Question: How would you synthesize olestra from sucrose?

Olestra is a carbohydrate with a sweet taste and is used in table sugar. It is a polyester of sucrose and long-chain fatty acids.

The large numbers of ester groups present in olestra are clustered together in close proximity.

Due to this, the hydrolysis of the ester groups does not occur inside the body. Due to this, olestra cannot be metabolized and is removed from the body unchanged.

The reaction in which a hydroxyl group and a carboxyl group react to form an ester by the removal of a water molecule is called an esterification reaction.

When the esterification reaction is initiated by a proton, it is called Fischer esterification. The proton is added to the reaction mixture as mineral acids

Olestra is synthesized from long-chain fatty acids and sucrose by the esterification reaction. The reaction is catalyzed by sulphuric acid.

A large number of esterification reactions within the molecule give the polyester olestra.

Synthesis of olestra