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 notsuitable for frying. With Olestra®, the glycerol molecule of a fat is replaced by sucrose (p. 1201). In Olestra®, the sucrosemolecule has six, seven, or (most commonly) eight fatty acids esterified to its hydroxy groups. The fatty acids come fromhydrolysis of vegetable oils such as soybean, corn, palm, coconut, and cottonseed oils. This unnaturally bulky, fat-likemolecule does not pass through the intestinal walls, and digestive enzymes cannot get close to the sucrose center to bind itto their active sites. Olestra® passes through the digestive system unchanged, and it provides zero calories. Draw a typicalOlestra® molecule, using any fatty acids that are commonly found in vegetable oils.

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
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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. 1201). In Olestra®, the sucrose
molecule has six, seven, or (most commonly) eight fatty acids esterified to its hydroxy 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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