Olestra is a fat-based fat substitute that became available in snack foods such as potato chips in

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Olestra is a fat-based fat substitute that became available in snack foods such as potato chips in 1998. Previous fat substitutes were carbohydrate-based or protein-based mixtures that did not give as good a sensation in the mouth, and are not suitable for frying. With Olestra, the glycerol molecule of a fat is replaced by sucrose (p. 1135). In Olestra, the sucrose molecule has six, seven, or (most commonly) eight fatty acids esterified to its hydroxyl groups. The fatty acids come from hydrolysis of vegetable oils such as soybean, corn, palm, coconut, and cottonseed oils. This unnaturally bulky, fat-like molecule does not pass through the intestinal walls, and digestive enzymes cannot get close to the sucrose center to bind it to their active sites. Olestra passes through the digestive system unchanged, and it provides zero calories. Draw a typical Olestra molecule, using any fatty acids that are commonly found in vegetable oils.
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Organic Chemistry

ISBN: 978-0321768414

8th edition

Authors: L. G. Wade Jr.

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