Linked esterified alkoxylated polyols useful as reduced calorie fat substitutes

Reference Number: N 04-04

Inventors: Ferenz, Michael R.; Sekula, Bernard C.

Owner: NISTAC

USPTO Link: 5374446

Invention Summary

This invention provides a linked esterified alkoxylated polyol useful as a reduced calorie fat substitute comprised of at least one polyether glycol linking segment, at least two polyol segments, wherein each polyol segment is connected to a polyether glycol linking segment either directly or through an unesterified oxyalkylene segment, and at least one fatty substituent selected from fatty acid ester groups and fatty acid-esterified oxyalkylene segments attached to a polyol segment.

In a preferred embodiment, the fat substitute has a molecular weight of from 750 to 6000 and is comprised of:

(a) at least one polyether glycol linking segment having the general structure ##STR1## wherein n is an integer of from 1 to 20, Q and Q.sup.1 are the same or different and are independently selected from hydroxy groups, fatty acid ester groups, hydroxy-terminated oxyalkylene segments, and fatty acid-esterified oxyalkylene segments, a and b are different and are 0 or 1, c and d are different and are 0 or 1 and R.sup.1 and R.sup.2 are the same or different and are selected from hydrogen and C.sub.1 -C.sub.6 alkyl;

(b) from two to four polyol segments derived from an aliphatic polyol having from 3 to 8 hydroxyl groups, wherein each polyol segment is connected to a polyether glycol linking segment, either directly or through an unesterified oxyalkylene segment having the general structure ##STR2## wherein m is an integer of from 1 to 20 and R.sup.3 and R.sup.4 are the same or different and are independently selected from hydrogen and C.sub.1 -C.sub.6 alkyl; and

(c) at least one fatty acid-esterified oxyalkylene segment attached to a polyol segment having the general structure ##STR3## wherein R.sup.5 and R.sup.6 are the same or different and are independently selected from hydrogen and C.sub.1 -C.sub.6 alkyl, R.sup.7 is a C.sub.5 -C.sub.23 hydrocarbyl group, and p is an integer of from 1 to 20, wherein the number of polyether glycol linking segments is one less than the number of polyol segments and the number of fatty acid-esterified oxyalkylene segments is at least equal to the number of polyol segments.

The linked esterified alkoxylated polyols of this invention are obtainable, for example, by reaction of a polyepoxide-functionalized polyether glycol, a C.sub.2 -C.sub.6 aliphatic mono-epoxide, a polyol, and a fatty acid entity such as a free fatty acid, fatty acid halide, fatty acid ester, or fatty acid anhydride.

Also provided by this invention is a fat component useful for preparing a reduced calorie food product, said fat component comprising an edible triglyceride and the linked esterified alkoxylated polyol. The invention also furnishes a reduced calorie food product comprised of a fat component, said fat component comprising the aforedescribed linked esterified alkoxylated polyol fat mimetic.