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Fuchsine
Solid Basic Fuchsine
Solid Basic Fuchsine
Solid basic fuchsine
Basic Fuchsine in aqueous solution
Basic Fuchsine in aqueous solution
Basic fuchsine in aqueous solution
Names
IUPAC name
4-[(4-Aminophenyl)-(4-imino-1-cyclohexa-2,5-dienylidene)methyl]aniline hydrochloride
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.010.173 Edit this at Wikidata
EC Number
  • 209-321-2
KEGG
RTECS number
  • 8053-09-6
UNII
  • InChI=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?; ☒N
    Key: NIKFYOSELWJIOF-SVFFXJIWSA-N ☒N
  • 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?;
    Key: NIKFYOSELWJIOF-SVFFXJIWBQ
  • [Cl-].[NH2+]=C\1/C=C\C(C=C/1)=C(\c2ccc(N)c(C)c2)c3ccc(N)cc3
Properties
C20H19N3·HCl
Molar mass 337.86 g/mol (hydrochloride)
Appearance Dark green powder
Melting point 200 °C (392 °F; 473 K)
2650 mg/L (25 °C (77 °F))
log P 2.920
Vapor pressure 7.49×10−10 mmHg (25 °C)
2.28×10−15 atm⋅m3/mole (25 °C)
Atmospheric OH rate constant
 4.75×10−10 cm3/molecule⋅sec (25 °C)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Ingestion, inhalation, skin and eye contact, combustible at high temperature, slightly explosive around open flames and sparks.
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Fuchsine (sometimes spelled fuchsin) or rosaniline hydrochloride is a magenta dye with chemical formula C20H19N3·HCl.[1][2] There are other similar chemical formulations of products sold as fuchsine, and several dozen other synonyms of this molecule.[1]

It becomes magenta when dissolved in water; as a solid, it forms dark green crystals. As well as dying textiles, fuchsine is used to stain bacteria and sometimes as a disinfectant. In the literature of biological stains the name of this dye is frequently misspelled, with omission of the terminal -e, which indicates an amine.[3] American and English dictionaries (Webster's, Oxford, Chambers, etc.) give the correct spelling, which is also used in the literature of industrial dyeing.[4] It is well established that production of fuchsine results in development of bladder cancers by production workers. Production of magenta is listed as a circumstance known to result in cancer.[5]

History

[edit]

Fuchsine was first created by Jakub Natanson in 1856 from aniline and 1,2-Dichloroethane.[6] In 1858 August Wilhelm von Hofmann obtained it from aniline and carbon tetrachloride.[7][8] François-Emmanuel Verguin [fr] discovered the substance independently of Hofmann the same year and patented it.[9] Fuchsine was named by its original manufacturer Renard frères et Franc,[10] is usually cited with one of two etymologies: from the color of the flowers of the plant genus Fuchsia,[11] named in honor of botanist Leonhart Fuchs, or as the German translation Fuchs of the French name Renard, which means fox.[12] An 1861 article in Répertoire de Pharmacie said that the name was chosen for both reasons.[13][14]

Usage

[edit]

In the 21st century, it remains useful for biological chemistry, particularly for detecting glycogenic material.[6]

Historically, after its discovery it became widely-used in the textile industry in the late 1800s and 1900s for dyeing fabrics pink, and also for dyeing foodstuffs, particularly red wine, despite health concerns.[15]

Acid fuchsine

[edit]

Acid fuchsine is a mixture of homologues of basic fuchsine, modified by addition of sulfonic groups. While this yields twelve possible isomers, all of them are satisfactory despite slight differences in their properties. [citation needed]

Basic fuchsine

[edit]

Basic fuchsine is a mixture of rosaniline, pararosaniline, new fuchsine and magenta II [Wikidata].[16] Formulations usable for making of Schiff reagent 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 phenol (also called carbolic acid) as an accentuator[17] it is called carbol fuchsin and is used for the Ziehl–Neelsen and other similar acid-fast staining of the mycobacteria which cause tuberculosis, leprosy etc.[18] Basic fuchsine is widely used in biology to stain the nucleus, and is also a component of Lactofuchsin, used for Lactofuchsin mounting.

