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Coconut Oil and Medium Chain Fatty Acid Metabolism PDF
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contents
6 Coconut oil boom
Coconut oil, once reviled for its high saturated fat content, is now getting credit for all
kinds of health benefits. Inform reviews the scientific evidence.
Aqueous phase /
Water
Fine meal
Coarse meal
14 17 22
14 Aqueous enzymatic oil extraction as a green processing method
Using water and enzymes in place of chemical solvents preserves micronutrients and is easier on
the environment, so why is solvent-based extraction still the main method used to extract edible oils
from oilseeds?
22 3D micro X-ray images help answer questions about fried foods’ internal structure
X-ray micro-computed tomography sheds light on the internal pore structure and oil distribution in
potato disks during various frying times.
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Coconut oil
6 • inform May 2016, Vol. 27 (5)
Coconut is the oil du jour, attracting endorsements from athletes and celebrities for its alleged
health-promoting effects. The oil, once considered exotic outside of the tropics, is showing up in
supermarkets and health food stores everywhere, often advertised as a “functional food.” Yet not
long ago, coconut oil was reviled by health experts, lumped in the same unhealthful category as lard
and tallow because of its high content of saturated fat. As saturated fat has embarked on the long
road to exoneration, many people are starting to appreciate the unique physical and chemical
characteristics of coconut oil, not only as a cooking oil, but also as a cosmetic ingredient, an
antimicrobial agent, a biofuel, and even a possible medicine for ailments ranging from obesity to
Alzheimer’s disease. But does the scientific evidence of coconut oil’s benefits justify the hype?
Boom and bust
Although new to many consumers in the West, coconut oil has been used as
• Coconut oil is surging in popularity a food ingredient and folk medicine for millennia in the tropical regions
where coconut trees grow, such as India, the Philippines, Sri Lanka, Malaysia,
as a “health food,” after being
Polynesia, and Indonesia (Fig. 1). The oil attracted the attention of European
demonized since the 1950s because traders in the late 19th century, a time of increased demand for edible
of its high saturated fat content. oils and oils for soapmaking in Europe and the United States. As a result,
Europeans established coconut plantations in the Caribbean, Southeast
Asia, and the South Pacific from the 1890s to the 1920s, and coconut oil was
• Coconut oil has a variety of uses: widely used as a cooking oil in Europe and the United States until about 1940.
Then, World War II cut off the supply of coconut oil to the West. “There was
as a cooking oil, shortening, quite a desperate shortage of edible oil in the U.S., and the soy industry got a
nutritional supplement, personal huge boost from that,” says Mike Foale, a coconut consultant in Queensland,
care ingredient, antimicrobial Australia, and retired agronomist at Australia’s Commonwealth Scientific
and Industrial Research Organization (CSIRO). “The price of coconut oil was
agent, and biofuel. so high, and the soy oil industry expanded very rapidly indeed during that
period.”
• Many of the properties of coconut
oil can be traced to medium-chain
fatty acids (MCFAs) such as lauric
acid (C12:0), which are metabolized
differently from long-chain fatty
acids (LCFAs).
FIG. 1. Although larger operations are on the rise, much of the world’s coconut
oil is still produced by small operators with traditional methods, such as this
ox-driven coconut oil press in Myanmar.
Figure 1.
Among vegetable oils, coconut oil, palm oil, and palm “Most of the health benefits of coconut oil, whether VCO
kernel oil have the highest levels of saturated fat (coconut, or RBD coconut oil, have been attributed to the high content
93%; palm, 50%; palm kernel, 82%), making them semi-solid at of lauric acid,” says Fabian M. Dayrit, professor of chemistry at
room temperature. All three oils are derived from palm trees, Ateneo de Manila University, in Quezon City, Philippines.
but from different species or parts of the fruit: Coconut oil is “Additional health benefits of VCO have been attributed to the
extracted from the meat, or kernel, of the coconut fruit of the presence of polyphenols.”
palm Cocos nucifera, whereas palm and palm kernel oil are
derived from the pulp and kernel, respectively, of the fruit of
the oil palm Elaeis guineensis. Palm oil contains mostly LCFAs,
MCFA metabolism
such as palmitic acid (C16) at 44%, whereas coconut and palm About 60% of coconut TAGs contain the MCFAs lauric (C12)
kernel oils contain predominantly MCFAs, such as lauric acid or capric (C10) acid at the sn-1 or sn-3 positions (Fig. 4).
(C12) at about 48% and 46%, respectively (Dubois, V., et al., This placement is important because lipases in the body
http://doi.org/10.1002/ejlt.200700040, 2007) (Fig. 3, page 7). hydrolyze TAGs more rapidly if MCFAs occupy the sn-1 and sn-3
Coconut and palm kernel oils have similar fatty acid pro- positions, rather than LCFAs. Upon ingestion, TAGs undergo
files, but they have different triacylglyceride (TAG) composi- stepwise hydrolysis. First, lipases in the gastrointestinal tract
tions (Dayrit, F. M., http://doi.org/10.1007/s11746-014-2562-7, cleave off a fatty acid at the sn-1 or sn-3 position of the TAG to
2015). In one study, researchers found that the predominant yield a diacylglyceride and a free fatty acid. Then, lipases
TAGs in coconut oil are trilaurin (3C12), 1-capro,2,3-dilauryl hydrolyze a second fatty acid (sn-1 or sn-3) to produce 2-
glyceride (C10-C12-C12), and 1-capro,2-lauryl,3-myristyl monoacylglyceride and another free fatty acid. In the third
glyceride (C10-C12-C14). In contrast, palm kernel oil contains hydrolysis step, the fatty acid at the sn-2 position is hydrolyzed
mostly trilaurin (3C12), 1-myristyl,2-stearyl,3-lauryl glycer- to yield glycerol and the remaining free fatty acid. Alternatively,
ide (C14-C18-C12), and 1,3-oleyl,2-lauryl glyceride (C18:1- 2-monoacylglyceride can undergo isomerization to 1-mono-
C12-C18:1). Unlike coconut oil, palm kernel oil is not commonly acylglyceride, which can then be hydrolyzed to glycerol and
consumed in the diet because of the presence of residual a free fatty acid.
extraction solvents, says Foale. After lipases liberate fatty acids from TAGs, enterocytes
The two main types of coconut oil—copra and virgin—have of the small intestine absorb the free fatty acids. From there,
similar fatty acid profiles, but virgin coconut oil has a higher LCFAs and MCFAs have very different metabolic fates. LCFAs
content of bioactive components such as tocotrienols and are predominantly re-esterified into TAGs, and then combined
tocopherols (forms of vitamin E), sterols (precursors to fat- with phospholipids, proteins, and cholesterol to form com-
soluble vitamins and steroid hormones), and polyphenols plexes called chylomicrons. Chylomicrons enter the lymphatic
(antioxidants). The two types of coconut oil differ in their system, where they circulate in the bloodstream and enter
extraction processes (Table 1). Copra is produced by crushing tissues, contributing to fat accumulation. In contrast, MCFAs
dried coconut kernels to extract the oil, which is then typically are more water-soluble than LCFAs due to their shorter chain
refined, bleached, and deodorized (RBD). This coconut oil was length, so they do not require packaging into chylomicrons.
the type commonly used in the United States and Europe for Instead, most MCFAs are conducted to the hepatic portal vein,
frying and shortening in the early twentieth century. In con- which directly links the gastrointestinal tract to the liver. In
trast, virgin coconut oil (VCO) is made by pressing shredded wet experiments using rat intestine, the proportion of saturated
coconut kernel to squeeze out the oil and coconut milk, which fatty acids entering the portal vein was inversely correlated
form an emulsion that is then separated by various techniques. with carbon number: C12 (72%), C14 (58%), C16 (41%), and
Unlike RBD copra oil, VCO is not refined, and thus not subjected C18 (28%) (Dayrit, F. M., Philipp. J. Sci., 2014). As a result, most
to the high temperatures of free fatty acid distillation and ingested MCFAs are transported directly to the liver, where
deodorization, which can volatilize or otherwise destroy they are converted to energy and other metabolites rather
heat-labile components. than being stored as fat. Indeed, among fatty acids, lauric acid
re 3. contributes the least to fat accumulation.
