Structured Lipids–

Novel Fats
with Medical,
Nutraceutical, and
Food Applications
H.T. Osborn and C.C. Akoh

ABSTRACT: Generally, structured lipids (SLs) are triacylglycerols (TAGs) that have been modified to change the fatty acid
composition and/or their positional distribution in glycerol backbone by chemically and/or enzymatically catalyzed
reactions and/or genetic engineering. More specifically, SLs are modified TAGs with improved nutritional or functional
properties. SLs provide an effective means for producing tailor-made lipids with desired physical characteristics, chemical
properties, and/or nutritional benefits. The production, commercialization outlook, medical, and food applications of
SLs are reviewed here. Physical property measurements for SL in food systems and future research needs for increased
industrial acceptance are also included in this review.
Keywords: acidolysis, interesterification, lipases, modified fats, structured lipids

Introduction acids based on their potential benefits for improvements in nutri-

With the ability to combine the beneficial characteristics of
component fatty acids into 1 triacylglycerol molecule, lipid modi-
fication enhances the role fats and oils play in food, nutrition, and
health applications. Structured lipids are tailor-made fats and oils
with improved nutritional or physical properties because of modi-
fications to incorporate new fatty acids or to change the position
of existing fatty acids on the glycerol backbone.
Soybean and safflower oils have been used in making fat emul-
sions for total parenteral nutrition (TPN) and enteral administra-
tion. Later, a physical blend of medium chain triacylglycerols
(MCTs) and long chain triacylglycerols (LCTs) was used, with the
MCTs being readily metabolized for quick energy. More recently,
SLs were designed to provide simultaneous delivery of beneficial
long chain fatty acids (LCFAs) at a slower rate and medium chain
fatty acids (MCFAs) at a quicker rate (Babayan 1987; Akoh 1998).
SL synthesis yields novel triacylglycerol (TAG) molecules (Akoh
1998). SLs may provide the most effective means of delivering de-
sired fatty acids for nutritive or therapeutic purposes, and for tar-
geting specific diseases and metabolic conditions (Lee and Akoh
1998).
Improvements or changes in the physical and/or chemical char-
acteristics of a TAG can also be achieved when SLs are synthe-
sized. Lipid modification strategies for the production of function-
al fats and oils include chemically- or lipase-catalyzed interesteri-
fication and/or acidolysis reactions and genetic engineering of
oilseed crops. Interesterification is used to produce fats with desir-
able functional and physical properties for food applications. In-
terest in interesterification from nutritional and functional stand-
points is on the rise because of the possibility to produce trans-
free margarines, cocoa butter substitutes, and reduced calorie
foods; to improve functional and physical properties of foods; and
to improve the nutritional quality of fats and oils. Regardless of
the method used, all SLs are designed to incorporate various fatty
tion or physical characteristics.
This review covers a broad range of information concerning the
production of SLs, including component fatty acids, production
strategies, medical and nutraceutical applications, functional food
applications, commercialization outlook, and future prospects for
research and development in this field.
Component Fatty Acids
A variety of fatty acids are used in the synthesis of SLs, taking
advantage of the functions and properties of each to maximize the
benefits of a given SL. The component fatty acids and their posi-
tion in the TAG molecule determine the functional and physical
properties, the metabolic fate, and the health benefits of an SL.
Therefore, careful analysis of the function and metabolism of
component fatty acids is merited.
Short chain fatty acids
Short chain fatty acids (SCFAs) range from 2 to 6 carbons long,
and are also known as volatile fatty acids. Traditional sources of
SCFAs include bovine milk and butter fat. Due to their water solu-
ble nature, molecular size, and short chain length, they are more
rapidly absorbed in the stomach than other fatty acids. Addition-
ally, SCFAs attached to the sn-3 position of TAGs will be com-
pletely hydrolyzed in the lumen of the stomach and small intes-
tine, due to the positional and chain length specificity of human
pancreatic gastric lipase. SCFAs have lower heat of combustion
than other fatty acids, making them lower in calories. Caloric val-
ues of common SCFAs are as follows: C2:0, 3.5 kcal/g; C3:0, 5.0
kcal/g; C4:0, 6.0 kcal/g; and C6:0, 7.5 kcal/g (Akoh 1998).
Medium chain fatty acids
The primary sources of MCFAs, which range in length from

© 2002 Institute of Food Technologists Vol. 1, 2002—COMPREHENSIVE REVIEWS IN FOOD SCIENCE AND FOOD SAFETY 93

