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Olestra ® is a fat-based fat substitute that became
Chapter 26, Problem 25SP(choose chapter or problem)
Problem 25SP
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.
Questions & Answers
QUESTION:
Problem 25SP
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.
ANSWER:
Solution 25SP:
Here, we are going to draw the structure of Olestra ®
Step1:
Olestra is a non-digestible plastic,which is made of adding eight fatty acid molecules to the sugar molecule sucrose. The fatty acids block access to the sugar, so enzymes can't break it down. Therefore, the molecule behaves like a fat, but it can not be digested by intestinal bacteria. That is why it behaves like a mineral oil.