6

Flax 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, axseed is more often used than oil because of its better stability
and because of the presence of ber, lignans, and a-linolenic acid (ALA), which
have health benets. Cold pressed axseed oil is not considered suitable for
deep-frying, although Chinese use it in stir-frying (2). In this chapter, oilseeds of
ax, 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 specic 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
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 ber, linen cloth, and seed. Linseed is an
alternative name used for ax. Crops grown for seed are termed linseed in India
and in the United Kingdom and axseed in Canada and the United States, and
ax oil or ax 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 ber are generally called dual-purpose ax.
Initially, the same variety was used for both oil and ber production. Today, oil and
ber varieties are different and specically 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 ax 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 axseed our 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 axseed was about
3.4 million metric tons (MMT), which was more than sunower, 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, axseed was the third-most produced oil-
seed in the world by volume. Since then, world production of axseed has remained
between 2 and 3 MMT, and the production of other oilseeds has increased consid-
erably (4). In 20002001, world production of axseed 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 axseed for the past ten years was
2.52 MMT (5). The principal growing areas for axseed 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 axseed 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 axseed producers listed contributed up to 82%
of the total yearly axseed production.
282 FLAX OIL AND HIGH LINOLENIC OILS
Canada is one of the major axseed producers and exporters, where a minimal
amount of seeds is crushed to produce ax oil. Flax oil is mainly considered as a
health food product but not a commodity oil. Figure 2 shows yearly production of
axseeds in Canada for the past ten years. On average, Canada is producing above
800,000 MT (metric tons) of axseed 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 axseed in food product formulations. This is
Figure 1. Major world producers of axseed (Ten-year average from 1990 to 2000). Production
averaged 2.52 million metric tons/year.
a
Former U.S.S.R. Source: Canadian Grains Council,
Statistical Handbook 2001 (5).
19911992 1993199419951996199719981999 2000 2001
M
e
t
r
i
c

T
o
n
s

(
x
1
0
0
0
)
200
300
400
500
600
700
800
900
1000
1100
1200
Figure 2. Flaxseed production in Canada. Data include low linolenic axseed. Source: Canada
Grains Council Statistical Handbook 2001 (5).
FLAX 283
mainly because of the presence of ALA, dietetic ber, and plant lignans, which
according to scientic evidence provide important health benets.
2.3. Physicochemical Properties of Flax Oil
Some physicochemical properties of conventional axseed oil and low linolenic
varieties are presented in Table 1. The higher specic gravity of 0.935 observed
for axseed oil than other vegetable oils can be directly attributed to the high con-
tribution of linolenic acid. It is in line with the specic 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
ashpoints of vegetable oils. Melting temperature of oil is directly related to the
melting point of fatty acids, which decreases with unsaturation (7). The ash point
of axseed oil is relatively low compared with other vegetable oils; this can be
attributed to a high contribution of PUFA.
Unsaponiable matter content, saponication value, and iodine value are char-
acteristic for a high contribution of PUFA in the ax oil. The content of unsaponi-
able matter in ax oil is similar to other vegetable oils.
2.4. Chemical Composition of Flax Oil
Main components of vegetable oils, including ax oil, are triglycerols and usually
contribute more than 90% of all components (Table 1). Minor components in ax
oils were found to be at the similar level as in canola and soybean oils (10). The
presence of chlorophyll in ax oil usually indicates immaturity of axseed.
TABLE 1. Properties of Flaxseed Oils (69).
Linola
TM

Parameter Flaxseed Oil Crude RBD

Relative density (20

C/water at 4

C) 0.9250.935 0.921 0.920

Refractive Index (n
D
20

C) 1.4751.475 1.4657 1.4665

Melting Point (

C) 20 to 24
Flash Point, min. (

C, open cup) 120135

Viscosity (cp) 46.8 46.4
Iodine Value 182203 142 144
Unsaponiable Matter (%) 0.11.7 1.2 0.6
Saponication 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 <0.02
Triglyceride (%) 9498 9398 9698
RBDRened, bleached, and deodorized.
284 FLAX OIL AND HIGH LINOLENIC OILS
Fatty acid composition of regular ax 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, axseed and ax 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
ax oil (Linola), soybean, and sunower 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 axseed 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 Linola
TM
Canola Soybean Sunower
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 58

