Oleic acid, oleate structure

Of all mentioned prebiotic membranogenic molecules, the ones that have gained more attention in the literature are long-chain fatty acids. In addition to their prebiotic relevance, these compounds are relatively simple from the structural point of view, and most of them are easily available. We will see in the next chapter that these vesicles have acquired a particular importance in the held of the origin of life. In fact, the hrst inveshgations on self-reproducing aqueous micelles and vesicles were carried out with caprylate (Bachmann et al, 1992) and most of the recent studies on vesicles involve vesicles from oleic acid/oleate (for simplicity we will refer to them as oleate vesicles). In this section, I would like to illustrate some of the basic properties of these surfactant aggregates. 

A primary reason of interest and fascination is at the level of self-assembly and selforganization. This phenomenon, which we already know well for other structures, acquires in giant vesicles a particular dimension. One of the simplest giant vesicles was produced simply by dispersing oleic acid in water at pH 8.5 [1]. This was an oleic acid - oleate giant vesicle having a diameter of about 70 pm, as can be seen in Figure 1.1. 

In this example of spontaneous vesiculation, a total of about 10 oleic acid-oleate molecules are involved in the formation of one vesicle. It is self-assembly and self-organization in the highest form, and unprecedented in chemistry-unless we consider crystallization. It is useful to remember that this creation of order operates under thermodynamic control ordered structures are built by a process which is... 

Esters of the fatty acid oleic acid are components of membranes that are subject to autoxidation. Explain which hydrogens of an oleate ester you expect to be abstracted most readily by a radical. Show the structures of the major autoxidation products that would be formed from an oleate ester. 

Nicolau A, Martignago Mariath R, Agostini Martini E, dos Santos Martini D, Samios D.The polymerization products of epoxidized oleic acid and epoxidized methyl oleate with cis-l,2-cyclohexanedicarboxylic anhydride and triethylamine as the initiator chemical structures, thermal and electrical properties. Mater Sci Eng C 2010 30 951-962. 

Soft templates have also been used for the synthesis of ceria nanoplates. Murray and co-workers used a high-boiling solvent system for the synthesis of ceria nanocrystals. Oleic acid and oleylamine were chosen as the solvent and capping agents and sodium diphosphate or sodium oleate were used as mineralizers in the experiment. Square-shaped ceria nanoplates were prepared and assembled into wire-like structures. 

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