crfsfsv1n3ms20010544-Osborn-Akoh-AF.P65 93 11/6/2002, 10:55 AM

 CRFSFS: Comprehensive Reviews in Food Science and Food Safety
C6:0 to C12:0, are coconut and palm kernel oils. MCFAs are pref-
erentially transported via the portal vein to the liver, because of
their smaller size and greater solubility compared to LCFAs (Bell
and others 1991; Straarup and Hoy 2000). For entry into the mito-
chondria of all tissues, MCFAs are not carnitine-dependent (Ba-
bayan 1987; Bell and others 1997). Additionally, MCFAs are me-
tabolized as rapidly as glucose in the body with little tendency to
deposit as stored fat, because they are not readily re-esterified into
triacylglycerols. Although MCFAs may be useful in the control of
obesity, they can potentially raise serum cholesterol levels. There-
fore, it appears that MCFAs are most useful in a structured lipid
that combines their inherent mobility, solubility, and ease of me-
tabolism with more healthful polyunsaturated fatty acids (Cater
and others 1997; Akoh 1998).
Long chain fatty acids
Long chain fatty acids (LCFAs), ranging from C14 to C24, are
common to animal fats and vegetable and marine oils. LCFAs are
absorbed and metabolized more slowly than either medium or
short chain fatty acids; much of the LCFAs may be lost as calci-
um-fatty acid soap in the feces (Broun and others 1999). LCFAs
cannot be absorbed or transported in the blood, due to their in-
creased hydrophobic character compared to SCFA and MCFA. In-
stead they must be first packaged into micelles, and then enter the
intestinal cells where chylomicrons are formed. Chylomicrons are
secreted into the lymphatic system and ultimately enter the sys-
temic circulation. Carnitine is then required to transport LCFAs
into the mitochondria of cells.
Several types of LCFAs exist, and the important ones in SL pro-
duction will be discussed here. Omega-6 fatty acids cannot be
synthesized by humans and are therefore considered essential fat-
ty acids (EFAs). Linoleic acid (18:2n-6), found in most vegetable
oils and plant seeds, is an EFA that can be desaturated further, and
elongated to arachidonic acid (20:4n-6). Arachidonic acid is a
precursor for eicosanoid formation. Another type of EFA is the
omega-3 fatty acid, such as linolenic acid (18:3n-3), which is
found in soybean and linseed oils. Eicosapentaenoic acid, 20:5n-
3 (EPA), and docosahexaenoic acid, 22:6n-3 (DHA), found in fish
oil, are other n-3 polyunsaturated fatty acids (PUFAs) of interest in
SL production. The n-3 fatty acids are essential in growth and de-
velopment throughout the human life cycle and should be includ-
ed in the diet. The n-3 PUFAs inhibit tissue eicosanoid biosynthe-
sis and reduce inflammation. Diets rich in n-3 PUFAs also in-
crease high density lipoprotein (HDL) cholesterol, while decreas-
ing low density lipoprotein (LDL) and very low density lipoprotein
(VLDL) cholesterol levels. Omega-9 fatty acids, found as oleic
acid (18:1n-9) in many vegetable oils, are not EFAs, but play a
moderate role in reducing plasma cholesterol in the body.
Conjugated linoleic acid (CLA), which has been shown to ex-
hibit potent anticancer properties in animal models of carcino-
genesis, can also be used for designing SLs. The major dietary
source of this important class of PUFA is from the meats and fats
of ruminant animals. Commercial sources of foodgrade quantities
of this unusual non-methylene-interrupted fatty acid will be re-
quired before the therapeutic benefits are realized in humans
(Watkins and German 1998).
Long chain saturated fatty acids are generally believed to in-
crease serum cholesterol levels. However, stearic acid (18:0) is
neutral with respect to cholesterol levels in the blood, partly be-
cause it has a melting point that is higher than body temperature
and it is readily desaturated to oleic acid in vivo. Additionally,
TAGs with high amounts of long chain saturated fatty acids are
poorly absorbed in humans.
Controlling the positional distribution of component fatty acids
in the final TAG is also important. During digestion, TAGs are de-
graded to sn-2 monoacylglycerols (MAGs) and free fatty acids in
94 COMPREHENSIVE REVIEWS IN FOOD SCIENCE AND FOOD SAFETY—Vol. 3, 2002
crfsfsv1n3ms20010544-Osborn-Akoh-AF.P65 94
the small intestine by pancreatic lipase. The sn-2 MAG and free
fatty acids are then absorbed by the enterocytes. In the intestinal
mucosa cells, sn-2 MAGs are re-esterified with fatty acids of exog-
enous or endogenous origin to form new TAGs. These are then
packed into chylomicrons and excreted into the lymph. The rate
of hydrolysis of TAGs by pancreatic lipase is affected by chain
length and unsaturation of the fatty acids at the sn-1 and -3 posi-
tions, with medium chain triacylglycerols (MCTs) being degraded
faster than long chain triacylglycerols (LCTs) (Straarup and Hoy
2000).
Production of Structured Lipids
Chemical synthesis
Chemical interesterification is inexpensive and easy to scale
up; however, the reaction lacks specificity and offers little or no
control over the positional distribution of fatty acids in the final
product (Willis and Marangoni 1999). This process usually in-
volves hydrolysis of a mixture of MCTs and LCTs, and re-esterifi-
cation after random mixing of the MCFAs and LCFAs has oc-
curred, by the ester-interchange reaction (Akoh 1998; Lee and
Akoh 1998).
Ester-interchange:
R1-CO-OR2 + R3-CO-OR4 R1-CO-OR4 +R3-CO-OR2
This reaction, catalyzed by alkali metals or metal alkylates, re-
quires high temperatures and anhydrous conditions. In addition to
the desired randomized TAGs, a number of unwanted products
are also obtained from this reaction and may be difficult to re-
move (Akoh 1998).
Enzymatic synthesis
Lipases occur widely in nature and are active at the oil-water
interface in heterogeneous reaction systems. Lipase catalyzed in-
teresterification reactions offer the advantage of greater control
over the positional distribution of fatty acids in the final product,
due to lipases’ fatty acid selectivity and regiospecificity. Lipases
hydrolyze TAGs to monoacylglycerols, diacylglycerols (DAGs),
free fatty acids (FFA), and glycerol. In addition to the ester-inter-
change reaction discussed in the previous section, lipases can
also catalyze direct esterification, acidolysis, and alcoholysis re-
actions (Lee and Akoh 1998).
Direct esterification:
R1-CO-OH + R-OH R1-CO-OR + H20
Acidolysis:
R1-CO-OR + R2-CO-OH R2-CO-OR + R1-CO-OH
Alcoholysis:
R-CO-OR1 + R2-OH R-CO-OR2 + R1-OH
Lipase-catalyzed reactions are a combination of esterification
and hydrolysis (reverse reaction) reactions. Water must be contin-
uously removed from the reaction medium in order to increase
esterification reactions, while minimizing hydrolysis in order to
obtain high conversion rates to products. When excess water is
present, hydrolysis predominates, resulting in the accumulation of
glycerol, FFAs, MAGs, and DAGs. However, some water is essen-
tial for enzymatic catalysis because it maintains enzyme dynam-
ics during noncovalent interactions. To “optimize” 1-step lipase-
catalyzed reactions, it is necessary to strike a balance between
hydrolysis and esterification. Willis and Marangoni (1999) recent-
ly proposed splitting the reactions into 2 component hydrolytic
and esterification phases and then optimizing the reaction condi-
tions for each individual phase, in order to improve productivity
and potentially make lipase-catalyzed reactions economically vi-
able. The results of their study indicated that using chemical ester-
ification of oil for the 1st phase of the reaction and enzyme hy-
drolysis in the 2nd phase offered the best control over the fatty
11/6/2002, 10:55 AM
 Structured lipids. . .
acid positional distribution in the final product and required the
least amount of reaction time. There were drawbacks associated
with the chemical reaction, and further studies are needed in or-
der to reduce product charring, degree of hydrolysis, and decom-
position.
Structured lipids can be produced with lipases in organic sol-
vent, where substrates are soluble and hydrolysis can be mini-
mized. The type of organic solvent employed can dramatically af-
fect the reaction kinetics and catalytic efficiency of an enzyme.
The extent to which the solvent affects the activity or stability of
the enzyme and the effect of the solvent on the equilibrium posi-
tion of the desired reaction must both be considered when choos-
ing a solvent for biocatalysis. Hydrophilic or polar solvents can
penetrate into the hydrophilic core of proteins and alter their
functional structure. They also strip off the essential water of the
enzyme. Hydrophobic solvents are less likely to cause enzyme in-
activation in esterification reactions (Akoh 1998).
Most lipases are optimally active between 30 and 40 ⬚C (Shah-
ani 1975). As the temperature increases, enzyme molecules un-
fold by destruction of bonds, such as sulfide bridges, and may
lead to hydrolysis of peptide bonds and deamidation of aspar-
agine and glutamine residues. However, these processes can be
avoided in a water-free environment. Immobilization of enzymes
also results in greater thermostability. Additionally, genetically en-
gineered lipases are now available for the synthesis of SLs. It is
hoped that the use of biotechnology will reduce the cost of lipas-
es, making the enzymatic route to SLs economically viable.
Other factors affecting enzymatic activity and product yield in-
clude pH, substrate molar ratio, enzyme activity and load, incu-
bation time, specificity of enzyme to substrate type and chain
length, and regiospecificity (Akoh 1998). Two of the most attrac-
tive reasons for choosing enzymatic over chemically catalyzed re-
actions for SL production are the energy saved and minimization
of thermal degradation.
Genetic engineering of plant lipids
Limited fatty acid compositional modifications of crop plant
oils have been achieved in the past through traditional breeding
techniques. Breeders have made use of the natural diversity that
exists among plant varieties to transfer desirable characteristics
from one to another. Mutagenesis has been used to produce culti-
vars of sunflower containing 90% oleate and less than 7% satu-
rates. Sunflower oil normally contains only 16 to 20% oleate. This
high-oleate sunflower is now in production and does not require
catalytic hydrogenation for stabilization. Mutagenesis also en-
abled the production of flax that contains no linolenic acid, but
has an increased amount of linoleic acid. Recently, high stearate
soybean and high oleic sunflower oils with improved stability
have been produced. Low saturate and linolenic acid soybean
oils are desirable outcomes of genetic engineering.
Most of the genes relevant to the synthesis of plant storage lip-
ids have now been isolated. Genetic codes are available to intro-
duce double bonds, elongate carbon chains, synthesize eicosap-
entaenate, and produce fatty acid isomers not normally found in
common sources of edible oils. Plant engineers are now trying to
incorporate the principles used in chemical and enzymatic syn-
thesis of “tailor-made” structured lipids into their genetic engi-
neering techniques.
Researchers have targeted specific traits for incorporation into
oilseed crops. The temperate zone oilseed crops tend to have stor-
age lipids rich in unsaturated fatty acids, and thus liquid oils are,
in themselves, not suitable for products like shortenings and mar-
garines. Both palmitic and stearic acids are precursors to the un-
saturated fatty acids, making up the bulk of the oil found in seeds
from temperate zone crops. Pathways have now been engineered
that produce fewer unsaturated fatty acids and accumulate more
Vol. 3, 2002—COMPREHENSIVE REVIEWS IN FOOD SCIENCE AND FOOD SAFETY
crfsfsv1n3ms20010544-Osborn-Akoh-AF.P65 95
of the precursor palmitic and stearic acids in the TAGs.
PUFAs have beneficial effects on serum cholesterol, but are
highly susceptible to oxidation when not protected by antioxi-
dants. Since oleic acid (18:1) appears to have a similar effect on
cholesterol as linoleic acid (18:2n-6) and is not as susceptible to
oxidation, researchers increased the ratio of monounsaturated fat-
ty acids (MUFAs) to PUFAs in soybean and canola oil by modify-
ing the activity of a microsomal membrane-bound oleate desatu-
rase (Broun and others 1999).
The presence of trans fatty acids in the diet has recently be-
come a major health concern for consumers. Some well-publi-
cized studies have suggested that trans fatty acids contribute to
coronary heart disease by raising levels of LDL cholesterol and
lowering levels of HDL cholesterol (Kris-Etherton 1995). Trans fat-
ty acids are produced during the hydrogenation process used by
food companies that try to produce a more solid fat from vegeta-
ble oils for use in shortenings and margarines. Several companies
are actively pursuing the development of seed oils that contain
levels of saturated fatty acids high enough to permit the elimina-
tion of the need for hydrogenation, and, subsequently, the pro-
duction of trans fatty acids (Knauf and Del Vecchio 1998).
Cloning and characterizing genes for a family of thioesterases
was the 1st step toward the goal of incorporating MCFAs into oil
seed crops that naturally do not contain such fatty acids. A gene
from the California bay tree that produces MCFAs in its seeds was
incorporated into canola plants. The transgenic canola now accu-
mulates up to 65% more lauric acid in their seed TAGs (Voelker
and others 1996). The sn-2 acyltransferase has a high degree of
specificity for an unsaturated fatty acid; therefore, most of the ole-
ic acid found in these TAGs is at the sn-2 position. This oil was
commercialized by Calgene (now Monsanto) and marketed as
Laurical®. Initial functional screening of this new oil was con-
ducted to see if it would serve as a cocoa butter replacement in
coating and confectionery products. When evaluated in a stan-
dard confectionery coating versus commercial lauric fats (palm
kernel oil and coconut oil), significant improvements were ob-
served, including better compatibility with cocoa butter, signifi-
cant increases in flavor impact, increased shelf life because of de-
creased bloom, and preferred mouthfeel. Also, some negative dif-
ferences were found, including problems with demolding, less
snap, and less gloss (Knauf and Del Vecchio 1998). This oil can
also be used in coffee whiteners, whipped toppings, and filling
fats (Broun and others 1999). Unfortunately, Laurical® is not used
much in foods, probably because lauric acid has the tendency to
raise serum cholesterol levels. Laurical® may find more use in
nonfood products.
Other thioesterase genes have been isolated that encode C8
and C10 fatty acids. Rapeseed plants expressing this gene accu-
mulated significant amounts of these medium chain fatty acids
(Dehesh and others 1996). It seems likely that producing a wide
variety of MCFA will soon be possible in canola and other wild
and domesticated Cuphea plant varieties. One problem observed
in the above-mentioned transgenic plants is that MCFAs are ex-
cluded from the sn-2 position of the TAG. However, the genes en-
coding for lysophosphatidic acid sn-2 acyltransferases were re-
cently isolated and may prove useful for producing nutritionally
useful structured TAG molecules (Broun and others 1999).
With the identification and purification of so many genes in-
volved in plant seed lipid production, the possibilities for geneti-
cally engineered SLs may seem limitless. However, there are
some limits to what is practically possible, and feasibility is the
1st consideration when thinking of specific ways to modify seed
storage lipids (Knauf and Del Vecchio 1998). Lipids cannot be
modified in such a way that they interfere with the ability of seeds
to germinate or metabolize energy. A modified seed lipid will be
useless if the crop is not viable. When unusual fatty acids are in-
95
11/6/2002, 10:55 AM
 CRFSFS: Comprehensive Reviews in Food Science and Food Safety
corporated into the storage lipids during seed development, it is
highly likely that they will also become incorporated into the
structural lipids because their synthesis pathways share many
common steps. The structural lipids are essential to support
growth and for normal seed function. Therefore, re-engineering
TAG biosynthesis must not compromise the synthesis of the struc-
tural lipids necessary to support growth and viability. Another
type of limitation is the amount of oil obtainable from a crop,
since most of the oilseed crop breeders measure success by how
much seed is harvested per acre. Therefore, “designer” plants can-
not compromise crop yield.
Practical limitations also exist in this new field of genetic engi-
neering. Expertise from a variety of fields is required to successful-
ly produce genetically modified crops: plant physiology, enzy-
mology, molecular biology, gene transfer cell biology, prototype
evaluation, and plant breeding. Financial modeling and analyses
of the eventual value and return, versus development costs and
risk, may argue against ever starting certain projects. A major con-
cern associated with genetically modified crops is the potential
for cross-pollination to occur among genetically modified crops
and unmodified plants in neighboring fields. This phenomenon
would reduce the purity of both crops. Regulatory and political is-
sues are also major obstacles facing genetic engineering. Cost of
raw materials and synthetic capacities are factors to consider
when this approach is compared with chemically or enzymatical-
ly modified lipids. Genetically engineered crops are limited by
the number of acres that can be planted, and, in the latter case,
huge capital investments are required to form manufacturing
plants (Knauf and Del Vecchio 1998).
Medical and Nutraceutical Applications of Structured
Lipids
The relationship between stereospecific fatty acid location and
lipid nutrition suggests that the process of interesterification, or
acidolysis, could be used to improve the nutrition profile of cer-
tain TAGs. Manufacturers of specialty food ingredients for infant
formulas and enteral supplements should design fats with saturat-
ed fatty acids at the sn-2 position to provide increased caloric in-
take (Decker 1996).
Infant formulas
Ideally, the fat component of infant formulas should contain the
fatty acids, such as MCFAs, linoleic acid, linolenic acid, and PU-
FAs in the same position and amount as those found in human
milk. Human milk is comprised of 20 to 30% palmitic acid, with
33% at the sn-2 position (Willis and others 1998). The fat in most
infant formulas is of vegetable origin and tends to have unsaturat-
ed fatty acids in the sn-2 position. Innis and others (1994) found
that infants fed human milk had 26% palmitic acid in their plas-
ma TAGs, compared with 7.4% in infants fed vegetable oil-based
infant formula with the same total concentration of palmitic acid,
but not at the sn-2 position. When rats were fed a coconut oil and
palm olein SL, absorption was increased due to the increased pro-
portion of long-chain saturates at the sn-2 position (Lien and oth-
ers 1993). Therefore, SLs with high proportions of palmitic acid at
the sn-2 position would provide a fat with improved absorption
capability in infants (Willis and others 1998). Care must be taken
with regard to the concentrations of the saturates at the sn-2 posi-
tion, because palmitic acid is the only saturate that has been stud-
ied extensively, and other long chain saturates may have hyperc-
holesterolemic effects (Pai and Yeh 1997).
Enteral and parenteral nutrition
While MCTs have many advantages, a minimum amount of
LCT is still necessary to provide EFAs. Physical mixtures of MCTs
96 COMPREHENSIVE REVIEWS IN FOOD SCIENCE AND FOOD SAFETY—Vol. 3, 2002
crfsfsv1n3ms20010544-Osborn-Akoh-AF.P65 96
and LCTs have proven useful in the past for enteral (oral tube
feeding) and parenteral (intravenous feeding) nutrition. More re-
cently, structured TAGs comprised of LCFAs and MCFAs have
emerged as the preferred alternative to physical mixtures for treat-
ment of patients, although both products provide identical fat
contents. Structured lipids comprised of both LCFAs and MCFAs
are designed to provide simultaneous delivery of the fatty acids
and a slower, more controlled release of the MCFA into the
bloodstream (Babayan 1987). The advantages of enterally fed SLs
may well relate to differences in absorption and processing. Struc-
tured TAGs that contain MCFA may provide a vehicle for rapid hy-
drolysis and absorption, due to their smaller molecular size and
greater water solubility in comparison to long-chain TAGs (Jensen
and Jensen 1992). Structured lipids offer several advantages over
native oils and physical mixtures, including improved immune
function, decreased cancer risk, thrombosis prevention, cholester-
ol lowering, improved nitrogen balance, and no risk of reticu-
loendothelial system (RES) impairment (Kennedy 1991). Increases
in protein synthetic rates in both skeletal muscle and liver have
also been demonstrated in patients receiving SL (DeMichele and
others 1988). The more recent studies on SL for medical applica-
tions are an attempt to define the factors affecting the absorption
and metabolic fates of a structured TAG, and the effects they have
in vivo. The results of several such studies are summarized below,
and the TAG structure of the SL in each study is diagrammed in
Table 1.
Lee and others (2000) showed that although they have a similar
total fatty acid composition, enzymatically modified lipids and a
physical mixture of lipids have different metabolic pathways,
based on the structure and due to the difference in fatty acid com-
position at the sn-2 position of lipid molecules. In this study, soy-
bean oil was modified by incorporating caprylic acid (C8:0) at the
sn-1 and sn-3 positions; the LCFA remained intact at sn-2 posi-
tion. This SL was compared to a physical mixture of soybean oil
and tricaprylin. Caprylic acid was found in the livers and inguinal
adipocyte TAGs of the rats fed SL, whereas it was not present in
the rats fed a physical mixture. This suggests that the positional
distribution of C8:0 is important in the metabolism of TAGs and
may lead to different physiological influences. Conflicting results
regarding the influence positional distribution has on absorption
and metabolism have been reported, but may be due to differenc-
es in the oils and experimental conditions used (Jensen and others
1994; Christensen and others 1995; Tso and others 1999).
Straarup and Hoy (2000) extended this examination by compar-
ing the lymphatic transport of a specific SL, comprised of rape-
seed oil and decanoic acid (C10:0), a randomized fat, and a phys-
ical mixture, in normal and malabsorbing rats. All 3 lipids com-
pared in this study contained the same fatty acid profile. Rape-
seed oil was used as the control. In this study, the decanoic acid
was located mainly in the sn-1 and sn-3 positions in the specific
SL, but at all positions in the randomized lipid, which was synthe-
sized chemically. In normal rats, faster absorption rates of 18:1n-9
and 18:2n-6 fatty acids were obtained from the specific SL and
the physical mixture compared to the randomized and control
oils. The authors concluded that this was a result of faster hydroly-
sis of the specific TAG compared to the randomized and native
oils. The MCFA and the sn-2 MAG released after hydrolysis of
MCTs in the physical mixture may improve the emulsification of
LCTs and, therefore, account for the increased absorption rate of
the physical mixture. The recoveries of C18:3n-3 were similar for
the physical mixture and randomized oils, but significantly lower
than for the specific oil. This indicates that the TAG structure of
the oil and the presence of C10:0, not the level of individual fatty
acids, were the major determinants of the amount of fatty acid ab-
sorbed and transported. The specific SL had low amounts of
C10:0 at the sn-2 position, and dietary C10:0 from the sn-1 and
11/6/2002, 10:55 AM
 Structured lipids. . .