O sn-1 and sn-3: 4.9% and 54.3% of the fatty acids are C10:0
sn-1 O R1 . and C12:0, respectively
O
sn-2 sn-2: 1.6% and 44.1% of the fatty acids are C10:0 and C12:0,
O R2 .
O
respectively
sn-3 O R3 .
Coconuts are deshelled, and the meat, also known as the kernel Coconuts are deshelled.
or copra, is dried to a moisture content of 6% or below.
Copra is cut into small chips, which are fed into steam-jacketed Kernel is pared and dewatered. Coconut is passed through cutter
kettles and cooked at 70 oC for 30 min. to shred.
Cooked material is fed into expeller and pressed twice. Combined Shredded coconut is fed into screw/hydraulic press to extract fresh
oil is collected in tank. Or, copra is treated with solvents (solvent coconut milk (dry process). Or, pressing is done in the presence of
extraction). water (wet process).
Oil is filtered with filter press. Milk is filtered and centrifuged to separate coconut oil from milk. Or,
natural enzymes separate oil from milk in a fermentation process.
Upon arrival at the liver, MCFAs enter the mitochondria. such as the brain, muscle, and heart. There, enzymes can
Unlike LCFAs, MCFAs can freely diffuse across the mitochon- convert the ketone bodies to acetyl CoA for use as an energy
drial membrane without requiring carnitine-assisted transport. source. The second pathway, ω-oxidation, accounts for only
MCFAs are then rapidly metabolized by one of two pathways 10–20% of total liver fatty acid oxidation under normal
(Fig. 5). The major pathway, β-oxidation, yields acetyl CoA. Ace- conditions. This pathway produces 11- and 12-hydroxyl fatty
tyl CoA either enters the citric acid cycle to produce energy, or is acids, which can be further oxidized to dicarboxylic acids.
further metabolized to ketone bodies. Ketone bodies are three The ω-oxidation pathway may help remove excess fatty acids
water-soluble molecules (acetoacetate, β-hydroxybutyrate, and from the mitochondrial respiratory chain (Dayrit, F. M.,
acetone) that are transported from the liver to other tissues, Philipp. J. Sci., 2014).
Figure 5.
O
OH
Lauric acid
ω-oxidation
β-oxidation
O OH O
H3C S-CoA OH
11-Hydroxylauric acid
Citric acid cycle thiolase
O
HO
O O OH
Cellular energy
12-Hydroxylauric acid
OH
Acetoacetic acid
OH O
OH
β−Hydroxybutyric acid
Acetone
Ketone bodies
To extrahepatic organs:
brain, muscle, heart
Cellular energy
Antimicrobial properties Coconut oil also has applications in hair care. “Coconut oil
has a high affinity for hair proteins and, because of lauric
Lauric acid and its derivative monolaurin have antimicrobial
acid’s low molecular weight and straight linear chain, is able to
activity against gram-positive bacteria and some fungi and
penetrate inside the hair shaft,” says Oi-Ming Lai, professor of
viruses. Lauric acid is the most active antimicrobial among sat-
bioprocess technology at Universiti Putra Malaysia, in Serdang.
urated fatty acids, and monolaurin is more active than lauric
“Coconut oil reduces protein loss for both undamaged and
acid (Dayrit, F. M., http://doi.org/10.1007/s11746-014-2562-7,
damaged hair when used as a pre-wash and post-wash
2015). In fact, many commercial products contain lauric acid
grooming product.”
or monolaurin as antimicrobial agents. Synthetic monolaurin
is used as an antimicrobial compound in a number of food and
non-food applications. Food ingredient
The antimicrobial properties of lauric acid can be traced Coconut oil is perhaps best known for its use as a cooking oil,
to three main mechanisms: destruction of the cell membrane but it is also used extensively by the food industry in baked
of gram-positive bacteria and lipid-coated viruses, interfer- products, processed foods, and infant formulas. Because
ence with microbial processes such as transcription and signal coconut oil is almost completely saturated fat, it is much less
transduction, and stabilization of human cell membranes. Thus susceptible to heat-induced damage than unsaturated fats.
far, bacteria have not been able to evolve resistance to lauric The oil has a long shelf life, 2 years on average.
acid or monolaurin, possibly due to their multiple antimicro- Many people find coconut oil to have attractive sensory
bial mechanisms (Dayrit, F. M., http://doi.org/10.1007/s11746- attributes. “When coconut oil is solid, at room temperature,
014-2562-7, 2015). it’s pure white, and when it’s melted it looks just like water,”
Like its predominant fatty acid, coconut oil likewise has says Foale. “This lovely oil has a very gentle aroma and a subtle
antimicrobial properties, says A. G. Gopala Krishna, retired taste—a pleasant taste, but not a strong taste.” He says that
chief scientist at the Central Food Technological Research Insti- coconut oil can replace butter or shortening in “all manner of
tute (CSIR) in Mysore, India. “Coconut oil kills bacteria that recipes.”
cause diseases such as pneumonia, sore throats, dental cavi-
ties, urinary tract infections, meningitis, gonorrhea, and food
poisoning,” he says. “It also kills the causes of fungal infections
such as candida, ringworm, athlete’s foot, thrush, jock itch, DIFFICULT, COMPLEX DISTILLATION?
and diaper rash. It kills viruses having a lipid coating, such as CONTRACT WITH POPE SCIENTIFIC
herpes, HIV, hepatitis C, influenza, and mononucleosis.”
In the early twentieth century, a prominent American WE’RE UP TO THE CHALLENGE!
dentist named Weston A. Price traveled to the South Pacific
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COLUMN TECHNOLOGY.
of the fatty acids,” says Foale. The traditional Indian practice
• Highest possible purity and yield with
of “oil pulling,” or swishing coconut oil around in the mouth, heat-sensitive materials
is increasing in popularity. Although evidence of its efficacy • Newly expanded modern facility, GMP
is mostly anecdotal at this point, coconut oil pulling has been and kosher certified
reported to reduce or prevent bad breath, gingivitis, and tooth • Long term contracting, short runs,
decay. pilot process development, lab
services
• Equipment also offered for sale
Personal care worldwide
• Global leaders in professional
Coconut oil is a common ingredient in personal care products customer service, experience, and
such as soaps, lotions, and cosmetics. Also, lauric acid and its results with:
derivatives (e.g., lauryl sulfate) are used as detergents and Edible & Essential Oils • Esters • Flavors
surfactants in cleansers. Rubbing VCO directly on the skin can Fragrances • Foods • Pharmaceuticals
Biomaterials • Polymers • Extracts
boost the skin’s moisture and lipid content, similar to mineral Waxes • Vitamins • Nutraceuticals
oil (Agero, A. L., and Verallo-Rowell, V. M., Dermatitis, 2004). Lubricants • Biofuels • Specialty
Coconut oil may confer antiseptic properties to lotions or Chemicals • Others
moisturizers that could benefit people with certain skin PARTNER WITH AND OUTSOURCE TO POPE. MINIMIZE RISK, COSTS AND
conditions. TIME-TO-MARKET WHILE MAXIMIZING PRODUCT QUALITY, VALUE & SUCCESS!
www.popeinc.com +1-262-268-9300
12 • inform May 2016, Vol. 27 (5)
Biodiesel residual water, and it must not have been subjected to high
temperatures [above 60 oC] during preparation.”