5
-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
Cool temperatures during the 1025 days after owering are the main cause for
higher amounts of linolenic acid in ax oils (14). For the same reason, axseed
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-
ower, canola, and soybean (7, 13, 14). Similarly, a wide variation in fatty acid
composition in Australian axseed samples was observed: 1325% of 18:1 and
4664% of 18:3 (6).
Analysis performed on varieties of axseeds collected from different ax 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 ax, 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 sunower 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 ax oils,
with a contribution of about 80% to the total amount. This makes ax oil compar-
able with soybean oil. Among unique antioxidants detected in ax 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 efcient
antioxidant than any tocopherols isomer (15). A low content of tocopherols in ax-
seed did not make them more susceptible to oxidation; experiments showed that
milled axseed 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 ax oils at a level lower than those in many
vegetable oils, 2.3 mg/g in axseed 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 the
main component followed by campesterol and
5
-avenasterol. Brassicasterol was
found in trace amounts in ax 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 ax 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 ax 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
matairesinol (MAT), are the main compounds among axseed 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
axseed, in far higher amounts than other oils, oilseeds, and cereals.
Lignans from axseed 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 ax oil makes it nutritionally more valuable
than any other oil. When high levels of ALA and linoleic acid are considered in
the whole equation, axseed oil serves as the best oil in terms of its nutritional
and health value.
The Food and Drug Administration (FDA) regulations allow inclusion of ax-
seed in food products, but the amount allowed is limited to 12% (34).
TABLE 3. Composition of Triacyglycerols
in Flaxseed Oil (17).
Triacyglycerols
1
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
1
Abbreviations of fatty acid: Ppalmitic; Lnlinolenic;
Llinoleic; Ooleic; Sstearic.
FLAX 287
OR
OR
OH
OCH
3
H
3
CO
HO
OH
OH
OH
HO
OH
OCH
3
H
3
CO
HO
O
O
OH
HO
O
O
Bacterial
Fermentation
Bacterial
Fermentation
Bacterial
Fermentation
Secoisolariciresinol
Diglycoside (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
2.5. Low Linolenic Flaxseed Oil
Low linolenic acid varieties with yellow-seed coat ax trademarked Linola were
developed by the Commonwealth Scientic 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 axseed dark brown color. The generic com-
mon name Solin has been assigned by Flax Council of Canada for all low linolenic
ax 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 ax and linseed varieties are currently
cultivated (35, 36). The climate in northern Europe is highly suitable for production
of Linola, where sunower 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 modied, 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-
ower and soybean oils (Table 2). Linola has been found to be more resistant to
oxidation than regular ax oil, and its stability is comparable with soybean, canola,
and sunower oils (Przybylski, unpublished data).
Rening of crude Linola oil by conventional steps, namely, degumming, alkali
rening, bleaching, and deodorization, produces colorless and odorless oil, which
has good oxidative stability (9). In addition, properties of crude and rened,
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 benecial 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 brous 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
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 axseed, and it decomposes glucosides to many products, including
hydrocyanic acid, one of the most toxic substances. Newly developed varieties of
ax 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 difcult and
often double pressing is required to efciently remove oil from the seeds. Proces-
sing steps for ax 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 ne particles when seeds are cracked or aked and will maximize
removal of oil from them. Moisturized seeds are passed through sets of corrugated
and smooth rolls to be cracked and aked, respectively. From the next processing
step, production of ax oil is differentiated from that for Solin/Linola oil (7). The
ax oil for human consumption is cold-pressed, and further purication 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 35

C and pressing
is 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 axseed to produce cold-pressed ax oil.
290 FLAX OIL AND HIGH LINOLENIC OILS
Oil from expeller is ltered, 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, ax oil is considered as a health food oil.
When ax oil is processed for industrial use, standard processing steps are
applied as described in Figure 6. Flaxseeds are tampered and then aked, passing
through a set of smooth rolls. Flaked seeds are sent to a cooker where they are
heated to a temperature of 80100

