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{{For|the sodium sulfonate derivative|acid fuchsin}}
{{Distinguish|fuscin}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 402135077
| Watchedfields = changed
| ImageFile = Rosaniline hydrochloride.png
| verifiedrevid = 425367120
| ImageSize =
| ImageFile = Rosaniline hydrochloride.svg
| ImageSize = 200px
| ImageFileL1 = Sample of Basic Fuchsine.jpg
| ImageSizeL1 = 100px
| ImageNameL1 = Solid Basic Fuchsine
| ImageCaptionL1 = Solid basic fuchsine
| ImageFileR1 = Basic Fuchsine in aqueous solution.jpg
| ImageSizeR1 = 100px
| ImageNameR1 = Basic Fuchsine in aqueous solution
| ImageCaptionR1 = Basic fuchsine in aqueous solution
| IUPACName = 4-aniline hydrochloride | IUPACName = 4-aniline hydrochloride
| OtherNames = | OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8UUC89LHB2 | UNII = 8UUC89LHB2
| InChIKey = NIKFYOSELWJIOF-ZTQQLSIABC | InChIKey = NIKFYOSELWJIOF-SVFFXJIWBQ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C20H19N3.ClH/c1-13-12-16(6-11-19(13)23)20(14-2-7-17(21)8-3-14)15-4-9-18(22)10-5-15;/h2-12,21H,22-23H2,1H3;1H/p+1/b20-14-,21-17?; | StdInChI = 1S/C20H19N3.ClH/c1-13-12-16(6-11-19(13)23)20(14-2-7-17(21)8-3-14)15-4-9-18(22)10-5-15;/h2-12,21H,22-23H2,1H3;1H/b20-14-,21-17?;
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = NIKFYOSELWJIOF-SVFFXJIWSA-O | StdInChIKey = NIKFYOSELWJIOF-SVFFXJIWSA-N
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 632-99-5 | CASNo = 632-99-5
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=21106314 | ChemSpiderID = 10468578
| ChEBI_Ref = {{ebicite|correct|EBI}}
| PubChem =
| ChEBI = 87665
| SMILES = Cl.=C\1/C=C\C(C=C/1)=C(\c2ccc(N)c(C)c2)c3ccc(N)cc3
| PubChem = 12447
| InChI = 1/C20H19N3.ClH/c1-13-12-16(6-11-19(13)23)20(14-2-7-17(21)8-3-14)15-4-9-18(22)10-5-15;/h2-12,21H,22-23H2,1H3;1H/p+1/b20-14-,21-17?;
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| RTECS = 8053-09-6
| ChEMBL = 1979636
| EINECS = 209-321-2
| KEGG = C19252
| SMILES = .=C\1/C=C\C(C=C/1)=C(\c2ccc(N)c(C)c2)c3ccc(N)cc3
| InChI = 1/C20H19N3.ClH/c1-13-12-16(6-11-19(13)23)20(14-2-7-17(21)8-3-14)15-4-9-18(22)10-5-15;/h2-12,21H,22-23H2,1H3;1H/b20-14-,21-17?;
| RTECS = 8053-09-6
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>20</sub>H<sub>20</sub>N<sub>3</sub>·HCl | Formula = C<sub>20</sub>H<sub>19</sub>N<sub>3</sub>·HCl
| MolarMass = 337.86 g/mol (hydrochloride) | MolarMass = 337.86 g/mol (hydrochloride)
| Appearance = | Appearance = Dark green powder
| Density = | Density =
| MeltingPt = 200°C | MeltingPtC = 200
| BoilingPt = | BoilingPt =
| Solubility = 2650 mg/L (25°C) | Solubility = 2650 mg/L ({{convert|25|C}})
| LogP = 2.920 | LogP = 2.920
| VaporPressure = 7.49E-10 mm Hg (25°C) | VaporPressure = {{val|7.49|e=-10|u=mmHg}} (25 °C)
| HenryConstant = 2.28E-15 atm-m<sup>3</sup>/mole (25°C) | HenryConstant = {{val|2.28|e=-15|u=atm⋅m<sup>3</sup>/mole}} (25 °C)
| AtmosphericOHRateConstant = 4.75E-10 cm<sup>3</sup>/molecule-sec (25°C) | AtmosphericOHRateConstant = {{val|4.75|e=-10|u=cm<sup>3</sup>/molecule⋅sec}} (25 °C)
}}
| Section3 = {{Chembox Hazards
| MainHazards = Ingestion, inhalation, skin and eye contact, combustible at high temperature, slightly explosive around open flames and sparks.
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 0
| NFPA-O =
| FlashPt =
| Autoignition =
}} }}
|Section3={{Chembox Hazards
| MainHazards = Ingestion, inhalation, skin and eye contact, combustible at high temperature, slightly explosive around open flames and sparks.
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 0
| NFPA-S =
| FlashPt =
| AutoignitionPt =
}}
}} }}
'''Fuchsine''' or '''rosaniline hydrochloride''' is a ] ] with ] C<sub>20</sub>H<sub>19</sub>N<sub>3</sub>·HCl.<ref name="nih-basic">. ''Discovery Series'' online database, Developmental Therapeutics Program, U.S. National Institutes of Health. Retrieved on 2007-10-08.</ref><ref>Goyal, S.K. . ''Journal of Environmental Monitoring'', '''3''', 666-670, DOI: 10.1039/b106209n. Retrieved on 2007-10-08.</ref> There are other similar chemical formulations of products sold as fuchsine, and several dozen other synonyms of this molecule.<ref name="nih-basic" />