Coconut oil can be used directly as a fuel, or can be converted
According to Krishna, rancidity can be a problem for
into methyl esters that have similar combustion properties as
low-quality coconut oil. “If moisture is removed carefully
diesel, says Dayrit. “Coco-biodiesel” offers many advantages
before extraction of the oil, or not allowed to come in
over diesel, including reduced emissions of particulates,
contact with the oil, a good-quality oil can be prepared,” he
carbon monoxide, and nitric oxide; reduced toxicity; and
says. “Hydrolytic rancidity causes the oil to stink very badly
improved safety due to a higher flash point. In addition to
and become unfit for human consumption or for use in
reducing air pollution, coco-biodiesel is environmentally
cosmetic applications.” Krishna adds that a good-quality oil
friendly from the standpoint that is it renewable and
should have a bland or slightly coconut aroma, be light to
biodegradable. “The use of coco-biodiesel is already being
slightly brown in color, and have very low levels of free fatty
implemented in a number of countries,” says Dayrit. “In the
acids (below 1%).
Philippines, diesel fuel currently must contain at least 1%
Adulteration can also be a problem for VCO. Less-
coco-biodiesel.”
expensive oils such as palm kernel oil or RBD coconut oil can
be added to VCO to cut costs. “Because of the increased
Quality control demand for VCO in recent years, there is a need for methods
For someone choosing to consume coconut oil for its to detect adulterated VCO,” says Lai. Proposed techniques
suspected health benefits, VCO is a better choice than include Fourier transform infrared spectroscopy (FTIR), NMR,
RBD copra oil because of the higher content of polyphenols differential scanning calorimetry (DSC), and an electronic nose
and other bioactive compounds. But how can consumers be (Marina, A. M., et al., http://doi.org/10.1016/j.tifs.2009.06.003,
certain they are purchasing high-quality coconut oil? To ensure 2009).
quality, Codex Alimentarius has established standards for VCO.
Likewise, the Asian and Pacific Coconut Community (APCC), an Rediscovery
intergovernmental agency of 18 coconut-producing countries
Coconut oil has a long history of use in tropical regions, but
that oversees global trade and other aspects of the coconut
people elsewhere are now just discovering the varied uses
industry, has standards for VCO. “The guidelines are very
of the oil. “From a historical perspective, the current rise in
simple,” says Foale. “The oil must be perfectly clear, there
popularity of coconut oil in the U.S. and Europe can be seen
mustn’t be any cloudy material from suspended particles, no
as a rediscovery, driven by the dissatisfaction with currently
Information
Agero, A. L., and Verallo-Rowell, V. M. (2004) “A random- Dubois, V., et al. (2007) “Fatty acid profiles of 80
ized double-blind controlled trial comparing extra virgin vegetable oils with regard to their nutritional potential.”
coconut oil with mineral oil as a moisturizer for mild to Eur. J. Lipid Sci. Technol. 109: 710–732.
moderate xerosis.” Dermatitis 15: 109–116. http://dx.doi.org/10.1002/ejlt.200700040.
Assunção, M. L., et al. (2009) “Effects of dietary coconut Fernando, W. M., et al. (2015) “The role of dietary coconut for
oil on the biochemical and anthropometric profiles of the prevention and treatment of Alzheimer’s disease: potential
women presenting abdominal obesity.” Lipids 44: 593– mechanisms of action.” Br. J. Nutr. 114: 1–14.
601. http://doi.org/10.1007/s11745-009-3306-6. http://doi.org/10.1017/S0007114515001452.
Cassiday, L. (2015) “Big fat controversy: changing Hashim, S. A., et al. (1960) “Effect of a saturated medium-
opinions about saturated fat.” Inform 26: 343–349, 377 chain triglyceride on serum lipids in man.” Lancet 1:
(June 2015). 1105–1108.
Dayrit, F. M. (2014) “Lauric acid is a medium-chain fatty Liau, K. M., et al. (2011) “An open-label pilot study to assess
acid, coconut oil is a medium-chain triglyceride.” the efficacy and safety of virgin coconut oil in reducing
Philipp. J. Sci. 143: 157–166. visceral adiposity.” ISRN Pharmacol. 2011, 94686.
http://doi.org/10.5402/2011/949686.
Dayrit, F. M. (2015) “The properties of lauric acid and
their significance in coconut oil.” J. Am. Oil Chem. Soc. 92:
1–15. http://doi.org/10.1007/s11746-014-2562-7.
inform May 2016, Vol. 27 (5) • 13
The use of water in place of solvent is highly desirable as In addition to the green benefits gained from using water
a green processing method for oil extraction from various oil- as an extraction medium, the use of enzymes imparts its own
bearing materials. Abundant studies have shown great interest green benefits. As summarized by Simpson et al. (2012), the
in this method as compiled and discussed in review papers by advantages of using enzymes are listed as follows.
Rosenthal et al. (1996) and Mat Yusoff et al. (2015). More ongo-
ing studies concerning this approach were also reported in the • Enzymes always act only on their substrates due to their
case of pumpkin seeds (Jiao et al., 2014), tiger nuts (Ezeh et al., selective characteristics. Consequently, fewer co-products
2016), Lophira lanceolata seeds (Nonviho et al., 2015), and and waste products are formed during the production of food
sesame seeds (Ribeiro et al., 2016). Recent studies also focused products.
on the use of enzymes for the separation of the emulsified oil, • Enzymes are relatively nontoxic, which makes their use in
as in the case of emulsified oils from maize germ (Matsakidou foods and as processing aids acceptable to consumers.
et al., 2015). This de-emulsification method is discussed thor- • Enzymes function even at low concentrations and under mild
oughly in the review paper done by Mat Yusoff et al. (2015). processing or reaction conditions, which are easier on the
In light of the use of water as the extraction medium, the environment and allow for the use of less expensive stainless
advantages of the AEE method are summarized as follows. steel vessels.
• Enzymes are composed of natural protein structures which
•W ater is much safer and friendlier to the environment than are readily deactivated after use. They can also be immobi-
solvents, which leads to safer and flexible operations. lized for further recovery and re-use, which reduces process-
• T he use of water is economical, requires mild operational con- ing costs.
ditions, and the oil does not need to undergo further refining.
These factors contribute to lower energy consumption, lower Despite the advantages of AEE as a green processing
operational costs, lower capital investment, and consequently method, AEE is only used commercially in the extraction of
a lower overall cost of processing. olive and avocado oil. Two key factors limiting large-scale
• AEE can be applied to a variety of oil-bearing materials, commercial application of AEE to other oil-bearing materials
and the use of mild operating conditions results in valuable have been identified.
co-products such as non-toxic meal and value-added fiber
and protein.
60
50
40
Oil yield (% w/w)
Aqueous extracon
30
Aqueous enzymac
20
extracon
10 Solvent extracon
0
Moringa oleifera Sesame seeds Sunflower seeds
kernels
Oil-bearing materials
FIG. 2. The oil yields of different oil-bearing materials from aqueous extraction, aqueous enzymatic extraction, and solvent extrac-
tion methods. Although several enzymes were tested, the oil yields depicted are only those of the enzymes that achieved the
highest yields for each material: protease (Protex 7L) for Moringa oleifera kernels (Latif et al., 2011), protease (Alcalase 2.4L) for
sesame seeds (Latif and Anwar, 2011), and a mixture of carbohydrases (Viscozyme L) for sunflower seeds (Latif and Anwar, 2009).
