Paper Chromatography of 2,4-Dinitrophenylhydrazones of Saturated Aliphatic Aldehydes

Ellis, Rebecca; Gaddis, A. M.; Currie, G. T.

doi:10.1021/ac60136a006

Cited by 62 publications

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“…Acetone separates in the alkanal class, and methanol and ethanal come out in the alk-2-enal class (19). As a result, when the classes are separated into individual compounds (13), mixtures of ethanal-acrolein, acetone-propanal, and acetonebutanal are obtained (19). However, the presence of acetone, methanol, and ethanal in the mixture of monocarbonyl DNPH's can be detected by the partial extraction of these compounds from carbon tetrachloride with a 2 N HC'I solution of 2,4-dinitrophenylhydrazine (18).…”

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“…Spectrophotometric studies in neutral solution and in alcoholic alkali (13,26) are useful in the detection of such mixtures, and where necessary corrections can be applied. Over-all, the methods of Ellis, Gaddis, and Currie (13) and Gaddis and Ellis (19) result in a powerful tool for rapid identification and estimation of classes and individual compounds. In the freezer-stored pork fat (18) examined so far, acrolein has not been detected, and methanol, ethanal, acetone, and methyl ethyl ketone are usually present only in trace amounts.…”

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“…EXPERIMENTAL Solvents and reagents. A. C. S. grades of carbon tetrachloride, benzene, methanol, and commercial absolute ethanol, Skellysolve C ( b 91 " -95") were purified as described by Ellis, Gaddis, and Currie (13). Technical grade petroleum ether was distilled and the fraction boiling 37" -40" C.…”

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CARBONYLS IN OXIDIZING FAT. I. SEPARATION OF STEAM VOLATILE MONOCARBONYLS INTO CLASSES^a

Gaddis

Ellis

Currie

1959

Journal of Food Science

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Carbonyl compounds influence the flavor and quality of many foods and natural products. They are believed to be largely responsible for the rancid flavors developed in oxidizing fat and fatty tissue. However, relatively little is known concerning the influence of composition, treatments, and conditions on the kinds and amounts of carbonyls formed in fat, and their relationship to odor and flavor (11,18,23,30,38). The objectives of this work were to determine some of the changes occurring in fractions of the steam volatile carbonyls of freezer-stored pork fat.There is considerable need for a more specific objective method of determining rancidity. The shortcomings of the organoleptic methods (1,2,21, 34,35) have been fully described elsewhere (4,24,36,47). Peroxide values can be used to follow the amount of oxidation, but they do not constitute a specific determination of rancidity (31,32,33,36,38). Rancidity has been found to appear at different peroxide levels. Carbonyls are produced as a result of the decomposition of the peroxides, and apparently their nature depends on the kind of hydroperoxides, conditions, and other variables (38).In recent years the sensitivity of methods involving 2, 4-dinitro-phenylhydrazone derivatives of carbonyls has been applied. Pool and Klose (40) have devised a method for determining total monocarbonyls, Neumer and Dugan (37) have reported a procedure for total volatile carbonyls, and Chang and Kummerow (10) a method for total and volatile carbonyls. I n general, applications of the above methods have indicated a close relationship between peroxides and carbonyl values. Total carbonyl values, therefore, also appear not to be specific for rancidity.Consideration of these facts, together with the well-known sensitivity of taste, leads to the assumption that rancid flavors may be due to some particular type of carbonyls (8,9,14,15,27), the proportions and rate of formation of which are influenced by the composition of the glycerides, catalysts, enzymes, and anti-oxidants present, and processing and storage conditions. Henick, Benca, and Mitchell (23) have developed a method for determination of total saturated and unsaturated carbonyls as hexanal and crotonaldehyde.Applications (23,38) of this method showed the rate of increase of saturated carbonyls exceeded that of the 2-enal class. The method does not take into account other classes of carbonyls that may be present.In studies of autoxidative mechanisms (6,8,9,22,25,27,28,44,45,46) one or more compounds of the following classes have been identified : saturated aliphatic aldehydes, saturated ketones, 2-en-l-als, 2,4-dienals, and dicarbonyls.

