2.4- Dinitrophenylhydrazine deriv

Ekstrom T, Warholm M, Kronevi T, et al. 1988. Recovery of malondialdehyde in urine as a 2,4-dinitrophenylhydrazine derivative after exposure to chloroform or hydroquinone. Chem Biol Interact 67 25-31. 

Sample extract buffered to pH 3 and derivatized with 2,4-dinitrophenylhydrazine derivative extracted and determined by UV at 360 nm... 

Cordis, G.A., Das, D.K., and Riedel, W. 1998a. High-performance liquid chromato-graphic peak identification of 2,4-dinitrophenylhydrazine derivatives of lipid peroxidation aldehydes by photodiode array detection. J. Chromatogr. 798 117-123. 

Investigation of the chloroform fraction [3] in Figure 1 resulted in the isolation of compounds 4 5 and 6. This was achieved through extensive column chromatography on silica gel. Compounds 4 and 5 were present in the oily chromatographic fraction which had the characteristic smell of cinnamon. Compound 4 was isolated as an oil and identified as cinnamaldehyde by formation of the 2,4-dinitrophenylhydrazine derivative which melted at 251-253° [lit(7) m.p. 255°c]. NMR, IR, and UV data were consistent with this assignment. Further proof was provided by air oxidation to form a white crystalline material which was. shown to be identical with compound 5 which upon IR, NMR, and UV comparison with an authentic sample (Aldrich Chemical Company) was shown to be cinnamic acid. 

R18. Roe, J. H., and Kuether, C. A., The determination of ascorbic acid in whole blood and urine through the 2,4-dinitrophenylhydrazine derivative of dehydroascorbic acid.. Biol. Chem. 147, 399-407 (1943). 

Preparation of 2,4-Dinitrophenylhydrazine Derivatives of Highly Oxygenated Carbonyl Compounds, M. L. Wolfrom and G. P. Arsenault,/. Org. Chem., 25, 205-208... 

An apparatus for simultaneously coating a plate with two adjacent layers of different adsorbents was accomplished by placing a plastic insert into a commercial spreader, thus forming two independent chambers. For this reason, combinations of two adsorbents, such as cellulose, silica gel, alumina, charcoal, silicic acid, magnesium silicate, etc. as a function of the sample were used. Then, the two eluents systems were optimized for the two development directions, e.g., 2-D separation of some ketones on a bilayer (charcoal/ silicic acid) with benzene-ether-acetic acid (82 9 9, v/v) in the first direction (on charcoal) and with benzene-ether (85 15, v/v) in the second direction (on silicic acid). In another paper, the first adsorbent was silica gel (air-dried) and the second adsorbent was deactivated aluminum oxide. The same solvent system, toluene-ethyl acetate (3 1, v/v), was used in the two directions. In this condition, a mixture of 2,4-dinitrophenylhydrazine derivatives of hydroxycarbonyl compounds was resolved. 

Aldehydes can be determined with great sensitivity in ethoxylated surfactants by HPLC of the 2,4-dinitrophenylhydrazine derivatives. This procedure allows individual determination of formaldehyde, acetaldehyde and propionaldehyde. (Formaldehyde is not a byprod-... 

The most satisfactory chemical methods for ascorbic acid analysis are based on the reduction of 2,6-dichlorophenolindophenol or on the formation of a colored dinitrophenylhydrazine derivative. A large number of other reactions, mostly with other oxidizing agents, have been used but have not found general favor (R21). 

Suspend 0 25 g. of 2 4-dinitrophenylhydrazine in 5 ml. of methanol and add 0-4 0-5 ml. of concentrated sulphuric acid cautiously. FUter the warm solution and add a solution of 0 1-0-2 g. of the carbonyl compound in a small volume of methanol or of ether. If no sohd separate within 10 minutes, dUute the solution carefuUy with 2N sulphuric acid. CoUect the solid by suction filtration and wash it with a little methanol. RecrystaUise the derivative from alcohol, dUute alcohol, alcohol with ethyl acetate or chloroform or acetone, acetic acid, dioxan, nitromethane, nitrobenzene or xylene. 

Aldehydes, ketones Apply sample solution and moisten with 2 N 2,4-dinitrophenylhydrazine in acetic acid After reacting, dry and chromatograph the 2,4-DNPH derivatives [14]... 

Forsyth et al. found that gelsemicine contains three active hydrogen atoms (Zerewitinov determination), yields a non-basic, monobenzoyl derivative, m.p. 232°, and behaves as a secondary base giving JV-methyl-gelsemicine hydriodide, m.p. 227°, on treatment with methyl iodide. It does not react with either hydroxylamine or 2 4-dinitrophenylhydrazine. On hydrogenation in dry acetic acid in presence of Adams s platinic oxide catalyst it absorbs three molecules of hydrogen. 

The most popular reagent for the formation of aldehyde and ketone derivatives is 2,4-dinitrophenylhydrazine which forms hydrazones containing strong chromophores. 

By far the most common examples of this are with derivatives of NH3, particularly those like HONH2, NH2CONHNH2, PhNHNH2, etc., which have long been used to convert liquid carbonyl compounds into solid derivatives, for their characterisation 2,4-dinitrophenylhydrazine, (N02)2C6H3NHNH2, is particularly useful in this respect. 

In the early days, greatest interest was focused on the acid-catalyzed hydrolysis (by hydrochloric acid in the presence of 2,4-dinitrophenylhydrazine) of Reissert compounds to aldehydes and the corresponding heterocyclic carboxylic acid derivatives. This reaction is fairly general for compounds of quinoline (178) and isoquinoline (179) (Table 18), but it is not applicable to pyridines as they rarely form Reissert compounds. The 3-hydroxyquino-line Reissert compound does not yield benzaldehyde, probably because acylation of the 3-hydroxy group prevents formation of the required cyclic intermediate (180). Some nitroquinolines and isoquinolines give low yields of benzaldehyde. Rather curiously, disub-stituted quinoline Reissert compounds yield less of the aldehyde than of the corresponding... 

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