Trans Fatty Acids

TRANS FATTY ACIDS:
WHAT THEY ARE AND HOW

DO YOU AVOID THEM?
Animal fats are rich in saturated fatty
acids, whereas plant oils (for example,
corn, soybean, canola, olive, and palm
oil) are rich in unsaturated fatty acids.
Fats are added to processed foods to
provide a desirable firmness along with
a moist texture and pleasant taste.

To supply the demand for dietary fats
of the appropriate consistency, the cis
double bonds of vegetable oils are
partially hydrogenated.
The greater the extent of hydrogenation,
the higher the MP of the triglyceride.

The extent of hydrogenation is carefully
controlled, usually by employing a Ni
catalyst and a calculated amount of H2 as
a limiting reagent.

Under these conditions, the H2 is used up
before all double bonds are reduced, so
that only partial hydrogenation and the
desired overall consistency is achieved.
For example, by controlling the degree of
hydrogenation, an oil with a melting
point below room temperature can be
converted to a semisolid or even a solid
product.

The mechanism of catalytic hydrogena-
tion of alkenes follow several steps. A
key step in the mechanism involves
interaction of the carbon-carbon double
bond of the alkene with the metal
catalyst to form a metal-carbon bond.
Because the interaction of a carbon-
carbon double bond with the Ni catalyst
is reversible, many of the double bonds
remaining in the oil may be isomerized
from the less stable cis configuration.
Thus equilibration between cis and trans
configurations may occur when H2 is the
limiting reagent.

For ex., elaidic acid is the trans C
18
fatty
acid analog of oleic acid, a common C
18

cis fatty acid.

C
17
H
33
COOH oleic acid(one double bond)

O

HO
1 9 18
Elaidic acid
(a trans C
18
fatty acid)
The oils used for frying in fast-food
restaurants are usually partially
hydrogenated plant oils and, therefore,
contain substantial amount of trans
fatty acids that are transferred to the
foods cooked in them.

Other major sources of trans fatty acids
in the diet include stick margarine,
certain commercial bakery products,
creme-filled cookies, potato and corn
chips, frozen breakfast foods, and cake
mixes.
Recent studies have shown that consu-
ming a significant amount of trans fatty
acids can lead to serious health prob-
lems related to serum cholesterol levels.

Low over-all serum cholesterol and a
decreased ratio of low-density lipopro-
tein (LDL) cholesterol to high-density
lipoprotein (HDL) cholesterol are asso-
ciated with good cardio-vascular health.
High serum cholesterol levels and an
elevated ratio (LDL)-cholesterol to
(HDL) cholesterol are linked to a high
incidence of cardiovascular disease,
especially atherosclerosis.

Research has indicated that consuming
a diet high in either saturated fatty
acids or trans fatty acids substantially
increases the risk of cardiovascular
disease.
The FDA recently announced that
processed foods must list the amount of
trans fatty acids they contain, so that
consumers can make better choices
about the food they eat.

A diet low in satd and trans fatty acids is
recommended, along with consumption
of more fish, whole grains, fruits and
vegetables, and especially daily exercise,
which is tremendously beneficial
regardless of diet.
Monounsaturated and polyunsaturated
fatty acids have not produced similar
health risks in most studies, although too
much fat or any kind of fat in the diet can
lead to obesity, a major health problem
that is associated with several diseases,
one of which is diabetes.

Some polyunsaturated (cis) fatty acids,
such as those found in certain types of
fish, have even been shown to have
beneficial effects in some studies.

These are the so-called omega-3 fatty
acids. Here, the last carbon of the last
double bond of the hydrocarbon chain
ends three carbons in from the methyl
terminal end of the chain.

The last C of the chain is called the
omega (the last letter of the Greek
alphabet) carbonhence the designa-
tion of omega-3. The two most
commonly found in health food supple-
ments are eicosapentaenoic acid and
docosahexaenoic acid.
Eicosapentaenoic acid, C
20
H
30
O
2,
is an
impt fatty acid in the marine food chain
and serves as a precursor in humans of
several members of the prostacyclin and
thromboxane families.

Note how the name of this fatty acid is
derived. Eicosa- is the prefix, indicating
20 C in the chain; pentaene indicates 5
C=C double bonds; and oic acid shows
the carbonyl functional group.

Docosahexaenoic acid, C
22
H
32
O
2
, is found
in fish oils and many phospholipids.

It is a major structural component of
excitable membranes in the retina and
brain and synthesized in the liver from
linoleic acid.

O

20 17 14 11 8 5 1

OH
EICOSAPENTAENOIC ACID

22 19 16 13 10 7

4 1
COOH

DOCOSAHEXAENOIC ACID

Trans Fatty Acids

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TRANS FATTY ACIDS:

WHAT THEY ARE AND HOW

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