'''Fuchsine''' (sometimes spelled '''fuchsin''') or '''rosaniline hydrochloride''' is a ] ] with ] C<sub>20</sub>H<sub>19</sub>N<sub>3</sub>·HCl.<ref name="nih-basic">. ''Discovery Series'' online database, Developmental Therapeutics Program, U.S. National Institutes of Health. Retrieved on 2007-10-08.</ref><ref>Goyal, S.K. . ''Journal of Environmental Monitoring'', '''3''', 666–670, {{doi|10.1039/b106209n}}. Retrieved on 2007-10-08.</ref> There are other similar chemical formulations of products sold as fuchsine, and several dozen other synonyms of this molecule.<ref name="nih-basic" />
It becomes magenta when dissolved in ]; as a ], it forms dark ] ]s. As well as dying ]s, fuchsine is used to ] ] and sometimes as a ]. In the literature of biological stains the name of this dye is frequently misspelled, with omission of the terminal e, which indicates an amine<ref>Baker JR (1958) Principles of Biological Microtechnique. London: Methuen.</ref> American and English dictionaries (Webster's, Oxford, Chambers etc.) give the correct spelling, which is also used in the literature of industrial dyeing.<ref>Hunger K (2003) Industrial Dyes. Chemistry, Properties, Applications. Weinheim: wiley-VHC.</ref>

It becomes magenta when dissolved in ]; as a ], it forms dark ] ]s. As well as dying ]s, fuchsine is used to ] ] and sometimes as a ]. In the literature of biological stains the name of this dye is frequently misspelled, with omission of the ], which indicates an ].<ref>Baker JR (1958) Principles of Biological Microtechnique. London: Methuen.</ref> American and English dictionaries (Webster's, Oxford, Chambers, etc.) give the correct spelling, which is also used in the literature of industrial dyeing.<ref>Hunger K (2003) Industrial Dyes. Chemistry, Properties, Applications. Weinheim: wiley-VHC.</ref> It is well established that production of fuchsine results in development of bladder cancers by production workers. Production of magenta is listed as a ].<ref>{{cite book|title=MAGENTA AND MAGENTA PRODUCTION|year=2010|volume=99|series=IARC MONOGRAPHS ON THE EVALUATION OF CARCINOGENIC RISKS TO HUMANS|pages=297 to 324|url=http://monographs.iarc.fr/ENG/Monographs/vol99/mono99-12.pdf|access-date=January 12, 2013|author=|publisher=International Agency for Research on Cancer, World Health Organization|quote=Magenta production is carcinogenic to humans (Group 1).}}</ref>


