Crystal violet
Names | |
---|---|
Preferred IUPAC name
4-{Bis[4-(dimethylamino)phenyl]methylidene}-N,N-dimethylcyclohexa-2,5-dien-1-iminium chloride | |
Other names
| |
Identifiers | |
3D model (
JSmol ) |
|
3580948 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard
|
100.008.140 |
EC Number |
|
KEGG | |
MeSH | Gentian+violet |
PubChem CID
|
|
RTECS number
|
|
UNII |
|
UN number | 3077 |
CompTox Dashboard (EPA)
|
|
| |
| |
Properties | |
C25H30ClN3 | |
Molar mass | 407.99 g·mol−1 |
Melting point | 205 °C (401 °F; 478 K) |
4 g/L at 25 °C[1] | |
Pharmacology | |
D01AE02 (WHO) G01AX09 (WHO) | |
Hazards | |
GHS labelling: | |
Danger | |
H302, H318, H351, H410 | |
P273, P280, P305+P351+P338, P501 | |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
|
1.2 g/kg (oral, mice) 1.0 g/kg (oral, rats)[2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
Crystal violet or gentian violet, also known as methyl violet 10B or hexamethyl pararosaniline chloride, is a
The name gentian violet was originally used for a mixture of methyl pararosaniline dyes (methyl violet), but is now often considered a synonym for crystal violet. The name refers to its colour, being like that of the petals of certain gentian flowers; it is not made from gentians or violets.
Production
A number of possible routes can be used to prepare crystal violet.
The dye can also be prepared by the condensation of formaldehyde and dimethylaniline to give a leuco dye:[3][4][7]
- CH2O + 3 C6H5N(CH3)2 → CH(C6H4N(CH3)2)3 + H2O
Second, this colourless compound is oxidized to the coloured cationic form (hereafter with oxygen, but a typical oxidizing agent is manganese dioxide, MnO2):
- CH(C6H4N(CH3)2)3 + HCl + 1⁄2 O2 → [C(C6H4N(CH3)2)3]Cl + H2O
Dye colour
Crystal violet (pH indicator) | ||
below pH −1.0 | above pH 2.0 | |
−1.0 | ⇌ | 2.0 |
When dissolved in water, the dye has a blue-violet colour with an
The different colours are a result of the different charged states of the dye molecule. In the yellow form, all three nitrogen atoms carry a positive charge, of which two are protonated, while the green colour corresponds to a form of the dye with two of the nitrogen atoms positively charged. At neutral pH, both extra protons are lost to the solution, leaving only one of the nitrogen atoms positive charged. The pKa for the loss of the two protons are approximately 1.15 and 1.8.[8]
In
Applications
Non-medical
Crystal violet is used as a textile and paper dye, and is a component of navy blue and black inks for printing, ball-point pens, and inkjet printers. It is sometimes used to colourize diverse products such as fertilizer, antifreeze, detergent, and leather.[citation needed]
The dye is used as a
When conducting
In biomedical research, crystal violet can be used to stain the nuclei of adherent cells.[11] In this application, crystal violet works as an intercalating dye and allows the quantification of DNA which is proportional to the number of cells.[citation needed]
In
In body piercing, gentian violet is commonly used to mark the location for placing piercings, including surface piercings.[citation needed]
Medical
Gentian violet has
- Marking the skin for surgery preparation and allergy testing;
- Treating jock itch);
- Treating impetigo; it was used primarily before the advent of antibiotics, but still useful to persons who may be allergic to penicillin.
