C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
99/156, 260/483,
C07C 69/33 (2006.01) A23D 7/00 (2006.01) A23L 1/30 (2006.01) A23L 1/308 (2006.01) C07C 69/58 (2006.01)
Patent
CA 1311238
Abstract Esterified epoxide-extended polyols (EEEPs) of the formula P(OH)a+c(EPO)n(FE)b where P is a polyol having a = 2 - 8 primary hydroxyls, c = 0 - 8 secondary and tertiary hydroxyls, a + c is in the range of 3 - 8, EPO is a C3-C6 epoxide, FE is a fatty acid acyl moiety, n is the minimum epoxylation index average number having a value generally equal to or greater than a and is a number sufficient that greater than 95% of the primary hydroxyls of the polyol are converted to secondary or tertiary hydroxyls, and 2 < b ? a + c, methods of preparation thereof, and their use as non-digestible fat substitutes (fat mimatics) having non-caloric food values, which have good organoleptic characteristics, are substantially resistant to intestinal absorption, and do not appreciably hydrolyze in the digestive tract. Suitable polyols include sugars, glycerides or saccharides which are reacted (etherified) with C3-C6 epoxides such as propylene oxide, butylene oxide, isobutylene oxide, pentene oxide, and the like to produce epoxide-extended polyols (EEPs) having an epoxylation index number, n, generally in the range of 2 - 8. Acylation with C8-24 fatty acids such as octanoic, stearic, palmitic, oleic, and/or heptadecanoic, or fatty acids from soybean oil, fish oil, coconut oil, cotton seed oil, corn oil, sunflower oil, safflower oil, jojoba oil and the like, produce the end product ester with physical properties ranging from a liquid oil, through fats and greases, and ultimately to waxes. Best mode example are acylated propoxylated glycerol compound mixtures (APGs) which are resistant to pancreatic lipase in vitro, and feeding studies show them to be suitably resistant to overall digestion. The resultant EEPEs are useful in food formulations and for cooking as they have a good mouth feel and characteristics similar to vegetable oils and fats. Being relatively non-absorbable, non-digestible, and non-toxic they may be substituted for natural or processed oils and fats, but have low caloric value.
536602
Pollard Michael R.
White John F.
Atlantic Richfield Company
Osler Hoskin & Harcourt Llp
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