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6Flax Oil and
High Linolenic Oils
Roman Przybylski
University of Manitoba
Winnipeg, Manitoba, Canada
1. INTRODUCTION
Many species in the Europhorbiaceae and Labiatae families
produce seeds with a
high content of oil and contribution of linolenic acid of up to
76% (1). Flaxseed has
been used for years in the production of paints, varnishes,
inks, and linoleum. In
food applications, flaxseed is more often used than oil because
of its better stability
and because of the presence of fiber, lignans, and a-linolenic
acid (ALA), whichhave health benefits. Cold pressed flaxseed oil is
not considered suitable for
deep-frying, although Chinese use it in stir-frying (2). In this
chapter, oilseeds of
flax, perilla, camelina, and chia are discussed as sources of
oils with elevated con-
tent of ALA. These oilseeds are produced in industrial
quantities and can be con-
sidered as potential sources of new oils with specific
nutritional and functional
properties.
Baileys Industrial Oil and Fat Products, Sixth Edition, Six
Volume Set.Edited by Fereidoon Shahidi. Copyright# 2005 John Wiley
& Sons, Inc.
281
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2. FLAX
2.1 Origin
Flax, widely adapted to warm and cool climates, has been
cultivated for centuries in
various parts of the world for its stem fiber, linen cloth, and
seed. Linseed is an
alternative name used for flax. Crops grown for seed are termed
linseed in India
and in the United Kingdom and flaxseed in Canada and the United
States, and
flax oil or flax seed is used in many European countries.
Flaxseed/linseed is the annual cultivar of Linum usitatissimum
L. Flax is a mem-
ber of the Linaceae family that includes ten genera and more
than 150 species (3).
Approximately 200 species of Linum are known (3).
The crops grown for both seed and fiber are generally called
dual-purpose flax.
Initially, the same variety was used for both oil and fiber
production. Today, oil and
fiber varieties are different and specifically designed to serve
the actual end use.
Fiber varieties usually have longer stem, 80120 cm tall, with
fewer branches,
fewer seed capsules, and smaller seeds. Although oil type has
shorter and heavily
branched stems, 6080 cm tall, with a higher number of seed
capsules and larger
seeds.
All registered flax varieties in Canada have a dark brown seed
coat. There are
available yellow seed-coated varieties grown in other countries
such as the Omega
variety in the United States. Transition to different color is
mainly esthetic, lighter
colored flaxseed flour is produced from these seeds, and
appearance of the product
is less affected when it is applied as an ingredient.
2.2 Production
More than 60 years ago, the average world production of flaxseed
was about
3.4 million metric tons (MMT), which was more than sunflower,
2.5 MMT, and
slightly lower than rapeseed, 3.8 MMT. In the same period,
soybean was produced at
a level of 12.6 MMT (4). In those years, flaxseed was the
third-most produced oil-
seed in the world by volume. Since then, world production of
flaxseed has remained
between 2 and 3 MMT, and the production of other oilseeds has
increased consid-
erably (4). In 20002001, world production of flaxseed was 2.34
MMT, with Canada
being the largest producer and exporter of this oilseed (See
graph in Canola
chapter).
The total average yearly world production of flaxseed for the
past ten years was
2.52 MMT (5). The principal growing areas for flaxseed are
Canada, China, India,
Argentina, the United States, the United Kingdom, former USSR,
and some
European countries (5). The average contribution of mentioned
countries in the
world production of flaxseed is presented in Figure 1. Among
mentioned producers,
Canada, China, and India contributed 34.9%, 18.7%, and 11.9%,
respectively, to the
world production. The eight main flaxseed producers listed
contributed up to 82%
of the total yearly flaxseed production.
282 FLAX OIL AND HIGH LINOLENIC OILS
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Canada is one of the major flaxseed producers and exporters,
where a minimal
amount of seeds is crushed to produce flax oil. Flax oil is
mainly considered as a
health food product but not a commodity oil. Figure 2 shows
yearly production of
flaxseeds in Canada for the past ten years. On average, Canada
is producing above
800,000 MT (metric tons) of flaxseed per year (5). Part of this
production is low
linolenic acid varieties, which contribute from 10% to 15% to
the total production.
Recently, the food industry in North America and Europe has
shown an
increased interest in utilization of flaxseed in food product
formulations. This is
Figure 1. Major world producers of flaxseed (Ten-year average
from 1990 to 2000). Production
averaged 2.52 million metric tons/year. aFormer U.S.S.R. Source:
Canadian Grains Council,
Statistical Handbook 2001 (5).
19911992 1993199419951996199719981999 2000 2001
Met
ric T
ons
(x100
0)
200300400500600700800900
100011001200
Figure 2. Flaxseed production in Canada. Data include low
linolenic flaxseed. Source: Canada
Grains Council Statistical Handbook 2001 (5).
FLAX 283
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mainly because of the presence of ALA, dietetic fiber, and plant
lignans, which
according to scientific evidence provide important health
benefits.
2.3. Physicochemical Properties of Flax Oil
Some physicochemical properties of conventional flaxseed oil and
low linolenic
varieties are presented in Table 1. The higher specific gravity
of 0.935 observed
for flaxseed oil than other vegetable oils can be directly
attributed to the high con-
tribution of linolenic acid. It is in line with the specific
density of fatty acids that
increases from 0.895 to 0.9038 and to 0.914 for oleic, linoleic,
and linolenic acids,
respectively (7).
The amount of polyunsaturated fatty acids (PUFA) affects both
melting and
flashpoints of vegetable oils. Melting temperature of oil is
directly related to the
melting point of fatty acids, which decreases with unsaturation
(7). The flash point
of flaxseed oil is relatively low compared with other vegetable
oils; this can be
attributed to a high contribution of PUFA.
Unsaponifiable matter content, saponification value, and iodine
value are char-
acteristic for a high contribution of PUFA in the flax oil. The
content of unsaponifi-
able matter in flax oil is similar to other vegetable oils.
2.4. Chemical Composition of Flax Oil
Main components of vegetable oils, including flax oil, are
triglycerols and usually
contribute more than 90% of all components (Table 1). Minor
components in flax
oils were found to be at the similar level as in canola and
soybean oils (10). The
presence of chlorophyll in flax oil usually indicates immaturity
of flaxseed.
TABLE 1. Properties of Flaxseed Oils (69).