In resource-limited settings, gentian violet is used to manage burn wounds,
Veterinary
Because of its antimicrobial activity, it is used to treat ich in fish. However, it usually is illegal to use in fish intended for human consumption.[22]
Biological research
Crystal violet can be used as an alternative to Coomassie brilliant blue (CBB) in staining of proteins separated by SDS-PAGE, reportedly showing a 5x improved sensitivity vs CBB.[23]
History
Synthesis
Crystal violet is one of the components of methyl violet, a dye first synthesized by Charles Lauth in 1861.[24] From 1866, methyl violet was manufactured by the Saint-Denis-based firm of Poirrier et Chappat and marketed under the name "Violet de Paris". It was a mixture of the tetra-, penta- and hexamethylated pararosanilines.[25]
Crystal violet itself was first synthesized in 1883 by Alfred Kern (1850–1893) working in Basel at the firm of Bindschedler and Busch.[6] To optimize the difficult synthesis which used the highly toxic phosgene, Kern entered into a collaboration with the German chemist Heinrich Caro at BASF.[5] Kern also found that by starting with diethylaniline rather than dimethylaniline, he could synthesize the closely related violet dye now known as C.I. 42600 or C.I. Basic violet 4.[26]
Gentian violet
The name "gentian violet" (or Gentianaviolett in German) is thought to have been introduced by the German pharmacist Georg Grübler, who in 1880 started a company in Leipzig that specialized in the sale of staining reagents for histology.[27][28] The gentian violet stain marketed by Grübler probably contained a mixture of methylated pararosaniline dyes.[29] The stain proved popular and in 1884 was used by Hans Christian Gram to stain bacteria. He credited Paul Ehrlich for the aniline-gentian violet mixture.[30] Grübler's gentian violet was probably very similar, if not identical, to Lauth's methyl violet, which had been used as a stain by Victor André Cornil in 1875.[31]
Although the name gentian violet continued to be used for the histological stain, the name was not used in the dye and textile industries.[32] The composition of the stain was not defined and different suppliers used different mixtures. In 1922, the Biological Stain Commission appointed a committee chaired by Harold Conn to look into the suitability of the different commercial products.[27] In his book Biological Stains, Conn describes gentian violet as a "poorly defined mixture of violet rosanilins".[32]
The German
In 1902, Drigalski and Conradi found that although crystal violet inhibited the growth of many bacteria, it has little effect on Bacillus coli (
Precautions
One study in mice demonstrated dose-related
"Like MG (malachite green), CV (crystal violet) is readily absorbed into fish tissue from water exposure and is reduced metabolically by fish to the leuco moiety, leucocrystal violet (LCV). Several studies by the National Toxicology Program reported the carcinogenic and mutagenic effects of crystal violet in rodents. The leuco form induces renal, hepatic and lung tumor in mice."[40][41]
In 2019, Health Canada found medical devices that use gentian violet to be safe for use but recommended to stop using all drug products that contain gentian violet, including on animals, causing Canadian engineering schools to revisit the usage of this dye during orientation.[42][43]
See also
References
- OCLC 911335305.
- PMID 5034986.
- ^ a b Colour Index 3rd Edition Volume 4 (PDF), Bradford: Society of Dyers and Colourists, 1971, p. 4391, archived from the original (PDF) on 2011-07-19
- ^ ISBN 978-3-527-30385-4
- ^ ISBN 0-7923-6602-6, archivedfrom the original on 2022-02-28, retrieved 2020-10-30
- ^ a b US 290856, Caro, H. & Kern, A., "Manufacture of dye-stuff", issued 1883
US 290891, Kern, A., "Manufacture of dye-stuff or coloring-matter", issued 1883
US 290892, Kern, A., "Manufacture of purple dye-stuff", issued 1883 - ISBN 978-0-471-48494-3[permanent dead link]. Also available from Scribd Archived 2012-11-04 at the Wayback Machine.
- ^ .
- PMID 70939.
- S2CID 28700868.
- PMID 24482381.
- PMID 7175462.
- ISSN 0361-0268.
- ISBN 978-1-77025-374-2, archivedfrom the original on 2021-07-14, retrieved 2021-07-14.
- PMID 2272286
- PMID 24118276.