Properties

[edit]
Basic fuchsine pieces. The two magenta stains on the paper were made by placing one drop of ethanol-water azeotrope, 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 CI 42500. Their structure differs from the structure shown above by the absence of the methyl group on the upper ring, otherwise they are quite similar.

They are soft, with a hardness 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

[edit]

Fuchsine is an amine salt and has three amine groups, two primary amines and a secondary amine. If one of these is protonated to form ABCNH+, 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 aromatic rings terminated by a primary amine group.[clarification needed] Other resonance 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 basic 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

[edit]

References

[edit]

Further reading

[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Fuchsine

View on Grokipedia
from Grokipedia
Fuchsine, also known as basic fuchsin or C.I. Basic Violet 14, is a synthetic characterized by its brilliant red-violet hue and C₂₀H₁₉N₃Cl. It appears as a dark green powder or metallic green crystals, is slightly soluble in but more soluble in alcohol, and decomposes above 392°F without a defined . First synthesized in 1856 by Polish chemist Jakub Natanson, and independently in 1859 by French chemist François-Emmanuel Verguin in through the oxidation of mixtures of and toluidines, fuchsine marked an early milestone in the synthetic industry following William Perkin's discovery of three years earlier. Verguin obtained a French for its production, naming it after the flower, and it quickly gained popularity for its vibrant color and fastness on and . Independent syntheses were reported around the same time by chemists like August Wilhelm von Hofmann with and , though Verguin's method enabled commercial-scale manufacturing. As a basic dye, fuchsine exhibits high water solubility and good light fastness but poorer wash fastness, making it suitable for applications on synthetic fibers, , , and wood. Its primary uses include dyeing for reds, purples, and browns; biological staining in and , such as in the Ziehl–Neelsen stain for acid-fast ; and as a or agent in medical contexts. Additionally, it serves as a filter dye in and a in chemical laboratories. Despite its historical significance, modern concerns over its potential and carcinogenicity have led to restrictions in some applications, prompting research into safer alternatives.

Introduction and Properties

Definition and Nomenclature

Fuchsine is a synthetic magenta-colored classified within the triarylmethane family, typically encountered as the hydrochloride salt with the general molecular \ceC20H19N3⋅HCl\ce{C20H19N3 \cdot HCl}. This compound represents one of the earliest artificial derived from derivatives, marking a pivotal shift from natural pigments to industrially produced colorants through . In its basic form, fuchsine acts as a cationic , characterized by its positively charged that enables strong binding to negatively charged substrates. The nomenclature of fuchsine encompasses several historical and commercial synonyms, including rosaniline hydrochloride, magenta I, and red, reflecting its composition as a primarily of rosaniline and homologues. These names highlight its origins in -based chemistry and its vivid red hue. An alternative spelling, "fuchsin," is also commonly used, particularly in . The of "fuchsine" traces back to its resemblance to the color of the flower, with the name coined by French chemist François-Emmanuel Verguin upon its discovery in 1859. Shortly thereafter, it was renamed "" to honor the French victory at the in June 1859, linking the dye's nomenclature to both botanical inspiration and a significant military event. This dual naming convention underscores fuchsine's role as a landmark in dye chemistry, distinguishing it as a purely synthetic entity without natural precedents.

