Molecular modeling studies of triacylglycerols

Abstract

The methods of molecular mechanics and semiempirical quantum mechanics have been used to investigate the steric and electrostatic features for a group of lipid-like molecules. Included in this group were trilaurin (LLL), tridecyl 1,2,3-propanetricarboxylate (TPT), and a family of short and long acid triacylglycerol molecules (SALATRIM). Computational studies on all of the molecules in the gas phase indicated that the hydrophobic interactions between the fatty acid chains were dominant in determining the molecular conformation. Analysis also showed that the triacylglycerols (LLL and SALATRIM) have similar molecular electrostatic potentials (EP). This electronic similarity suggests that one might expect similar reactivity toward lipase-mediated hydrolysis. A very different EP map was found for TPT, a compound which has each ester linkage molecularly reversed. TPT appears to be resistant to lipolysis, as evidenced by the near total lack of digestibility of this type of lipid in published in-vivo studies conducted in rodents.

Structure and functionality of edible fats

“…Many modeling studies have been carried out on triacylglyceride (TAG) systems. [67][68][69][70] An open problem is to model the condensation of TAG molecules into a crystal and the identification of the various polymorphic forms. We carried out simulations in order to see to what extent the assumption that the liquid oil was homogeneous when the distance, d, (Fig.…”

Structure and Mechanical Properties of Fat Crystal Networks

“…Methods to determine triglyceride and fatty acid composition in fat crystal networks are well established and well reviewed in the book by Christie(Chnstie, 1982). In addition, methods to determine the fatty acid positional distribution within a triglyceride have been established by two separate groups (Brockerhoff, 1965; Lands et al, 1966 Soest, 1978;de Song et al, 1991 ;Hagemann and Rothfus, 1992;van Soest et al, 1990;Yan et al, 1994), but to bis date there has been no predictive use of such methods.…”

Nanoscale characteristics of triacylglycerol oils: phase separation and binding energies of two-component oils to crystalline nanoplatelets

“…Triacylglycerol (TAG) polycrystalline particles in TAG oils find extensive use in the food industry. Although modelling studies of TAG systems have been carried out, [1][2][3][4] none have attempted to address a problem of central concern to food science and technology: the ''oil binding capacity'' of a system. In a many-component oil the existence of a solid fat surface could induce phase separation on a nanoscale in the oil.…”