16 • inform May 2016, Vol. 27 (5)
• Most studies reported a lower oil recovery from an AEE pro- In the case of palm oil, using water as an extraction medium
cess as compared to solvent extraction (Fig. 2, page 15). In most could contribute to a reduction in the use of chemicals through-
cases, the cell wall and membrane were not fully hydrolyzed out the entire palm-oil-extraction process. This could potentially
by the enzymes, which prevented further oil release into the reduce the production of Green House Gas (GHG), potentially
water. offsetting the lower oil extraction rate. Although further de-
• A portion of the released oil formed an oil-in-water emul- emulsification could require a longer dragging-time, the amount
sion with the water. This requires a further de-emulsification of gas released would probably be lower than that released dur-
method for higher total oil recovery. This downstream process ing solvent extraction. Production of a lower GHG value is of
may results in higher operational costs. great market demand, which could contribute to lower expendi-
tures for maintaining the biogas plant in the future. Such advan-
As discussed by Dalsgaard and Abbotts (2003), in food indus- tages are encouraging. (Personal communication, 2016).
try, energy consumption is highly dependent on the types of food Despite its disadvantages, AEE offers great potential for sig-
processed and the processing steps involved. AEE for oil-bearing nificant long-term benefits to both the environment and health of
seeds has only been done at laboratory scale due to the disad- operators. These potential benefits gave rise to several ongoing
vantages highlighted above. Limited resources have made it dif- studies aimed at overcoming the limitations of AEE during the last
ficult to evaluate overall energy costs and to identify any partial few decades.
energy-savings that could potentially be incorporated into the
process—aside from those related to the use of water as the Masni Mat Yusoff is a PhD student in the Department of Food
extraction medium. Also, because solvent extraction has been and Nutritional Sciences, University of Reading, Reading, United
the main oil-extraction method for oil seeds for decades, convert- Kingdom. She is also a tutor in the Faculty of Food Science and
ing to a new extraction method would involve unknowns with Technology, Universiti Putra Malaysia, UPM Serdang, Malaysia.
respect to time, costs, energy expenditures, consultation experts, She can be contacted at m.matyusoff@pgr.reading.ac.uk., or
production losses, and rate of success. masniyusoff@upm.edu.my
Understanding the
oil-gelling properties
of natural waxes
Ashok R. Patel
Oil-structuring strategies aimed at creating structures with the functionality of fats, but with the
nutritional profile of liquid oils (low in saturated fats and high in unsaturated fats) represent an
important area of research that is highly relevant from the product development point of view.
In the last few years, the field of oil structuring (oleogelation) has experienced rapid growth, with
a more than 5-fold increase in scientific publications related to this field. Of all the structuring
agents explored so far, natural waxes can be regarded to be the most promising oleogelators
(Fig. 1, page 18), owing to their efficient oil-gelling functionality (effective at concentrations as low
as 0.5 %wt), natural origins (food-approved status), and ease of availability (most are agricultural
and industrial by-products). Moreover, gels formed using waxes have interesting properties such
as themoreversibility and emulsion stabilization, which further justifies the popularity of waxes as
oleogelators for vegetable oils. However, as the use of wax to gel liquid oils is a relatively recent
concept, a sufficient understanding of the gelling properties of waxes is still lacking. In the following
section, results from chemical analysis, thermal behavior, microstructure studies, and rheological
characterization are compared to gain new insights into the gelling behavior of natural waxes.
Unlike other low-molecular-weight gelators, waxes have a
multi-component chemical nature comprised of major compo-
• Natural waxes are promising oleogelators due nents such as hydrocarbons (HCs), wax esters (WEs), fatty acids
(FAs), and fatty alcohols (Falcs). Such chemical diversity makes
to their efficient oil-gelling functionality, natu- the characterization of wax-based organogels very complicated.
ral origins, and availability. In our study, we looked at six waxes differing in the proportion of
major components (Fig. 2a, page 18) to gel high-oleic sunflower
oil. As seen from the melting profiles (Fig. 2b, page 18), sunflower
• Results from chemical analysis, thermal be- wax (SFW) was predominantly rich (> 95 %wt) in WEs and showed
havior, microstructure studies, and rheological a single melting and corresponding crystallization peak (not
shown). Consequently, SFW was classified as a mono-component
characterization were recently compared to wax. Based on the melting ranges, the waxes were further cat-
gain new insights into the gelling behavior of egorized into wax with low-, mid-, and high-melting components
(lmc, mmc and hmc, respectively).
natural waxes. On comparing the critical gelling concentrations (Fig. 3, page
19), SFW and candelilla wax (CLW)—with high levels of wax esters
and hydrocarbons, respectively—displayed the lowest values,
• This article describes what was learned.
while berry wax (BW) and fruit wax (FW), with no wax esters or
hydrocarbons, showed much higher values (6 and 7 %wt). This
suggests that wax esters and hydrocarbons are responsible for
the efficient gelling properties of natural waxes. In case of car-
nauba wax (CRW), the presence of a polar component (Falc) inter-
fered with the crystallization of wax esters, resulting in a more
aggregated crystal morphology. Hence, CRW required a
18 • inform May 2016, Vol. 27 (5)
To conclude, the rheological behavior of wax-based oleo- might show “ductile-type” or “brittle-type” deformation
gels can be assumed to have characteristics of both floc- under applied shear depending on the uniformity of bonding
culated suspension (at low volume fractions of colloidal strength connecting the aggregated particles (as seen in floc-
particles) as well as semi-dilute polymer solution. At a certain culated suspension). The Cg and the rheological behavior are
concentration, Cg (analogous to C* in case of semi-dilute poly- strongly influenced by the morphology of primary crystalline
mer solution), a 3D network or agglomeration of aggregated particles as well as the subsequent aggregation of these pri-
crystalline particles is created to form a viscoelastic gel which mary particles, which in turn, depends on the chemical com-
ponents present in waxes. The information obtained through
this work will help us in setting criteria for selecting waxes.
For instance, it is not the melting range but the relative
proportion of individual chemical constituents that deter-
mine the rheological properties of obtained gels (wax esters
and hydrocarbons have a dominant role in microstructure
development of gels). For example, because of the presence
of a high proportion of WEs (> 95 %wt), SFW forms rod-like
crystalline particles which facilitates efficient gel formation at
FIG. 5. a) Gelation and peak crystallization temperatures of much lower crystalline mass fraction, whereas BW forms large
oleogels and b) Elastic modulus at the crossover (gelation) spherical crystals because of a high proportion of low melting
point of oleogels FAs (> 95 %wt) and thus, a relatively higher crystalline mass
fraction is required for oil gelation.
The waxes studied in this work are of natural origins
and they can therefore be used for potential applications in
bio-related products such as food, pharmaceuticals, and
cosmetics. For instance, the gelling of edible oils at such low
concentration of waxes can be exploited in formulation of
food products with low-saturated-fat content. However,
since these gels are rather “weak” in nature, with high shear
sensitivity and low thixotropic recovery, incorporation of high-
melting fats will be necessary to obtain structured oil systems
(i.e., hybrid systems) with desired properties for actual food
applications.
Recommended reading
1. Patel, A.R. and Dewettinck, K. “Edible oil structuring: An overview and recent updates,” Food & Function 7: 20–29 (2016).
2. Patel, A.R., Babaahmadi, M., Lesaffer, A., and Dewettinck, K. “Rheological profiling of organogels prepared at critical gelling
concentrations of natural waxes in a triacylglycerol solvent,” J. Agric. Food Chem. 63: 4862–4869 (2015).
3. Chi, D.D., Van de Walle, D., Dewettinck, K., and Patel, A.R. “Evaluating the oil gelling properties of natural waxes in rice bran oil:
Rheological, thermal and microstructural study,” J. Am. Oil Chem. Soc. 92: 801–811 (2015).
4. B
lake, A., Co, E., and Marangoni, A. “Structure and physical properties of plant wax crystal networks and their relationship to oil
binding capacity,” J. Am. Oil Chem. Soc. 91: 885–903 (2014).
5. Hwang, H.-S.; Kim, S.; Singh, M.; Winkler-Moser, J. and Liu, S. “Organogel formation of soybean oil with waxes,” J. Am. Oil Chem.
Soc. 89: 639–647 (2012).