Table 1—Triacylglycerol structure of structured and comparison lipids used in recent studies on enteral and parenteral nutri-
tion.
Source Structured Lipida Comparison Lipid(s)
Lee and others 2000 8:0 or LCFA LCFA
18:2n-6 (63%), 18:1n-9 (23%), 18:3n-3 (6%) 18:2n-6 (66%), 18:1n-9 (24%), 18:3n-3 (5%)
8:0 or LCFA LCFA
Soybean Oil
8.0
8.0
8.0

Straaup and Hoy 2000 10:0 10:0

18:1n-9 (42%), 18:2n-6 (22%), 18:3n-3 (10%) 10:0
10:0 10:0
Specific SL
LCFA, 10:0 LCFA
10:0 (45%), 18:1n-9 (30%), 18:2n-6 (12%) 18:1n-9 (47%), 18:2n-6 (35%), 18:3n-3 (15%)
LCFA, 10:0 LCFA
Randomized SL Rapeseed Oil

Mu and Hoy 2000 8:0, 10:0, or 12:0 LCFA

18:1n-9 or 18:2 18:2 (75%), 18:1n-9 (11%)
8:0, 10:0, or 12:0 LCFA
Safflower Oil
LCFA
18:1n-9 (90%), 18:2 (7%)
LCFA
High Oleic Sunflower Oil

Sandstrom and others 1993, MCFA, LCFA LCFA

Bellantone and others 1999, MCFA, LCFA LCFA
Chambrier and others 1999, MCFA, LCFA LCFA
Kruimel and others 2000, Structolipid (Pharmacia & Upjohn AB, MCFA
Rubin and others 2000 Stockholm, Sweden), or FE 73403 MCFA
(Kabi Pharmacia AB, Stockholm, Sweden) MCFA
Intralipid (pharmacia & Upjohn AB)
Lipofundin (Braun Melsungen AG,
Melsungen, Germany), or Medialipide 20%
(B. Braun Inc., Boulongne, France)

Lee and others 1999 PUFA LCFA

8:0 (64.3%), 20:5n-3 (17.8%), 22:6n-3 (15%) 18:2n-6 (66%), 18:1n-9 (25 %), 18:3n-3 (5%)
PUFA LCFA
Soybean Oil