Physical and Chemical Properties

Fuchsine, in its solid form as the salt, appears as a dark crystalline . When dissolved in , it produces a deep magenta-colored solution, characteristic of its nature. The compound exhibits high in polar solvents such as (approximately 4 g/L at 25°C) and (up to 30 g/L at 25°C), but it is insoluble in non-polar solvents like . This profile facilitates its use in aqueous and alcoholic solutions. Fuchsine demonstrates sensitivity to light and oxidizing agents, which can lead to decolorization through photochemical oxidation or reduction to leuco-bases. It also shows pH-dependent color variations, transitioning from to between pH 1.0 and 3.1, and becoming colorless in strongly basic environments. The melting point is approximately 250°C, at which point it decomposes. The molecular weight of the hydrochloride form is 337.85 g/mol. In terms of spectral properties, fuchsine in has an absorption maximum at approximately 543 nm, accounting for its vivid hue. Regarding , fuchsine is a potential irritant to and eyes, necessitating the use of protective gloves, , and adequate ventilation during handling. It is classified as a possible human () based on sufficient evidence in experimental animals.

Chemical Aspects

Molecular Structure

Fuchsine, commonly referred to as basic fuchsin, belongs to the triarylmethane class of dyes and features a core structure consisting of a central carbon atom bonded to three phenyl rings, each substituted with amino groups at the para positions relative to the central carbon. In the leuco (colorless) form, this is a derivative, but the intensely colored cationic form predominant in solution involves delocalization where the central carbon becomes planar and sp² hybridized, with one phenyl ring transforming into a quinoid structure bearing an group. This configuration is exemplified by , described structurally as 4-[bis(4-aminophenyl)methylidene]cyclohexa-2,5-dien-1-iminium. The molecular formula of the free base for rosaniline, a key component, is C20H19N3C_{20}H_{19}N_3, while pararosaniline has C19H17N3C_{19}H_{17}N_3; the hydrochloride salt, widely used, is protonated as C20H19N3+Cl−C_{20}H_{19}N_3^+ Cl^- for rosaniline hydrochloride. Fuchsine is not a single compound but a mixture of isomeric triarylmethane homologues, primarily pararosaniline (lacking a methyl substituent on the quinoid ring) and rosaniline (bearing a methyl group at the meta position of the quinoid ring), along with minor variants such as magenta II (methyl on one peripheral ring) and new fuchsin (methyls on two peripheral rings). These isomers differ in the degree and position of methylation on the aromatic rings but share the same triarylmethane backbone with primary amino (-NH₂) substituents. The vibrant color of fuchsine stems from the formed by the extended conjugation across the three aromatic systems in the resonance-stabilized cationic form, where electron delocalization from the amino donors to the central acceptor enhances visible absorption. This is central to the dye's classification within the triarylmethane family, enabling its applications as a histological and colorant.

Synthesis and Production

The original synthesis of fuchsine, also known as magenta or rosaniline , involves the oxidation of a mixture of , ortho-toluidine, and para-toluidine, along with their hydrochlorides, in the presence of or at elevated temperatures around 180–200°C. This forms the triarylmethane framework, with nitrobenzene acting as both solvent and oxidant, often catalyzed by iron salts such as ferrous chloride or ferric chloride. Alternatively, arsenic acid was historically used in place of nitrobenzene for the initial heating step with aniline hydrochloride. The key reaction pathway begins with the formation of a leuco base through the condensation of an aromatic aldehyde intermediate—derived from the oxidation of aniline—with additional aniline and toluidine molecules, yielding a colorless triarylmethane precursor. This leuco base is then oxidized, typically with agents like sodium dichromate or potassium chlorate in hydrochloric acid, first to the carbinol base and subsequently to the colored quinoid dye structure. For pararosaniline, the unsubstituted analog, the overall process can be simplified as 3\ceC6H5NH2+3 \ce{C6H5NH2} + oxidizing agent →\rightarrow pararosaniline, though practical syntheses incorporate toluidines to produce the commercial fuchsine mixture. In industrial production, modern methods rely on controlled oxidation of and mixtures using and metal chloride catalysts under conditions, followed by acidification and to isolate the crude dye. Purification occurs through recrystallization from hot solutions, resulting in the soluble salt form that is the standard commercial product. Traditional arsenic acid-based processes achieved yields of 25–42%, while optimized contemporary approaches have improved efficiency, though specific modern yields are not widely reported; historical production scales reached tens of tonnes annually in facilities like those in the during the mid-20th century. The historical reliance on arsenic acid in fuchsine manufacturing has been phased out since the late due to its toxicity and associated health risks, including links to occupational among workers. Current eco-friendly alternatives emphasize nitrobenzene-based oxidations with enhanced catalyst systems and waste minimization, reducing environmental discharge of aromatic amines and while maintaining purity above 90% in commercial grades.