LinolaTM
Parameter Flaxseed Oil Crude RBD
Relative density (20C/water at 4C) 0.9250.935 0.921
0.920Refractive Index (nD 20
C) 1.4751.475 1.4657 1.4665Melting Point (C) 20 to 24Flash
Point, min. (C, open cup) 120135Viscosity (cp) 46.8 46.4
Iodine Value 182203 142 144
Unsaponifiable Matter (%) 0.11.7 1.2 0.6
Saponification Value (mgKOH/g) 187195 185 185
Phosphorus (ppm) 1.030 300 1.0
Chlorophyll (ppm) 0.01.5 0.4 0.1
Free Fatty Acids (% of oleic) 0.12.0 0.3
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Fatty acid composition of regular flax oil is different from
other commercial oils
because of the very high contribution of ALA, usually above 50%
(Table 2).
Because of the high content of this unique fatty acid, flaxseed
and flax oil are often
used as food supplements, where enrichment with omega-3 fatty
acids is needed.
This fatty acid is susceptible to oxidation; it oxidizes 2040
times faster than oleic
acid and 24 times faster than linoleic acid (8). This property
makes the oil a good
material for paint and plastic production where fast oxidation
is required. Flax oil
contains low amounts of saturated fatty acids (SFA) compared
with low linolenic
flax oil (Linola), soybean, and sunflower oils; however, it is
higher than canola
oil (Table 2). Canola oil contains the lowest amount of SFA
among all commercial
oils.
The contribution of linolenic acid in flaxseed oil showed a wide
range and was
affected by the growing conditions. Flax varieties grown in
Western Canada, aver-
age from 495 samples analyzed, contained 5% palmitic acid
(16:0), 3% stearic acid
(18:0), 17% oleic acid (18:1), 15% linoleic acid (18:2), and 59%
linolenic acid
(18:3) (11). Although similar varieties were grown in North
Dakota, the 11 cultivars
assessed showed the following fatty acid composition: 56% of
16:0, 36% of 18:0,
1929% of 18:1, 1418% of 18:2, and 4552% of 18:3 (12).
TABLE 2. Composition of Flaxseed and Major Oils (6, 10,
Przybylski Unpublished Data).
Component Flax LinolaTM Canola Soybean Sunflower
Fatty Acids (%)
C16:0 5.3 6.1 3.8 11.2 6.0
C18:0 3.3 3.8 1.7 4.1 4.0
C18:1 17.9 15.5 58.2 24.3 16.5
C18:2 14.7 71.3 20.1 54.6 72.4
C18:3 58.7 2.0 9.6 8.3 0.5
SFA 9.0 10.0 6.2 15.6 11.2
MUFA 18.1 17.1 64.2 23.4 16.7
PUFA 72.9 72.9 29.6 61.0 72.1
Tocopherols (ppm)
Alpha 20 15 272 116 613
Gamma 200 200 423 737 19
Delta 7 5 275
Plastochromanol-8 120 110 75
Total 347 330 770 1128 632
Phytosterols (%)
Brassicasterol 1 1 14
Campesterol 27 23 28 18 7
Stigmasterol 8 4 1 15 7
b-Sitosterol 50 54 52 54 585-Avenasterol 10 18 5 2 4
Total sterols (g/kg) 2.3 2.2 6.9 2.6 3.1
Abbreviations: Fatty Acids: SFAsaturated; MUFAmonounsaturated;
PUFApolyunsaturated; Plasto-
chromanol-8derivative of gamma tocotrienol with longer side
chain.
FLAX 285
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Cool temperatures during the 1025 days after flowering are the
main cause for
higher amounts of linolenic acid in flax oils (14). For the same
reason, flaxseed
grown in the Canadian prairies, northern latitude, produce oils
with higher levels
of polyunsaturated fatty acids and lower contributions of oleic
acid and saturated
fatty acids. This phenomenon was also observed for other
oilseeds such as sun-
flower, canola, and soybean (7, 13, 14). Similarly, a wide
variation in fatty acid
composition in Australian flaxseed samples was observed: 1325%
of 18:1 and
4664% of 18:3 (6).
Analysis performed on varieties of flaxseeds collected from
different flax grow-
ing regions of the world and later grown in Morden, Manitoba,
Canada, showed
even wider distributions of oleic acid 1460%, linoleic acid
321%, and ALA
3172% (13). All of these data indicate that within flax, there
is a wide distribution
of fatty acids, and this variability can be used for developing
specialty oils based on
traditional breeding and to avoid GMO oils.
Flaxseed oils contain much lower amounts of tocopherols, half of
the amount
present in sunflower and canola oils and one-third of that
present in soybean oil
(Table 2). A lower content of these antioxidants makes these
oils even more suscep-
tible to oxidation. Gamma-tocopherol was found as the main
tocopherol in flax oils,
with a contribution of about 80% to the total amount. This makes
flax oil compar-
able with soybean oil. Among unique antioxidants detected in
flax oils was plasto-
chromanol-8. This compound is a derivative of gamma tocotrienol
with twice as
long unsaturated side chain. Plastochromanol-8 was found to be a
more efficient
antioxidant than any tocopherols isomer (15). A low content of
tocopherols in flax-
seed did not make them more susceptible to oxidation;
experiments showed that
milled flaxseed could be stored for 28 months at ambient
temperatures without
measurable changes in oxidation products. This can be attributed
to the presence
of antioxidants other than tocopherols in the seeds (16).
Sterols or phytosterols are present in flax oils at a level
lower than those in many
vegetable oils, 2.3 mg/g in flaxseed oil versus 4.1 to 6.9 mg/g
in other oils (Table 2).
The composition of sterols was similar to other oils, where
b-sitosterol was themain component followed by campesterol and
5-avenasterol. Brassicasterol wasfound in trace amounts in flax
oil. This phytosterol is characteristic to plants from
the Brassica family and often is used as a marker for oil
adulteration (Table 2).
As discussed above, triacyglycerols are the main components of
vegetable oils
and the composition of flax acylglycerols is presented in Table
3.
As expected from fatty acid composition, the main
triacylglycerols contain lino-
lenic acid in their molecules and 84% of all triacylglycerols
have this acid in their
structure (Table 3). Among them, 21% of total acylglycerols
contained three ALA
in molecule, second by contribution were acylglycerols with two
ALA, and linoleic
acid had the second-most abundant fatty acid present in the flax
oil (17).
