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Studies of Heated Milk III. Mode of Formation of Certain Furan Compounds¹

Department of Dairy Husbandry, The Pennsylvania Agricultural Experiment Station, State College, Pennsylvania

ABSTRACT

The mechanism by which furfuryl alcohol and hydroxymethylfurfural are heat-generated in condensed skimmilk and certain lactose systems has been studied. The importance of pH and buffer capacity in the reactions concerned has been demonstrated and discussed. Condensed skimmilk and weakly alkaline lactose systems produced both furfuryl alcohol and hydroxymethylfurfural. Acidified condensed skimmilk and neutral or acidic lactose systems yielded significant quantities of hydroxymethylfurfural but no furfuryl alcohol.

The structure of the lactose molecule or that of a similar sugar, maltose, was shown to be rather specifically required in furfuryl alcohol formation.

A proposed mechanism for the conversion of lactose to furfuryl alcohol has been presented schematically. In this mechanism the production of furfuryl alcohol is related to that of formic acid. It is suggested that a variation of the mechanism accounts for the conversion of lactose to hydroxymethylfurfural.

¹ Authorized for publication as paper no. 1601 on May 25, 1950, in the Journal Series of The Pennsylvania Agricultural Experiment Station.