Kenler and others 1996, MCFA, 20:5n-3, 20:6n-3 8:0, 10:0

Swails and others 1997 MCFA, 20:5n-3, 20:6n-3 8:0, 10:0
MCFA, 20:5n-3, 20:6n-3 8:0, 10:0
Corn or soybean LCFA
Corn or soybean LCFA
Corn or soybean LCFA
Osmolite HN (Ross Products Division,
Columbus, Ohio, U.S.A.)
a MCFA = medium chain fatty acid, LCFA = long chain fatty acid

sn-3 positions was thought to be absorbed directly through the
portal vein; therefore, less C10:0 was expected in the lymph as a
result of SL feeding, compared to randomized oil and physical
mixture diets. However, similar amounts of C10:0 were observed
in the mesenteric lymph from the 3 oils, which indicates better
hydrolysis and higher absorption rates of the specific SL, as well
as acyl migration in the TAG during hydrolysis. The intragastric
administration of fat to the rats excluded the activation of lingual
lipase in this study, and rats have only trace amounts of gastric li-
pase. Therefore, all hydrolysis of test oils measured in this study
was a result of pancreatic lipase. The preduodenal lipases prefer-
entially hydrolyze short and medium chain fatty acids from the
sn-3 position, so improved recovery from the specific SL would
be expected in patients when these lipases are also contributing
to hydrolysis. Clinical treatment of short-bowel patients is one
promising area for this type of SL, because these patients fre-
Vol. 3, 2002—COMPREHENSIVE REVIEWS IN FOOD SCIENCE AND FOOD SAFETY
quently have compromised EFA status (Jeppesen and others
1997, 1998).
Mu and Hoy (2000) compared the intestinal absorption of dif-
ferent SLs in vivo. They studied the lymphatic transport of fatty ac-
ids from specific SL containing different MCFA varying from ca-
prylic acid (8:0) to lauric acid (12:0) in the sn-1,3 positions and
LCFAs in the sn-2 position, to investigate the effect of chain length
of MCFAs on the absorption of LCFAs and the distribution of MC-
FAs between the portal vein and lymphatics in rats with normal
fat absorption. The results of this study showed that the chain
length of MCFAs located in the primary positions does not affect
the lymphatic transport of LCFAs in the sn-2 position. This result
suggests that similar type SLs may be used to provide different
LCFAs according to clinical demand. Similar intestinal absorption
of different LCFAs can be expected in other SLs that contain MC-
FAs at the sn-1 and sn-3 positions. It appears that it is possible to
97

crfsfsv1n3ms20010544-Osborn-Akoh-AF.P65 97 11/6/2002, 10:55 AM

 CRFSFS: Comprehensive Reviews in Food Science and Food Safety
manufacture SLs with different MCFAs to direct the fatty acids from
the sn-1 and sn-3 positions toward the liver through the portal
vein or toward the muscle or adipose tissues through formation of
chylomicrons, without affecting the transport of the long-chain fat-
ty acid in the sn-2 position.
The TAGs in total parenteral nutrition (TPN) are normally ad-
ministered as an emulsion. These emulsions are suspected of sup-
pressing the immune function because pneumonia and wound in-
fection often occurs in patients treated with TPN. However, the
influence of various lipid emulsions on leukocyte function is still
unclear. Kruimel and others (2000) attempted to explain this phe-
nomenon through in vitro studies of lipid emulsions containing
fatty acids with different chain lengths on the production of radi-
cals by polymorphonuclear leukocytes. Emulsions made from
LCT, a physical mixture of LCT and MCT, and an SL were com-
pared in this study. The results indicated that physical mixtures
caused higher peak levels and faster production of oxygen radi-
cals, compared to LCT and SL emulsions. Chambrier and others
(1999) conducted a similar study comparing the effect of physical
mixtures and SL on postoperative patients. They did not see the
hepatic function disturbances in patients given the SL, which are
often observed with TPN. The plasma TAG levels remained normal
in patients given SL, whereas they significantly increased with the
physical mixture. Bellantone and others (1999) gave lipid emul-
sions to patients after colorectal surgery. The differences between
the SL and physical mixture groups were less marked in this study.
Structured lipids synthesized from fish oil and MCTs were ad-
ministered to patients undergoing surgery for upper gastrointesti-
nal malignancies. This diet was compared to a control diet that
differed only in its fat source. The SL diet was tolerated signifi-
cantly better, led to improved hepatic and renal function, and re-
duced the number of infections per patient (Kenler and others
1996). Lee and others (1999) fed female mice diets supplemented
with an SL containing n-3 PUFAs and caprylic acid or soybean oil
for 21 d. The effect of the diet on serum lipids and glucose con-
centrations were determined at the end of the feeding period. In
spite of the higher content of caprylic acid in the SL, 8:0 was not
detected in the livers of the SL fed mice. High amounts of n-3 PU-
FAs were found in the livers of the SL fed mice. These findings
suggest that the 8:0 was metabolized quickly for energy, and that
different fatty acids (FAs) in the diet may eventually lead to
change in fatty acid composition of the liver. SLs containing MC-
FAs and n-3 PUFAs could be a therapeutic or medical lipid
source, and may be useful in enteral and parenteral nutrition. This
SL could decrease serum cholesterols and TAGs. It may also re-
duce the rate of body weight gain, because the MCFAs were me-
tabolized more rapidly in the body compared to soybean oil.
Swails and others (1997) demonstrated significant reductions in
prostaglandin production in postsurgical patients receiving an en-
teral SL formula containing EPA and DHA. This downregulation in
prostaglandin production did not predispose the patients to any
postoperative events, such as higher incidence of infection or an
inability to heal wounds. In fact, improved liver function was re-
ported in the SL patients. The physiological function of the SL ap-
pears to be due in part to the n-3 fatty acids acting through al-
tered prostaglandin release from mononuclear cells.
Diets containing an SL composed of MCFAs and linoleic acid
led to improved absorption of EFAs in patients with cystic fibrosis.
These patients experience malabsorption as a result of impaired
pancreatic function. However, the SL provided an efficient way to
supplement linoleic acid and to provide energy from the MCTs,
which were the preferred substrate for oxidative metabolism (Bell
and others 1997). No signs of central nervous system toxicity
were noted in patients given the SL, and there was no tendency to
ketosis (Sandstrom and others 1993).
Recently, a long-term study (4 wk treatment) was conducted on
98 COMPREHENSIVE REVIEWS IN FOOD SCIENCE AND FOOD SAFETY—Vol. 3, 2002
crfsfsv1n3ms20010544-Osborn-Akoh-AF.P65 98
the efficacy and safety of an SL prepared from coconut oil and
soybean oil. Patients receiving the SL were compared to other pa-
tients given LCT. This double-blind, randomized, crossover study
indicated that the SL was safe and efficient when provided to pa-
tients on home parental nutrition on a long-term basis and that it
may be associated with possible reduction in liver dysfunction
(Rubin and others 2000).
Reduced calorie fats
With increasing consumer awareness of the risks associated
with high fat intake, a market for reduced calorie fats and fat re-
placers has opened up. Carbohydrate and protein-based fat re-
placers are currently available, but cannot be exposed to high
temperatures. Therefore, lipid-based fat substitutes are the only
option for use in cooking and deep-frying applications and for
mimicking all the attributes of a natural fat. Reduced calorie SLs
are designed by taking advantage of either limited absorption of
long-chain saturates or the low caloric value of SCFAs.
The majority of reduced calorie fats and fat substitutes available
today contain fatty acids that are not naturally present in edible
oils and fats, but may match the chemistry and functions of natu-
ral fats. Typically, such products lack nutritionally important EFAs.
For example, Akoh and Yee (1997) interesterified tristearin with
tricaprin (C10:0) or tricaprylin (C8:0) with sn-1,3-specific immo-
bilized lipase to produce a low calorie SL.
One group of researchers (Kanjilal and others 1999) synthe-
sized an SL from natural vegetable oils so it would contain EFAs
and natural antioxidants. They incorporated behenic acid into the
sn-1 and sn-3 positions of sunflower oil through a transesterifica-
tion reaction catalyzed by lipases. The synthesized product deliv-
ered 5.36 kcal/g and had an improved plastic nature, which in-
creases the potential food applications for such a product, espe-
cially since it is a trans-free solid fat. After producing the SL, it
was fed to rats and compared to a control group fed sunflower oil.
No differences were observed in the amount of food consumed,
which indicates that the palatability and taste of the SL was very
similar to the native sunflower oil. Additionally, no differences
were observed between the groups regarding the levels of major
fatty acids of the plasma total lipids.
Functional Structured Lipids
Plastic fats for food applications
Margarine, modified butters, and shortenings are “plastic,” that
is, they have the appearance of solids in that they resist small
stresses, but yield to a deforming stress above a certain minimal
value (the yield stress) to flow like liquid. The relative proportion
of solid to liquid crystals is the dominant controlling factor for
hardness, followed by crystal size and polymorphic form (Johnson
1998). Manufacturers need fats with a steep solid fat content
(SFC) curve for margarine production. They want their product to
be solid in the refrigerator, but spread easily upon removal and
melt quickly in the mouth. The spreadability of margarine at re-
frigerator temperatures is related to its content of solid fats at 2
and 10 ⬚C. The solid content at 25 ⬚C influences plasticity at room
temperature (Brekke 1980). Desired spreadability occurs within a
range of roughly 15 to 35% solids (de Man 1992). The fat should
crystallize as a ␤’ polymorph.
Interesterification is useful for producing plastic fats and oils
suitable for use in margarines and shortenings, because chemical
properties of the original fat are relatively unaffected and the fatty
acids’ inherent properties are not changed. Additionally, unsatura-
tion levels stay constant in the fatty acids, and there is no cis-trans
isomerization. When short or medium chain fatty acids and
LCFAs are incorporated, they can produce TAGs with good
11/6/2002, 10:55 AM
 Structured lipids. . .