Flaxseed is the richest source of plant lignans containing 75800
times more
than that in other oilseeds, cereals, legumes, fruits, and
vegetables (18). These plant
origin components act in mammalians as hormone-like
phytoestrogens. Lignans are
compounds with a dibenzylbutane skeleton, which have been found
in many higher
plants (1820). Plant lignans, namely, secoisolariciresinol
diglycoside (SDG) and
286 FLAX OIL AND HIGH LINOLENIC OILS
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matairesinol (MAT), are the main compounds among flaxseed
lignans. Both are
structurally different from animal and human lignans, enterodiol
(ED) and entero-
lactone (EL). Mammalian lignans are formed by intestinal
microorganisms from
plant precursors (Figure 3). The concentration of mammalian
lignan precursors is
measured by adding a particular food ingredient to the model of
the intestinal
microorganism and assessing the amounts of released ED and EL
(18). Similarly,
excretion of animal lignans in urine may be measured (18, 19).
Figure 4 shows urin-
ary excretion of ED and EL when different plant components were
included in the
diet. Flax oil is the second dominant source of mammalian
lignans excreted after
flaxseed, in far higher amounts than other oils, oilseeds, and
cereals.
Lignans from flaxseed have been shown to reduce mammary tumor
size by more
than 50% and tumor number by 37% in carcinogen-treated rats (19,
20). Further-
more, it has been suggested that lignans have antimiotic,
antiestrogenic, antiviral,
antibacterial, antifungal, and antioxidant properties
(2033).
The presence of plant lignans in flax oil makes it nutritionally
more valuable
than any other oil. When high levels of ALA and linoleic acid
are considered in
the whole equation, flaxseed oil serves as the best oil in terms
of its nutritional
and health value.
The Food and Drug Administration (FDA) regulations allow
inclusion of flax-
seed in food products, but the amount allowed is limited to 12%
(34).
TABLE 3. Composition of Triacyglycerols
in Flaxseed Oil (17).
Triacyglycerols1 Contribution (%)
PLnLn 7.6
PLLn 6.7
PLL 1.5
POL 1.6
LnLnLn 20.9
LLnLn 13.8
LLLn 3.7
OLnLn 8.4
LLL 0.9
OLLn 5.3
OLL 0.9
SLLn 1.1
OOL 3.4
OOLn 7.3
POLn 4.0
SLnLn 3.2
POL 1.6
PLL 1.5
OOO 3.3
1Abbreviations of fatty acid: Ppalmitic; Lnlinolenic;
Llinoleic; Ooleic; Sstearic.
FLAX 287
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OROR
OHOCH3
H3CO
HO
OHOH
OH
HO
OHOCH3
H3CO
HOO
O
OH
HOO
O
BacterialFermentation
BacterialFermentation
BacterialFermentation
SecoisolariciresinolDiglycoside (SDG)
Matairesinol
Enterodiol (ED) Enterolactone (EL)
Plant Lignans
Mammalian Lignans
Figure 3. Mammalian lignan formation in digestive tract and
their plant precursors (19).
Figure 4. Total excretion of human lignans in the urine of rats
after diet was supplemented with
various foods (18).
288 FLAX OIL AND HIGH LINOLENIC OILS
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2.5. Low Linolenic Flaxseed Oil
Low linolenic acid varieties with yellow-seed coat flax
trademarked Linola were
developed by the Commonwealth Scientific and Industrial Research
Organization
(CSIRO) in Australia and distributed elsewhere under this name
by United Grain
Growers, Canada (4). The Linola seed color has been changed to
yellow to make
it distinguishable from the traditional flaxseed dark brown
color. The generic com-
mon name Solin has been assigned by Flax Council of Canada for
all low linolenic
flax varieties produced in Canada. Developmental work on Solin
(Linola is a brand
name within Solin family) is continuing mainly to reduce
saturated fatty acid and to
increase linoleic acid content above the 70% level and to
increase the content of
antioxidants as well as to enhance nutritional properties of the
meal.
The new oilseed crop is grown wherever flax and linseed
varieties are currently
cultivated (35, 36). The climate in northern Europe is highly
suitable for production
of Linola, where sunflower and corn/maize cannot be produced.
Linola seed can be
processed by existing crushing plants using similar processing
parameters. Linola
meal is used for ruminant feed in the same way as linseed
meal.
The fatty acid composition of the new crop has been modified,
and the level of
linolenic acid has been reduced from over 50% to 2% (6). This
greatly improves
oxidative stability of the oil, which by fatty acid composition
is very close to sun-
flower and soybean oils (Table 2). Linola has been found to be
more resistant to
oxidation than regular flax oil, and its stability is comparable
with soybean, canola,
and sunflower oils (Przybylski, unpublished data).
Refining of crude Linola oil by conventional steps, namely,
degumming, alkali
refining, bleaching, and deodorization, produces colorless and
odorless oil, which
has good oxidative stability (9). In addition, properties of
crude and refined,
bleached, and deodorized (RBD) Linola oil are comparable with
other commodity
oils (Table 1).
The FDA granted Generally Recognized as Safe (GRAS) status for
Solin/Linola
oil in 1998 (38). This oil can be used as an ingredient in food
product formulations
such as salad oil, cooking, and frying oil, and in fat phase to
formulate margarine,
spreads, and shortenings (19, 37).
Because of several beneficial nutritional properties, mainly
related to the high
level of linoleic acid and lignans, there is a growing interest
to use Linola seeds
and oil in bakery and confectionery applications. The
golden-yellow-colored Linola
seeds can serve as an attractive and appealing topping for
baking goods. It seems
evident that Linola/Solin seed and oil can have promising future
applications in
food products (35).
2.6. Processing of Flaxseed and Oil
Flaxseed is covered with fibrous hull accounting for 25 to 45%
of the seed weight
and contains 27% by weight of water-soluble carbohydrates. These
components
called mucilage can interfere during processing (38). Flaxseed
contains approxi-
mately 25% protein, 10% moisture, and 3545% of oil (6, 38, 11).
In immature
FLAX 289
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seeds, cyanogenic glucosides such as linamarin, linustatin, and
neolinustatin can be
present at the level of 200650 mg/100 g of seeds (9). Enzyme
linase is always pre-
sent in flaxseed, and it decomposes glucosides to many products,
including
hydrocyanic acid, one of the most toxic substances. Newly
developed varieties of
flax have lower amounts of glucosides in the seed. During
processing, small
amounts of glucoside can be transferred into oil, whereas these
compounds are
water-soluble.
Flaxseed contains a high amount of oil, but expressing oil from
it is difficult and
often double pressing is required to efficiently remove oil from
the seeds. Proces-
sing steps for flax oil production are presented in Figure 5.
