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 (see Arene substitution pattern) 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.
Safranines are the azonium compounds of symmetrical 2,8-dimethyl-3,7-diaminophenazine. 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 red or violet. They are strong bases and form stable monacid salts. Their alcoholic solution shows a yellow-red fluorescence.[3]
Phenosafranine is not very stable in the free state[citation needed]; its chloride forms green plates[clarification needed]. It can be readily diazotized, and the diazonium salt when boiled with alcohol yields aposafranine or benzene induline, C18H12N3. Friedrich 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 an 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 dichromate and sulfuric acid.[3]
Mauveine was converted to parasafranine (1,8-dimethylsafranine) by Perkin in 1878 by oxidative/reductive loss of the 7N-para-tolyl group.[4] Another well known safranin is phenosafranine (C.I. 50200, 3,7-diamino-5-phenylphenazinium chloride) widely used as a histological dye, photosensitizer and redox probe.[5]
References
^ abcd"Safety Data Sheet: Safranin O" (PDF). LabChem. Retrieved 10 March 2016.
^Rosenberg L (1971). . J Bone Joint Surg Am. 53 (1): 69–82. doi:10.2106/00004623-197153010-00007. PMID 4250366. Archived from the original (abstract) on 2008-04-17.
^ abOne or more of the preceding sentences incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). "Safranine". Encyclopædia Britannica. Vol. 23 (11th ed.). Cambridge University Press. p. 1000.
^Zucca, Paolo; Vinci, Carla; Rescigno, Antonio; Dumitriu, Emil; Sanjust, Enrico (14 April 2010). "Is the bleaching of phenosafranine by hydrogen peroxide oxidation catalyzed by silica-supported 5,10,15,20-tetrakis-(sulfonatophenyl)porphine-Mn(III) really biomimetic?". Journal of Molecular Catalysis A: Chemical. 321 (1–2): 27–33. doi:10.1016/j.molcata.2010.01.015.
February 18, 2023
safranin, basic, biological, stain, used, histology, cytology, used, counterstain, some, staining, protocols, colouring, cell, nuclei, this, classic, counterstain, both, gram, stains, endospore, staining, also, used, detection, cartilage, mucin, mast, cell, gr. Safranin 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 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 2 mucin and mast cell granules Safranin Solid safranin Safranin in aqueous solutionNamesPreferred IUPAC name 3 7 Diamino 2 8 dimethyl 5 phenylphenazin 5 ium chlorideIdentifiersCAS Number 477 73 6 Y3D model JSmol Interactive imageChEBI CHEBI 33601 NChemSpider 2005991 YECHA InfoCard 100 006 836PubChem CID 2723800UNII XTX0YXU2HV YCompTox Dashboard EPA DTXSID60874047InChI 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 YKey OARRHUQTFTUEOS UHFFFAOYSA N YInChI 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 1HKey OARRHUQTFTUEOS UHFFFAOYARInChI 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 1SMILES Cl n1c4c n c2c1cc c N c2 C c3ccccc3 cc c c4 C NPropertiesChemical formula C 20H 19Cl N 4Molar mass 350 85 g mol 1Solubility in water SolubleHazardsGHS labelling Pictograms 1 Signal word Danger 1 Hazard statements H315 H318 1 Precautionary statements P264 P280 P302 P352 P305 P351 P338 P310 P332 P313 P362 1 NFPA 704 fire diamond 200Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references 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 see Arene substitution pattern 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 EditSafranines are the azonium compounds of symmetrical 2 8 dimethyl 3 7 diaminophenazine 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 red or violet They are strong bases and form stable monacid salts Their alcoholic solution shows a yellow red fluorescence 3 Phenosafranine is not very stable in the free state citation needed its chloride forms green plates clarification needed It can be readily diazotized and the diazonium salt when boiled with alcohol yields aposafranine or benzene induline C18H12N3 Friedrich 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 an 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 dichromate and sulfuric acid 3 Mauveine was converted to parasafranine 1 8 dimethylsafranine by Perkin in 1878 by oxidative reductive loss of the 7N para tolyl group 4 Another well known safranin is phenosafranine C I 50200 3 7 diamino 5 phenylphenazinium chloride widely used as a histological dye photosensitizer and redox probe 5 References Edit a b c d Safety Data Sheet Safranin O PDF LabChem Retrieved 10 March 2016 Rosenberg L 1971 Chemical Basis for the Histological Use of Safranin O in the Study of Articular Cartilage J Bone Joint Surg Am 53 1 69 82 doi 10 2106 00004623 197153010 00007 PMID 4250366 Archived from the original abstract on 2008 04 17 a b One or more of the preceding sentences incorporates text from a publication now in the public domain Chisholm Hugh ed 1911 Safranine Encyclopaedia Britannica Vol 23 11th ed Cambridge University Press p 1000 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 Zucca Paolo Vinci Carla Rescigno Antonio Dumitriu Emil Sanjust Enrico 14 April 2010 Is the bleaching of phenosafranine by hydrogen peroxide oxidation catalyzed by silica supported 5 10 15 20 tetrakis sulfonatophenyl porphine Mn III really biomimetic Journal of Molecular Catalysis A Chemical 321 1 2 27 33 doi 10 1016 j molcata 2010 01 015 Retrieved from https en wikipedia org w index php title Safranin amp oldid 1136787465, wikipedia, wiki, book, books, library,
