Lipase Catalyzed Methanolysis of Tri-(12-Hydroxy Stearoyl)-Glycerol in Organic Solvents

Abstract

Castor oil is the source of numerous products and is the only commercial source of the fatty acid ricinoleate, 12-hydroxy-oleate. Hydrogenated castor oil is similarly useful as the source of 12-hydroxy-stearic acid, best known as a component of lithium grease. Mono- and diacylglycerols are derived from castor oil and are useful in development of lubricants and emulsifiers for cosmetics, pharmaceutical and food use. Acylglycerols derived from hydrogenated castor oil may be similarly useful, albeit with different physical and chemical properties. We have evaluated the use of immobilized lipases to generate acylglycerols, using organic solvents to modulate the action of lipase to produce mono- and diacylglycerols, using tri-(12-hydroxy stearoyl)-glycerol as a model for hydrogenated castor oil. The presence of an alkylated oxygen in the solvent appears to be an important factor in supporting lipase activity, with diisopropyl ether providing the best yield of di-(12-hydroxy stearoyl)-glycerol.