Before crushing, cleaned
seeds are tempered to achieve a moisture level of 9.5% to 10%,
this will minimize
the formation of fine particles when seeds are cracked or flaked
and will maximize
removal of oil from them. Moisturized seeds are passed through
sets of corrugated
and smooth rolls to be cracked and flaked, respectively. From
the next processing
step, production of flax oil is differentiated from that for
Solin/Linola oil (7). The
flax oil for human consumption is cold-pressed, and further
purification of oil is
not applied. According to industry standards, cold pressing is
achieved when the
temperature of oil coming from the extruder does not exceed 35C
and pressingis performed under protection from oxygen, usually
under a blanket of nitrogen.
Good practice requires utilization of expellers, which have the
ability to cool parts
of the press, which are in contact with seeds and oil to control
the temperature
during processing (38).
Figure 5. Processing of flaxseed to produce cold-pressed flax
oil.
290 FLAX OIL AND HIGH LINOLENIC OILS
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Oil from expeller is filtered, packaged under nitrogen or other
neutral gas into bot-
tles protecting from light exposure, and ready for distribution.
Flax oil is very suscep-
tible to oxidative deterioration, and treatment to eliminate
oxygen needs to be
applied. On the North American continent, flax oil is considered
as a health food oil.
When flax oil is processed for industrial use, standard
processing steps are
applied as described in Figure 6. Flaxseeds are tampered and
then flaked, passing
through a set of smooth rolls. Flaked seeds are sent to a cooker
where they are
heated to a temperature of 80100C to inactivate enzymes and help
release theoil during pressing. At this stage, formation of toxic
substances is prevented. The
cooked seeds are transferred to the expeller, and expelled oil
through filtration is
placed in a storage tank, where it is combined with oil from
solvent extraction.
Cake/meal after pressing is fed to the solvent extractor, where
hexane is used as
Figure 6. Processing of flaxseed to produce refined, bleached,
and deodorized flax oil.
FLAX 291
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a solvent. From the extractor, cake is moved to the desolvatizer
where the solvent
is removed at 100C. Meal is then cooled and used as an animal
feed ingredient.Combined oils are purified by the standard refining
process, typical to all vegetable
oils (7). Degumming is applied to remove phospholipids, refining
to lower the
content of free fatty acids, bleaching to eliminate chlorophylls
and other pigments
as well as to decompose hydroperoxides, and deodorizing to make
the oil
odorless through elimination of oxidation products (Figure 6).
Processing of
low linolenic flaxseed oil is similar to that described for flax
oil and other com-
modity oils.
3. PERILLA OIL
3.1. Origin and Application
Perilla, Perilla frutescens, L. Britton, is a member of the mint
family, Lamiaceae
(Labiatae). This plant is a common annual weed in the eastern
United States (1). In
Asia, perilla is considered a commercial crop where seeds are
used to produce oil
and plant parts are used as garnish, flavoring, and sources of
nutritional components
in combination with cereals or vegetables. In the United States,
perilla food pro-
ducts are available in the Korean ethnic markets, and red-leafed
plants are used
in landscaping. After the Second World War, the United States
imported perilla
oil, which was used as a drying oil (1). Perilla plant and seed
is used in Asia as
seeds for birds and human consumption; seed oil is used as a
fuel, a drying oil,
or a cooking oil; leaves are used as a pot-herb, for medicine,
food coloring, flavor-
ing dishes, and source of functional nutrients; foliage is
distilled to produce an
essential oil for flavoring.
Wilson et al. (39) isolated the toxin, perilla ketone, which
causes pulmonary
edema (fluid in the lung cavity) in many animal species,
although not in pigs
and dogs (40). In Japan, 2050% of long-term workers in the
perilla industry devel-
oped dermatitis on their hands because of contact with
perillaldehyde (41). Small
amounts of these components have been detected in perilla oil
where it works as an
efficient antioxidant.
Perilla was never grown commercially as an oilseed in the United
States; how-
ever, several agronomists have investigated the crop (42, 43).
Rabak and Lowman
(43) determined that perilla is well adapted to the climate of
the southeastern
United States; it would be unprofitable to cultivate it, unless
seed shattering can
be controlled. Seed yields ranged from 220 to 1400 kg/ha in
Illinois (44), 1020
to 1440 kg/ha in Korea (45), and 1110 to 1670 kg/ha in Japan
agricultural produc-
tion (41). Perilla was also experimentally grown as a crop in
many parts of the
British Empire (46, 47). Production of perilla seeds and oil has
been continued
in Korea for a long time (48, 45). Annual production of perilla
seed is approxi-
mately 40,000 MT, and perilla oil is the third largest among
edible oils used in
the Korean market (49). Perilla plant and seed is widely used in
Asian countries
as food ingredients, including Japan, China, and India.
292 FLAX OIL AND HIGH LINOLENIC OILS
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3.2. Perilla Seed and Oil
The seed of perilla contains 3151% of oil, which is similar in
composition to
flaxseed oil, with a higher contribution of PUFA of over 70%
(Table 4). The
oil is highly unsaturated, with an iodine value of 192208-g
iodine /100-g oil
(Table 4). Perilla oil contains over 60% linolenic acid with
equal amounts of
both linoleic and oleic acids (Table 4). Specific gravity of
this oil is higher than
flax oil because of a higher contribution of PUFA. Other
physical parameters of
this oil reflect the composition of its fatty acids.
TABLE 4. Composition and Properties of Perilla, Camelina, and
Chia Oils.
Parameter Perillaa Camelinab Chiac
Fatty Acids (%)
C16:0 7 6 6
C18:0 2 2 3
C18:1 14 13 7
C18:2 17 16 20
C18:3 61 39 63
Saturated 8 12 9
Monounsaturated 14 34 8
Polyunsaturated 78 54 83
Tocopherols (ppm)
a-Tocopherol 31 46g-Tocopherol 461 420d-Tocopherol 7 10Total 499
500
Lipid Classes (%)
Sterol Esters 2
Glycerides 91 97
Glycolipids 4 2
Phospholipids 2 0.9
Sterols (%)
Cholesterol 5
Brassicasterol 4
Campesterol 25
Stigmasterol 3
b-Sitosterol 525-Avenasterol 11
Total Sterols (mg/kg) 3604
Physicochemical Properties
Refractive Index (nD 20C) 1.4761 1.4698 1.4753
Specific Gravity (at 15.5C/15.5C) 0.937 0.925 0.936Iodine Value
192208 127155 190199
Saponification Value (mgKOH/g) 188197 180190 180192
Unsaponifiable Matter (%) 1.31.5 1.21.5 1.11.3
Oil Content (%) 3550 3542 3240
Protein Content (%) 1728 2530 2030
Camelina contains 15% of eicosenoic acid (C20:1) and 35% of
erucic acid (C22:1).
