SYNTHESIS AND INVESTIGATION OF POTENTIALLY NEW SWEETENING AGENTS FROM LACTOSE
Abstract
Lactose was chemically modified according to predictive sweetness theory and based upon previous chlorosucrose experiments for the purpose of increasing its relative sweetness. Lactose was first isomerized to lactulose which was then chlorinated with triphenylphosphine and carbon tetrachloride in pyridine. Reaction products were characterized by thin layer chromotography, ('1)H-n.m.r. spectroscopy, ('13)C-n.m.r. spectroscopy, mass spectroscopy and elemental analysis. Substitution was observed at 3 primary sites. Two of the sites were occupied by chlorine and the third by phenylphosphine, presumably formed by the reaction of a previously substituted chlorine and triphenylphosphine. Lactose was reduced to lactitol which was chlorinated in the same manner. Products displayed various degrees of chloro and phenylphosphine substitution. Isopropylidene cyclic acetals of lactulose were made. A mono- and a diisopropylidene derivative were characterized as 2',3':3,4-di-O-isopropylidene lactulose and 3,4-O-isopropylidene lactulose. Enhancement of sweetness was not observed. Bitterness was attributed to C-6 chlorine and phenylphosphine substitution.
Degree
Ph.D.
Subject Area
Food science
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