Variants

Basic Fuchsine

Basic fuchsine, also known as basic magenta, is the primary non-sulfonated form of the fuchsine dye family, consisting of a mixture of rosaniline hydrochloride (C20H19N3·HCl), pararosaniline hydrochloride (C19H17N3·HCl), magenta II, and new fuchsine. This mixture forms a cationic dye where the positive charge resides on the triarylmethane , enabling electrostatic interactions with negatively charged substrates. It is prepared directly through the oxidation of and hydrochlorides, typically using oxidizing agents such as stannic chloride or under acidic conditions, without the introduction of groups that characterize the acid variant. Unlike the anionic acid fuchsine, basic fuchsine binds preferentially to acidic tissue components due to its cationic nature, making it suitable for applications requiring strong basic staining properties. Commercial grades of basic are standardized by metrics such as content (typically >85% by titanometry), color intensity (absorption maximum around 540 nm), and in or , with the Colour Index designation CI 42510. In solution, it exhibits pH-dependent behavior: in alkaline conditions, the proton is lost to form a colorless carbinol base, which reverts to the characteristic color upon acidification.

Acid Fuchsine

Acid fuchsine is a sulfonated derivative of basic fuchsine, consisting of a mixture of sulfonated rosaniline homologues, primarily as disodium salts with the representative formula C20_{20}H17_{17}N3_{3}Na2_{2}O9_{9}S3_{3}. This anionic dye arises from the introduction of sulfonic acid groups (-SO3_{3}H), typically two to three per molecule, rendering it water-soluble without the need for chloride counterions associated with the basic form. The preparation involves treating basic fuchsine with fuming () to facilitate sulfonation, adding the SO3_{3}H groups to the aromatic rings, followed by neutralization with to form the sodium salts. This process can yield up to twelve possible isomers from the four basic fuchsine homologues (, rosaniline, magenta II, and new fuchsine), each potentially bearing one to three sulfonic groups, though commercial products are variable mixtures rather than pure isomers. It is classified under Colour Index number 42685 and often supplied at lower purity levels (e.g., ≥60% dye content) suitable for histological staining applications. Key properties include high water solubility (approximately 14 g/100 mL) and a range of 3-4 in , with a magenta-red color and absorption maximum around 546 nm. As an anionic , it preferentially stains acidic tissue structures such as fibers, binding via electrostatic interactions with positively charged sites. The sulfonic groups reduce its metachromatic tendencies compared to the basic form, minimizing color shifts in staining and enhancing specificity for acidophilic components. Due to its hydrosoluble nature, acid fuchsine serves as a xylem-mobile dye in plant physiology studies, distributing with water via transpiration to visualize ascending flow in the xylem and demonstrate the trajectory of captured water to and within leaves; see the Applications section for further details.