Source: a(49); b(50, 51); c(5054).
PERILLA OIL 293
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The amount of tocopherols in perilla oil is higher compared with
flax oil, and a
similar contribution of gamma-tocopherol, above 90%, was
observed (Table 4).
Shin and Kim (49) analyzed perilla oil for lipid composition and
established that
it contained more than 90% triacylglycerols, 4% glycolipids, and
2% of each phos-
pholipids and sterol esters.
Perilla oil has been used as a drying oil in paints, varnishes,
linoleum, printing
ink, lacquers, and for protective waterproof coatings on cloth.
It has also been used
for cooking and as fuel (56). The meal produced after oil
extraction is often used as
an animal feed ingredient.
3.3. Perilla Oil Processing
Perilla oil in Korea is processed like other cold-pressed oils,
where pressing and
filtration are the main processing steps. To improve the flavor
of perilla oil used
in food applications, roasting of seeds is practiced. This will
provide oil with a
distinctive roasted, nutty flavor and improved stability.
Roasting of perilla seeds
is often applied in Korea and China (57). Kim et al. (57)
analyzed different
parameters of roasting and established that temperature above
170C providedthe best flavor and stability for the oil.
Nonenzymatic browning components are
mainly responsible for flavor and antioxidant activity (52).
When perilla oil is pro-
duced for the industrial applications, additional processing
such as refining, bleach-
ing, and deodorization is carried out (58).
4. CAMELINA
Standard oilseed crops are not often suitable to marginal lands
where factors such
as low moisture, low fertility, and saline soils play an
important role in the possible
crop to be grown. In recent years, there has been increasing
interest in developing
agronomic systems with low requirements for fertilizer,
pesticides, and energy,
which provide better soil erosion control than conventional
systems. Camelina
can grow in these extreme conditions and provide oilseed with
enhanced nutritional
value (59, 60).
4.1. Origin
Camelina sativa (L.) Crantz., plant from the Brassicaceae
family, known as false
flax, linseed dodder, and Gold-of-Pleasure, originated in the
Mediterranean area
and Central Asia (61). Seeds are small (0.7 mm 1.5 mm), pale
yellow-brown,oblong, rough, and with a ridged surface. Camelina is
listed as being adapted to
the flax-growing region on the Prairies, in Europe, and other
countries (59, 62).
It is primarily a minor weed in flax, which does not have seed
dormancy (63).
Camelina is short-seasoned, 85100 days, so it could be
incorporated into double
cropping systems during cool periods in warmer environments
(55).
Cultivation of camelina probably began in Neolithic times, and
by the Iron Age
in Europe, when the number of crop plants approximately doubled,
this crop was
294 FLAX OIL AND HIGH LINOLENIC OILS
-
commonly used as an oil-supplying plant. Cultivation, as
evidenced from carbo-
nized seed, has been shown to occur in regions surrounding the
North Sea during
the Bronze Age (64). Camelina monoculture occurred in the Rhine
River Valley as
early as 600 B.C. Camelina probably spread in mixtures with flax
and as monocul-
tures, similar to small grains, which also often spread as crop
mixtures. It was cul-
tivated in antiquity from Rome to Southeastern Europe and the
Southwestern Asian
(64).
Camelina production declined during medieval times because of
unknown fac-
tors, but it continued to coevolve as a weed with flax, and this
is the possible intro-
duction of it to the Americas. Like rapeseed oil, camelina oil
has been used as an
industrial oil after the industrial revolution (64). The seeds
have been fed to caged
birds, and the straw has been used for fiber. There has been
scattered production of
camelina in Europe in modern times, mostly in Germany, Poland,
and the USSR. In
the 1980s, breeding and germplasma screening were applied to
modify fatty acid
composition and the content of glucosinolates in camelina seeds
(6569).
Camelina has been evaluated in Canada, North Dakota, and
Minnesota for its
agronomical performance (63, 70, 50). Recent interest in the
species is mainly
because of the demand for alternative low-input oilseed crops
with the potential
for food and nonfood utilization of the seed oil (60, 71).
Unique agronomic features
such as compatibility with reduced tillage and cover crop and
competitiveness with
weeds or winter surface seeding showed suitability of camelina
for sustainable agri-
culture systems. Furthermore, the species has a potential as a
low-cost crop for
green manuring (60).
Long-term yield of camelina cultivars in North America has been
averaging
from 1100 to 1200 kg/ha with a maximum of about 2000 kg/ha. It
should be noted
that the yield of many commodity oilseeds, especially B. napus,
has been improved
through plant breeding, whereas camelina has not been modified
yet (63).
4.2. Seed Composition
The oil content of camelina seed ranges from 29% to 45% in North
American
crops, and in Germany, it is between 37% and 44%. The seed
protein content varies
from 23% to 30% (60, 50, 71, 72). Camelina protein content and
composition is
similar to flax, although higher sulfur content has been
observed for camelina oil
(63). Camelina meal is comparable with soybean meal, containing
4547% crude
protein and 1011% fiber (73). Like other cruciferous plants,
camelina meal con-
tains glucosinolates at levels of 1520 mmol/g (74). This is a
low content of gluco-sinolates compared with other brassicaceous
species, hence making the utilization
of meals easier (73, 75).
4.3. Fatty Acid Composition and Use of the Oil
Camelina oil has a unique fatty acid pattern and is
characterized by a linolenic
acid (C18:3) content ranging from 30% to 40%, eicosenic acid
(C20:1) content
CAMELINA 295
-
of around 15%, and less than 4% erucic acid (21). The fatty
acids in camelina oil are
primarily unsaturated, with only about 12% being saturated
(Table 4). About 54%
of the fatty acids are polyunsaturated, primarily linoleic
(18:2) and linolenic (18:3),
and 34% are monounsaturated, primarily oleic (18:1) and
eicosenoic (20:1).