C to inactivate enzymes and help release the

oil during pressing. At this stage, formation of toxic substances is prevented. The
cooked seeds are transferred to the expeller, and expelled oil through ltration 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 axseed to produce rened, bleached, and deodorized ax oil.
FLAX 291
a solvent. From the extractor, cake is moved to the desolvatizer where the solvent
is removed at 100

C. Meal is then cooled and used as an animal feed ingredient.

Combined oils are puried by the standard rening process, typical to all vegetable
oils (7). Degumming is applied to remove phospholipids, rening 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 axseed oil is similar to that described for ax 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, avoring, 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, avor-
ing dishes, and source of functional nutrients; foliage is distilled to produce an
essential oil for avoring.
Wilson et al. (39) isolated the toxin, perilla ketone, which causes pulmonary
edema (uid 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
efcient 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 unprotable 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
3.2. Perilla Seed and Oil
The seed of perilla contains 3151% of oil, which is similar in composition to
axseed 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). Specic gravity of this oil is higher than
ax oil because of a higher contribution of PUFA. Other physical parameters of
this oil reect the composition of its fatty acids.
TABLE 4. Composition and Properties of Perilla, Camelina, and Chia Oils.
Parameter Perilla
a
Camelina
b
Chia
c
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 46
g-Tocopherol 461 420
d-Tocopherol 7 10
Total 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 52

5
-Avenasterol 11
Total Sterols (mg/kg) 3604
Physicochemical Properties
Refractive Index (n
D
20

C) 1.4761 1.4698 1.4753

Specic Gravity (at 15.5

C/15.5

C) 0.937 0.925 0.936

Iodine Value 192208 127155 190199
Saponication Value (mgKOH/g) 188197 180190 180192
Unsaponiable 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
The amount of tocopherols in perilla oil is higher compared with ax 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
ltration are the main processing steps. To improve the avor of perilla oil used
in food applications, roasting of seeds is practiced. This will provide oil with a
distinctive roasted, nutty avor 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 170

C provided
the best avor and stability for the oil. Nonenzymatic browning components are
mainly responsible for avor and antioxidant activity (52). When perilla oil is pro-
duced for the industrial applications, additional processing such as rening, 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
ax, linseed dodder, and Gold-of-Pleasure, originated in the Mediterranean area
and Central Asia (61). Seeds are small (0.7 mm1.5 mm), pale yellow-brown,
oblong, rough, and with a ridged surface. Camelina is listed as being adapted to
the ax-growing region on the Prairies, in Europe, and other countries (59, 62).
It is primarily a minor weed in ax, 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 ax 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 ax, 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 ber. 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 modied 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 ax, although higher sulfur content has been observed for camelina oil
(63). Camelina meal is comparable with soybean meal, containing 4547% crude
protein and 1011% ber (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 inuenced 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 signicant, they are rela-
tively small in absolute terms and have no signicant 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 ax oil but
more than sunower 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 identied 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 ax oil (Tables
4 and 2). The total content of tocopherols in camelina oil is higher than canola, ax,
soybean, and sunower.
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 avor is acceptable in India and other
Asian countries, but in Europe and North America, it is difcult to nd acceptability
among consumers, mainly because of a different expectation from vegetable oils.
However, commercial camelina oil needs to be rened and deodorized to produce
an odorless and colorless product as expected by consumers (76). Crude camelina
oil, rened following typical steps as described for ax 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 65

C with crude and rened canola and linseed and camelina

oils (76). Conjugated dienes, peroxide, and p-anisidine values were determined.
The results indicated that the storage stability of camelina oil was similar to ax
oil, but it was less stable than canola oil. Crude camelina oil showed a higher
oxidative stability than the rened product (76). During storage, rened camelina
oil had a 30% higher peroxide level when compared with crude camelina oil (76).
Comparison with sh oil, which is rich in omega-3 fatty acids, proved that camelina
oil is much more resistant to oxidative deterioration than sh 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 ax 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 rst 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 avor (76).
Rened 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-avors 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-avor formation (76).
Taking into consideration that camelina oil production will be less expensive and
the oil is more stable than sh 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 ber similar to axseed 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 ber, may possibly contain lignans,
and is similar to ax (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; the
content of this fatty acid is higher than ax 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).
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