Table 2—Plastic fats produced by chemical and enzymatic reactions or genetic engineering
Structured Lipid
Stearic Acid and High-Laurate
Canola Oil
High Palmitic Soybean Oil
Palm Stearin-Sunflower Oil
Stearic Acid and Triolein
Butterfat-Canola Oil
Triolein and Tripalmitin
Production Method
Genetic engineering of high-
laurate canola; acidolysis with stearic
acid and a nonspecific lipase
Genetic engineering using
the fap5 allele
Transesterification catalyzed by
sn-1,3 specific and nonspecific
lipases
Acidolysis with sn-1,3 specific
lipase; interesterification with stearic
acid methyl ester and a
nonspecific lipase
Chemical interesterification
Enzymatic interesterification in a
canola lecithin-hexane
reverse micelle system
Food Application Reference
Production of trans-free Fomuso and Akoh 2001
margarine.
Production of trans-free Stoltzfus and others 2000
margarine-type fats
Softening and improved melting Lai and others 1998
characteristics of a component
for shortening, pastry, margarine,
and other edible fats
Production of trans-free Seriburi and Akoh 1998
margarine-type fats
Improved cold-temperature Rousseau and others 1996
spreadability of butter
Adapt technology for Marangoni and others 1993
modification of vegetable
oils and dairy fat

spreadability and temperature stability. Table 2 summarizes exper-
iments conducted using chemical and enzymatic reactions, or ge-
netic engineering to produce plastic fats.
Cocoa butter alternatives
Cocoa butter is the fat of choice in the confectionery industry.
Its polymorphism greatly affects the physical properties of choco-
late products, such as gloss, snap, contraction, heat resistance,
quick and sharp melting in the mouth, and bloom-resistance
(Koyano and others 1990; Loisel and others 1998). The availabili-
ty of cocoa butter, which affects cost, has prompted much re-
search on alternatives that can be used as cocoa butter replace-
ments or extenders in chocolate and confectionery coatings.
There are no naturally occurring fats with similar physical proper-
ties to cocoa butter; all alternatives are made by blending and/or
modifying fats. When using enzymatic processes for producing
cocoa butter alternatives, several factors need to be taken into
consideration. The melting behavior has to be very similar to co-
coa butter in order to achieve the same cooling effect in the
mouth. An alternative fat that is to be used in conjunction with co-
coa butter should not interfere with the correct crystallization of
the cocoa butter during tempering. ␤ crystals are the desirable
polymorph in the confectionery industry.
The most common cocoa butter equivalents to date include
palm oil, palm mid-fractions, illipe (Shorea stenoptera) fat, shea
(Butyrospermum parkii) butter, sal (Shorea robusta) fat, and ko-
kum (Garcinia indica) butter. There are also some commercially
blended alternatives available. When these natural fat sources are
modified by incorporating either palmitic or stearic acid, using
sn-1 and sn-3 selective lipases, it is possible to produce a cocoa
butter-like fat, in which the fatty acid composition closely resem-
bles that of cocoa butter. An extensive review of cocoa butter al-
ternatives was published by Lipp and Anklam (1998). Foglia and
others 1993 suggested beef tallow as a possible base fat for pro-
ducing SLs that could be used as cocoa butter alternatives. Un-
published data (Osborn and Akoh 2002) from our laboratory in-
dicate that SLs enzymatically made by randomizing beef tallow or
by incorporating stearic acid into beef tallow may be useful as a
cocoa butter extender, because “chocolates” produced with the
SL had some physical properties similar to chocolates produced
with only cocoa butter.
Frying oils
Kubow (1993) noted that PUFAs and plant sterols may form po-
tentially toxic products when exposed to oxidative stress, either
thermally or through aeration. High oleic acid sunflower oil, dis-
cussed previously in the genetically engineered SL section, shows
excellent behavior with respect to thermooxidation and frying sta-
bility (Dobarganes and others 1993). Canola plants that express
80% 18:1 in their seed TAG have much improved heat stability
over traditional canola oil. When measured according to the ac-
tive oxygen method (AOM) for fat stability, conventional soybean
oil is rated 10 to 20 h, whereas the high-oleic transgenic lines
have been rated up to 140 h (Fitch 1997). Warner and Mounts
(1993) found that genetically modified soybean and canola oils
had higher flavor characteristics when used in potato frying tradi-
tional oils. Other studies have also been published on genetically
modified frying oils, such as high-oleic corn oil and low-linolenic
soybean oils with improved frying characteristics (Mounts and
others 1994; Warner and Knowlton 1997).
Physical properties
In the above sections on the food applications of SLs, it should
have become obvious that methods for testing the physical prop-
erties of novel lipids are needed during the development stages.
Fats and oils are usually modified to attain a certain functionality,
such as improved spreadability, a specific melting point, or a par-
ticular solid fat content and temperature profile. It is important to
know the thermal characteristics, rheology, crystal habit, texture,
and appearance of a new SL when determining its suitability for
use in a certain food application.
The Mettler dropping point is a simple, yet effective method of
measuring the effect of interesterification on fats (AOCS 1989a).
In this procedure, liquefied fats are crystallized in sample cups
and heated until they reach the dropping point, which is the point
when a sample begins to flow under its own weight (Rousseau
and Marongoni 1998a). The slip melting point measures the tem-
perature at which a column of fat moves in an open capillary
when heated. The drop or slip point of a fat usually occurs at a
lower temperature than the melting point, because they will begin
flowing at temperatures where 5% solid fat still exists (Timms
1985). Some researchers used dropping point as a verification of
complete interesterification (List and others 1995). However, this
may not be an accurate measurement for all SLs. Rousseau and
others (1996) found that a linear increase in the proportion of
canola oil did not lead to a linear reduction in dropping point.
The amount of solids in a TAG sample can be determined by
pulsed nuclear magnetic resonance (NMR) (AOCS 1989b). Differ-