The fatty acid composition of camelina oil can be influenced by
both environ-
ment and variety, although the effects detected were small. Nine
varieties were
tested, and the maximum differences between oleic, linoleic and
linolenic acid
levels were 3%, 2.4%, and 2.2%, respectively (76). Also, a 2%
less linolenic
acid was observed in camelina grown during a dry warm year
compared with the
normal year. Although these differences are statistically
significant, they are rela-
tively small in absolute terms and have no significant effect on
the properties of the
extracted oil (68, 50, 76).
With its high contribution of polyunsaturated fatty acids,
mainly linoleic and
linolenic, and relatively low saturated fatty acid content,
camelina oil could be con-
sidered a high-quality edible oil. Camelina oil is less
unsaturated than flax oil but
more than sunflower or canola oils (Tables 2 and 4). This oil
seems to be unique
among vegetable oils in having a high content of 11-eicosenoic
acid. Most of the
camelina lines assessed contain 24% erucic acid (Table 4), which
is higher than
the maximum limits for canola-quality rapeseed oil. However,
screened germplasm
of camelina showed that lines with zero erucic acid content are
available and,
through plant breeding, zero erucic varieties can be
obtained.
Plant sterols identified in this oil consist mainly of
b-sitosterol and campesterol(Table 4). About 4% brassicasterol was
detected in the oil, which is typical for
Brassica family plants (51). The total content of sterols in oil
is comparable with
other commercial oils (Tables 2 and 4). The presence of
cholesterol in camelina oil
makes it unique among vegetable oils, where only a trace has
been detected in some
tropical oils (51).
Composition and content of tocopherols in camelina oil was
similar to perilla
oil, where more than 80% of all tocopherols were gamma isomer
(Table 4). Alpha
and delta tocopherols were detected as minor antioxidants (77).
The total content of
tocopherols was comparable with perilla oil, and higher than
that in flax oil (Tables
4 and 2). The total content of tocopherols in camelina oil is
higher than canola, flax,
soybean, and sunflower.
4.4. Processing of Camelina Seed, Oil Stability, and
Utilization
Cold-pressed camelina oil had an attractive yellow color, a
mustard-like taste, and a
characteristic pleasant odor. This type of flavor is acceptable
in India and other
Asian countries, but in Europe and North America, it is
difficult to find acceptability
among consumers, mainly because of a different expectation from
vegetable oils.
However, commercial camelina oil needs to be refined and
deodorized to produce
an odorless and colorless product as expected by consumers (76).
Crude camelina
oil, refined following typical steps as described for flax oil
(Figure 6), afforded a
product similar to typical commercial oils (76).
296 FLAX OIL AND HIGH LINOLENIC OILS
-
To establish storage stability of camelina oil, an accelerated
Schaal Oven storage
test was carried out at 65C with crude and refined canola and
linseed and camelinaoils (76). Conjugated dienes, peroxide, and
p-anisidine values were determined.
The results indicated that the storage stability of camelina oil
was similar to flax
oil, but it was less stable than canola oil. Crude camelina oil
showed a higher
oxidative stability than the refined product (76). During
storage, refined camelina
oil had a 30% higher peroxide level when compared with crude
camelina oil (76).
Comparison with fish oil, which is rich in omega-3 fatty acids,
proved that camelina
oil is much more resistant to oxidative deterioration than fish
oil (76). At room
temperature, crude camelina oil was far more stable than could
be expected
from its high linolenic acid content. This unusual oxidative
stability can be attrib-
uted to the presence of natural antioxidants. However, the
content of tocopherols
discussed above was in the middle range compared with other
commercial
oils but slightly higher than that of flax oil (Tables 2 and 4).
Oxidative stability
is not only related to the content and composition of
tocopherols, but also to pre-
sence of other components, such as phenolic acids and
polyphenols. The content of
antioxidants in oils is also affected by the processing, and the
amounts of antiox-
idants can be lowered even by 50% when particular processing
conditions are
applied (15).
The frying performance of camelina oil was compared with soybean
oil and
assessed under deep frying conditions. Oil deterioration was
monitored by asses-
sing changes in viscosities, free fatty acids, p-anisidine
values, and the formation
of oxidized triacylglycerols (76). During the first 5 days of
frying, camelina oil
deterioration was similar to that of soybean oil. After that
time of frying, camelina
oil deteriorated much faster than soybean oil, probably because
its antioxidants
were depleted. In fact, after 7 days of frying, the levels of
oxidized triacylglycerols
in camelina oil reached the level permitted in Europe, 25%, and
in soybean the
amount of these components was at 14% (76). Similarly, viscosity
of camelina
oil increased 100% by the end of the heating period, whereas in
soybean oil, it
increased only by 30%. Total carbonyl level, measured by
p-anisidine values,
was three times higher in camelina oil than in soybean oil. In
addition, deterioration
of camelina oil during 5 days of potato frying caused formation
of the strong and
objectionable paint-like flavor (76).
Refined camelina oil was blended into fat phase to produce
margarines and
spreads enriched in omega-3 fatty acids. The resulting spreads
had physical proper-
ties similar to a product based on typical commercial oils. The
stability of the new
product was satisfactory, and off-flavors were not detected
after 6 months of storage
(76).
Camelina oil was also included in formulation of salad
dressings. Produced dres-
sings showed a similar stability to conventional products during
several months of
storage at ambient temperature without off-flavor formation
(76).
Taking into consideration that camelina oil production will be
less expensive and
the oil is more stable than fish oil, this oil can be an
excellent ingredient to enrich
spreads, margarines, and other fat-containing food products, in
omega-3 fatty acids,
and by this way change the ratio of omega-3 to omega-6 fatty
acids.
CAMELINA 297
-
5. CHIA
5.1. Origin
Chia (Salvia hispanica L.) is an annual herbaceous plant from
the mint family,
Labiatae, and it is native to southern Mexico, northern
Guatemala, and can be
grown in South America and the Southwestern United States (52).
This plant
was used by the Aztec and other tribes of Central America as an
important crop
not only for food, but also for medicine and paint. Chia oil is
a century-old ingre-
dient that has been rediscovered today as a potential ingredient
for cosmetic and
food industries (52). Although chia has been cultivated for
several centuries, pre-
sently it is cultivated only in some states in Mexico. The total
area cultivated is less
than 450 hectares per year. Trials to adopt this cultivar to
other regions of America
have been done with positive results (52). Chia seeds and oil
are available on the
American continent in health food stores.
5.2. Oil and Seed Composition
Chia seed contains 2540% oil and 1830% protein. The chia meal is
high in pro-
tein and fiber similar to flaxseed and soybean (52, 53). Chia
seed, oil, and meal can
be used as ingredients with high nutritional value for human
food and animal feed.
