Eosin Y

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Eosin Y
Eosin Y.svg
Eosin Y 2.jpg
Names
IUPAC name
2-(2,4,5,7-tetrabromo-6-oxido-3-oxo-3H-xanthen-9-yl)benzoate [in its deprotonated form]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.037.629 OOjs UI icon edit-ltr-progressive.svg
MeSH Eosine+Yellowish-(YS)
PubChem CID
UNII
  • InChI=1S/C20H8Br4O5.2Na/c21-11-5-9-13(7-3-1-2-4-8(7)20(27)28)10-6-12(22)17(26)15(24)19(10)29-18(9)14(23)16(11)25;;/h1-6,25H,(H,27,28);;/q;2*+1/p-2 Yes check.svgY
    Key: SEACYXSIPDVVMV-UHFFFAOYSA-L Yes check.svgY
  • InChI=1/C20H8Br4O5.2Na/c21-11-5-9-13(7-3-1-2-4-8(7)20(27)28)10-6-12(22)17(26)15(24)19(10)29-18(9)14(23)16(11)25;;/h1-6,25H,(H,27,28);;/q;2*+1/p-2
    Key: SEACYXSIPDVVMV-NUQVWONBAJ
  • c1ccc(c(c1)c2c3cc(c(c(c3oc-4c(c(=O)c(cc24)Br)Br)Br)[O-])Br)C(=O)[O-].[Na+].[Na+]
Properties
C20H6Br4Na2O5
Molar mass 647.89052
AppearanceRed powder
Density 1.018 g·cm−3
Melting point 295.5 °C (563.9 °F; 568.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Eosin Y, also called C.I. 45380 [1] [2] or C.I. Acid Red 87, [2] [1] is a member of the triarylmethane dyes. It is produced from fluorescein by bromination. [3]

Contents

Use

Eosin Y is commonly used as the red dye in red inks.

It is commonly used in histology, most notably in the H&E (Haematoxylin and Eosin) stain. [1] Eosin Y is also widely used in the Papanicolaou stain (or Pap stain used in the Pap test) and the Romanowsky type cytologic stains. [1] [2] It is also used as a photosensitizer in organic synthesis. [4]

See also

Related Research Articles

Histology Study of the microscopic anatomy of cells and tissues of plants and animals

Histology, also known as microscopic anatomy or microanatomy, is the branch of biology which studies the microscopic anatomy of biological tissues. Histology is the microscopic counterpart to gross anatomy, which looks at larger structures visible without a microscope. Although one may divide microscopic anatomy into organology, the study of organs, histology, the study of tissues, and cytology, the study of cells, modern usage places all of these topics under the field of histology. In medicine, histopathology is the branch of histology that includes the microscopic identification and study of diseased tissue. In the field of paleontology, the term paleohistology refers to the histology of fossil organisms.

Acridine 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.

Haematoxylin Chemical compound

Haematoxylin or hematoxylin, also called natural black 1 or C.I. 75290, is a compound extracted from heartwood of the logwood tree with a chemical formula of C
16
H
14
O
6
. This naturally derived dye has been used as a histologic stain, ink and as a dye in the textile and leather industry. As a dye, haematoxylin has been called Palo de Campeche, logwood extract, bluewood and blackwood. In histology, haematoxylin staining is commonly followed (counterstained), with eosin, when paired, this staining procedure is known as H&E staining, and is one of the most commonly used combinations in histology. In addition to its use in the H&E stain, haematoxylin is also a component of the Papanicolaou stain which is widely used in the study of cytology specimens.

Eosin Groups of chemical compound used as dyes

Eosin is the name of several fluorescent acidic compounds which bind to and form salts with basic, or eosinophilic, compounds like proteins containing amino acid residues such as arginine and lysine, and stains them dark red or pink as a result of the actions of bromine on eosin. In addition to staining proteins in the cytoplasm, it can be used to stain collagen and muscle fibers for examination under the microscope. Structures, that stain readily with eosin, are termed eosinophilic. In the field of histology, Eosin Y is the form of eosin used most often as a histologic stain.

Dimethylaniline Chemical compound

N,N-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline. It consists of a tertiary amine, featuring 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.

Staining Technique used to enhance visual contrast of specimens observed under a microscope

Staining is a technique used to enhance contrast in samples, generally at the microscopic level. Stains and dyes are frequently used in histology and in the medical fields of histopathology, hematology, and cytopathology that focus on the study and diagnoses of disease at a microscopic level. Stains may be used to define biological tissues, cell populations, or organelles within individual cells.