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CARBONYLS IN OXIDIZING FAT. I. SEPARATION OF STEAM VOLATILE MONOCARBONYLS INTO CLASSES^a

Gaddis

Ellis

Currie

1959

Journal of Food Science

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“…There are few references to systems suitable for further separating such a mixture, though zinc carbonate columns and/or chromatoplates (van Duin 1958 ;Badings 1959), and the reverse phase chromatographic system of Ellis, Gaddis, and Currie (1958) hydrazones and developed with a mixture of methanol and water. When only amall quantities (1-20 pg) of compounds are available or when limited information on a fraction rather than characterization of its constituents is required, sheetpaper chromatograms are suitable.…”

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“…Table 1 lists fifteen binary and Table 2 two quaternary mixtures separated on alumina columns. Eight of the binary mixtures (marked with an asterisk in Table 1) were also separated by the method of Ellis, Gaddis, and Currie (1958) with both ascending and descending development. TKO chromatographic systems can be successfully combined for the purification of unknown mixtures of 2,4-dinitrophenylhydrazonex.…”

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Fractionation of complex mixtures of 2,4-dinitrophenylhydrazones

Forss¹,

Dunstone²,

Stark³

1960

Aust. J. Chem.

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The advantages of partition over adsorption chromatographic columns for the initial fractionation of mixtures of 2,4-dinitrophenylhydrazones have been increasingly appreciated during the last few years. The literature however reveals little awareness that while partition systems will separate the members of an homologous series, they will not effectively separate dinitrophenylhydrazones of different classes of carbonyl compounds of similar chain-length. The compositions of the fractions obtained from such mixtures will depend on the partition system used (eg. Kramer and van Duin 1954 ; Monty 1958) but it would be possible to have included in the one fraction the dinitrophenylhydrazones of, for instance, a C, alkan-2-one, a On+, walkanal, a C,,, alk-2-enal, and a On+, alka-2,4-dienal.There are few references to systems suitable for further separating such a mixture, though zinc carbonate columns and/or chromatoplates (van Duin 1958 ;Badings 1959), and the reverse phase chromatographic system of Ellis, Gaddis, and Currie (1958) have been used with success.

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Acetaldehyde

Hagemeyer

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Acetaldehyde is a product of most hydrocarbon oxidations. It occurs in trace amounts in all ripe fruits that have a tart taste before ripening. Acetaldehyde is also an intermediate product of fermentation. It may form in wine and other alcoholic beverages after exposure to air, imparting an unpleasant taste. Acetaldehyde occurs in trace quantities in blood. Acetaldehyde is a colorless, mobile liquid having a pungent, suffocating odor that is somewhat fruity and quite pleasant in dilute concentrations. It is a highly reactive compound undergoing numerous condensation, addition, and polymerization reactions. The liquid‐phase oxidation of ethylene is the process of choice for the manufacture of acetaldehyde. Acetaldehyde appears to paralyze respiratory muscles, causing panic. When breathed in high concentration, it causes headache and sore throat. In 1976 acetic acid production represented 60% of the acetaldehyde demand, which has diminished as a result of the rising cost of ethylene as feedstock.

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Paper Chromatography of 2,4-Dinitrophenylhydrazones of Saturated Aliphatic Aldehydes

Cited by 62 publications

References 39 publications

CARBONYLS IN OXIDIZING FAT. I. SEPARATION OF STEAM VOLATILE MONOCARBONYLS INTO CLASSES^a

CARBONYLS IN OXIDIZING FAT. I. SEPARATION OF STEAM VOLATILE MONOCARBONYLS INTO CLASSES^a

Fractionation of complex mixtures of 2,4-dinitrophenylhydrazones

Acetaldehyde

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Paper Chromatography of 2,4-Dinitrophenylhydrazones of Saturated Aliphatic Aldehydes

Cited by 62 publications

References 39 publications

CARBONYLS IN OXIDIZING FAT. I. SEPARATION OF STEAM VOLATILE MONOCARBONYLS INTO CLASSESa

CARBONYLS IN OXIDIZING FAT. I. SEPARATION OF STEAM VOLATILE MONOCARBONYLS INTO CLASSESa

Fractionation of complex mixtures of 2,4-dinitrophenylhydrazones

Acetaldehyde

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Product

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CARBONYLS IN OXIDIZING FAT. I. SEPARATION OF STEAM VOLATILE MONOCARBONYLS INTO CLASSES^a

CARBONYLS IN OXIDIZING FAT. I. SEPARATION OF STEAM VOLATILE MONOCARBONYLS INTO CLASSES^a