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What happens to food and its microstructure when it is fried is a complicated process, both
scientifically and mathematically speaking? While consumers want a product that is crispy and
tasty, food scientists seek to get a closer glimpse into what exactly is going on inside the food
during frying in order to improve products.
Pawan Takhar, a food scientist at the University of Illinois
at Urbana–Champaign, is interested in the food’s uptake of
• Frying food is a complex process that affects oil during frying and how that oil gets distributed through-
out the food. “Through conventional lab techniques we can
the internal microstructure of food. already see how much oil content is in food material, but we
didn’t know how it gets distributed throughout the mate-
rial,” he says.
• Food scientists seek to improve the To understand the distribution of oil better, Takhar
healthfulness and taste of fried foods by and his lab recently conducted a study using X-ray micro-
understanding what takes place in the computed tomography (micro-CT) to gain 3D images of the
microstructure of fried potato disks after they had been
food material’s internal structure when fried for various lengths of time (Fig. 1).
it is fried. During deep frying, as food is immersed in hot oil, water
in that food quickly evaporates and steam pressure builds.
This pressure affects the microstructure, including the
• Researchers at the University of Illinois at porosity—the number and size of pores in the food—as well
as the twistiness of the pathways between those pores (tor-
Urbana–Champaign, Illinois, USA, use X-ray
tuosity). This determines how and how much oil gets taken
micro-computed tomography (micro-CT) up into the food. For the study, russet potatoes cut into
to study the internal pore structure and oil disks that were 45-mm in diameter and 1.65 mm thick were
fried at 190 degrees Celsius for 20, 40, 60, or 80 seconds,
distribution in potato disks during various freeze dried, and scanned. Takhar says about 986 2D images
of the potato samples were collected and then combined to
produce 3D images. Using the 3D images, they were able to
gain more information about the pores and pore networks
in the material.
inform May 2016, Vol. 27 (5) • 23
FIG. 1. From left to right: X-ray microtomograph of potato disks fried at different frying times.
Image courtesy of Pawan Takhar
The researchers observed that as frying time increased, texture of crispiness outside and softness inside. At the
pore size increased, allowing for greater uptake of oil. They same time you want to reduce the oil content to make the
also saw a correlation between oil content and how the net- food healthier. With this network study we wanted to see
work of pathways between the pores changed throughout how those networks are formed, because networks are also
the frying time. These pathways act like channels for water related to texture.” It’s a combination of the oil content and
and vapor flow and oil penetration in the food. air pockets in the pore structure that provide the desired
“As you fry the material, you can see how those pore crispy texture.
structures are forming,” Takhar says. “We found that in the The findings from the potato disks in the study can
beginning of frying, the pore network is very complicated. also be applied to other fried foods, Takhar says. His lab has
The waviness in the pathway, the tortuosity, is very complex done previous research on frying using chicken nuggets and
in the beginning so the material resists oil penetration. But French fries.
as the frying progresses, those pathways become simpler. While Takhar and his lab have done mathematical mod-
Pores open up and are easily accessible from the outside and eling of what happens during frying—just one previous paper
oil can be taken up.” (Fig. 2, page 24) outlines over 100 mathematical equations involved in the
Takhar also explains that oil was observed distributed process—he says this study provides some experimental
across the full thickness of the potato disks. In thicker mate- validation as to what is happening inside the food material.
rials with lots of moisture (like chicken nuggets and French The resulting paper, “Microstructural characterization of
fries), they have observed the oil to remain near the surface fried potato disks using X-Ray micro computed tomography,”
as continuous evaporation helps to resist oil penetration. was published online in February 2016 in the Journal of Food
“It is not easy to make a product that has no oil and still Science ( http://dx.doi.org/10.1111/1750-3841.13219.) It was
provides taste, flavor, and texture that consumers enjoy,” he coauthored by Tanjila Alam, a former graduate student at the
says. “People like that fried flavor and the University of Illinois.
24 • inform May 2016, Vol. 27 (5)
FIG. 2. 3D image of potato disks showing pores as holes; and pore network model.
Image courtesy of Pawan Takhar
“I would say we still only understand about 10 percent of Stephanie Henry is a news writer at the College of Agricultural,
what is taking place during frying,” says Takhar. He and his lab Consumer, and Environmental Sciences at the University of Illi-
have studied the effects of frying for 10 years. “For an engi- nois at Urbana–Champaign, Illinois, USA. She can be contacted
neer or a food scientist, it’s the ultimate problem because it’s so at slhenry@illinois.edu.
complicated.
“Our aim is to make these products healthier, so that they Funding was provided by USDA-NIFA. The researchers
have the same taste and texture but, at the same time, have acknowledge Beckman Institute at University of Illinois for
lower fat content. That is our long-term goal with our research,” providing assistance with the micro CT scanning experiments.
Takhar says.
inform May 2016, Vol. 27 (5) • 25
New
Oxidative Stability and Shelf Life Release
of Foods Containing Oils and Fats
Edited by Min Hu and Charlotte Jacobsen
February 2016 | ISBN 9781630670566
Oxidative Stability and Shelf Life of Foods Containing Oils and Fats is the first book
to address the critical role of oils and fats in the successful development, and
improvement of, food and pet food products. From ensuring products are consumer
acceptable in nutritional and sensory aspects to extending the lifespan between
production and consumption, oxidative stability provides important options for foods
containing oils and fats. This book explores both analytical and evaluative methods for
bulk oils and fats, frying oils and fried foods, and food emulsions as well as for specific
food product categories. Featuring 13 chapters written by renowned experts, this
reference offers valuable insights into the latest research and applications.
Key Features:
● Presents the challenges of assessing oxidative stability and strategies for
minimizing lipid oxidation and extending the shelf life of various food products
● Discusses lipid co-oxidation with protein (many food products contain both
lipids and proteins)
● Includes new information on packaging technologies to control lipid oxidation
● Directed toward scientists working in the food and pet food industries
EI
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in high demand, and are highly respected AO
CS SA
Indeed, observational studies (e.g., the Framingham HDL cholesterol group harbored this mutation. When the team
study; Gordon, T., et al., Am. J. Med., 1977) have shown that sequenced an additional cohort of 1,282 subjects, they again
high serum HDL cholesterol levels correlate with reduced risk found that the SCARB1 P376L mutation was significantly over-
of coronary heart disease, whereas high LDL cholesterol lev- represented in people with high HDL cholesterol levels. Nearly
els associate with increased risk. However, recent studies of all of the people with this mutation were of Ashkenazi Jew-
people with very high serum levels of HDL cholesterol (greater ish descent. Rader estimates that the P376L mutation occurs
than about 100 mg/dl) have indicated that the relationship in 3–5 people per 100 with this ethnic background, but is
between HDL cholesterol and heart disease may not be so extremely rare in the general population.
simple. In particular, a study that appeared in the March 11, The researchers established in cell lines and in mice that
2016, issue of Science has shown that a genetic mutation in the P376L mutation results in a complete loss of function of
the human SCARB1 gene raises HDL cholesterol levels but, the SR-BI receptor, such that cholesterol uptake from HDL is
paradoxically, increases the risk of coronary heart disease dramatically reduced. They next performed a meta-analysis of
(Zanoni, P., et al., http://dx.doi.org/10.1126/science.aad3517). genotyping studies encompassing 49,846 coronary heart dis-
SCARB1 encodes SR-BI (scavenger receptor class BI), the ease patients and 88,149 controls. Rader and colleagues found
major receptor for HDL cholesterol. SR-BI promotes the uptake that P376L carriers had an 80% higher risk of developing coro-
of cholesterol into the liver, where it can be excreted. Knock- nary heart disease compared with noncarriers. The research-
out mice lacking SR-BI have elevated HDL cholesterol lev- ers concluded that HDL function and cholesterol flux may be
els and increased atherosclerosis. However, the relationship more important than absolute HDL levels in protecting against
among SR-BI, HDL metabolism, and coronary heart disease coronary heart disease. Furthermore, enhancing SR-BI expres-
risk in humans was unknown. So Daniel J. Rader at the Univer- sion may be a new therapeutic strategy for reducing heart
sity of Pennsylvania, in Philadelphia, USA, and his colleagues disease risk.
examined the sequence of the SCARB1 gene in two groups of Gerald McNeill, vice president of research and develop-
people: 328 participants with very high HDL cholesterol levels ment at IOI Loders Croklaan, in Channahon, Illinois, USA, calls
(>95th percentile, mean HDL cholesterol level of 106.8 mg/dl), the study “very interesting.” He points out that the high HDL
and a control group of 398 subjects with low HDL cholesterol levels seen in individuals with the SR-BI mutation result from
(<25th percentile, mean HDL cholesterol of 30.4 mg/dl). the HDL cholesterol “being unable to enter the liver and having
The researchers identified five individuals in the high nowhere to go. In effect, there is no active HDL in the serum.”