Vol. 3, 2002—COMPREHENSIVE REVIEWS IN FOOD SCIENCE AND FOOD SAFETY 99

crfsfsv1n3ms20010544-Osborn-Akoh-AF.P65 99 11/6/2002, 10:55 AM

 CRFSFS: Comprehensive Reviews in Food Science and Food Safety
ential scanning calorimetry (DSC) and dilatormetry techniques are
also available to estimate the percentage of solid fats in an SL sam-
ple. Knowing the solid fat content of an SL is important for pre-
dicting the organoleptic properties it will impart to a food. In order
to avoid this problem, fats should be completely melted at 36 ºC
(body temperature). The SFC of a fat also contributes to the cool-
ing sensations that will be associated with a product in the
mouth. This “coldness” is important in margarines and chocolate
products. In margarines, a large difference between the SFC at 15
and 25 ⬚C is correlated to increased cooling sensations (Idris and
others 1996). In chocolates, a sharp melting point is indicative of
intense cooling sensations in the mouth.
As previously mentioned, the polymorphic behavior of an SL is
important in food systems. TAGs can form 1 of 3 major polymor-
phic forms: ␣, ␤, and ␤’. Different polymorphs are needed for dif-
ferent food applications. For example, the ␤ polymorph should be
avoided in margarines, because it causes graininess in the final
product (de Man 1983). However, this same crystal is the one de-
sired for chocolate production. Similarly, the ␤’ crystal, which is
associated with softening and low melting points in chocolate
products, is the desired polymorph for margarine production. X-
ray diffraction is a simple, rapid, and nondestructive method for
determining polymorphic structure in fat samples. Although this
technique is used for research purposes (Ali and others 2001), the
instrumentation is costly and therefore not widely used by indus-
try. DSC is the method of choice for determining crystal structure
by most lipid manufacturers. The melting profiles of different co-
coa butter crystal polymorphs have been correlated to definitive
x-ray determinations (Talbot 1995). Polarized light microscopy
can also be used to observe the morphology of crystals in a fat.
Interesterification leads to noticeable modifications in crystal
morphology. Lard consists of large crystals before interesterifica-
tion, but contains tiny, delicate crystals afterward (Rousseau and
Marangoni 1998a).
Viscous and elastic components are measured to determine the
rheology of a fat. Rheology plays an important role in the percep-
tion of taste, flavor, smoothness, and graininess of margarines, sal-
ad dressings, mayonnaise, and chocolate products produced
with SLs. Therefore, controlled stress rheology measurements pro-
vide a means for relating changes in molecular structure to pro-
cess behavior and for predicting product performance (Narine
and Marangoni 1999). For example, Fomuso and others (2001)
recently compared the rheological properties of mayonnaise and
Italian salad dressing made from SL (caprylic acid incorporated
into olive oil by acidolysis reaction) to the same foods made with
unmodified olive oil. The structured lipid mayonnaises and salad
dressings displayed similar viscoelastic properties to their olive
oil-based counterparts, which indicate similar structural and tex-
tural properties between the samples. Fomuso and Akoh (2001)
also used rheology to measure the liquid and solid behaviors of
trans-free margarine prepared with an enzymatically synthesized
SL comprised of high-laurate canola oil and stearic acid.
Texture of an SL can be measured with cone penetrometry, an
Instron testing machine, or a texture analyzer. Hardness and co-
hesiveness are important textural measurements for spreadable
materials and chocolate products. If an SL is brittle and not
spreadable, it will have low cohesive values. Lohman and Hartel
(1994) demonstrated a link between SFC of a fat and hardness in
chocolate. The same may be true for SL used in “chocolate.”
Mechanical measurements are important for determination of
suitability of SLs for certain food applications, but the importance
of consumer acceptability cannot be stressed enough. Sensory
tests are needed to determine threshold levels for SL incorpora-
tion and to describe sensory characteristics such as flavor, odor,
and texture. Instrumental analysis of samples may detect no
change in physical properties, but the sensory properties of a food
100 COMPREHENSIVE REVIEWS IN FOOD SCIENCE AND FOOD SAFETY—Vol. 3, 2002
crfsfsv1n3ms20010544-Osborn-Akoh-AF.P65 100
could be altered when an SL is substituted for a natural oil. A
good example of this phenomenon was documented by Rous-
seau and Marangoni (1998b). They interesterified canola oil and
butterfat to reduce the hardness of butter, but the product led to a
rancid, metallic flavor. Free fatty acid removal and steam injection
under vacuum successfully removed these undesirable flavors.
Unfortunately, all the desirable flavor components were removed
at the same time, and the final product was tasteless. The same au-
thors later compared the physical and sensory properties of but-
terfat SLs produced chemically and enzymatically. Chemical inter-
esterification led to greater changes in physical and sensory at-
tributes than enzymatic interesterification. In both cases, butter fla-
vor degradation must be minimized before the process would be
suitable for commercial production of butterfat SLs (Rousseau and
Marangoni 1999).
Some cocoa butter substitutes have a SFC that decreases over a
broader range of temperatures, compared to the sharp decrease in
solid fat in cocoa butter near body temperature. Sensory analysis
is therefore necessary to determine if such SLs are suitable for use
in chocolate manufacturing, because consumers may perceive
this remaining solid fat as a waxy mouthfeel.
Commercial Outlook for Structured Lipids
Commercial product examples
Many SLs, produced from a variety of methods, are now com-
mercially available. Genetic engineering allowed Calgene (Mon-
santo Co.) to market Laurical®, which was described in detail in a
previous section of this review. Esterification reactions catalyzed
by chemicals have also been used to produce SLs commercially.
Structolipid (Pharmacia & Upjohn AB, Stockholm, Sweden),
comprised of randomized MCFAs and LCFAs, is produced for
medical use in TPN treatments. Kabi Pharmacia AB (Stockholm,
Sweden) produces a similar product, FE 73403. These products
provide physicians with alternative lipid sources for TPN formu-
las, which are normally formulated with LCTs or physical mix-
tures of MCTs and LCTs.
Procter & Gamble’s (Cincinnati, Ohio, U.S.A.) Caprenin is a
structured lipid containing C8:0, C10:0, and C22:0 fatty acids es-
terified randomly to a glycerol backbone. Coconut, palm kernel,
and rapeseed oils were chemically transesterified to produce this
SL, which contains only 5 kcal/g. The behenic acid is partially ab-
sorbed by the body and is responsible for the reduced caloric val-
ue of the product.
Nabisco Foods Group (East Hanover, N.J., U.S.A.) used similar
principles to produce Salatrim® from C2:0, C3:0, C4:0, and
C18:0 fatty acids and glycerol. This product, now marketed as
Benefat by Cultor Food Science (Ardsley, N.Y., U.S.A.), provides 5
kcal/g and is intended for use in baking chips, chocolate-flavored
coatings, baked and dairy products, dressings, dips, and sauces,
or as a cocoa butter substitute (Bell and others 1997).
Captex 810D is a reduced calorie SL produced by Abitec Corp.
(Columbus, Ohio, U.S.A.). Akoh and others (1998) found that a
Captex diet resulted in increased heat production and altered en-
ergy metabolism in obese Zucker rats. McKenna and others
(1985) also reported improved absorption of 18:2n-6 when Cap-
tex was administered to cystic fibrosis patients.
Another reduced-calorie SL containing oleic (C18:0) and be-
henic (C22:0) acids, Bohenin, was designed to slow or prevent fat
bloom formation in chocolate products. It promotes the formation
of stable ␤ crystals and provides 5 kcal/g.
The Stepan Food Co. (Maywood, N.J., U.S.A.) markets the
Neobee MCTs. The 1095 line prevents bloom formation in choco-
late, while the M-5 option prevents uncoated nutritional bars
from sticking to packaging material by migrating to the surface of
11/6/2002, 10:55 AM
 Structured lipids. . .
these products.
SL emulsions, such as Structolipid (Pharmacia/Upjohn, Uppsa-
la, Sweden) and Intralipid (Pharmacia/Upjohn, Uppsala, Sweden),
may have clinical and metabolic advantages for stressed and/or
septic patients (Sandstrom and others 1993). Structolipids 20%
contains structured fractionated interesterified MCFA from puri-
fied coconut oil and LCFA from purified soybean oil in a ratio of
50:50 (mol%). Intralipid 20% contains 100% LCTs from fraction-
ated soybean oil. Both SL emulsions contain the same phospho-
lipid emulsifier consisting of natural glycerophospholipids, main-
ly phosphatidylcholine and phosphatidylethanolamine. The SLs
are administered to patients as part of a total parental nutrition
regimen (Rubin and others 2000). Nordenstrom and others (1995)
found no change in serum cholesterol, but an increase in serum
TAGs in healthy subjects infused with FE 73403 (Pharmacia AB,
Stockholm, Sweden), another SL emulsion source that contains
27% caprylic and 10% capric acids.
Betapol (Loders Croklaan, Glen Ellyn, Ill., U.S.A.) was the 1st
commercially available enzymatically synthesized SLs. It was
made by reacting tripalmitin with unsaturated fatty acids using an
sn-1,3 specific lipase. This SL was designed to mimic the fatty
acid distribution of human milk for use in infant formulas.
Commercialization of the enzymatic process
The majority of SLs available commercially are produced
through chemical interesterification/acidolysis or genetic engi-
neering techniques. The growth rate of enzymatic lipid modifica-
tion processes adopted by industry has not kept pace with the re-
search conducted on using enzymes to produce novel fats. The
main reasons for limited application are as follows: few industri-
ally promising applications and few high-value-added products,
high cost of commercial lipases, limited market for the specialty
lipids, lack of mainstream use, and low efficiency of available
processes. Large-scale enzymatic synthesis of SLs presents some
downstream processing problems. Lipase-catalyzed reactions re-
sult in a mixture of desirable and unreacted substrates that make
the purification of SL difficult for large-scale productions (Akoh
1998). Examples of unreacted substrates and undesirable products
that must be removed from the SL upon completion of the esterifi-
cation reaction include: FFA, fatty acid methyl esters, diacylglyc-
erols, and TAGs. Conventional methods for fractionation result in
oxidation of PUFAs in SLs that have not been stabilized with anti-
oxidants. Akoh and Moussata (2001) were unable to restore the
stability of SL to premodification values, but did improve oxidative
stability compared to the control SL, which did not have antioxi-
dants added.
The 1st step toward making lipase-catalyzed reactions more
suitable for industrial application was the immobilization of en-
zymes. Immobilization increases their stability to pH and heat,
