Triolein structure

Figure 3.3 shows that the log /fow-log sw plot for compounds with log Kow > 5 deviates from linearity. This phenomenon is also observed for plots of log bioconcentration factor (BCF) versus log Ko (Connell, 1990). Chiou (1985) has shown that a similar deviation occurs in a triolein-water system alone, at log Ko > 5.5, as a result of solute-triolein incompatibility. Similarly, Banerjee and Baughman (1991) argued that BCFs of large molecules are smaller than expected on the basis of their hydrophobicity as a result of their disrupting effect on the structure of the lipid phase. The curvilinearity is not likely to be caused by sorption to DOC in the experimental systems (Section 3.4.), because deviations from linearity already occur at log /fow 5, whereas the effect of DOC-bo mA contaminants can only be expected at log /fow values > 7. 

This structure shows a triglyceride with three identical saturated fatty acids. Tripalmitin, in which all fatty acids are palmitic acid (n = 14), provides one example of a fat. Triolein is an oil containing only oleic acid moieties esterified to glycerol. In contrast to these two examples, it is by no means necessary that the three fatty acid groups be derived from only one fatty acid. For example, we might have a triglyceride that contains one saturated fatty acid, say palmitic acid, one monounsaturated fatty acid, say oleic acid, and one polyunsaturated fatty acid, perhaps arachidonic acid. 

Figures 7, 8 and 9 are plots at 25 C of specific conductance and density versus volume fraction of methanol in 2/1 triolein/ surfactant systems which are 4/1 molar ratios of 2-octanol to bis(2-ethylhexyl) sodium sulfosuccinate, triethylammonium linoleate and tetradecyldimethylammonium linoleate, respectively. For each surfactant system, a maximum for specific conductance and a minimum for density was observed at the same volume fraction, but this volume fraction of methanol varied between the three surfactant systems. At volume fractions of methanol above these abrupt changes, each system exhibited translucence, and it appears that gel-like structures form. These data are consistent for microemulsion structures that are based largely on geometric considerations (16-18).

Fomuso, L. B., and Akoh, C. C., Enzymatic modification of triolein Incorporation, of caproic and butyric acids to produce reduced-calorie structured lipids, J. Am. Oil Chem. Soc., 3, 269-272 (1997). 

Porcine lipase exhibits a series of unusual properties (142). The most interesting one, directly connected with its structure, is certainly its specific interactions with emulsified esters. When an aqueous solution of lipase at pH 5 is mixed with an excess of a triolein emulsion and when the cream is separated by centrifugation, no lipase can be detected in the clear aqueous lower phase. All activity is in the cream. But it returns at once into water when the emulsion is broken (145). This simple experiment suggests that lipase is adsorbed at the oil/water interface of the emulsion and that this interface may be the normal site of its action. Such an assiunption is confirmed by a series of experiments with substrates and inhibitors. 

None of the venoms, however, showed any interaction with films of cholesterol or protein, nor did hydrolysis occur in films of tripalmitin, triolein, cerebron, or sphingomyelin. The reaction with lecithin is highly specific. Not only is it sensitive to the chemical structure of the film, but the reaction rate may also be greatly altered by slight changes in the orientation of the molecules in the film or by changes in the pH of the solution or of the concentration of venom. 

The three corresponding esters or fats are tripalmitin, tristearin, and triolein, the general structural formula being ... 

Based on thermodynamic arguments, it has been suggested that octanol does not accurately represents fish lipids [81]. Lipid solubility has been proposed as an additional parameter based on the argument that lipids are more structured than octanol [82]. Partition coefficients with other solvents (triolein-water) and membrane vesicles are measured and related to as well as to BCF [32, 83, 84]. In general, these latter partition coefficients fairly correlate with Kq with systematic lower values at high These differences may lead to an apparently lower BCR The consequences are that overestimates bioaccumulation for very hydrophobic compounds. 

The methatesis of vegetable oils with ethylene is a very interesting way to obtain new unsaturated structures to be transformed into new polyols via the epoxidation - alcoholysis route. Trioleine was used as a model compound (the triester of glycerol with oleic acid), the methatesis reaction with ethylene being catalysed by a special ruthenium catalyst [72]. The resulting triglyceride, with terminal double bonds, after removal of the 1-decene formed, is transformed into polyols by epoxidation, followed by alcoholysis with methanol (reactions 17.27 and 17.28). 

Zlatanic, A. Z.S. Petrovic K. Dusek. Structure and properties of triolein-based polyurethane networks, 2002, 3, 1048-1056. 

Ahmadi, L Wright, AJ Marangoni, AG. Structural and mechanical behavior of tristearin/triolein-rich mixtures and the modification achieved by interesterification. FoodBiophys, 2009 4 64—76. 

Enzymatic catalysis can be regio-(l, 3 or 2-position) and fatty acid-specific and can result in products with better-defined chemical structure and composition (Ray et al., 2013). This flexibility allows the use of specific lipases to prepare fully acylated glycerin, such as triolein, as well asmono- or diglycerides that are used in the formulation of healthier products and as a first step in the production of structured lipids (Rodrigues and Femandes-Lafiiente, 2010). 

Draw the condensed structural formula for glyceryl trioleate (triolein), a triacylglycerol that uses oleic acid. 

Figure 1. Molecular structure of triolein, vernonia oil, and epoxidized soybean oil.

We were interested in the drying mechanism of vernonia oil since it has two functionalities unsaturated double bonds and epoxy rings. For this purpose, we have compared the drying characteristics of triolein, vernonia oil, and epoxidized soybean oil in the presence of 0.5% cobalt drier under baking conditions at 150 C for one hour. The molecular structures of these three oils are shown in Figure 1. 

Triglycerides are mostly derived from nature (- fats and oils) or are made by - esterification or - transesterification, if special structures and properties are desired. Triolein (- olein) or tristearin (- stearin) are made this way. Purity depends on the quality of the fatty acid or methyl ester used. 

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