = Liudmila| last3 = Tchipeva| first3 = Rositsa}}</ref>{{Failed verification|date=July 2019}} which is {{transl|uk|zelenka}} ({{wikt-lang|uk|зеленка}}) in Ukrainian.

A 1% solution in 60% alcohol can be used for treatment of skin. 0.5% solution is used for mucous membranes or for infants.<ref name="Narat1931"/>

Brilliant green is a visible light-activated photocatalyst in organic synthesis.<ref>{{Cite journal|last1=Rogers|first1=David A.|last2=Bensalah|first2=Adam T.|last3=Espinosa|first3=Alvaro Tomas|last4=Hoerr|first4=John L.|last5=Refai|first5=Fares H.|last6=Pitzel|first6=Amy K.|last7=Alvarado|first7=Juan J.|last8=Lamar|first8=Angus A.|date=2019-06-07|title=Amplification of Trichloroisocyanuric Acid (TCCA) Reactivity for Chlorination of Arenes and Heteroarenes via Catalytic Organic Dye Activation|journal=Organic Letters|language=en|volume=21|issue=11|pages=4229–4233|doi=10.1021/acs.orglett.9b01414|pmid=31140821|s2cid=169034253 }}</ref>

==Safety and toxicity==

Brilliant green is effective against [[Biology:Gram-positive bacteria|Gram-positive bacteria]].<ref>{{Cite journal|last=|first=|date=June 1984|title=Martindale: The extra pharmacopeia, 28th Ed. Edited By James E. F. Reynolds and Anne B. Prasad. The Pharmaceopeial Press, 1 Lamberth High Street, London, SE1 7JN. Distributed in the U.S. by Rittenhouse Book Distributors, Inc., King of Prussia, PA 19406. 1982.|url=http://dx.doi.org/10.1002/jps.2600730653|journal=Journal of Pharmaceutical Sciences|volume=73|issue=6|pages=862|doi=10.1002/jps.2600730653|issn=0022-3549|via=}}</ref> The main advantage of brilliant green over the more common antiseptics such as [[Chemistry:Iodine|iodine]] is that it does not irritate mucous membranes as harshly on accidental contact. Soviet medical doctrine deemed it "not for use on mucosa" and cautions that it can cause eye damage and ophthalmic chemical burns and burns to an eye, at least in the typical formulations produced for medical use.{{Citation needed|date=July 2019}}

Brilliant green induces vomiting when swallowed and is toxic when ingested.<ref name="Narat1931">{{cite journal | pmc = 1391517| year = 1931| last1 = Narat| first1 = J. K.| title = Brilliant Green: A Clinical Study of Its Value As a Local Antiseptic| journal = Annals of Surgery| volume = 94| issue = 6| pages = 1007–1012| doi=10.1097/00000658-193112000-00003| pmid=17866691}}</ref> The compound may lead to serious injuries if it comes in contact with an eye, even resulting in bilateral [[Medicine:Blindness|blindness]] due to corneal opacification.<ref>{{PubChem|12449}}</ref>

== Politics ==
{{main|Chemistry:Zelyonka attack}}
In {{wipe|Russia}} and sometimes in {{wipe|Ukraine}}, {{transl|ru|zelyonka}} has been used to physically attack political opponents.<ref>{{cite web|url=https://intpolicydigest.org/2017/05/06/how-the-soviet-era-antiseptic-zelyonka-became-a-political-weapon-in-russia-and-ukraine|title=How the Soviet-Era Antiseptic "Zelyonka" Became a Political Weapon in Russia and Ukraine|date=6 May 2017|publisher=|access-date=26 September 2017|archive-date=23 November 2020|archive-url=https://web.archive.org/web/20201123093230/https://intpolicydigest.org/2017/05/06/how-the-soviet-era-antiseptic-zelyonka-became-a-political-weapon-in-russia-and-ukraine/|url-status=dead}}</ref>  Since 2016, many opponents of the Russian government have been splashed with {{transl|ru|zelyonka}}, including Alexei Navalny, Igor Kalyapin, liberal activists, Nadya Tolokonnikova, Maria Alekhina, Lyudmila Ulitskaya, Ilya Varlamov and Mikhail Kasyanov.<ref>{{cite news | url = https://www.economist.com/blogs/economist-explains/2017/05/economist-explains-7 | title = Why are Russian opposition leaders' faces turning green? | newspaper = [[Finance:The Economist|The Economist]] | date = May 10, 2017 | access-date = May 11, 2017}}</ref>

==References==
<references />

[[Category:Triarylmethane dyes]]
[[Category:Antiseptics]]
[[Category:Staining dyes]]
[[Category:Anilines]]
[[Category:Diethylamino compounds]]

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{{Sourceattribution|Brilliant green (dye)}}