Reduced calorie fat mimetics with an average number of oxyalkylene groups per molecule of no more than five

Reference Number: N 04-04

Inventors: Sekula, Bernard Charles

USPTO Link: 6268010

Invention Summary

The present invention relates to fat substitutes comprising esterified alkoxylated polyols, particularly esterifiedpropoxylatedglycerol, which is susceptible to hydrolysis during digestion thus being partially digestible. This is accomplished by only partially propoxylating the polyol backbone such that the average number of oxypropylene (oxyalkylene) groups per molecule is no more than 5, and preferably between about 2 and 5, and subsequently esterifying with fatty acids. At this level of propoxylation, the number of primary hydroxyl groups that are converted to secondary and tertiary hydroxyls, can be limited to about between 61 percent to 95 percent of the total number of hydroxyl groups on the molecule, such that the amount of primary hydroxyl groups on the molecule is between 5 percent and 39 percent of the total number of hydroxyl groups. The compositions of the invention have a porcine pancreatic lipase hydrolysis index of less than about 15 based on an olive oil standard of 100.

Esterified alkoxylated polyols are prepared, preferably esterified propoxylated glycerin compositions, wherein the propoxylation of the polyol is carefully controlled to ensure that the average number of oxypropylene groups per molecule is no more than 5. Thereafter, the propoxylated polyol is esterified with fatty acids. By carefully controlling the propoxylation of the polyol, including esterified propoxylated glycerin compositions, the number of primary hydroxyl groups that are converted to secondary and tertiary hydroxyls can be limited to from 61 percent to about 95 percent. Primary hydroxyl esters are significantly more sensitive to lipase activity than secondary and/or tertiary esters, and, thus, are more susceptible to in vivo hydrolysis. Increasing the degree of hydrolysis of the esterified alkoxylated polyol increases tiff hydrophilicity of the compound. Accordingly, by only partially alkoxylating the polyol backbone, the conversion of primary hydroxyl esters to secondary hydroxyl esters and/or tertiary hydroxyl esters is limited which results in more susceptibility to in vivo hydrolysis and reduces and/or obviates undesirable gastrointestinal side effects, such as oil intolerance and anal leakage.

The fat replacement compositions of the invention can be comprised of one, or a mixture of two or more, fatty acid-esterified alkoxylated polyol compositions, including esterified alkoxylated glycerin compositions and esterified propoxylated glycerin compositions, that can be used to replace all or a portion of the natural or artificial fats in various food products.

The fatty acid-esterified alkoxylated polyol compositions are made by incorporating alkylene oxide groups into a typical triglyceride fat as described in White. The average number of alkylene oxide groups which are incorporated into a compound is called the alkoxylation number. The melting point, melting profile and other characteristics of the composition can be modified by adjusting the alkoxylation number, the fatty acid chain length and level of unsaturation. Similarly, two or more different fatty acid-esterified alkoxylated polyol compositions (i.e., having different alkoxylation numbers) of the same fatty acid, two or more fatty acid-esterified alkoxylated polyol compositions of different fatty acids having the same or different alkoxylation numbers, and any combination thereof which provides the desired fat replacement characteristics may be utilized.

The most suitable fatty acid-esterified alkoxylated polyol composition or combination of fatty acid-esterified alkoxylated polyol compositions will vary depending upon the type of fat being replaced in a particular food product. The selection of the most suitable fatty acid-esterified alkoxylated polyol compositions or combination of fatty acid-esterified alkoxylated polyol compositions according to the invention is based on the particular food application as will be apparent to those skilled in the art.