Fluorescein Synthetic organic compound used as dye and fluorescent tracer

Fluorescein is an organic compound and dye. It is available as a dark orange/red powder slightly soluble in water and alcohol. It is widely used as a fluorescent tracer for many applications.

Malachite green Organic dye

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.

Crystal violet Triarylmethane dye used as a histological stain and in Grams method of classifying bacteria

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.

Acid dye

Acid dyes are anionic, soluble in water and are essentially applied from acidic bath. These dyes possess acidic groups, such as SO3H and COOH and are applied on wool, silk and nylon when ionic bond is established between protonated –NH2 group of fibre and acid group of dye. Overall wash fastness is poor although lightfastness is quite good. As dye and fibre contain opposite electrical nature, strike rate and uptake of acid dye on these fibres is faster; electrolyte at higher concentration is added to retard dye uptake and to form levelled shades. Acid generates cation on fibre and temperature helps to substitute negative part of acid with anionic dye molecules.

Pararosaniline Chemical compound

Pararosaniline, Basic Red 9, or C.I. 42500 is an organic compound with the formula [(H2NC6H4)3C]Cl. It is a magenta solid with a variety of uses as a dye. It is one of the four components of basic fuchsine. (The others are rosaniline, new fuchsine and magenta II.) It is structurally related to other triarylmethane dyes called methyl violets including crystal violet, which feature methyl groups on nitrogen.

Light green SF Chemical compound

Light green SF, also called C.I. 42095, light green SF yellowish, is a green triarylmethane dye.

Bismarck brown Y also called C.I. 21000 and C.I. Basic Brown 1, is a diazo dye with the idealized formula [(H2N)2C6H3N2]2C6H4. The dye is a mixture of closely related compounds. It was one of the earliest azo dyes, being described in 1863 by German chemist Carl Alexander von Martius. It is used in histology for staining tissues.

Papanicolaou stain Histological staining method

Papanicolaou stain is a multichromatic (multicolored) cytological staining technique developed by George Papanicolaou in 1942. The Papanicolaou stain is one of the most widely used stains in cytology, where it is used to aid pathologists in making a diagnosis. Although most notable for its use in the detection of cervical cancer in the Pap test or Pap smear, it is also used to stain non-gynecological specimen preparations from a variety of bodily secretions and from small needle biopsies of organs and tissues. Papanicolaou published three formulations of this stain in 1942, 1954, and 1960.

H&E stain Histological stain method

Hematoxylin and eosin stain is one of the principal tissue stains used in histology. It is the most widely used stain in medical diagnosis and is often the gold standard. For example, when a pathologist looks at a biopsy of a suspected cancer, the histological section is likely to be stained with H&E.

Xanthene Chemical compound

Xanthene (9H-xanthene, 10H-9-oxaanthracene) is the organic compound with the formula CH2[C6H4]2O. It is a yellow solid that is soluble in common organic solvents. Xanthene itself is an obscure compound, but many of its derivatives are useful dyes.

Triphenylmethanol 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.

Triarylmethane dyes are synthetic organic compounds containing triphenylmethane backbones. As dyes, these compounds are intensely colored. They are produced industrially as dyes.

Naphthol Green B Chemical compound

Naphthol Green B is a coordination complex of iron that is used as a dye.

Triphenylcarbenium

In chemistry, triphenylcarbenium, triphenylmethyl cation, tritylium , or trityl cation is an ion with formula [C
19
H
15
]+
or (C
6
H
5
)
3
C+
, consisting of a carbon atom with a positive charge connected to three phenyl groups. It is a charged version of the triphenylmethyl radical (C
6
H
5
)
3
C
. The name is often abbreviated to triphenylmethyl or trityl in salts, although these names also denote the chemical group in compounds like triphenylmethyl chloride that do not contain the cation.

References

  1. 1 2 3 4 Bancroft, John; Stevens, Alan, eds. (1982). The Theory and Practice of Histological Techniques (2nd ed.). Longman Group Limited.
  2. 1 2 3 Lillie, Ralph Dougall (1977). H. J. Conn's Biological stains (9th ed.). Baltimore: Williams & Wilkins. pp. 692p.
  3. Gessner, Thomas; Mayer, Udo (2000). "Triarylmethane and Diarylmethane Dyes". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a27_179.
  4. Diercxsens, Nicolas (2017-04-10), "Eosin Y", Encyclopedia of Reagents for Organic Synthesis, Chichester, UK: John Wiley & Sons, Ltd, pp. 1–3, doi:10.1002/047084289x.rn02033, ISBN   978-0-470-84289-8