Chia seed contains mucilage and water-soluble fiber, may
possibly contain lignans,
and is similar to flax (53). Trials conducted in 1995 and 1996
showed yield and
oil contents to be affected by growing conditions and harvested
yields were up to
1500 kg/ha (52).
Chia oil is high in polyunsaturated fatty acids, particularly
a-linolenic acid; thecontent of this fatty acid is higher than flax
oil (Table 4). Linoleic acid is the sec-
ond-most abundant acid in chia with a contribution of 1726%,
which gives PUFA
content of 83%, the highest amount among edible oils.
Additionally, chia oil has the
lowest content of saturated fatty acids (Tables 2 and 4).
The physical properties of chia oil are similar to perilla and
camelina with
the same effect of PUFA discussed above. Lipid class composition
in chia oil is
also typical for vegetable oils where triacylglycerols are the
main components
(Table 4)(52).
REFERENCES
1. J. M. Hagemann, F. R. Earle, and I. A. Wolff, Lipids, 2, 371
(1967).
2. Q. Pan, Flax Production, Utilization and Research in China,
53, 5963 (1990).
3. T. P. Freeman, in S. C. Cunnane and L. U. Thompson, eds.,
Flaxseed in Human Nutrition,
AOCS Press, Champaign, Illinois, 1995, pp. 1121.
4. T. L. Krawczyk, Inform, 10, 1029 (1999).
5. Canada Grains Council, Statistical Handbook, 2001.
6. A. G. Green and D. R. Marshall, Aust. J. Agric. Res., 32, 599
(1981).
298 FLAX OIL AND HIGH LINOLENIC OILS
-
7. N. A. M. Eskin, B. E. McDonald, R. Przybylski, L. J.
Malcolmson, R. Scarth, T. Mag,
K. Ward, and D. Adolph, in Y. H. Hui, ed., Baileys Industrial
Oil and Fat Products, Wiley,
New York, 1996, p. 1.
8. E. N. Frankel, Trends Food Sci. Technol., 4, 220 (1993).
9. A. G. Green, and P. J. C. Dribnenki, Lipid Technol., 6, 29
(1994).
10. F. D. Gunstone, J. L. Harwood, and F. B. Padley, eds., The
Lipid Handbook, Chapman and
Hall, London, 1994.
11. D. R. Declercq, J. K. Daun, and K. H. Tipples, in Crop
Bulletin, Canadian Grain
Commission, Winnipeg, Manitoba, Canada, No. 202, 1992, p. 1.
12. N. S. Hettiarachy, G. A. Hareland, A. Ostenson, and G.
Baldner-Shank, in Proceedings of
the 53rd Annual Flax Institute of the US Meeting, Fargo, North
Dakota, 1990, p. 36.
13. D. G. Dorrell, Fette Seifen Anstrichm., 77, 258 (9175).
14. A. G. Green, Crop Sci., 26, 961 (1986).
15. D. Olejnik, M. Gogolewski, and M. Nogala-Kalucka, Nahrung,
41, 101104 (1997).
16. N. A. M. Eskin and R. Przybylski, in N. A. M. Eskin and D.
S. Robinson, eds., Food Shelf
Life Stability, CRC Press, Boca Raton, Florida, 2001, p.
175.
17. R. B. Tarandjiiska, I. N. Mrekov, B. M. N. Damyanova, and B.
S. Amidzhin, J. Sci Food
Agric., 72, 403 (1996).
18. L. U. Thompson, P. Robb, M. Serraino, and F. Cheung, Nutr.
Cancer, 16, 43 (1991).
19. M. Axelson, J. Sjovall, B. E. Gustafsson, and K. D. R.
Setchell, Nature, 298, 659 (1982).
20. K. D. R. Setchell, in S. C. Cunnane and L. U. Thompson,
eds., Flaxseed in Human
Nutrition, AOCS Press, Champaign, Illinois, 1995, p. 82.
21. L. U. Thompson, S. E. Rickard, L. J. Orcheson, and M. M.
Seidl, Carcinogenesis, 17, 1373
(1996).
22. L. U. Thompson, M. M. Seidl, S. Rickard, L. Orcheson, and H.
H. S. Fong, Nutr. Cancer,
26, 159 (1996).
23. W. R. Phipps, M. C. Martini, J. W. Lampe, J. L. Slavin, and
M. S. Kurzer, J. Clin.
Endocrinol., 77, 1215 (1993).
24. Y. Mousavi and H. Adlercreutz, J. Steroid. Biochem. Mol.
Biol., 41, 615 (1992).
25. M. E. Martin, M. Haourigui, C. Pelissero, C. Benassayag, and
E. A. Nunez, Life Sci., 58,
429 (1996).
26. T. Fotsis, M. Pepper, and H. Adlercreutz, Proc. Natl. Acad.
Sci. USA, 90, 2690 (1993).
27. T. Hirano, K. Fukuoka, K. Oka, and Y. Matsumoto, Cancer
Invest., 9, 145 (1991).
28. K. Prasad, Mol. Cell Biochem., 168, 17 (1997).
29. G. Block, B. Patterson, and A. Subar, Nutr. Cancer, 50, 207
(1992).
30. D. M. Parkin, C. S. Muir, S. L. Whelan, Y. Gao, J. Ferlay,
and J. Powell, in Cancer
Incidence in Five Continents, Vol VI, International Agency for
Research on Cancer, Lyon,
France, 1992, p. 865.
31. H. Adlercreutz, T. Fotsis, and J. Lampe, Scand. J. Clin.
Lab. Invest., 53, 5 (1993).
32. H. Adlercreutz, H. R. Heikkinen, and M. Woods, Lancet, 2,
1295 (1982).
33. K. D. R. Setchell and H. Adlercreutz, in I. R. Rowland, ed.,
Role of the Gut Flora in
Toxicity and Cancer, Academic Press, London, 1988, pp.
315345.
34. J. E. Vanderveen, in S. C. Cunnane and L. U. Thompson, eds.,
Flaxseed in Human
Nutrition, AOCS Press, Champaign, Illinois, 1995, p. 363.
REFERENCES 299
-
35. B. F. Haumann, Inform, 1, 934 (1990).
36. E. A.Weiss, Oils & Fat Int., 9, 23 (1993).
37. Inform, 9, 628 (1998).
38. P. P. Kolodziejczyk and P. Fedec, in S. C. Cunnane and L. U.
Thompson, eds., Flaxseed in
Human Nutrition, AOCS Press, Champaign, Illinois, 1995, p.
