Food Lipids: Chemistry, Nutrition, and Biotechnology

Figure 18 Preparation of structured triacylglycerols for use as nutraceuticals by lipasecatalyzed
transesterification.
Structured triacylglycerols containing two molecules of caprylic acid and one
molecule of erucic acid have been prepared by lipase-catalyzed esterification of
caprylic acid to monoerucin; the resulting triacylglycerols yield upon subsequent
hydrogenation of the erucoyl moieties to behenoyl moieties products resembling
Caprenin, a commercially available low-calorie triglyceride (125). Structured triacylglycerols
of the type monoglyceride diacetates and diglyceride monoacetates are
prepared using sn-1,3-specific lipase by transesterification of plant oils with triacetin
(126) or an alkyl acetate, e.g., ethyl acetate (127), as shown in Fig. 20.
2. Bioesters, Long Chain Esters, and Flavor Esters
Esterification reactions catalyzed by a nonspecific lipase from Candida antarctica
(Fig. 21) is being used commercially to produce a wide variety of fatty acid esters,
the ‘‘bioesters,’’ such as isopropyl myristate, isopropyl palmitate, octyl palmitate,
octyl stearate, decyl oleate, and cetyl palmitate, which are used in personal care
products (128).
Short chain esters have numerous applications in food industries as flavoring
components. Lipase-catalyzed esterification and interesterification for the synthesis
of these esters have received considerable attention (129–137).
3. Wax Esters and Steryl Esters
Esterification of mixtures of long chain and very long chain monounsaturated fatty
acids with the corresponding mixtures of alcohols using a lipase from Rhizomucor
miehei (Lipozyme) as catalyst provides wax esters (Fig. 22) in almost theoretical
yields (138).
The high rates of interesterification of triacylglycerols with a long chain alcohol
(96) indicate that alcoholysis reactions should be useful for the production of wax
esters of good commercial value. Using Lipozyme as biocatalyst, wax esters resembling
jojoba oil are obtained in high yield by alcoholysis of seed oils from Sinapis
Figure 19 Preparation of structured triacylglycerols for use in infant foods and nutraceuticals
by lipase-catalyzed transesterification.
Copyright 2002 by Marcel Dekker, Inc. All Rights Reserved.