Newer synthetic approaches to surfactants, lipids, and related compounds based on C‐3 building blocks: Recent advances related to fatty chemistry

Euro J Lipid Sci & Tech

2003

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Studies on design of liquid crystalline block molecules with non-conventional mesophase morphoplogies have been proposed by Tschierske and co-workers. These block molecules have a rigid core, a lateral substituent, and an alkyl chain segmenting blocks from each other. Related to this, diglyceryl alkyl ethers found by us have glycerol as a rigid core, a lateral substituent, and an alkyl chain similar to the Tschierske design. These two cases are compared with each other with regard to the relationship between the molecular structure and the liquid crystalline morphologies and other properties. Recently, new soft materials suitable for liquid crystals exhibiting self-assembly of phase-segregated structures have been designed. Typical examples of such "block" molecules containing glycerol having a C-3 building block include: (i) undecyl-glycerylether-modified siloxane derivatives with a siloxane segment as the rigid core and alkyl chains with 2,3-dihydroxypropoxy group as a hydrophilic group at a lateral or terminal position of the siloxane segment; (ii) novel hyper branched dendrimers forming the basis of polyglycerol nanocapsules with a core-shell molecular architecture; (iii) carbon nanotubes based on cyclodextrins (CDs); (iv) polymerizable amphiphilic diacetylene-containing phospholipids suitable for construction of functional nanocomposites. This is done by self-assembly and polymerization of diacetylene creating a "block molecular structure" with a polyacetylene chain as a rigid core segment, the lipid headgroups as the hydrophilic segment, and terminal flexible alkyl chains. On the basis of these results, future potential of block molecules as a soft building material for liquid crystalline structures was discussed.

Section: Liquid Crystals the Fourth State Of Matters And Their Futurmentioning

confidence: 81%

Section: Liquid Crystals the Fourth State Of Matters And Their Futurmentioning

confidence: 99%

Unique block molecules based on glycerol skeleton as C‐3 building blocks for liquid crystals formation by self‐assembly and their future potential for the “nano‐chemistry”

Euro J Lipid Sci & Tech

2003

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“…Glycerin is one of the simplest molecules bearing three -OH groups and can participate in reactions yielding amphiphilic esters (glycerides) and/or ethers (glyceryl ethers). In the past few decades, an industrial process for the preparation of fatty alkyl glyceryl ethers and their derivatives has been developed (9). In studies on the application of fatty alkyl glyceryl ethers as emulsifiers, Tsutsumi et al (10) found that synthetic methyl-branched isostearyl glyceryl ethers (GE-IS), where the methylbranched isostearyl moiety is CH 3 (CH 2 ) m CH(CH 3 )(CH 2 ) n -(m is an integer of 2-14, n is an integer of 2-10, and m + n is 10-16), gave stable water-in oil (W/O) emulsions with water contents as high as 98%.…”

mentioning

confidence: 99%

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

Takaishi

2002

J Surfact & Detergents

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Biological structures from proteins through viruses to cellular organelles with dimensions of 1 to 100 nm require molecular self-assembly and self-organization to form nanostructures. In contrast to covalent bonding, noncovalent interactions such as hydrogen bonding and hydrophobic association involve lower bond energies (2-20 kcal/mol) to attain the mobility and fluidity properties of biological structures. Noncovalent interactions are also well-known with amphiphilic molecules bearing both hydrophilic head groups and hydrophobic groups and are responsible for the formation of several types of self-assemblies such as micelles, liquid crystals, and lipid bilayers. As typical amphiphiles with a glycerin skeleton as a C-3 building block, alkyl glyceryl ethers and their derivatives have been of interest since they show unique self-assembly structures such as liquid crystals with hitherto unknown character.

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

Eur. J. Lipid Sci. Technol.

Takaishi

2001

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Cholesterol is one of the most widely distributed natural materials and has a unique chemical structure such as a steroid skeleton. Many types of chemical transformations of cholesterol functional groups have been developed. There is an interest in the derivatization of cholesterol and to introduce alkyl branched fatty acids into the molecule. These have found applications in the formulation of cosmetics and toiletries over the past few decades. An extraordinary interesting case is related to cholesteryl esters and their use in gene therapy delivery systems. These results can be attributed to their potential for forming cell-mimic membranes, because cholesterol is the most important building block of living cell membranes. In terms of organic synthesis, cholesterol is a strategically useful material. A typical case is remote functionalization by chemical reactions or by biocatalysis. In the future, cholesterol should be considered as a key compound, a building block for the construction of artificial lipid-like membranes by self-assembly. Also, as cholesterol is one of the members of the fat and oil family, fat and oil chemists should study and develop cholesterol chemistry even further.