History

Discovery and Early Research

Fuchsine, the first synthetic dye produced in , was discovered in by the François-Emmanuel Verguin while working in . Building on William Henry Perkin's groundbreaking synthesis of in 1856, Verguin experimented with the oxidation of , initially using stannic chloride as the oxidizing agent to produce a vibrant magenta-colored compound from derivatives. This marked a significant advancement in , as Verguin's method yielded a more stable and brilliant red hue compared to earlier attempts, though he later refined the process using cheaper oxidants like to achieve yields of 25-42% fuchsine hydrochloride. Verguin initially named the dye "fuchsine," drawing from the flower of the plant, which reflected its striking pinkish-red color, and he patented it in 1859. In English-speaking regions, it became known as "magenta" to honor the French victory at the in June 1859 during the Second , a naming choice that quickly popularized the dye internationally. Independently, German chemist August Wilhelm von Hofmann had obtained a similar crimson product earlier in 1858 by reacting with , but his version remained impure and unrefined for practical use. Early research on fuchsine revealed significant challenges, as the dye was not a single compound but an impure mixture of homologues derived from and toluidines, leading to inconsistencies in color and . Researchers identified as a primary component, a key triarylmethane derivative responsible for the dye's intense coloration, though separating it from contaminants like residues—up to 6% from the method—proved difficult. In the 1870s, brothers and Otto Fischer provided crucial insights by elucidating the molecular structures of fuchsine and related compounds, confirming their triarylmethane nature through systematic degradation and synthesis experiments in . Their work laid the foundation for understanding the dye's chemistry, resolving earlier uncertainties about its composition.

Commercialization and Industrial Impact

Following the discovery of fuchsine in 1858, François-Emmanuel Verguin partnered with the dyers Renard frères et , who secured a French for its production process on April 8, 1859, marking the onset of commercial manufacturing in a dedicated factory in . This covered not only the synthesis but also its application in and , enabling rapid scale-up from laboratory experiments to industrial output. The dye, initially named after the flower and later associated with the 1859 , quickly transitioned into a key product for the emerging synthetic colorants sector. By the early 1860s, production spread globally as German firms, including precursors to and Hoechst, began manufacturing fuchsine despite the French patent, dominating the market through efficient processes and exports to and the . , founded in 1865, built on earlier efforts from 1861 to produce fuchsine as one of its initial dyes, while Hoechst launched with magenta as its first product, contributing to Germany's capture of approximately 50% of world synthetic dye production by 1870. This expansion ignited a boom in the synthetic industry, transforming coal-tar derivatives into a multi-million-mark sector by the and laying the groundwork for modern chemical manufacturing. Intense legal disputes, dubbed the "Battle for Magenta," erupted between French patentees like Renard and Verguin and competing producers in Germany and England from 1859 to 1865, centering on process infringements and resolved in favor of English firms through court rulings that clarified scopes. These lawsuits highlighted the challenges of enforcing s amid rapid , ultimately spurring further international competition. Fuchsine production peaked in the late but declined as superior synthetic reds emerged and toxicity concerns, including residues from early methods, limited its use; the French monopoly firm Société La Fuchsine collapsed in the due to overcapitalization and internal strife. Today, commercial output is restricted to niche applications like , yet fuchsine's legacy endures as a foundational milestone in dye chemistry, influencing the development of safer, scalable .