and allows for easy recovery and reuse of the lipase. Cellulose,
sephadex, Duolite, carboxylic acid ion-exchange resin, and
macroporous ion-exchange resins are the materials typically used
as supports for lipases (Lee and Akoh 1998). New developments
in the production of high-quality lipases by genetic engineering,
improvement of lipase stability by protein engineering, and theo-
retical insights and practical improvements of microaqueous me-
dia have also occurred recently. Therefore highly stable lipases at
relatively low prices should soon be available for commercial ap-
plication (Xu and others 1998c). Use of plant biocatalysts may
have advantages, owing to their lower cost and ready availability,
in comparison to their microbial and animal counterparts. Carica
papaya latex (CPL), a plant exudate well known for its proteolytic
activity, also exhibits lipase activity and was used to successfully
produce low-calorie SLs in a solvent-free reaction system (Man-
gos and others 1999).
There are many factors that influence yield in the enzyme-cata-
Vol. 3, 2002—COMPREHENSIVE REVIEWS IN FOOD SCIENCE AND FOOD SAFETY
crfsfsv1n3ms20010544-Osborn-Akoh-AF.P65 101
lyzed synthesis or modification of lipids. These parameters that in-
fluence the reaction equilibrium are reasonably well understood,
but knowledge about the control and kinetics of the reaction is
still rather limited. Response surface methodology (RSM) can be
used to investigate the relationships between factors (such as wa-
ter content, reaction time, reaction temperature, substrate molar
ratio, and enzyme amount) affecting SL synthesis and to deter-
mine the optimum conditions for transesterification reactions
(Shieh and others 1995). Xu and others (1998b) used this method
to determine what factors affected acyl migration in lipase-cata-
lyzed interesterification reactions. From this data, they proposed a
quadratic model that expresses acyl migration for enzymatic inter-
esterification in a batch reactor. Based on the importance of water
levels on enzyme activity that was determined by RSM, Han and
Yamane (1999) explored the use of vacuum to control the water
level in their reaction system during production of an SL contain-
ing eicosapentaenoic acid.
Fixed bed reactors have been investigated and applied in a
wide range of enzymatic applications, both in the laboratory and
in industry, especially for immobilized enzymes. Lipase-catalyzed
lipid modifications in fixed bed reactors have also been proposed
and studied to some extent in systems with and without solvents
present (Xu and others 1998a, 1998c). A canola oil SL containing
caprylic acid (Xu and others 2000a) was produced. Similarly, ca-
prylic acid was incorporated into menhaden oil (Xu and others
2000b). Fixed bed reactors are very promising for future develop-
ments of lipase-catalyzed lipid modifications.
Combinations of lipase-catalyzed reactions with genetic engi-
neering and/or chemical-catalysis may be required to produce nu-
tritionally optimized products at a reasonable price on a commer-
cial basis. Additionally, more collaboration between industry and
academia would hasten and increase successful commercializa-
tion of enzymatic processes for SL production.
Future Prospects
Continued improvements to the enzymatic catalyzed reaction
for producing SLs are necessary before it is more widely accepted
by industry. Isolation and genetic engineering of new lipases that
allow for more specific tailoring of TAG structure could increase
the potential market for SLs. Isolation of inexpensive plant lipases,
with similar functionality to microbial lipases, may alleviate some
of the high production cost burden that is currently warding off
potential investors considering commercialization of an enzymat-
ically-catalyzed SL reaction. Further investigation of the safety and
efficacy of SLs produced for medical, functional and nutraceutical
applications is warranted. The ability to increase absorption and
combine the beneficial characteristics of component fatty acids
into 1 TAG make SLs very attractive to the medical community.
Researchers have generated numerous articles on SLs, and, in
many cases, a potential food application is given for their prod-
uct. However, few have taken the next step and studied how the
SL actually behaves when used in a particular food application.
The opportunity for more studies on the kinetics, physical proper-
ties, and functionality of food systems containing structured lipids
definitely exists.
Some researchers are now studying the addition of novel mole-
cules to SLs to impart even more functionality to the lipid. For ex-
ample, Houte and others (2000) recently strategized that more ef-
fective chemopreventive compounds could be developed by in-
corporating bioactive derivatives into naturally occurring pharma-
cologically active carrier molecules. They hypothesized that such
analogues would manifest intramolecular synergism of the con-
stituent fragments. They were able to successfully esterify ␤-Apo-
8’-carotenoic acid and 7-selenacapryloic acid with glycerol to
highly unsaturated stable di- and triacylglycerols. Biological data
101
11/6/2002, 10:55 AM
 CRFSFS: Comprehensive Reviews in Food Science and Food Safety
is now needed to confirm the expected properties of these antiox-
idant lipids. This work on designing lipids that contain caro-
tenoids opens the door for development of countless new SLs that
serve as immunopotentiators against diseases, sunscreens, radio-
protectives, food stabilizers, cosmetics, and dietary supplements
for humans and animals.
Conclusions
Although much remains unstudied in the field of SLs, one can-
not read this review and feel that the consumers will not benefit
from at least one aspect of SLs. Whether it be through improve-
ment in functionality or physical properties of a food, reduction in
caloric value of foods that normally contain high amounts of fat,
or the medicinal properties of rapidly absorbing TAGs composed
of MCFAs and PUFAs, structured lipids definitely provide at-
tributes that consumers will find valuable. Therefore, it is impor-
tant that further research be conducted that will allow for better
understanding and more control over the various esterification
processes and reduction in costs associated with large-scale pro-
duction of SLs.
References
Akoh CC and Yee LN. 1997. Enzymatic synthesis of position-specific low-calorie structured
lipids. J Am Oil Chem Soc 74(11):1409-1413.
Akoh CC. 1998. Structured lipids. In: Akoh CC and Min DB, editors. Food lipids chemistry,
nutrition, and biotechnology. New York: Marcel Dekker. P 699-727.
Akoh CC, Long KD, Flatt WP, Rose BS, Martin RJ. 1998. Effects of a structured lipid, Captex,
and a protein-based fat replacer, Simplesse, on energy metabolism, body weight, and se-
rum lipids in lean and obese Zucker rats. Nutr Biochem 9(5):267-275.
Akoh CC, Moussata CO. 2001. Characterization and oxidation stability of enzymatically
produced fish and canola oil-based structured lipids. J Am Oil Chem Soc 78(1):25-30.
Ali A, Selamat J, Che Man YB, Suria AM. 2001. Effect of storage temperature on texture,
polymorphic structure, bloom formation and sensory attributes of filled dark chocolate.
Food Chem 72(4):491-497.
AOCS. 1989a. Official methods and recommended practices of the American Oil Chemists’
Society. 4th ed. Champaign, IL: American Oil Chemists’ Society. Cc 18-80.
AOCS. 1989b. Official methods and recommended practices of the American Oil Chemists’
Society. 4th ed. Champaign, IL: American Oil Chemists’ Society. Cd 16-81.
Babayan VK. 1987. Medium chain triglycerides and structured lipids. Lipids 22(6):417-420.
Bell SJ, Macioli EA, Bistrian BR, Babayan VK, Blackburn GL. 1991. Alternative lipid sourc-
es for enteral and parenteral nutrition: long- and medium-chain triglycerides, structured
triglycerides, and fish oils. J Am Dietetic Assoc 91(1):74-78.
Bell SJ, Bradley D, Forse RA, Bistrain BR. 1997. The new dietary fats in health and disease.
J Am Dietetic Assoc 97(3):280-286.
Bellantone R, Bossola M, Carriero C, Malerba M, Nucera P, Ratto C, Crucitti P, Pacelli F,
Doglietto GB, Crucitti F. 1999. Structured versus long-chain triglycerides: a safety, toler-
ance, and efficacy randomized study in colorectal surgical patients. J Parenteral Enteral
Nutr 23(3):123-127.
Brekke OL. 1980. Soybean oil food products - their preparation and uses. In: Erickson DR,
Pryde EH, Brekke OL, Mounts TL, Falb RA, editors. Handbook of soy oil processing and
utilization. St. Louis, Mo. and Champaign, Ill: American Soybean Association
and American Oil Chemist’s Society. P 383-427.
Broun P, Gettner S, Somerville C. 1999. Genetic engineering of plant lipids. Annu Rev Nutr
19(1):197-216.
Cater NB, Howard JH, Denke MA. 1997. Comparison of the effects of medium-chain tria-
cylglycerols, palm oil, and high oleic acid sunflower oil on plasma triacylglycerol fatty
acids and lipid and lipoprotein concentrations in humans. Am J Clin Nutr 65(1):41-45.
Chambrier C, Guiraud M, Gibault JP, Labrosse H, Bouletreau P. 1999. Medium- and long-
chain triacylglcyerols in postoperative patients: structured lipids versus a physical mixture.
Nutr 15(4):274-277.
Christensen MS, Mullertz A, Hoy C. 1995. Absorption of triglycerides with defined or ran-
dom structure by rats with biliary and pancreatic diversion. Lipids 30(6):521-526.
Decker EA. 1996. The role of stereospecific saturated fatty acid positions on lipid nutrition.
Nutrition Reviews 54(4):108-110.
Dehesh K, Jones A, Knutzon DS, Voelker TA. 1996. Production of high levels of 8:0 and 10:0
fatty acids in transgenic canola by overexpression of chfatb2, a thioesterase cDNAfrom
Cuphea hookeriana. Plant J 9(2):167-172.
de Man JM. 1983. Consistency of fats: a review. J Am Oil Chem Soc 60(1):82-87.
de Man JM. 1992. Fats and oils: chemistry, physics, and applications. In: Hui YH, editor.
Encyclopedia of food science and technology. New York: John Wiley & Sons, Inc.
P 818-828.
DeMichele SJ, Karistad MD, Babayan VK, Istfan NW, Blackburn GL, Bistian BR. 1988. En-
hanced skeletal muscle and liver protein synthesis with structured lipid in enterally fed
burned rats. Metabolism 37(8):787-795.
Dobarganes MC, Marquez-Ruiz G, Perez-Camino MC. 1993. Thermal stability and frying
performance of genetically modified sunflower seed ( Helianthus annus L.) oils. J Agric
Food Chem 41(4):678-681.
Fitch, HB. 1997. Bioengineered oilseed acreage escalating. Inform 8(8):804-811.
Foglia TA, Petruso K, Feairheller SH. 1993. Enzymatic interesterification of tallow-sunflow-
er oil mixtures. J Am Oil Chem Soc 70(3):281-285.
102 COMPREHENSIVE REVIEWS IN FOOD SCIENCE AND FOOD SAFETY—Vol. 3, 2002
crfsfsv1n3ms20010544-Osborn-Akoh-AF.P65 102
Fomuso LB, Akoh CC. 2001. Enzymatic modification of high-laurate canola to pro-
duce margarine fat. J Agric Food Chem 49(9):4482-4487.
Fomuso LB, Corredig M, Akoh CC. 2001. A comparative study of mayonnaise and Italian
dressings prepared with lipase-catalyzed transesterified olive oil and caprylic acid. J Am
Oil Chem Soc 78(7):771-774.
Han JJ, Yamane T. 1999. Enhancement of both reaction yield and rate of synthesis of struc-
tured triacylglycerol containing eicosapentaenoic acid under vacuum with water activity
control. Lipids 34(9):989-995.
