Brilliant green (dye)

Last updated
Brilliant green
Brilliant green (dye) Structural Formula V1.svg
Names
Other names
Malachite green G, Emerald green, Solid green JJO, Diamond green G, Aniline green, Benzaldehyde green, Fast green J
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.010.174 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=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 Yes check.svgY
    Key: NNBFNNNWANBMTI-UHFFFAOYSA-M Yes check.svgY
  • 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
    Key: NNBFNNNWANBMTI-REWHXWOFAJ
  • [O-]S(=O)(=O)O.[N+](=C/1\C=C/C(C=C\1)=C(/c2ccccc2)c3ccc(N(CC)CC)cc3)(\CC)CC
Properties
C 27 H 33 N 2.HO 4 S
Molar mass 482.64 g/mol
Melting point 210 °C (410 °F; 483 K) (decomposes)
100 g/L a 20 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Brilliant green (also known as zelyonka or zelenka) is one of the triarylmethane dyes. It is closely related to malachite green. [1]

Contents

Uses

Zelyonka Brilliant green 1a.jpg
Zelyonka

Brilliant green has been used to color silk and wool.

It is indicated for disinfection of fresh postoperative and post-traumatic scars, 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, blepharitis, pyoderma, local furunculosis, carbunculosis, staphylococcal infection. [2] It is applied externally, the drug is applied to the damaged surface, capturing the surrounding healthy tissue.[ citation needed ]

In Russia and Ukraine (and much of the rest of the former Soviet Union), the dilute alcoholic solution of brilliant green is sold as a topical antiseptic, also known under a Latin name solutio viridis nitentis spirituosa and the colloquial Russian name of zelyonka ( зелёнка , lit.'green stuff' in Russian), [3] [ failed verification ] which is zelenka ( 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. [4]

Brilliant green is a visible light-activated photocatalyst in organic synthesis. [5]

Safety and toxicity

Brilliant green is effective against Gram-positive bacteria. [6] The main advantage of brilliant green over the more common antiseptics such as 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 ]

Brilliant green induces vomiting when swallowed and is toxic when ingested. [4] The compound may lead to serious injuries if it comes in contact with an eye, even resulting in bilateral blindness due to corneal opacification. [7]

Politics

In Russia and sometimes in Ukraine, zelyonka has been used to physically attack political opponents. [8] Since 2016, many opponents of the Russian government have been splashed with zelyonka, including Alexei Navalny, Igor Kalyapin, liberal activists, Nadya Tolokonnikova, Maria Alekhina, Lyudmila Ulitskaya, Ilya Varlamov and Mikhail Kasyanov. [9]

Related Research Articles

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Phenol is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group bonded to a hydroxy group. Mildly acidic, it requires careful handling because it can cause chemical burns.

<span class="mw-page-title-main">Acridine</span> Chemical compound

Acridine is an organic compound and a nitrogen heterocycle with the formula C13H9N. Acridines are substituted derivatives of the parent ring. It is a planar molecule that is structurally related to anthracene with one of the central CH groups replaced by nitrogen. Like the related molecules pyridine and quinoline, acridine is mildly basic. It is an almost colorless solid, which crystallizes in needles. There are few commercial applications of acridines; at one time acridine dyes were popular, but they are now relegated to niche applications, such as with acridine orange. The name is a reference to the acrid odour and acrid skin-irritating effect of the compound.

<span class="mw-page-title-main">Dimethylaniline</span> Chemical compound

N,N-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline. It is a tertiary amine, featuring a dimethylamino group attached to a phenyl group. This oily liquid is colourless when pure, but commercial samples are often yellow. It is an important precursor to dyes such as crystal violet.

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<span class="mw-page-title-main">Fluorescein</span> Synthetic organic compound used as dye and fluorescent tracer

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<span class="mw-page-title-main">Coomassie brilliant blue</span> Chemical compound

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<span class="mw-page-title-main">Rhodamine</span> Family of derivatives of xanthene used as dyes, indicators and fluorescent tracers

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Malachite green is an organic compound that is used as a dyestuff and controversially as an antimicrobial in aquaculture. Malachite green is traditionally used as a dye for materials such as silk, leather, and paper. Despite its name the dye is not prepared from the mineral malachite; the name just comes from the similarity of color.

<span class="mw-page-title-main">Triphenylmethane</span> Chemical compound

Triphenylmethane or triphenyl methane (sometimes also known as Tritan), is the hydrocarbon with the formula (C6H5)3CH. This colorless solid is soluble in nonpolar organic solvents and not in water. Triphenylmethane is the basic skeleton of many synthetic dyes called triarylmethane dyes, many of them are pH indicators, and some display fluorescence. A trityl group in organic chemistry is a triphenylmethyl group Ph3C, e.g. triphenylmethyl chloride (trityl chloride) and the triphenylmethyl radical (trityl radical).

