Ether lipids based on the glyceryl ether skeleton: Present state, future potential

Abstract

AbstractLipids from natural sources consist mainly of saponifiable substances, such as glycerides, along with some unsaponifiable lipids, some of which are ether lipids. Typical ether lipids are monoalkyl ethers of glycerin, also called alkyl/alkenyl glyceryl ethers. Alkyl/alkenyl glyceryl ethers have also been reported in marine organisms and in human feces. Several chemical syntheses of such ether lipids have been reported. Typical examples are alkyl glyceryl ether formation by the addition reaction of alkyl glycidyl ether and the telomerization reaction of butadiene with glycerin and a transition metal catalyst. Characteristic chemical structures, such as terpene alkyl glyceryl ethers, archaebacterial macrocyclic ether lipids, and glyceryl ethers of condensed cyclic planar molecules, have been obtained as well. Over the past few decades, industry has shown much interest in the chemistry and application of highly branched fatty acids. For example, isostearyl glyceryl ether (GE‐IS) with methyl branching in the middle chain was already known, but it is now prepared at an industrial scale by proprietary alkyl glycidyl ether methods. The characteristic behavior of GE‐IS toward water, such as formation of water‐in‐oil emulsions containing large amounts of water and of liquid crystals, has made it applicable for use in hair and skin‐care cosmetics. Based on these studies and considerations, glyceryl ether lipids, which are rarely investigated, may become one of the most important and useful lipids in the industry.