Organic Chemist’s Explorations of Lipids Research

This presentation is a recap of highlights of my experiences for the past 44 years in the lipids research in both academia and industry, studying the fundamental aspects and developing applications in creating new and value-added products. The fundamental studies include the synthesis of stereospecific glycerol derivatives, exploration of polymorphism of stereospecific homologous glycerol derivatives to reveal the influence of structure on molecular packing and properties. Synthesis of pure chiral glycerol esters, mono-, di- and tri-acyl-sn-glycerols (TAG) by employing various strategies and novel reagents to prevent acyl migration will be presented. Systematic studies of these compounds to understand how the structure and molecular packing influenced the properties and polymorphic behavior in stable β and meta stable β’ and α states. The influence of the glycerol conformation on physical properties was studied. We were the first to resolve the mixed acid TAG single crystal structures of PP2 and PP14, in β and β’ states respectively. The molecular arrangement of these two polymorphs markedly differed from the accepted chair conformation of mono-acid TAG.
The second aspect refers to application of structure-function knowledge to create commercial products: how several chemical transformations such as trans-esterification, cyclo-propanation, cyclization, epoxidation and branching can be used to generate structural heterogeneity, variation of molecular size, steric hindrance to disrupt molecular packing, and change in polarity to result in required functionality for a chosen application. Creating new value-added products from concept to commercialization resulted in new coatings, lubricants, and plasticizers. The successful as well as failed commercial product development ideas will be presented with examples. During this journey AOCS acted as a catalyst and helped me to accomplish many of these collaborative projects.