- ^ Gorgas, Ferdinand J. S. (1901), "Pyoctanin – Methyl-Violet – Pyoctanine", Dental Medicine. A Manual Of Dental Materia Medica And Therapeutics, 7th edition, chestofbooks.com, archived from the original on 2011-07-08, retrieved 2011-03-15.
- PMID 24475556.
- PMID 24392520.
- PMID 21210170.
- ^ Berman, Stephen; Nyquist, Christine; Lynch, Julia A.; Gentile, Ángela. Module 5. Management of Prevalent Infections in Children Following a Disaster (PDF). American Association of Pediatrics. p. 22. Archived (PDF) from the original on 8 August 2014. Retrieved 24 July 2014.
- ^ Erdely, Holly; Sanders, Pascal. "5. Gentian violet – Food and Agriculture Organization" (PDF). Food and Agriculture Organization. Archived (PDF) from the original on 2017-08-30. Retrieved 2017-08-30.
Residues in food and their evaluations – Conditions of use
- S2CID 53944873.
- ^ Lauth, C. (1867), "On the new aniline dye, 'Violet de Paris'", Laboratory, vol. 1, pp. 138–139
- ^ Gardner, W. M., ed. (1915), The British coal-tar industry : its origin, development, and decline, Philadelphia: Lippincott, p. 173
- ^ US 290893, Kern, A., "Manufacture of dye-stuff or coloring-matter", issued 1883; Also available from Google.
- ^ from the original on 2022-02-28, retrieved 2022-02-13
- PMID 11615369
- S2CID 29539186
- ISBN 0-683-01705-5(Earlier editions were authored by H.J. Conn)
- ^ Cornil, V. (1875), "Sur la dissociation du violet de méthylaniline et sa séparation en deux couleurs sous l'influence de certains tissus normaux et pathologiques, en particulier par les tissus en dégénérescence amyloïde", Comptes Rendus de l'Académie des Sciences (in French), vol. 80, pp. 1288–1291, archived from the original on 2022-02-15, retrieved 2022-02-13
- ^ a b Conn, H.J. (1925), Biological stains: a handbook on the nature and uses of the dyes employed in the biological laboratory, Geneva, NY: Commission on Standardization of Biological Stains, pp. 68–69
- ^ Council on Pharmacy and Chemistry (1937), New and Nonofficial Remedies, Chicago: American Medical Association, pp. 210–211
- ^ Stilling, J. (1890), Anilin Farbstoffe als Antiseptica und ihre Anwendung in der Praxis (in German), Strassbourg: Mittheilung, archived from the original on 2022-02-13, retrieved 2022-02-13
- ^ R. L. Berrios, J. L. Arbiser: Novel antiangiogenic agents in dermatology. In: Archives of Biochemistry and Biophysics. 508.2, 2011, S. 222–226, doi:10.1016/j.abb.2010.12.016.
- S2CID 22908909
- PMID 19867569
- from the original on 2022-02-28, retrieved 2019-06-30
- ^ "Carcinogenic Potency Database (CPDB)". Archived from the original on 2020-06-08. Retrieved 2022-02-13.
- ^ Questions and Answers on FDA's Import Alert on Farm-Raised Seafood From China: What evidence is there that malachite green, gentian violet and nitrofuran cause cancer?, US Food and Drug Administration, 2009, archived from the original on 2010-05-28, retrieved 2010-08-18
- ^ How FDA Regulates Seafood (PDF), US Food and Drug Administration, 2007, archived (PDF) from the original on 2015-09-24, retrieved 2014-10-27
- ^ "Health Canada warns Canadians of potential cancer risk associated with gentian violet". Government of Canada. 2019-06-11. Archived from the original on 2019-07-13. Retrieved 12 July 2019.
- Canadian Press. Archivedfrom the original on 11 July 2019. Retrieved 12 July 2019.
Further reading
- "Methylrosanilinium chloride (gentian violet)", WHO model prescribing information: drugs used in skin diseases, Geneva: World Health Organization, 1997, p. 70, ISBN 92-4-140106-0.