HDL cholesterol group that had a particular genetic mutation In other words, although HDL cholesterol levels are high in
(P376L) in the SCARB1 gene. None of the individuals in the low people with the SR-BI mutation, HDL cannot effectively unload
inform May 2016, Vol. 27 (5) • 29
Alternating Copolymer
a. [By Minihaa - created with Inkscape., CC0, https://commons.wikimedia.org/w/index.php?curid=37637257]
Block Copolymer
b. [By Minihaa - created with Inkscape., CC0, https://commons.wikimedia.org/w/index.php?curid=37637257]
Random Copolymer
c. [Aushulz - BY-SA 3.0, https://commons.wikimedia.org/w/index.php?curid=20548316]
Graft Copolymer
d. [By Minihaa - created with Inkscape., CC0, https://commons.wikimedia.org/w/index.php?curid=37637259]
FIG. 1. Some polymer architectures: (a) alternating copolymer; (b) block copolymer; (c) random copolymer; and (d) graft copolymer.
In the personal care cosmetic industry, polymers are • S imple Vinyl Polymers are designated by attaching the
defined by nomenclature conventions listed in INCI dictionary prefix poly to the monomer name (e.g., polyalkylenes
(explained in the April 2016 issue of Inform, pages 57–59); they " carbon-chain polymers with double bonds along the
are organized into a number of different classifications: organic monomer chain -C=C- (e.g., polystyrene, polyethylene,
polymers, inorganic polymers, siloxane polymers, and naturally and polypropylene, polyolefin).
occurring polymers. These classifications are further divided • Hetero-chain polymers that contain more than one atom
into the following sub-classes defined below. type in their backbone are grouped according to the types
of atoms and chemical groups (e.g., carbonyl, amide,
• Homopolymer—consisting of chain extension by one type of or ester) located along the backbone (e.g., Acrylate/
monomer (e.g., Polyisobutene, Polystyrene) Acrylamide Copolymer, Styrene/ Acrylamide Copolymer)
• Copolymer—consisting of at least 2 monomers, “/” is used •C rosspolymer " One or more of the monomeric constituents
between each monomer, and listed in alphabetical order are multifunctional.
(e.g., Acrylates/Aminoacrylates/C10-30 Alkyl PEG-20 Itaconate • Monomeric cross-linkers are identified in the assigned
Copolymer). Other examples include: monograph definition (e.g., Acrylates Crosspolymer –
• Acrylamides Copolymer is a copolymer of two or more Glycol Methacrylate as the cross-linker).
monomers consisting of acrylamide or simple alkyl • Polymeric cross-linkers are incorporated in the INCI
derivatives of acrylamide. assigned monograph (e.g. Acrylates/VA Crosspolymer,
•A crylates Copolymer is a copolymer of two or more Adipic Acid/Diethylene Glycol/Glycerin Crosspolymer).
monomers consisting of acrylic acid, methacrylic acid or • “Poly-Generic” " Four or more monomeric molecules
one of their simple esters. (e.g., Polyamides, Polyacrylic(ate), Polyester, Polyurethane,
Polyquaternium, Polyimide)
32 • inform May 2016, Vol. 27 (5)
• Polyacrylate-X is a co-polymeric acrylate that has a } Sucrose (one glucose and one fructose unit)
primary acrylic component represented as part of the } Lactose (one glucose and one galactose unit)
copolymer composition. • Polysaccharides have a polyether linkage of monosaccha-
• Polyquaternium-X is a co-polymeric quaternary ammo- rides and generally occur in nature (e.g., Glycogen).
nium salt that has a primary quaternium component as • Homopolysaccharides (same monosaccharide)
part of the copolymer composition as part of the } Starch derived from Glucose (e.g., Hydrolyzed Starch,
copolymer composition. Oryza Sativa (Rice) Starch)
•A lkoxylated Homopolymeric Ethers of ethylene oxide, } Cellulose built up from glucose units but differs from
propylene oxide, or aziridine starch in the configuration around the ether oxygen
• “PEG-X” is the polyethylene glycol fraction; “-X’ denotes bonds (e.g., Cellulose Gum, Methyl Cellulose)
the average number of moles of ethylene oxide. • Heteropolysaccharides—found in terrestrial and oceanic
• “PPG-Y” is the polypropylene glycol fraction; “-Y” denotes plants [gums and natural polymers] and animal king-
the average number of moles of propylene oxide. dom sourced, include Chitin and a large group of complex
• “PEI-Z” is the polyethylene imine fraction; “Z-“ denotes polysaccharides which are chemically bound to proteins
the average number of moles of ethylene imine (aziridine). (e.g., hyaluronic acid, Biosaccharide-X)
• Mixed Alkoxylate Polymer Ethers • Peptides - named based on the number of repeating
• Block Copolymer process named as PEG-X PEG-Y units of amino acid residues. In the definition is listed
Copolymer the amino acids in alphabetical order. If the sequence is
•R andom Copolymer process named as PEG/PPG- the same as a human peptide, there are special rules to
X/Y Copolymer communicate to the consumer that it is the same or a
• “ Carboxylic acid" or “Carboxylate” are the PEG and PPG replicate of a human gene sequence.
polymers or their derivatives in which one of the terminal } consisting of two to ten amino acid residues and is
primary alcoholic groups (CH2OH) has been oxidized to the named using the appropriate prefix, di-, tri-, tetra-,
carboxy group (-COOH) (e.g., PEG-10 oxidized to carboxylic etc., followed by the term peptide and an arbitrary
acid would be named PEG-10 Carboxylic Acid). number (e.g., Dipeptide-2, Acetyl Octapeptide-3)
• Naturally-Derived are biological polymers built-up from } consisting of 11 to 100 amino acids and is designated
naturally occurring monomers. Including all the sugar by the term oligopeptide, followed by an arbitrary
carbohydrates and starches, gums, cellulosic, protein type number (Oligipeptide-X)
biological polymers. } consisting of more than 100 amino acids and is
• Monosaccharides, or simple sugars, are represented by designated by the term polypeptide, followed by an
an aldose (aldehyde) derivative or ketose (ketone) arbitrary number (Polypeptide-X)
derivative (e.g., Glucose, Fructose). • Human-Sourced ingredients are defined from the original
• Disaccharides (Ethers of two monosaccharides) source of components or genes.
} Maltose (two glucose units)
FIG. 2. Products that are used by consumers for beautification and topical improvements of skin and hair. Source: Abruutyn, E., “The INCI
process: a chairman’s perspective,” Cosmetic & Toiletries 122: 22; September 2007.
inform May 2016, Vol. 27 (5) • 33
Stay connected!
inform May 2016, Vol. 27 (5) • 35
order to bring the liquid cooking oil into the process, and the batter
patents
coating retains the incorporated liquid cooking oil during process-
ing to impart a fat fried texture, appearance and taste to the baked
food product.
seven IF samples contain species of broader mass range (from 728 to SM at combating the detrimental effects of a high-fat diet in mice.
