Biochemistry of Fatty Acids

WHAT IS FATTY ACID?

Fatty Acids, common name for a group of organic acids that includes the saturated
(hydrogenated), straight-chain acids, with a single carboxyl (COOH) group, that are produced
by the hydrolysis of fats. The group also includes all other saturated straight-chain acids and
acids with a branched chain or cyclic structure. Methanoic (formic) acid, HCOOH, and
ethanoic (acetic) acid, CH3COOH, are the simplest fatty acids1. Both have a sour taste, irritate
the skin, and have a sharp smell. Of more complicated structure are butanoic, hexanoic and
octanoic acids, all of which have unpleasant odours. Stearic, palmitic, oleic, and naphthenic
acids are greasy materials with little odour. A growing source of fatty acids is tall oil, a by-
product of the pinewood used to make paper pulp.

Fatty acids are useful in preparing biodegradable detergents, thickeners for paints, and
lubricants. Stearic acid is used to combine rubber with other substances, such as pigments,
or materials that control the flexibility of rubber products; it is also used in the
polymerization of phenylethene (styrene) and butadiene in making artificial rubber. New
uses for fatty acids include ore flotation and the manufacture of disinfectants, varnish driers,
and heat stabilizers for vinyl resins. Fatty acids are also used in plastic products, such as
coatings for wood and metal, and in car parts ranging from air-cleaner housings to
upholstery.

FATTY ACIDS IN OILS AND FATS2

1
http://uk.encarta.msn.com/encnet/refpages/RefArticle.aspx?refid=761576432
2
http://uk.encarta.msn.com/media_121621355/Fatty_Acids_in_Oils_and_Fats.html
 Biochemistry of Fatty Acids

TYPES
Fatty acids can be saturated3 and unsaturated, depending on double bonds. In addition, they
also differ in length. Only unsaturated fatty acid will be discussed in-depth here.

UNSATURATED FATTY ACID

In unsaturated fatty acids, there are two ways the pieces of the hydrocarbon tail can be
arranged around a C=C double bond. In cis bonds, the two pieces of the carbon chain on
either side of the double bond are either both “up” or both “down,” such that both are on
the same side of the molecule. In trans bonds, the two pieces of the molecule are on
opposite sides of the double bond, that is, one “up” and one “down” across from each other.
Naturally-occurring unsaturated vegetable oils have almost all cis bonds, but using oil for
frying causes some of the cis bonds to convert to trans bonds. If oil is used only once like
when fry an egg, only a few of the bonds do this so it’s not too bad. However, if oil is
constantly reused, like in fast food French fry machines, more and more of the cis bonds are
changed to trans until significant numbers of fatty acids with trans bonds build up. The
reason this is of concern is that fatty acids with trans bonds are carcinogenic, or cancer-
causing4. The levels of trans fatty acids in highly-processed, lipid-containing products such as
margarine are quite high.

3
Saturated fatty acids have a chain of carbon atoms joined by single bonds, allowing for rotation
about the bonds.
4
Trans-fatty acids do not have the beneficial effects of cis-fatty acids such as glycemic control, energy
balance etc. It is therefore recommended (by Danish Nutrition Council) that intakes of trans-fatty
acids should not rise above the current average of about 2 per cent of energy intake.
 Biochemistry of Fatty Acids

MORE ABOUT TRANS FAT

Most trans fats are created artificially by a process called hydrogenation. It involves heating
regular vegetable oil and forcing hydrogen atoms onto the polyunsaturated fatty acid
molecules. This process turns the oil into a solid substance and improves the shelf life of the
fat.

Fully hydrogenating a vegetable oil will make it firm and not create trans fats. However, the
firmness of the fat makes it difficult to use in cooking. Partially hydrogenating an oil makes
for a softer product and is still widely used in baking and processing foods. Examples include
stick margarine and partially hydrogenated frying oils. Trans fats are commonly found in
donuts, snack cakes, cookies and processed foods.

Artificially created trans fats are the unhealthiest of fats, even worse than saturated fat 5.
Eating too many trans fats has been linked to increasing your risk of cardiovascular disease.

Not all trans fats are created in the lab. Small amounts of natural trans fats occur in milk and
beef. Conjugated linoleic acid is a well-known natural trans fat. The natural trans fats do not
appear to be as unhealthy as the artificial trans fats.

