サフラニン
WordNet
- any of a class of chiefly red organic dyes (同)safranin, saffranine
- a purplish red water-soluble dye used in microscopy
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/05/21 14:41:53」(JST)
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Safranin |
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Solid Safranin
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Safranin in aqueous solution
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Identifiers |
CAS number |
477-73-6 Y |
PubChem |
2723800 |
ChemSpider |
2005991 Y |
Jmol-3D images |
Image 1 |
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[Cl-].n1c4c([n+](c2c1cc(c(N)c2)C)c3ccccc3)cc(c(c4)C)N
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InChI=1S/C20H18N4.ClH/c1-12-8-17-19(10-15(12)21)24(14-6-4-3-5-7-14)20-11-16(22)13(2)9-18(20)23-17;/h3-11H,1-2H3,(H3,21,22);1H Y
Key: OARRHUQTFTUEOS-UHFFFAOYSA-N Y
InChI=1/C20H18N4.ClH/c1-12-8-17-19(10-15(12)21)24(14-6-4-3-5-7-14)20-11-16(22)13(2)9-18(20)23-17;/h3-11H,1-2H3,(H3,21,22);1H
Key: OARRHUQTFTUEOS-UHFFFAOYAR
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Properties |
Molecular formula |
C20H19ClN4 |
Molar mass |
350.84 g mol−1 |
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
Y (verify) (what is: Y/N?) |
Infobox references |
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Safranin (also Safranin O or basic red 2) is a biological stain used in histology and cytology. Safranin is used as a counterstain in some staining protocols, colouring all cell nuclei red. This is the classic counterstain in both Gram stains, and endospore staining. It can also be used for the detection of cartilage,[1] mucin and mast cell granules.
Safranin typically has the chemical structure shown at right (sometimes described as dimethyl safranin). There is also trimethyl safranin, which has an added methyl group in the ortho- position of the lower ring. Both compounds behave essentially identically in biological staining applications, and most manufacturers of safranin do not distinguish between the two. Commercial safranin preparations often contain a blend of both types.
Safranin is also used as redox indicator in analytical chemistry.
Safranines
Safranines are the azonium compounds of symmetrical 2,8-dimethyl-3,7-diamino-phenazine. They are obtained by the joint oxidation of one molecule of a para-diamine with two molecules of a primary amine; by the condensation of para-aminoazo compounds with primary amines, and by the action of para-nitrosodialkylanilines with secondary bases such as diphenylmetaphenylenediamine. They are crystalline solids showing a characteristic green metallic lustre; they are readily soluble in water and dye blue or violet. They are strong bases and form stable monacid salts. Their alcoholic solution shows a yellow-red fluorescence. Phenosafranine is not very stable in the free state; its chloride forms green plates. It can be readily diazotized, and the diazonium salt when boiled with alcohol yields aposafranine or benzene induline, C18H12N3. F. Kehrmann showed that aposafranine could be diazotized in the presence of cold concentrated sulfuric acid, and the diazonium salt on boiling with alcohol yielded phenylphenazonium salts. Aposafranone, C18H12N2O, is formed by heating aposafranine with concentrated hydrochloric acid. These three compounds are perhaps to be represented as ortho- or as para-quinones. The "safranine" of commerce is a ortho-tolusafranine. The first aniline dye-stuff to be prepared on a manufacturing scale was mauveine, which was obtained by Sir William Henry Perkin by heating crude aniline with potassium bichromate and sulfuric acid. Mauveine was converted to parasafranine (1,8-dimethyl Safranine) by Perkin in 1878 by oxidative/reductive loss of the 7-N-para-tolyl group.[2]
References
- ^ Rosenberg L (1971). "Chemical Basis for the Histological Use of Safranin O in the Study of Articular Cartilage" (abstract). J Bone Joint Surg Am. 53 (1): 69–82. PMID 4250366.
- ^ W. H. Perkin F.R.S. (1879). "LXXIV.—On mauveine and allied colouring matters". J. Chem. Soc., Trans. 35: 717–732. doi:10.1039/CT8793500717.
- This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press.
Stains
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Iron/Hemosiderin |
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Lipids |
- Sudan stain
- Sudan II
- Sudan III
- Sudan IV
- Oil Red O
- Sudan Black B
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Carbohydrates |
- Periodic acid-Schiff stain
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Amyloid |
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Bacteria |
- Gram staining
- Methyl violet/Gentian violet
- Safranin
- Ziehl–Neelsen stain/acid-fast
- Carbol fuchsin/Fuchsine
- Methylene blue
- Auramine-rhodamine stain
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Connective tissue |
- trichrome stain: Masson's trichrome stain/Lillie's trichrome
- Light Green SF yellowish
- Biebrich scarlet
- Phosphomolybdic acid
- Fast Green FCF
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Other |
- H&E stain
- Silver stain
- Grocott's methenamine silver stain
- Warthin–Starry stain
- Methyl blue
- Wright's stain
- Giemsa stain
- Gömöri trichrome stain
- Neutral red
- Janus Green B
- Alcian blue stain
- Movat's stain
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Tissue stainability |
- Acidophilic
- Basophilic
- Chromophobic
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International Chemical Identifier |
InChI= |
1/C20H18N4/c1-12-8-17-19(10-15(12)21)24(14-6-4-3-5-7-14)20-11-16(22)13(2)9-18(20)23-17/h3-11H,1-2H3,(H3,21,22)/p+1 |
InChIKey= |
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CASRN= |
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PIN= |
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UpToDate Contents
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English Journal
- Suppression of cartilage degeneration by intra-articular injection of heparan sulfate 6-O endosulfatase in a mouse osteoarthritis model.
- Otsuki S1, Murakami T2, Okamoto Y2, Hoshiyama Y2, Oda S2, Neo M2.
- Histology and histopathology.Histol Histopathol.2017 Jul;32(7):725-733. doi: 10.14670/HH-11-838. Epub 2016 Nov 3.
- PMID 27808352
- Histomorphology and Innate Immunity during the Progression of Osteoarthritis: Does Synovitis Affect Cartilage Degradation?
- Wang H1, Wang Q1, Yang M1, Yang L1, Wang W1, Ding H1, Zhang D1, Xu J1, Tang X2, Ding H2, Wang Q3.
- Journal of cellular physiology.J Cell Physiol.2017 May 17. doi: 10.1002/jcp.26011. [Epub ahead of print]
- PMID 28513840
- Inhibition of the TWEAK/Fn14 pathway attenuates autoimmune arthritis in a SKG mouse model.
- Park JS1, Kim SM1, Jung KA1, Lee J1,2, Kwok SK1,2, Cho ML3, Park SH1,4.
- Histology and histopathology.Histol Histopathol.2017 May;32(5):481-490. doi: 10.14670/HH-11-813. Epub 2016 Sep 20.
- PMID 27653285
Japanese Journal
- ゼラチンハイドロゲルシートによるPRP徐放投与の腱板修復促進効果
- Effect of cyclic compressive loading on redifferentiation of human chondrocytes in threedimensional cultured tissue
- 関節不安定性の制動が膝関節軟骨異化反応に及ぼす影響―組織学的・運動学的分析―
Related Links
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