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

Abstract

Lipids 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 [ipids 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, glycery[ ether lipids, which are rarely investigated, may become one of the most important and useful lipids in the industry. JAOCS 73, 819-830 (1996). KEY WORDS:Ether lipids, GE-IS, glyceryl ether, glycidyl ether, isostearic acid, isostearyl glyceryl ether, liquid crystal, W/O emulsion.Saponification of lipids from tissues and organs of many marine animals results in water-soluble soaps that have high levels of some unsaponifiable substances, which chiefly include hydrocarbons, such as squalene, sterols, and long-chain alcohols with one or more hydroxyl groups (1,2). Typical longchain alcohols that contain one or more hydroxyl groups are particularly present as monoalkyl ethers of glycerin:RO-CH2-CH-CH 2 cyl glycerol, and batyl alcohol as the major constituents in a mixture of free alkyl glyceryl ethers isolated from the sponge Desmapsamma anchorata, harvested in the Gulf of Mexico, and minor components consisted of Cls, Cl9, C20, and Czl alkyl glyceryl ethers (12). They also found that sponges such

Self‐assembly of compounds based on a glycerin skeleton as a C‐3 building block. Part I

“…These synthetic lipids are useful ingredients in cosmetics (16). Tsutsumi et al (11) studied the solution behavior of synthetic fatty α-monoalkyl glyceryl ethers with different kinds of alkyl branching in water by a polarizing microscopic technique, differential scanning calorimetry, electrical conductivity measurements, and binary phase diagram analysis.…”

Profiling of bioactive lipids of the wild edible land snails of the genus Helix

“…from Sagami Bay (Japan), contains in PE, 13% AGE, 53% plasmalogen form, and 34% diacyl form [34]. 1-O-Hexadecylglycerol (chimyl alcohol), 1-O-heptadecylglycerol and 1-Ooctadecyl-glycerol (batyl alcohol) have been identified as major native constituents in elasmobranch fish (sharks, skates and rays) [35], as well as in human milk, bone marrow, atherosclerotic aorta [36].…”

Cholesterol as synthetic building blocks for artificial lipids with characteristic physical, chemical and biological properties

“…Several types of artificial alkyl glyceryl ether lipids have been prepared and used as one of the most important ingredient for cosmetics [22]. The PTC method for alkyl glyceryl ethers lipids is based on the synthesis of alkyl glycidyl ether according to the Williamson ether synthesis.…”

“…These polyamine amides are also models for lipoplex formation with respect to gene delivery systems in gene therapy [80]. The second potential of the reaction of the cholesteryl glycidyl ether with nucleophiles is shown in the case of alcohol as the nucleophile to prepare 1-cholesteryloxy-3-alkoxy-2-propanols(1-cholesteryloxy-3-al koxy glyceryl ether) [22,23]. In relation to the theory of the evolution of biomembranes, Ourisson et al postulated in 1979 that terpenoids might play the same role in procaryotes as cholesterol in eucaryotes, that is, as membrane reinforcers.…”