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Fractionation of the Stale-Flavor Components of Dried Whole Milk¹

Department of Food Technology, University of Illinois, Urbana

ABSTRACT

The stale flavor of dried whole milk has been shown to exist in two forms which can be separated by CCl₄-vapor distillation and Girard's-T extraction. One is nonvolatile under the conditions employed but can be extracted from the milk fat with Girard's-T reagent; the other is volatile and is not recovered from the Girard's-T extract after hydrolysis of the resulting hydrazones.

The Girard's-T extractible component is recovered more completely from the fat when lower concentrations of Girard's-T reagent are used, a behavior similar to aldehydes. It can be separated by paper or column chromatography into a stationary and a mobile component which contains the flavor. The R_f value of the mobile component is similar to that of the reaction product of heptaldehyde. It is readily decomposed by alkali or 2,4-dinitrophenylhydrazine in 4 M HCl. On treatment with 2,4-dinitrophenylhydrazine, at least four carbonyl compounds were obtained as decomposition products and tentatively identified by paper chromatography as acetaldehyde, propionaldehyde, acetone, and either 2-butanone or 2-pentanone.

The CCl₄-vapor distillates were found to contain at least seven carbonyl compounds, five of which have been identified as formaldehyde, acetaldehyde, propionaldehyde, acetone, and 2-penatone. The remaining two compounds possess the spectra and chromatographic characteristics of a saturated monocarbonyl compound and either an unsaturated dicarbonyl or hydroxycarbonyl compound. The stale-flavor component of this fraction appears to behave like a dicarbonyl compound with Girard's-T reagent.

¹ Taken in part from the theses of S. H. Lombard presented in February, 1955, W. W. Nawar presented in February, 1959, and A. S. Ganguly, presented in May, 1961, in partial fulfillment of the requirements for the degrees of Doctor of Philosophy.

² Present address: Department of Food Technology, University of Massachusetts, Amherst, Massachusetts.

³ Present address: Division of Dairying, University of Pretoria, Pretoria, Republic of South Africa.

⁴ Present address: A/S Lidano, Kalundborg, Denmark.

⁵ Present address: Hindustan Lever, Ltd., Bombay, India.