Safranin

CA Index Name Phenazinium, 3,7-diamino-2,8-di-methyl-5-phenyl-, chloride (1 1) 

Other Names C.I. Basic Red 2 Phenazinium, 3,7-dia-mino-2,8-dimethyl-5-phenyl-, chloride Safranine O 2,8-Dimethylphenosafranine 3,7-Diamino-2,8-dimethyl-5-phenylphenazinium chloride Basic Pink Basic Red 2 Brilliant Safranine BR Brilliant Safranine G Brilliant Safranine GR C.I. 50240 Calcozine Red Y Cotton Red Duasyn Basic Red TH Gossypimine Hidaco Safranine Leather Red HT Lowacryl Red 2 Lowacryl Red 2 Cone Mitsui Safranine T Nippon Kagaku Safranine GK Nippon Kagaku Safranine T Safranin Safranin O Safranin T Safranine Safranine A Safranine B Safranine G Safranine GF Safranine J Safranine OK Safranine OK 70 100 Safranine Superfine G Safranine T Safranine TH Safranine TN Safranine TS Safranine Y Safranine YN Safranine Zh Tolusafranine 

Physical Form Dark red to dark green powder 

Solubility Soluble in water, ethanol, ethylene glycol, 

Staining Applications Antigen bacteria brain cellulose lignin mitochondria nucleated and non-nucleated blood cells nucleic acids proteins spinal cord hairs  

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Saffron [138-55-6] Safimax Safi ex Safe an Safranin Safranine dyes Safranine T Safranine T [477-73-6] Safrole [94-59-7]... 

The addition of 2,2, 4,4, 6-pentanitro-6 -methyldiphenylamine [64653-47-0] to seawater precipitates potassium (38). Aromatic amines, especially aminotetrahydronaphthalenes and their A[-aryl derivatives, are efficient flotation agents for quartz. The use of DPA for image formation in films has been patented (39,40). Diarylamines are used as intermediates (41) for azo, sulfur, oxidative base, triaryhnethane, oxazine, nitro, and safranine dyes (see Dyes and DYE INTERLffiDIATES). 

Mauveine is in a group of azines termed safranine dyes ie, it is a A/-phenyl-phenazonium chloride. Although the stmctures of these dyes are often written to show a positive charge on a particular hetero atom, the charge is in fact distributed through resonance throughout the molecule, thus accounting for their deep color. 

Azine dyes are relatively unimportant as a class of dyes but are used extensively as biological stains. Colors are mostly yellow to red. DurabiUty of some of these dyes is supported by the 1990 LATCC Buyers Guide pubflshed by the American Association of Textile Chemists and Colorists, which fists Basic Red 2, Safranine T [477-73-6] (13) and Basic Red 5, Neutral Red [553-24-2] (14), discovered in 1859 and 1879, respectively (1). Basic Red 2 is a safranine similar to mauveine (7). 

Historically the phenazine dyes have played an important part in the dyestuffs industry, although their use has largely been superseded by the more modern, color-fast dyes, in particular those dyes which become chemically bonded to the fibers of the materials being dyed. Amongst the earliest examples of phenazine dyes are those compounds known as the safranines. The discovery of the safranines has been attributed to Greville Williams in 1859 and they were apparently in commercial use shortly after that date, but it was not until 1886 that it was recognized that phenosafranine (138) was indeed a phenazine containing system. 

Numerous dyes structurally related to the safranines, such as the eurodines, e.g. (141), the indulines, e.g. (142), the nigrosines (143) and aniline black, a pigment of unknown structure used in the printing industry, are well known and a detailed account of their chemistry and applications has been presented (57HC(ll)l). 

Saccharin, 2-methyl-reduction, 6, 152 Saccharin, 6-nitro-reduction, 6, 154 Saccharin, thio-hydrolysis, 6, 161 methylation, 6, 160 Safranines applications, 3, 196 Safrole derivatives toxicity, 1, 139-140 occurrence, 6, 781 Safrole, 1-hydroxy-toxicity, 1, 140 Salazosulfapyridine... 

Unloaded silica does not recover HPA from aqueous solution. The surface of silica gel modified with quarternary ammonium salts (QAS) gets anion-exchange properties. The aim of the work is the elaboration of solid-phase reagents on the base of ion associate of HPA with QAS immobilized onto silica surface for the determination of phosphoms and organic reductants. Heterocyclic (safranine and lucigenine) and aliphatic (trinonyloctadecyl ammonium iodide and tetradecyl ammonium nitrate) compounds have been examined as QAS. 

In this work hybrid method is suggested to determine anionic surfactants in waters. It is based on preconcentration of anionic surfactants as their ion associates with cationic dyes on the membrane filter and measurement of colour intensity by solid-phase spectrophotometry method. Effect of different basic dyes, nature and hydrophobicity of anionic surfactants, size of membrane filter pores, filtration rate on sensitivity of their determination was studied. Various cationic dyes, such as Methylene Blue, Crystal Violet, Malachite Green, Rhodamine 6G, Safranin T, Acridine Yellow were used as counter ions. The difference in reflection between the blank and the sample was significant when Crystal Violet or Rhodamine 6G or Acridine Yellow were used. 

Malachite green Metanil yellow Nigrosine Orange Y Paramido phenol Paraphenylendiamine Pyrogene violet brown Rosaniline Safranine... 

The indicator used is Safranine T with the following properties ... 

Figure 9 summarizes the electrode responses toward a variety of DNA-binding substrates [14c]. For intercalators (quinacrine, acridine orange, and safranin) and groove binders (spermine and spermidine), a steep rise followed by a saturation of the concentration response curve is commonly observed. If one compares the specific concentration which gives a 50% response in the increment of the cathodic peak current (A/p ) for each substrate, a selectivity order of quinacrine acridine orange > spermine > spermidine > safranin can be estimated. The binding constants measured in aqueous media for the affinity reaction with ds DNA are as follows quinacrine, 1.5 x 10 (38 mM NaCl)... 