Houte H, Partali V, Sliwka HR, Quartey EGK. 2000. Synthesis of structured lipids and ether-
lipids with antioxidants: combination of a selena fatty acid and a selena fatty alcohol with
a carotenoic acid in glyceride molecules. Chem Phys Lipids 105(3):105-113.
Idris NA, deMan L, Tang TS, Chong CL. 1996. Chemical composition and physical proper-
ties of soft (tub) margarines sold in Malaysia. J Am Oil Chem Soc. 73(8):995-1001.
Innis SM, Nelson CM, Rioux MF, King DJ. 1994. Development of visual acuity in relation to
plasma and crythrocyte _-6 and _-3 fatty acids in healthy term gestation infants. Am J Clin
Nutr 60(3):347-352.
Jensen GL, Jensen RG. 1992. Specialty lipids for infant nutrition. II. Concerns, new develop-
ments, and future applications. J Pediatr Gastroenterol Nutr 15(4):382-394.
Jensen GL, McGarvey N, Taraszewski R, Wixon SK, Seidner DL, Pai T, Yeh YY, Lee TW,
DeMichele SJ. 1994. Lymphatic absorption of enterally fed structured triacylglcerol com-
pared with physical mix in a canine model. Am J Clin Nutr 60(4):518-524.
Jeppesen PB, Christensen MS, Hoy CE, Mortensen PB. 1997. Essential fatty acid deficiency
in patients with severe fat malabsoption. Am J Clin Nutr 65(3):837-843.
Jeppesen PB, Hoy CE, Mortensen PB. 1998. Essential fatty acid deficiency in patients receiv-
ing home parenteral nutrition. Am J Clin Nutr 68(1):126-133.
Johnson LA. 1998. Recovery, refining, converting, and stabilizing edible fats and oils. In:
Akoh CC and Min DB, editors. Food lipids chemistry, nutrition, and biotechnology. New
York: Marcel Dekker. P 181-228.
Kanjilal S, Prasad RBN, Kaimal TNB, Ghafoorunissa, Rao SH. 1999. Synthesis and estimation
of caloric value of structured lipid-potential reduced calorie fat. Lipids 34(10):1045-1055.
Kenler AS, Swails WS, Driscoll DS, DeMichele SJ, Daley B, Babinead TJ, Peterson MB, Bis-
trian BR. 1996. Early enteral feeding in postsurgical cancer patients: fish oil structured lip-
id-based polymeric formula versus a standard polymeric formula. Ann Surg 223(3):316-
333.
Kennedy JP. 1991. Structured lipids: fats of the future. Food Tech 45(11):76-83.
Knauf VC, Del Vecchio AJ. 1998. Genetic engineering of crops that produce vegetable oil.
In: Akoh CC and Min DB, editors. Food lipids chemistry, nutrition, and biotechnology. New
York: Marcel Dekker. P 779-805.
Koyano T, Hachiya I, Sato K. 1990. Fat polymorphism and crystal seeding effects on fat
bloom stability of dark chocolate. Food Structure 9(3):231-240.
Kris-Etherton PM (editor). 1995. trans Fatty acids and coronary heart disease risk: report of
the expert panel on trans fatty acid and coronary heart disease. Am J Clin Nutr 62(3):651S-
708S.
Kruimel JW, Naber AH, Curfs JH, Wenker MA, Jansen JB. 2000. With medium-chain triglyc-
erides, higher and faster oxygen radical production by stimulated polymorphonuclear leu-
kocytes occur. J Parenteral and Enteral Nutr 24(2):107-112.
Kubow S. 1993. Lipid oxidation-products in food and atherogenesis. Nutr Rev 51(2):33-40.
Lai OM, Ghazali HM, Chong CL. 1998. Effect of enzymatic transesterification of the melt-
ing points of palm stearin-sunflower oil mixtures. J Am Oil Chem Soc 75(7):881-886.
Lee KT, Akoh CC. 1998. Structured lipids: synthesis and applications. Food Rev Int 14(1):17-
34.
Lee KT, Akoh CC, Dawe DL. 1999. Effects of structured lipid containing omega-3 and me-
dium chain fatty acids on serum lipids and immunological variables in mice. J Food Bio-
chem 23(2):197-208.
Lee KT, Akoh CC, Flatt WP, Lee JH. 2000. Nutritional effects of enzymatically modified soy-
bean oil with caprylic acid versus physical mixture analogue in obese zucker rats. J Agric
Food Chem 48(11):5696-5701.
Lien EL, Yuhas RJ, Boyle FG, Tomarelli RM. 1993. Corandomization of fats improves absorp-
tion in rats. J Nutr 123(11):1859-1867.
Lipp M, Anklam E. 1998. Review of cocoa butter and alternative fats for use in chocolate –
Part A. Compositional data. Food Chem 62(1):73-97.
List GR, Pelloso T, Orthoefer F, Chrysam M, Mounts TL. 1995. Preparation and properties of
zero trans soybean oil margarines. J Am Oil Chem Soc. 72(3):383-384.
Loisel C, Lecq G, Keller G, Ollivon M. 1998. Dynamic crystallization of dark chocolate as
affected by temperature and lipid additives. J Food Sci 63(1):73-79.
Lohman MH, Hartel RW. 1994. Effect of milk fat fractions on fat bloom in dark chocolate. J
Am Oil Chem Soc 71(3):261-276.
Mangos TJ, Jones KC, Foglia TA. 1999. Lipase-catalyzed synthesis of structured low-calorie
triacylglycerols. J Am Oil Chem Soc 76(10):1127-1131.
Marangoni AG, McCurdy RD, Brown ED. 1993. Enzymatic interesterification of triolein with
tripalmitin in canola lecithin-hexane reverse micelles. J Am Oil Chem Soc 70(8):737-744.
McKenna MC, Hubbard VS, Pieri JG. 1985. Linoleic acid absorption from lipid supplements
in patients with cystic fibrosis with pancreatic insufficiency and in control subjects. J Pe-
diatr Gastroenterol Nutr 4(1):45-51.
Mounts TL, Warner K, List GR, Neff WE, Wilson RF. 1994. Low-linolenic acid soybean oils
– alternatives to frying oils. J Am Oil Chem Soc 71(5):495-499.
Mu H, Hoy CE. 2000. Effects of different medium-chain fatty acids on intestinal absorption
of structured triacylglycerols. Lipids 35(1):83-89.
Narine SS, Marangoni AG. 1999. Relating structure of fat crystal networks to mechanical
properties: a review. Food Res Int 32(4):227-248.
Nordenstrom J, Thorne A, Olivecrona T. 1995. Metabolic effects of infusion of a structured
triglyceride emulsion in healthy subjects. Nutr 1(3)1:269-274.
Osborn HT, Akoh CC. 2002. Enzymatically modified beef tallow as a substitute for
cocoa butter. J Food Sci (Forthcoming).
Pai T, Yeh YY. 1997. Stearic acid modifies very low-density lipoprotein lipid compo-
sition and particle size differently from shorter chain saturated fatty acids in
cultured rat hepatocytes. Lipids 32(2):143-149.
Rousseau D, Forestiere K, Hill AR, Marangoni AG. 1996. Restructuring butterfat through
blending and chemical interesterification: 1. Melting behavior and triacylglycerol modi-
fications. J Am Oil Chem Soc. 73(8):963-972.
Rousseau D, Marangoni AG. 1998a. In: Akoh CC and Min DB, editors. Food lipids chemis-
try, nutrition, and biotechnology. New York: Marcel Dekker. P 251-281.
11/6/2002, 10:55 AM
 Structured lipids. . .
Rousseau D, Marangoni AG. 1998b. Tailoring the textural attributes of butterfat-canola oil
blends via Rhizopus arrhizus lipase-catalyzed interesterification. 2. modifications of phys-
ical properties. J Agric Food Chem 46(6):2375-2381.
Rousseau D, Marangoni AG. 1999. The effects of interesterification on physical and senso-
ry attributes of butterfat and butterfat-canola oil spreads. Food Res Int 31(5):381-388.
Rubin M, Moser A, Vaserberg N, Greig F, Levy Y, Spivak H, Ziv Y, Lelcuk S. 2000. Structured
triacylglycerol emulsion, containing both medium- and long- chain fatty acids, in long-
term home parenteral nutrition: a double-blind randomized cross-over study. Nutrition
16(2):95-100.
Sandstrom R, Hyltander A, Korner U, Lundhom K. 1993. Structured triglycerides to postop-
erative patients: a safety and tolerance study. J Parenteral and Enteral Nutr 17(2):153-157.
Seriburi V, Akoh CC. 1998. Enzymatic transesterification of triolein and stearic acid and solid
fat content of their products. J Am Oil Chem Soc 75(4):511-516.
Shahani KM. 1975. Lipases and esterases. In: Reed G, editor. Enzymes in food processing.
2nd ed. New York: Academic Press. P 182-221.
Shieh CJ, Akoh CC, Koehler PE. 1995. Four-factor response surface optimization of the en-
zymatic modification of triolein to structured lipids. J Am Oil Chem Soc 72(6):619-623.
Stoltzfus DL, Fehr WR, Welke GA, Hammond EG, Cianzio SR. 2000. A fap5 allele for elevat-
ed palmitate in soybean. Crop Sci 40(3):647-650.
Straarup EM, Hoy CE. 2000. Structured lipids improve fat absorption in normal and malab-
sorbing rats. J Nutr 130(11):2802-2808.
Swails WS, Kenler AS, Driscoll DF, DeMichelle SJ, Babineau J, Utsunamiya T, Chavali S, Forse
RA, Bistrain BR. 1997. Effect of fish oil structured lipid-based diet on prostaglandin release
from mononuclear cells in cancer patients after surgery. J Parenteral and Enteral Nutr.
21(3):266-274.
Talbot, G. 1995. Fat eutectics and crystallisation. In: Beckett ST, editor. Physico-Chemical
Aspects of Food Processing, 1st ed. York, UK: Chapman & Hall. P 142-166.
Timms, RE. 1985. Physical properties of oils and mixtures of oils. J Am Oil Chem Soc
62(2):241-249.
Tso P, Karistad M, Bistrian BR, DeMichele SJ. 1999. Intestinal digestion, absorption, and
transport of structured triglycerides and cholesterol. Am J Physiol 268(4):G568-G577.
Voelker TA, Hayes TR, Cranmer AM, Turner JC, Davies HM. 1996. Genetic engineering of a
quantitative trait: metabolic and genetic parameters influencing the accumulation of lau-
rate in rapeseed. Plant J 9(2):229-241.
Warner K, Mounts TL. 1993. Frying stability of soybean and canola oils with mod-
Vol. 3, 2002—COMPREHENSIVE REVIEWS IN FOOD SCIENCE AND FOOD SAFETY
crfsfsv1n3ms20010544-Osborn-Akoh-AF.P65 103
ified fatty acid compositions. J Am Oil Chem Soc 70(10):983-988.
Warner K, Knowlton S. 1997. Frying quality and oxidative stability of high-oleic
corn oils. J Am Oil Chem Soc. 74(10):1317-1322.
Watkins SM, German JB. 1998. In: Akoh CC and Min DB, editors. Food lipids chemistry,
nutrition, and biotechnology. New York: Marcel Dekker. P 463-493.
Willis WM, Lencki RW, Marangoni AG. 1998. Lipid modification strategies in the
production of nutritionally functional fats and oils. Crit Rev Food Sci Nutr
38(8):639-674.
Willis WM, Marangoni AG. 1999. Assessment of lipase- and chemically catalyzed lipid
modification strategies for the production of structured lipids. J Am Oil Chem Soc
76(4):443-450.
Xu X, Balchen S, Hoy CE, Alder-Nissen J. 1998a. Pilot batch production of specific-structured
lipids by lipase-catalyzed interesterificaton: preliminary study on incorporation and acyl
migration. J Am Oil Chem Soc 75(2):301-308.
Xu X, Skands ARH, Hoy CE, Balchen S, Adler-Nissen J. 1998b. Production of specific-struc-
tured lipids by enzymatic interesterification: elucidation of acyl migration by response
surface design. J Am Oil Chem Soc 75(9):1179-1186.
Xu X, Balchen S, Hoy CE, Adler-Nissen J. 1998c. Production of specific-structured lipids by
enzymatic interesterification in a pilot continuous enzyme bed reactor. J Am Oil Chem Soc
75(11)1573-1579.
Xu X, Fomuso LB, Akoh CC. 2000a. Synthesis of structured triacylglycerols by lipase-cata-
lyzed acidolysis in a packed bed bioreactor. J Agric Food Chem 48(1):3-10.
Xu X, Fomuso LB, Akoh CC. 2000b. Modification of menhaden oil by enzymatic acidolysis
to produce structured lipids: optimization by response surface design in a packed bed re-
actor. J Am Oil Chem Soc 77(2):171-176.
MS 20010544 Submitted 10/1/01, Revised 1/12/02, Accepted 1/20/02, Received
1/23/02
This work is based in part upon work supported by the Cooperative State Research, Education, and
Extension Service, U.S. Dept. of Agriculture, under Agreement Nr 2001-35503-10037.
The authors are with the Univ. of Georgia, Dept. of Food Science and
Technology, Food Science Building, Athens, GA 30602-7610. Direct inquir-
ies to author Akoh (E-mail: cmscakoh@arches.uga.edu).
103
11/6/2002, 10:55 AM