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Crystal violet or gentian violet, also known as methyl violet 10B or hexamethyl pararosaniline chloride, is a triarylmethane dye used as a histological stain and in Gram's method of classifying bacteria. Crystal violet has antibacterial, antifungal, and anthelmintic (vermicide) properties and was formerly important as a topical antiseptic. The medical use of the dye has been largely superseded by more modern drugs, although it is still listed by the World Health Organization.

<span class="mw-page-title-main">Brilliant blue FCF</span> Chemical compound

Brilliant blue FCF is a synthetic organic compound used primarily as a blue colorant for processed foods, medications, dietary supplements, and cosmetics. It is classified as a triarylmethane dye and is known under various names, such as FD&C Blue No. 1 or acid blue 9. It is denoted by E number E133 and has a color index of 42090. It has the appearance of a blue powder and is soluble in water and glycerol, with a maximum absorption at about 628 nanometers. It is one of the oldest FDA-approved color additives and is generally considered nontoxic and safe.

<span class="mw-page-title-main">Eosin Y</span> Chemical compound

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<span class="mw-page-title-main">Triphenylmethanol</span> Chemical compound

Triphenylmethanol is an organic compound. It is a white crystalline solid that is insoluble in water and petroleum ether, but well soluble in ethanol, diethyl ether, and benzene. In strongly acidic solutions, it produces an intensely yellow color, due to the formation of a stable "trityl" carbocation. Many derivatives of triphenylmethanol are important dyes.

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<span class="mw-page-title-main">Chloroauric acid</span> Chemical compound

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<span class="mw-page-title-main">Polyhexanide</span> Pharmaceutical compound

Polyhexanide is a polymer used as a disinfectant and antiseptic. In dermatological use, it is spelled polihexanide (INN) and sold under various brand names. PHMB has been shown to be effective against Pseudomonas aeruginosa, Staphylococcus aureus, Escherichia coli, Candida albicans, Aspergillus brasiliensis, enterococci, and Klebsiella pneumoniae. Polihexanide, sold under the brand name Akantior is a medication used for the treatment of Acanthamoeba keratitis.

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<i>Zelyonka</i> attack Form of political protest in Russia and Ukraine

A zelyonka attack is a form of protest, provocation or violent assault, defined as throwing a solution of brilliant green, a triarylmethane antiseptic dye, on the body of a victim. On top of potential danger of vision loss, it is very hard to remove quickly; the complete natural removal may take up to a week. In the 2010s, zelyonka attacks became widespread in Russia and Ukraine by pro-government activists against anti-government political and other personalities.

References

  1. Gessner, T.; Mayer, U. (2002), "Triarylmethane and Diarylmethane Dyes", Ullmann's Encyclopedia of Industrial Chemistry 6th Edition, Weinheim: Wiley-VCH, doi:10.1002/14356007.a27_179, ISBN   3527306730
  2. "Malachite Green".
  3. Balabanova, Maria; Popova, Liudmila; Tchipeva, Rositsa (2004). "Dyes in dermatology". Disease-a-Month. 50 (6): 270. doi:10.1016/j.disamonth.2004.05.002.
  4. 1 2 Narat, J. K. (1931). "Brilliant Green: A Clinical Study of Its Value As a Local Antiseptic". Annals of Surgery. 94 (6): 1007–1012. doi:10.1097/00000658-193112000-00003. PMC   1391517 . PMID   17866691.
  5. Rogers, David A.; Bensalah, Adam T.; Espinosa, Alvaro Tomas; Hoerr, John L.; Refai, Fares H.; Pitzel, Amy K.; Alvarado, Juan J.; Lamar, Angus A. (2019-06-07). "Amplification of Trichloroisocyanuric Acid (TCCA) Reactivity for Chlorination of Arenes and Heteroarenes via Catalytic Organic Dye Activation". Organic Letters. 21 (11): 4229–4233. doi:10.1021/acs.orglett.9b01414. PMID   31140821. S2CID   169034253.
  6. "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". Journal of Pharmaceutical Sciences. 73 (6): 862. June 1984. doi:10.1002/jps.2600730653. ISSN   0022-3549.
  7. CID 12449 from PubChem
  8. "How the Soviet-Era Antiseptic "Zelyonka" Became a Political Weapon in Russia and Ukraine". 6 May 2017. Archived from the original on 23 November 2020. Retrieved 26 September 2017.
  9. "Why are Russian opposition leaders' faces turning green?". The Economist . May 10, 2017. Retrieved May 11, 2017.