Applications

Histological and Biological Uses

Fuchsine, particularly in its variant, serves as the primary stain in the Ziehl-Neelsen method for detecting acid-fast bacilli, such as , where it imparts a red color to the lipid-rich cell walls of these after heat application to facilitate dye penetration. This technique differentiates acid-fast organisms, which retain the dye despite decolorization with acid-alcohol, from non-acid-fast that counterstain blue with . In histological applications, basic fuchsine stains cell nuclei by targeting DNA, as seen in the Feulgen reaction where acid hydrolysis exposes aldehyde groups on deoxyribose, allowing selective binding to produce a magenta color specific to chromatin. Acid fuchsine, conversely, is employed in the Van Gieson method to stain collagen fibers bright red, providing contrast against yellow-stained muscle and cytoplasm from picric acid, which aids in visualizing connective tissue architecture. The staining mechanism of fuchsine relies on electrostatic interactions: the cationic basic form binds to negatively charged phosphate groups in DNA and RNA, while the anionic acid form attaches to positively charged amino groups in proteins like collagen via ionic and hydrogen bonding. In collagen, acid fuchsine forms hydrogen bonds with the fibrous structure, enabling rapid dye exchange, whereas cytoplasmic proteins favor hydrophobic interactions that slow diffusion. Standard protocols require preparation of stock solutions, such as 1 g basic fuchsine dissolved in 200 mL boiling for Schiff's reagent, cooled and treated with HCl and metabisulfite to decolorize, or a 0.1% solution in 100 mL for general use; tissues must be fixed, typically with formalin for or heat-fixed smears for , to preserve structure before staining. Biologically, the Ziehl-Neelsen method using is essential for tuberculosis diagnosis, enabling rapid detection of acid-fast in smears to initiate treatment and monitor efficacy in resource-limited settings. Additionally, basic fuchsine exhibits in , shifting from red to purple upon binding polyanionic glycosaminoglycans in the matrix, which highlights extracellular components in connective tissues. also serves as a and agent in medical applications, such as treating infections due to its phenolic components enhancing antimicrobial activity. In plant physiology, acid fuchsin is utilized as a hydrosoluble tracer to visualize water movement within the xylem. Its solubility in water allows it to distribute with the transpiration stream, enabling the observation of ascending flow and the trajectory of captured water to and within leaves. Typically prepared as a 0.1% aqueous solution, the dye is infused into stems or roots and moves rapidly through conductive vessels, staining them red for microscopic analysis of water-conducting pathways.

Textile and Industrial Applications

Fuchsine, particularly in its basic form, has been traditionally employed in the textile industry for dyeing protein fibers such as silk and wool, where it imparts vibrant red-violet shades. The process typically involves preparing a dye bath with the fiber immersed in a solution containing 1-2% basic fuchsine (on weight of fiber) in an acidic medium, such as acetic acid, to promote dye uptake. Dyeing occurs by entering the material at 60°C and gradually raising the temperature to 80°C for 30-60 minutes. Light fastness of fuchsine-dyed textiles is moderate, often fading under prolonged exposure, but can be improved through after-treatments such as chroming with sodium bichromate or , which form more stable complexes with the . Acid fuchsine, a sulfonated variant, allows for direct without mordants on these fibers, simplifying the process while achieving similar red hues with better in acidic baths. In modern textile applications, basic fuchsine remains in limited use for specialty and colorations, though its overall role has diminished due to stability issues. For and , fuchsine variants are used for producing shades through direct application, bypassing mordants and enabling straightforward immersion or brushing at temperatures of 25-60°C. On , it is applied in neutral or slightly acidic baths, followed by rinsing and oiling for suppleness, while on , it serves as a for vibrant tinting in substrates. These uses leverage fuchsine's strong affinity for in and cellulosic materials in , though emphasizes short contact times to avoid over-staining. Beyond materials coloring, fuchsine finds industrial roles in ink formulations, where basic fuchsine provides intense pigmentation for applications, and as a in processes requiring color change detection between 1.0 and 3.1 ( to ). Its use in is minor, primarily in temporary hair dyes or formulations needing stabilization for product integrity. In contemporary industry, fuchsine has been largely supplanted by more stable azo dyes for broad and needs, but persists in niche areas such as testing for penetration and specialty s. Additionally, basic fuchsine is used as a filter in to absorb green light and enhance red-violet tones, and as a reagent in for detecting aldehydes via the .

References

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  49. https://www.bloomtechz.com/chemical-reagent/laboratory-reagent/basic-fuchsin-dye-cas-632-99-5.html
  50. https://www.sciencedirect.com/science/article/abs/pii/S1572665720310213
  51. https://www.avantorsciences.com/us/en/product/46818152/basic-fuchsin-indicator-ph-10-31
  52. https://pubmed.ncbi.nlm.nih.gov/31060332/
  53. https://www.mdpi.com/2076-3417/11/14/6255
  54. https://www.sigmaaldrich.com/US/en/product/sial/b0904
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