2-Fatty Acrylic Acids: New Highly Derivatizable Lipophilic Platform Molecules

This paper reports the incorporation of an alpha-methylene unit into fatty acid skeletons. Since the new olefin is conjugated with the carboxylate, it is susceptible to 1,4-(Michael) additions. We have used multifunctional thiols and amines for additions at the methylene. The resulting products possess clusters of functionality grouped at one end of a hydrophobic tail. These structural patterns will be of use in the design of new types of bio-based surfactants and polymers. One particularly promising pattern of functionality that can be obtained through oxidation and reduction chemistry is a 2-fatty 1,2,3-propanetriol, or a lipophilized glycerol moiety.