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Chemistry / Organic Chemistry 2 / Chapter 26 / Problem 26.53

Organic Chemistry | 2nd Edition | ISBN: 9781118454312 | Authors: David R. Klein

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Olestra is a noncaloric oil substitute that is produced by

Chapter 26, Problem 26.53

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QUESTION:

Olestra is a noncaloric oil substitute that is produced by esterifying sucrose with eight equivalents of fatty acids obtained from the hydrolysis of vegetable oils. The eight fatty acid residues give Olestra the consistency and flavor of cooking oil, but the steric bulk of the compound prevents digestive enzymes from hydrolyzing the ester groups. As a result, Olestra passes through the digestive tract unaltered. Draw the structure of a molecule of Olestra that contains eight lauric acid residues. Is this compound chiral?

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QUESTION:

Olestra is a noncaloric oil substitute that is produced by esterifying sucrose with eight equivalents of fatty acids obtained from the hydrolysis of vegetable oils. The eight fatty acid residues give Olestra the consistency and flavor of cooking oil, but the steric bulk of the compound prevents digestive enzymes from hydrolyzing the ester groups. As a result, Olestra passes through the digestive tract unaltered. Draw the structure of a molecule of Olestra that contains eight lauric acid residues. Is this compound chiral?

ANSWER:

Step 1 of 2

Olestra (a food additive) is produced by esterifying sucrose with eight equivalents of fatty acids.

First draw the structure of sucrose (a disaccharide) and then replace each of the eight available hydroxyl groups with a lauryl ester.

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