Ether lipids based on the glyceryl ether skeleton: Present state,future potential |
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Authors: | Kouichi Urata Naotake Takaishi |
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Affiliation: | (1) Tochigi Research Laboratory, Kao Corporation, 2606, Akabane, Ichikaimachi, Haga-gun, 321-34 Tochigi, Japan;(2) Tokyo Research Laboratory, Kao Corporation, Sumida-ku, 131 Tokyo, Japan |
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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 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. |
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Keywords: | Ether lipids GE-IS glyceryl ether glycidyl ether isostearic acid isostearyl glyceryl ether liquid crystal W/O emulsion |
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