1035 Da). Our study indicates that two types of DHA were used in Additionally, distal gut microbiota is altered with milk SM and this
the seven IF products surveyed and that there is very large difference may have contributed to the lower serum LPS observed.
in molecular species distribution in different IF products that may
influence the fine nutritional profile and biological functions of IF
products.
Lipid Oxidation
Milk sphingomyelin improves lipid
metabolism and alters gut microbiota Physicochemical properties and antioxidant
in high fat diet-fed mice potential of phosvitin resveratrol
Norris, G.H., J. Nutr. Biochem. 30: 93–101, 2016. complexes in emulsion system
http://dx.doi.org/10.1016/j.jnutbio.2015.12.003. Duan, X., et al., Food Chem. 206: 102–109, 2016,
High dietary fat intake can cause elevated serum and hepatic http://doi.org/10.1016/j.foodchem.2016.03.055.
lipids, as well as contribute to gut dysbiosis, intestinal barrier Egg yolk phosvitin is the most highly phosphorylated protein
dysfunction, and increased circulating lipopolysaccharide (LPS). found in the nature. The physicochemical properties of phosvitin–
Dietary milk sphingomyelin (SM) has been shown to inhibit lipid resveratrol complexes and their synergistic antioxidant activities
absorption in rodents. We evaluated the effects of milk SM on lipid in microemulsions were investigated. The particle diameters of
metabolism and LPS levels in C57BL/6J mice fed a high-fat diet microemulsions containing 0.5%, 1.0% and 2.0% phosvitin were
for 4 weeks and compared it with egg SM. Mice were fed a high-fat 2.660, 0.501 and 0.414μm, respectively. The emulsifying activity
diet (45% kcal from fat) (CTL, n=10) or the same diet modified to index increased largely from 3.72 to 21.5m2/g with increasing phos-
contain 0.25% (wt/wt) milk SM (MSM, n=10) or 0.25% (wt/wt) vitin concentration from 0.5% to 2.0%. Fourier transform infrared
egg SM (ESM, n=10). After 4 weeks, MSM had gained significantly spectroscopy and thermal analyses indicated that the microemul-
less weight and had reduced serum cholesterol compared to CTL. sions underwent a conformational change during homogenization.
ESM had increases in serum cholesterol, triglycerides, phospholip- Antioxidant assays showed that phosvitin–resveratrol microemul-
ids, and SM compared to CTL. MSM significantly decreased, while sions exhibited a higher antioxidant activity than that of phosvitin–
ESM increased, hepatic triglycerides. This may have been related to resveratrol primary emulsions. The MTT assay indicated that HepG2
induction of hepatic stearoyl-CoA desaturase-1 mRNA observed cell viability remained higher than 80% at phosvitin concentration
in ESM. MSM displayed intestinal and hepatic gene expression below 1.0mg/ml. This suggested that phosvitin, when coupled with
changes consistent with cholesterol depletion. MSM had signifi- polyphenol, can effectively inhibit lipid oxidation in food emulsions,
cantly lower serum LPS compared to CTL, which may have been which provided valuable insights into deep processing and applica-
due to altered distal gut microbiota. Fecal Gram-negative bacteria tion of egg proteins in food industry.
were significantly lower, while fecal Bifidobacterium were higher, in
MSM. These results suggest that milk SM is more effective than egg
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This Code has been adopted by AOCS to define the rules of professional conduct for its members.
AOCS Code of Ethics • Chemistry and its application by scientists, engineers, and technologists have for their prime objective the advancement of science
and benefit of mankind. Accordingly, the Society expects each member: 1) to be familiar with the purpose and objectives of the Society as expressed in
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2016 MbrApp-1p-INF.indd
44 • inform May 2016, Vol. 27 (5)
Lipids (March)
• Tian, T., Y. Zhao, Q. Huang, and J. Li, n-3 polyunsaturated fatty • J ia, Z., et al., Structure of sphingolipids from sea cucumber
acids improve inflammation via inhibiting sphingosine kinase 1 Cucumaria frondosa and structure-specific cytotoxicity against
in a rat model of parenteral nutrition and CLP-induced sepsis human HepG2 cells
• Fukunaga, K., et al., Hypolipidemic effects of phospholipids • Newie, J., M. Kasanmascheff, M. Bennati, and I. Feussner,
(PL) containing n-3 polyunsaturated fatty acids (PUFA) are not Kinetics of bis-allylic hydroperoxide synthesis in the iron-
dependent on esterification of n-3 PUFA to PL containing lipoxygenase 2 from Cyanothece and the effects
• Faris, R., et al., Mitochondrial glycerol-3-phosphate acyltransfer- of manganese substitution
ase-dependent phospholipid synthesis modulates phospholipid • J amilian, M., et al., Vitamin D and evening primrose oil
mass and IL-2 production in Jurkat T cells administration improve glycemia and lipid profiles in women
• de França S.A., et al., A low-protein, high-carbohydrate diet with gestational diabetes
stimulates thermogenesis in the brown adipose tissue of rats via • Lagutin, K., H. Wong, M. Vyssotski, and A. MacKenzie, Absolute
ATF-2 stereochemistry of 1,2-diols from lipids of thermomicrobia
• López-Olmos, V., et al., Increased HDL size and enhanced apo
A-I catabolic rates are associated with doxorubicin-induced
proteinuria in New Zealand white rabbits
inform May 2016, Vol. 27 (5) • 45
Publications
• El-Sayed, R., A. Shaldom, and L.A. Mazrouee, Synthesis of
ecofriendly functionalized oxadiazole, imidazole, triazole
and pyridine derivatives
• Zhi, L., Q. Li, Y. Sun, and S. Yao, Mixed stability and antimicrobial
properties of gluconamide-type cationic surfactants
• Sathyam Reddy, Y., P. Sujitha, C.G. Kumar, S. Kanjilal,
P. Vijayalakshmi, Synthesis and evaluation of surface and
biological properties of some lactic acid-based anionic
surfactants
• Abdel-Rahem, R.A., A.M. Altwaiq, E.S. Zaben, and M.M.
