Esterified alkoxylated polyol fat substitutes having high primary ester content

Reference Number: N 04-04

Inventors: Cooper, Charles F.; Harris, Stephen H.

USPTO Link: 5512313

Invention Summary

We have now found that esterified alkoxylated polyols based on C.sub.3 -C.sub.10 1,2-alkylene oxides, but containing a high proportion of primary ester linkages, are useful as fat substitutes and mimetics. These substances have substantially reduced caloric content relative to natural fats and oils, yet exhibit comparable organoleptic and physical characteristics and are well-tolerated in the intestinal tract. The esterified alkoxylated polyol compositions of this invention thus exhibit a highly desirable balance of properties which heretofore has been quite difficult to attain in practice.

Our invention also provides an esterified alkoxylated polyol composition obtainable by reacting a C.sub.3 -C.sub.10 1,2-alkylene oxide with a polyol in the presence of a cationic ring-opening polymerization catalyst to form an alkoxylated polyol intermediate wherein at least 40% (more preferably, at least 60%; most preferably, at least 80%) of the hydroxyl end-groups of said alkoxylated polyol intermediate are primary hydroxyl end-groups and reacting the alkoxylated polyol intermediate with a fatty acid or fatty acid equivalent. In a preferred embodiment, the 1,2-alkylene oxide is propylene oxide and the polyol is glycerin.

Our invention additionally provides a reduced calorie fat substitute comprising a fatty acid ester of an alkoxylated polyol wherein (a) the polyol has from 2 to 8 hydroxyl groups, (b) from 1 times X to 7 times X oxyalkylene units derived from a C.sub.3 -C.sub.10 1,2-alkylene oxide are attached by ether linkages to the polyol, (c) each alkoxylated polyol is attached through ester linkages to from 0.67 times X to 1.0 times X fatty acid acyl groups, and (d) at least 40% of the ester linkages are primary ester linkages.

Also provided is a reduced calorie fat substitute comprising an esterified alkoxylated polyol having the general formula ##STR1## wherein oxyalkylene is derived from a C.sub.3 -C.sub.10 1,2-alkylene oxide, X is zero or an integer selected such that X times n is from 0 to 56, n is an integer of from 2 to 8, Q is a polyol residue, R.sup.1 and R.sup.2 are different and are hydrogen or C.sub.1 -C.sub.6 alkyl, with the proviso that R.sup.1 and R.sup.2 are selected such that at least 40% of R.sup.2 groups are hydrogen, and R.sup.3 is a C.sub.5 -C.sub.23 hydrocarbyl group.

The invention additionally provides a reduced calorie food product comprised of a fat component, wherein said fat component is comprised of the esterified alkoxylated polyol composition described hereinabove. Also provided is a fat component useful for preparing a reduced calorie food product wherein said fat component is comprised of an edible triglyceride such as a natural vegetable or animal fat or oil and the aforementioned esterified alkoxylated polyol composition.