261.
39. B. J. Wilson, J. E. Garst, R. D. Linnabary, and R. B.
Channell, Britton. Sci., 197, 573
(1977).
40. J. E. Garst, W. C. Wilson, N. C. Kristensen, P. C. Harrison,
J. E. Corbin, J. Simon, R. M.
Philpot, and R. R. Szabo, Anim. Sci., 60, 248 (1985).
41. N. Okazaki, M. Matsunaka, M. Kondo, and K. Okamoto, Skin
Res., 24, 250 (1982).
42. H. A. Gardener, U.S. Cir., 52, 1 (1917).
43. Rabak, F. and M. S. Lowman, in Perilla, USDA, Agriculture
Research Administration,
Bureau of Plant Industry, Soils, and Agricultural Engineering,
Beltsville, Maryland, 1945.
44. R. O. Weibel and W. L. Burlison, Soybean Dig., 8, 14
(1948).
45. I. S. Choi, S. Y. Son, and O. H. Kwon, Korean Soc. Hort.
Sci., 25, 68 (1980).
46. Imperial Institute, Bul. Imp. Inst., 18, 479 (1920).
47. Imperial Institute, Bul. Imp. Inst., 24, 205 (1926).
48. Yu, I. S. and S. K. Oh, Res. Rpt. Off. Rural Dev., 18, 187
(1976).
49. H. S. Shin and S. W. Kim, J. Amer. Oil Chem. Soc., 71, 619
(1994).
50. E. C. Leonard, Inform, 9, 831 (1998).
51. V. K. S. Shukla, P. C. Dutta, and W. E. Artz, J. Amer. Oil
Chem. Soc., 79, 965 (2002).
52. W. Coates, and R. Ayerza, J. Amer. Oil. Chem. Soc., 75, 1417
(1998).
53. A. A. Bushway, A. M. Wilson, L. Houston, and R. J. Bushway,
J. Food Sci., 49, 555 (1984).
54. R. Ayerza, J. Amer. Oil Chem. Soc, 72, 1079 (1995).
55. H. S. Park, J. G. Kim, and M. J. Cho, J. Korean Agric. Chem.
Soc., 24, 224 (1981).
56. Publications and Information Directorate, in The Wealth of
India, Vol.7, New Delhi, India,
1966.
57. S. J.Kim, H. N. Yoon, and J. S. Rhee, J. Amer. Oil Chem.
Soc., 77, 451 (2000).
58. S. J. Kim, S. H. Song, H. N. Yoon, and U. Y. Kong, Inform,
6, 514 (1995).
59. National Research Council (NRC), in Alternative
Agriculture/Committee on the Role of
Alternative Farming Methods in Modern Production Agriculture,
National Academy
Press, Washington, D.C., 1989.
60. D. H. Putnam, J. T. Budin, L. A. Field, and W. M. Breene, in
J. Janick and J. E. Simon, eds.,
New Crops, Wiley, New York, 1993, pp. 314322.
61. J. Schultze-Motel, Archaeo-Physika, 8, 267 (1979).
62. North Central Regional Technical Committee NC-121, Weeds of
the North Central States,
North Central Regional Res. Pub. 281, Bul. 772, Agr. Expt. Sta.,
Univ. Illinois, Urbana-
Champaign, Illinois, 1981.
63. R. G. Robinson, Minnesota Agr. Expt. Sta. Bull., 579
(1987).
64. K. H. Knorzer, Bererichte der Deutschen Botanischen
Gesellschaft, 91, 187 (1978).
65. R. Seehuber and M. Dambroth, Landbauforschung Voelkenrode,
37, 219 (1987).
66. G. Enge and G. Olsson, Sveriges Utsadesforenings Tidskrift,
96, 220 (1986).
67. B. G. Kartamyshev, Selektsiya i Semenovodstvo, 6, 9
(1985).
300 FLAX OIL AND HIGH LINOLENIC OILS
-
68. R. Seehuber and M. Dambroth, Landbauforschung Volkenrode,
33, 183 (1983).
69. R. Seehuber and M. Dambroth, Landbauforschung Volkenrode,
34, 174 (1984).
70. R. K. Downey, J. Amer. Oil Chem. Soc., 48, 718 (1971).
71. R. Seehuber, Fette-Seifen-Anstrichmittel, 86, 177
(1984).
72. R. Marquard and H. Kuhlmann, Fette Seifen Anstrichmittel,
88, 245 (1986).
73. G. O. Korsrud, M. O. Keith, and J. M. Bell, Can. J. Anim.
Sci., 58, 493 (1978).
74. J. Zubr, Indust. Crops Products, 6, 113 (1997).
75. R. Lange, W. Schumann, M. Petrzika, H. Busch, and R.
Marquard, Fat Sci. Technol., 97,
146 (1995).
76. J. G. Crowley and A. Frohlich. (2002, November 29). Factors
Affecting the Composition
and Use of Camelina. Technical Report, Crops Research Centre,
Oak Park, Carlow,
Ireland. Available:
http://www.teagasc.ie/research/reports/crops/4319/eopr-4319.htm.
77. J. T. Budin, W. M. Breene, and D. H. Putnam, J. Amer. Oil
Chem. Soc., 72, 309 (1995).
REFERENCES 301
Front MatterTable of ContentsVolume 1. Edible Oil and Fat
Products: Chemistry, Properties, and Health EffectsVolume 2. Edible
Oil and Fat Products: Edible Oils2.1 Butter2.2 Canola Oil2.3
Coconut Oil2.4 Corn Oil2.5 Cottonseed Oil2.6 Flax Oil and High
Linolenic Oils2.6.1 Introduction2.6.2 Flax2.6.3 Perilla Oil2.6.4
Camelina2.6.5 ChiaReferences
2.7 Olive Oil2.8 Palm Oil2.9 Peanut Oil2.10 Rice Bran Oil2.11
Safflower Oil2.12 Sesame Oil2.13 Soybean Oil2.14 Sunflower Oil
Volume 3. Edible Oil and Fat Products: Specialty Oils and Oil
ProductsVolume 4. Edible Oil and Fat Products: Products and
ApplicationsVolume 5. Edible Oil and Fat Products: Processing
TechnologiesVolume 6. Industrial and Nonedible Products from Oils
and FatsIndex