==History== ==History==


Fuchsine, named by its original manufacturer Renard frères et Franc,<ref>Béchamp, M. A. (January–June 1860.) '']'', Mallet-Bachelier: Paris, tome 50, page 861. Retrieved on 2007-09-25.</ref> is usually cited with one of two etymologies: from the color of the flowers of the plant genus '']'',<ref name="fuchsin2004">(2004.) ''The American Heritage Dictionary of the English Language, Fourth Edition,'' ], via dictionary.com. Retrieved on 2007-09-20</ref> named in honor of botanist ], or as the German translation ''Fuchs'' of the French name Renard, which means fox.<ref> (Website.) ''ARTFL Project: 1913 Webster's Revised Unabridged Dictionary''. Retrieved on 2007-09-25</ref> An 1861 article in ''Répertoire de Pharmacie'' said that the name was chosen for both reasons.<ref>Chevreul, M. E. (July 1860). ''Répertoire de Pharmacie'', tome XVII, p. 62. Retrieved on 2007-09-25.</ref> Fuchsine was first created by ] in 1856 from ] and ].<ref>{{Cite web|url=https://edu.rsc.org/feature/the-battle-for-magenta/2020242.article|title=The battle for magenta}}</ref> In 1858 ] obtained it from ] and ].<ref>{{cite journal | doi = 10.1002/prac.18590770130 | first = August Wilhelm | last = von Hofmann | title = Einwirkung des Chlorkohlenstoffs auf Anilin. Cyantriphenyldiamin | year = 1859 | journal = Journal für Praktische Chemie | volume = 77 | pages = 190–191 }}</ref><ref>{{cite journal | title = Action of Bichloride of Carbon on Aniline | journal = Philosophical Magazine | year = 1858 | pages = 131–142 | first = August Wilhelm | last = von Hofmann | url = http://zs.thulb.uni-jena.de/receive/jportal_jpvolume_00057523?XSL.view.objectmetadata=false&jumpback=true&maximized=true&page=PMS_1859_Bd17_%200089.tif }}</ref> {{ill|François-Emmanuel Verguin|||fr}} discovered the substance independently of Hofmann the same year and patented it.<ref>{{cite journal |author=<!--Staff writer(s); no by-line.--> |year=1865 |title= Necrologie. Verguin|journal=Le Moniteur Scientifique du Docteur Quesneville: Journal des Sciences pures et appliquées |trans-journal=The Scientific Monitor of Doctor Quesneville: Journal of Pure and Applied Sciences |url={{Google books |plainurl=yes |id=z-MEAAAAQAAJ |page=42 }} |language=fr |location= Paris, France |pages= 42–46}}</ref> Fuchsine was named by its original manufacturer Renard frères et Franc,<ref>Béchamp, M. A. (January–June 1860.) '']'', Mallet-Bachelier: Paris, tome 50, page 861. Retrieved on 2007-09-25.</ref> is usually cited with one of two etymologies: from the color of the flowers of the plant genus '']'',<ref name="fuchsin2004">(2004.) ''The American Heritage Dictionary of the English Language, Fourth Edition,'' ], via dictionary.com. Retrieved on 2007-09-20</ref> named in honor of botanist ], or as the German translation ''Fuchs'' of the French name Renard, which means fox.<ref> {{webarchive|url=https://web.archive.org/web/20070928233032/http://humanities.uchicago.edu/orgs/ARTFL/forms_unrest/webster.form.html |date=2007-09-28 }} (Website.) ''ARTFL Project: 1913 Webster's Revised Unabridged Dictionary''. Retrieved on 2007-09-25</ref> An 1861 article in ''Répertoire de Pharmacie'' said that the name was chosen for both reasons.<ref>Chevreul, M. E. (July 1860). ''Répertoire de Pharmacie'', tome XVII, p. 62. Retrieved on 2007-09-25.</ref><ref>{{cite journal | jstor = 4027004 | pages = 45–63 | last1 = Belt | first1 = H. V. D. | title = Why Monopoly Failed: The Rise and Fall of Société La Fuchsine | volume = 25 | issue = 1 | journal = The British Journal for the History of Science | year = 1992 | doi = 10.1017/S0007087400045325 | last2 = Hornix | first2 = Willem J. | last3 = Bud | first3 = Robert | last4 = Van Den Belt | first4 = Henk | s2cid = 80725880 }}</ref>


