Esterification and interesterification reactions catalyzed by acetone powder from germinating rapeseed

Article abstract of DOI:10.1007/BF02523520

Acetone powder from germinating rape (Brassica napus L.) seedlings exhibits essentially similar activity in lipolysis of triacylglycerols as the corresponding seedling homogenates. Acetone powder from rape seedlings catalyzes the esterification of a fatty acid, such as oleic acid, with n-butanol or a long-chain alcohol, such as oleyl alcohol. Furthermore, the acetone powder catalyzes alcoholysis of a methyl ester, such as methyl oleate with n-butanol or oleyl alcohol, and acidolysis of methyl oleate with a fatty acid, such as erucic acid. However, triacylglycerols are not accepted as substrates for interesterification reactions. In esterification of fatty acids with n-butanol, catalyzed by the acetone powder from rape seedlings, fatty acids having an olefinic bond next to the carboxyl group as a cis-6 double bond, e.g., γ-linolenic, gorlic and petroselinic acids, or those having a cis-4 double bond, e.g., docosahexaenoic acid, are strongly discriminated against as substrates. Such substrate selectivities can be utilized for the enrichment of definite fatty acids from mixtures, derived from naturally occurring oils, via kinetic resolution.