Reduced calorie fat mimetics comprising esterified propoxylated monoglycerides and diglycerides

Reference Number: N 04-04

Inventors: Sekula, Bernard C.

Owner: NISTAC

USPTO Link: 5858439

Invention Summary

The present invention relates to esterified propoxylated monoglycerides (EPMG) and diglycerides (EPDG) and reduced calorie food products comprising said compounds. EPMG may be prepared by reacting 3-Phenylmethoxy-1,2-propanediol with the desired number of equivalents of propylene oxide in the presence of an effective amount of a basic catalyst such as potassium hydroxide. The 3-phenylmethoxy-1,2-propanediol starting material can be obtained using the procedure described in Sowden, et al., "J. Am. Chem. Soc.", 63, 3244 (1941). The propoxylated 3-phenylmethoxy-1,2-propanediol is then reacted with hydrogen in the presence of a transition metal hydrogenolysis catalyst such as palladium. The benzyl ether group is converted to a hydroxyl group in this hydrogenolysis step. Subsequent esterification with fatty acid at an elevated temperature yields the desired product. EPDG may be prepared in an analogous manner using a glycerin-derived starting material having two benzyl ether groups. A more detailed discussion of the processes for producing the presently claimed fat mimetic compounds is set forth in copending patent application Ser. No. 07/600,462, entitled "Process for Producing Esterified Alkoxylated Polyols" by C. F. Cooper, assigned to ARCO Chemical Technology, Inc., and is hereby incorporated by reference.

Both EPMG and EPDG can be produced in a variety of forms including a liquid form, and can therefore be used for a variety of applications. These compounds are useful as partial or full substitutes for vegetable and other liquid oils, for purposes such as salad oils, cooking oils, anti-spattering or pan-release agents, or as ingredients in products such as mayonnaise, salad dressings, margarines, shortenings and peanut butter. Additionally, these compounds can withstand exposure to heat, and are therefore useful for baking, frying, sauteing and other related applications.

A benefit to the use of these compounds is the fact that both EPMG and EPDG are partially hydrolyzed within the body to fatty acids and nonabsorbable digestion residues which are more hydrophilic than the fully esterified substrate. By manipulation of the position and number of oxypropylene groups and types of fatty acids esterified, it is possible to produce fat mimetic compounds having a range of caloric values. Optimally, the fat mimetic compounds should possess minimum caloric value, while avoiding unpleasant side effects, such as vitamin stripping and anal leakage which are associated with non-hydrolyzable fat substitutes and mimetics.