If a section cut through a small sulfur-burned area of a lemon injured on the tree is examined microscopically, coagulation of protoplasm and cell collapse are apparent. Also, the injured tissue stains abnormally dark with safranin indicating the protoplasm has become more acidic than in normal tissue (18). Sides of the peel of lemons burned by sulfur on the tree were found to be higher in total sulfate than were uninjured sides of the same peel. The high total sulfate content of the peel was subsequently found to be due in part to soluble sulfate, as shown by analyses of the expressed cell solution (18). 

A modified method for determining Bayluscide in field trials was described by Strufe [59]. It involved the use of test kit containing safranin granulate and extracting with diethylcarbonate instead of ammonium acetate. The color reaction followed by a Zeiss-Ikon Polytest Colorimeter. 

Three methods for quantitative analysis of niclosamide at concentrations of 0.5-2.0 ppm were given. For in situ analysis, safranine dye solution was added to the sample and the extraction solution added which formed the upper phase. The niclosamide content was determined by the color intensity of the upper phase. The colors were compared with blanks of known concentration. When an accurate determination was required, niclosamide was extracted from the water sample with amylacetate, a methanol solution of sodium hydroxide was added to the extraction, and the resulting yellow color was measured at 385 mft in a spectrophotometer. Third method made use of a calibration curve [60],... 

The catalase-like activity of Fem-TAML activators does decrease in the presence of Safranine O (Fig. 16). The inset to Fig. 16 shows that the plot of the inverse rate vs. [Safranine O] is a straight line consistent with Eq. (23). 

Fig. 16. Retardation of the catalase activity of Fe-TAML activators by the dye Safranine O as an electron donor. Conditions [H202] 2.65 x 10-3 M [lk] 1.18 x 10 6M pH 10, 25°C. Inset shows that the rate of 02 evolution is inversely proportional to [Safranine O]. From Ref. (53).

The intercept and slope equal (k + km)lkikm and ku/ i m[H202], respectively. An estimate for the ratio ku/km is derived from the slope using the known value of k (e.g., 4.4 x 103M-1s-1 for lk). The kn/km ratio equals 52 for lk and indicates that the oxidized Fe-TAML is significantly more reactive to the ED, Safranine O, than to H202. This extremely important feature of the Fe-TAML activators eliminates unproductive decomposition of H202 in the oxidation of Safranine... 

Fig. 17. Kinetics of la-catalyzed bleaching of Safranine 0 (4.3 x 10-5M) by 0.012 M H2O2. Initial concentration of la (7.5 x 10-8 M) aliquots of the same amount of la were added after complete inactivation of the catalyst giving rise to the stepped dependence. The dashed line shows that addition of 0.012 M H2O2 does not resume the catalytic bleaching. Inset shows linearization of the data obtained after each addition of la in terms of Eq. (6) to give consistent values of k ( 3.3 x 10 3s 1). Conditions pH 11, 25°C. From Ref. (52).

The rate constants of kn and kx obtained using Eq. (24) reveal that (i) the activity of Fem-TAMLs in bleaching Safranine O (k ) increases more than 10-fold when the tail ethyl groups of la are replaced by fluorine atoms in lk. The rate constant kn for lk equals l(rM 1s 1 at 25°C, a value that corresponds to those found for the reactivity of horseradish peroxidase Compound II... 

Fig. 18. LFER between the rate constants k for bleaching Safranine 0 and ki for intramolecular inactivation in the series of head -substituted Fem-TAML catalysts with methyl tail groups. Conditions [H202] 0.012 M, 25°C, pH 11.0. The data point for la was ignored in the linear regression. From Ref. (52).

Fig. 19. (A) Simulated bleaching of a hypothetical dye using Eq. (24) at different concentrations of Feni-TAML catalyst (in M) with the rate constants ki (in s-1) and ku (in M-1s-1). The numerical values are indicated on the graph. (B) Normalized experimental and simulated bleaching of Safranine O (4.3 x 10-5M) by H202 (0.012 M) catalyzed by la at pH 11 and 25°C. Experimental data are shown as a and. The simulations, shown as solid lines, were made as in (A). From Ref. (52).

Fig. 19B shows the la-catalyzed bleaching of Safranine O at different [la] for comparison. The experimental and calculated curves agree and prove that complete bleaching of the dye is achievable by just increasing the la concentration. The required amount is still very low, specifically, 10-6 M for the difficult-to-oxidize dye Safranine O. 

A different approach is the combination of a Pt-carbonyl-cluster with a special dye, Safranine O (Saf 3,7-diamino-2,8-dimethyl-5-phenylphenazinium) in an aqueous/organic two-phase system [48]. The dye is reduced in the organic phase and subsequently, in a type of phase-transfer catalysis, it reduced the cofactor in the aqueous phase. In this example l-LDH is used as a production enzyme, reducing pyruvate to L-lactate (Scheme 43.6). Complete conversion was obtained within 48 h, the mixture containing pyruvate, NAD+ and the Pt-cluster catalyst in a 600 10 1 molar ratio. The TOF for NAD+ was 15 h-1. 

Gram Stain A staining procedure used in classifying bacteria. A bacterial smear on a slide is stained with a purple basic triphenyl methane dye, usually crystal violet, in the presence of iodine/potassium iodide. The cells are then rinsed with alcohol or other solvent, and then counter-stained, usually with safranin. The bacteria then appear purple or red according to their ability to keep the purple stain when rinsed with alcohol. This property is related to the composition of the bacterial cell wall. 

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