==Acid fuchsine== ==Acid fuchsine==
'''Acid fuchsine''' is a mixture of homologues of basic fuchsin, modified by addition of ] groups. While this yields twelve possible isomers, all of them are satisfactory despite slight differences in their properties. ] is a mixture of homologues of basic fuchsine, modified by addition of ] groups. While this yields twelve possible isomers, all of them are satisfactory despite slight differences in their properties. {{citation needed|date=September 2012}}


==Basic fuchsine== ==Basic fuchsine==
'''Basic fuchsine''' is a mixture of rosaniline, ], ] and ].<ref>Horobin RW & Kiernan JA 20002. ''Conn's Biological Stains'', 10th ed. Oxford: BIOS, p.184-191</ref> Formulations usable for making of ] must have high content of pararosanilin. The actual composition of basic fuchsine tends to somewhat vary by vendor and batch, making the batches differently suitable for different purposes. '''Basic fuchsine''' is a mixture of rosaniline, ], ] and ].<ref>Horobin RW & Kiernan JA 20002. ''Conn's Biological Stains'', 10th ed. Oxford: BIOS, p. 184–191</ref> Formulations usable for making of ] must have high content of pararosanilin. The actual composition of basic fuchsine tends to somewhat vary by vendor and batch, making the batches differently suitable for different purposes.


In solution with ] as an accentuator it is called carbol fuchsin and is used for the staining of the bacterium which causes ].<ref>Clark G 1973 ''Staining Procedures Used by the ]'', 3rd ed. Baltimore: Williams & Wilkins, pp. 252-254</ref> In solution with ] (also called carbolic acid) as an ]<ref>{{Cite web |url=http://stainsfile.info/StainsFile/theory/accent.htm |title=StainsFile - Stain theory - Accentuators |access-date=2012-06-28 |archive-url=https://web.archive.org/web/20161003122706/http://stainsfile.info/StainsFile/theory/accent.htm |archive-date=2016-10-03 |url-status=dead }}</ref> it is called ] and is used for the ] and other similar ] staining of the ] which cause ], ] etc.<ref>Clark G 1973 ''Staining Procedures Used by the ]'', 3rd ed. Baltimore: Williams & Wilkins, pp. 252–254</ref> Basic fuchsine is widely used in biology to stain the ], and is also a component of Lactofuchsin, used for ]ing.

==Properties==
]-water ], ''centre'', and water, ''right'', on the streaks remaining on the paper after the 'crystals' were removed. The 'crystals' were then replaced and the photograph taken.]]

The crystals pictured at the right are of basic fuchsine, also known as basic violet 14, basic red 9, pararosanaline or ]. Their structure differs from the structure shown above by the absence of the ] on the upper ring, otherwise they are quite similar.

They are soft, with a ] of less than 1, about the same as or less than talc. They possess a strong metallic lustre and a green yellow color. They leave dark greenish streaks on paper and when these are moistened with a solvent, the strong magenta colour appears.

==Chemical structure==
Fuchsine is an amine salt and has three amine groups, two ] and a ]. If one of these is ] to form ABCNH<sup>+</sup>, the positive charge is delocalized across the whole symmetrical molecule due to pi cloud electron movement.

The positive charge can be thought of as residing on the central carbon atom and all three "wings" becoming identical ]s terminated by a primary amine group.{{clarify|date=November 2012}} Other ] structures can be conceived, where the positive charge "moves" from one amine group to the next, or one third of the positive charge resides on each amine group. The ability of fuchsine to be protonated by a stronger acid gives it its ] property. The positive charge is neutralized by the negative charge on the chloride ion. The positive "basic fuchsinium ions" and negative chloride ions stack to form the salt "crystals" depicted above.


==See also== ==See also==
* ] and ] are related dyes * ] and ] are related dyes
* Fuchsine is a component in the ] * Fuchsine is a component in the ]
* Fuchsine is now often used in the ] procedure in ]. * Fuchsine is now often used in the ] procedure in ].
* Basic Fuchsine is a component in the ]


==References== ==References==
{{Reflist}} {{Reflist}}

==Further reading==
* {{Cite EB1911|wstitle=Fuchsine|volume=11|page=273}} This provides a detailed account of early experimentation on related chemicals.


{{Stains}} {{Stains}}
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