Journal of Surfactants and Detergents Alnass’a, Zinc corrosion in acidic solutions containing single and
mixed surfactants
(March) • Blagojević, S.N., S.M. Blagojević, and N.D. Pejić, Performance
and efficiency of anionic dishwashing liquids with amphoteric
and nonionic surfactants
• Kamal, M.S., A review of gemini surfactants: potential • Xu, J., F. Cao, T. Li, S. Zhang, C. Gao, and Y. Wu, Itaconic Acid
application in enhanced oil recovery based surfactants: i. synthesis and characterization of sodium
• Zhu, L., Y. Tang, and Y. Wang, Constructing surfactant systems n-octyl sulfoitaconate diester anionic surfactant
with the characteristics of gemini and oligomeric surfactants • Torres, M.D., and J. Seijo, By-products from the chestnut
through noncovalent interaction industry used to produce natural potassium soaps:
• Zarate-Muñoz, S., F. Texeira de Vasconcelos, K. Myint-Myat, J. physicochemical properties
Minchom, and E. Acosta, A simplified methodology to measure • Padasala, S., B. Kanoje B., K. Kuperkar, and P. Bahadur,
the characteristic curvature (Cc) of alkyl ethoxylate nonionic Mixed micellization study of alkyltrimethylammonium and
surfactants alkyltriphenylphosphonium bromides in aqueous solution
• Zhu, H., Z. Hu, X. Ma, J. Wang, and D. Cao, Synthesis, surface • Tang, W., T. Geng, Y. Jiang, H. Ju, Y. Wang, Properties of
and antimicrobial activities of cationic gemini surfactants with didecyldimethylammonium formate and sodium fatty
semi-rigid spacers alcohol ether carboxylate mixed systems
• Piecuch, A., E. Obła˛k, and K. Guz-Regner, Antibacterial activity • Tamer, Y., H. Berber Yamak, H. Ylldlrlm, Structural and
of alanine-derived gemini quaternary ammonium compounds physicochemical properties of a polymerizable surfactant
• Zheng, Y., Z. Ren, P. Mei, and L. Yu, Interactions between a synthesized from n-methylol acrylamide
sulfobetaine-type zwitterionic gemini surfactant and fatty • Shakil, Hussain S.M., et al., Synthesis, characterization and
acid alkanolamide in aqueous micellar solution surface properties of amidosulfobetaine surfactants bearing
• Lehanine, Z., and L. Badache, Effect of the molecular structure odd-number hydrophobic tail
on the adsorption properties of cationic surfactants at the • Ito, S., J. Kawata, M. Kameda, and M. Miyazawa, Lower
air–water interface irritation potential of laureth-3 carboxylate amino acid salt
• Staszak, M., A linear diffusion model of adsorption kinetics • S hyichuk, A., and D. Ziółkowska, Determination of anionic
at fluid/fluid interfaces surfactants by means of photometric titration with methylene
• Hou, B., et al., Surfactant-induced wettability alteration of blue dye
oil-wet sandstone surface: mechanisms and its effect on •M ostafalu, R., A. Banaei, M.H. Riazi, and F. Ghorbani,
oil recovery A modified method for the determination of n-
nitrosodiethanolamine in coconut diethanolamide
using HPLC with dual-wavelength UV–Vis detector
April 30–May 3, 2017. AOCS Annual Meeting and Industry For in-depth details on these and other upcoming meet-
Showcases, Rosen Shingle Creek, Orlando, Florida, USA. ings, visit http://aocs.org/meetings or contact the AOCS
Meetings Department (email: meetings@aocs.org; phone:
+1 217-693-4821; fax: +1 217-693-4865).
Latin America Update 46 • inform May 2016, Vol. 27 (5)
Q: What is palm oil, and what are its Q: Are there differences in the respective
applications in Brazilian cuisine? fatty acid profiles of palm oil from Brazil and
those from Malaysia and Indonesia?
A:
A:
Palm oil (dendê oil, in Portuguese), is derived from the
fruit of the palm tree Elaeis Guineensis, Jacq. Palm oil has a
The genus Elaeis comprises two species, namely
balanced fatty acid composition in which the level of satu-
E. guineensis and E. oleifera. Elaeis guineensis is native from
rated fatty acids is almost equal to that of the unsaturated
Africa and can be found in spontaneous populations or in
fatty acids. Palmitic acid (44–45%), oleic acid (39–40%), and
cultivated fields in all tropical regions of Africa, Southeast
linoleic acid (10–11%) are the major components. Crude palm
Asia, and South and Central America. The American oil palm,
oil also contains minor amounts of sterols, squalene, and
also known as Caiaué (Elaeis oleifera) is endemic to the humid
carotenoids (which are responsible for the reddish orange
tropical zone of Latin America. It occurs in spontaneous
color). This oil is also the richest source of tocotrienols among
populations from the south of Mexico to Amazon areas in
all vegetable oils.
Brazil and Colombia. The oil and fatty acids produced by
In Brazil and Africa, crude palm oil is often consumed in
Elaeis oleífera is more unsaturated and generally has lower
the crude form, and it is preferred for its taste and aroma. It
acidity than that produced by the African oil palm cultivars.
is an ingredient in most dishes from the state of Bahia, such
as moqueca, vatapá, xinxin de galinha, caruru, and akara.
The latter is a finger food that is a cultural icon of the city of
Salvador (Bahia, Brazil). As a flavoring ingredient, it is most Q: What are the health effects of palm oil?
commonly combined with coconut milk, chili peppers, and
cilantro. The combination of these ingredients leads to what
many people consider Bahiana cuisine. Furthermore, Dendê A: Palm oil is high in saturated fatty acids (44% palmitic
acid and 5% stearic acid). Consequently, many authors claim
oil is an important ritual food in the Afro-Brazilian religion
Candomblé. that palmitic acid intake may promote an increased risk of
hypercholesterolemia, liver disease, type 2 diabetes, and
other diseases. However, more recent investigations on the
Q: In which regions of Brazil is palm oil topic seem to have reconsidered the negative role of dietary
saturated fatty acids as a risk factor for cardiovascular
produced, and what is the annual production? diseases, and show that not only the type of fat, but also the
A:
triacylglycerol structure plays a role in these diseases.
An explanation as to why palm oil does not pose any
The major palm oil producers are Malaysia, Indonesia,
additional health risks is based on the particular location of
and Nigeria. However, African oil palm (and dendê oil) arrived
the fatty acids within the triacylglycerol molecule. The unsat-
in Brazil during the times of African slave trafficking.
urated fatty acids are located mostly at the sn-2 position
Palm oil production in Brazil is restricted to three states:
(> 58.25% of oleic acid and > 18.41% of linoleic acid), while
Pará, and Amazonas (North) and Bahia (Northeast). Pará has a
a high proportion (17–23%) of palmitic acid is at the sn-1,3
significant industrial complex and is notably the largest
position. Fatty acids at the sn-2 position are preferentially
Brazilian producer, responsible for approximately 90% of the
absorbed and are therefore more bioavailable than the fatty
total oil processed and produced in the country. The Amazo-
acids located at the sn-1,3 positions. On the assumption that
nas state has a low average yield due to its infant plantations
most saturated fatty acids in palm oil are located at the sn-1,3
and consequent small production scale. In the state of Bahia,
positions, the absorption of these fatty acid is actually low.
most of the palm production originates from spontaneous
groves comprising almost 50,000 hectares intertwined with
degraded tropical forest. There, plants of the Dura, a low-
yielding variety, are dominant, leading to low productivity Latin America Update is produced
and oil extraction rates (3–4 metric tons/ha/yr). by Leslie Kleiner, R&D Project
Currently, Brazilian production of palm oil and its deriva- Coordinator in Confectionery
tives corresponds to about 0.57% of the total production Applications at Roquette Americas, Inc.,
worldwide, making Brazil the 10th largest producer, with an Geneva, Illinois, USA, and a contributing
output of around 450,000 metric tons (MT). The domestic editor of Inform. She can be reached at
demand is 500,000 MT, with the majority of its use destined LESLIE.KLEINER@roquette.com.
for the food (80%) and chemical (20%) industries.
48 • inform May 2016, Vol. 27 (5)
Tips from
A doctoral student in food science wanted to know if bio-
diesel producers would be willing to pay a premium for
distillers corn oil with a lower free fatty acid (FFA) content.
Tips from inform|connect is a regular Inform column that features tips and other discussion
highlights from the community forum board at http://www.informconnect.org/home.
A:
using 1H NMR, J. Pharm. Biomed. Anal. 93: 95–101, 2014,
A:
A: I created two HPLC methods for silicone oil a few years http://dx.doi.org/10.1016/j.jpba.2013.09.005.
ago, one for characterization and a second one for
quantitation. Your sample matrix, of course, has much A: This reference can be useful: Gong, Z., G. Jiang, W.R.
to do with how you can analyze for this material. If it is Cullen, H.V. Aposhian, and X.C. Le, Determination of
water based, it may be possible to simply centrifuge it and arsenic metabolic complex excreted in human urine
inject 10 or more microliters onto the HPLC column using after administration of sodium 2,3-dimercapto-1-
the second method. We are now using the latest model propane sulfonate, Chem. Res. Toxicol. 15: 1318–23,
of the Corona charged aerosol, the Corona Veo, which may 2002, http://www.ncbi.nlm.nih.gov/pubmed/12387631.
be more sensitive for this application. The former detector
model was calibrated down to 78 ng on column, or 7.8 ppm
of liquid sample. A poster describing this analysis can be
found at http://tinyurl.com/gmnlrwx.
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