FOODS CONTRIBUTE TO TRANS FATTY ACID INTAKE6

Milk and cheese 18.8 Natural

Butter 5.9 Natural
Eggs 0.9 Natural
Meat and meat product 10.3 Natural
Oil and fats 35.5 Mainly resulting from hydrogenation
Biscuits and cakes 16.5 Mainly resulting from hydrogenation
Savoury pies, etc 3.5 Mainly resulting from hydrogenation
Chips, French fries 4.5 Mainly resulting from hydrogenation
Others 4.1 Mainly resulting from hydrogenation
TOTAL 100

TRANS FAT AND HEART

Recent studies have suggested that trans fatty acids (TFA) have a deleterious effect on
cholesterol levels and the risk of heart disease.

Ingestion of TFA is implicated in coronary heart disease (CHD) are based on changes induced
in plasma cholesterol levels. Within the range of intakes of 3-11 % of dietary energy there is
a dose-response relationship; an increase of 1 % of the total energy intake (at the expense of
oleic acid) increased low density lipoproteins (LDL) by 0.04 mmol/l and decreased high
density lipoproteins (HDL) by 0.013 mmol/l. This amounts to a 1 % reduction in HDL and a 1
% increase in LDL. TFA increase LDL to the same extent saturated fatty acid (SFA), but reduce
the beneficial HDL. In short, trans fatty acids turn out to increase total cholesterol levels and
LDL cholesterol levels, and to reduce HDL cholesterol levels.

5
Saturated fats are almost always found in foods that also contain cholesterol, so saturated fats offer
a "one-two" punch to heart health. On the other hand, trans fatty acids not only increase LDL
cholesterol, they also decrease HDL cholesterol
6
Information statement (2007) from Institute of Food Science and Technology Trust Fund, UK
 Biochemistry of Fatty Acids

OTHER NEGATIVE EFFECT OF TRANS FATTY ACID

1. Essential fatty acids (EFA)7 are transformed in the body by a series of reactions into long
chain polyunsaturated fatty acids essential for development of the nervous system and
eyesight. TFA compete with EFA for the enzyme systems involved in these reactions.
High intakes of TFA have been shown to influence the metabolism of EFA in
experimental animals when the EFA intake was low. Frank deficiency in EFA is only found
in abnormal circumstances in human adults. However, new-born infants, and especially
if premature, show borderline deficiency in EFA, and their TFA intake from the mothers
milk is related to her TFA intake.
2. There is conflicting evidence concerning the possible role of TFA in breast cancer. As
part of the EURAMIC (European Community Multicentre Study on Antioxidants,
Myocardial Infarction, and Breast Cancer) study, Kohlmeier et al (1997)8 investigated the
relationship between TFA and postmenopausal breast cancer in European populations
differing greatly in their dietary fat intakes. A case control study using adipose tissue
stores of TFA as a biomarker of exposure was conducted. Subjects included 698
postmenopausal incident cases of primary breast cancer and controls randomly drawn
from local population and patient registries, ages 50-74. Concentrations of individual
TFA in gluteal fat biopsies were measured in these women. The adipose concentration of
TFA showed a positive association with breast cancer, not attributable to differences in
age, body mass index, exogenous hormone use, or socio-economic status. The authors
conclude that these findings suggest an association of adipose stores of TFA with
postmenopausal breast cancer in European women, but point out that they require
confirmation in other populations, with concomitant consideration of the potential roles
of dietary saturated and monounsaturated fats.
3. Obesity: Research indicates that trans fat may increase weight gain and abdominal fat,
despite a similar caloric intake. A 6-year experiment revealed that monkeys fed a trans-
fat diet gained 7.2% of their body weight, as compared to 1.8% for monkeys on a mono-
unsaturated fat diet. Although obesity is frequently linked to trans fat in the popular
media, this is generally in the context of eating too many calories; there is no scientific
consensus connecting trans fat and obesity.
4. Liver Dysfunction: Trans fats are metabolized differently by the liver than other fats and
interfere with delta 6 desaturase. Delta 6 desaturase is an enzyme involved in converting
essential fatty acids to arachidonic acid and prostaglandins, both of which are important
to the functioning of cells.
5. Infertility: One 2007 study found, "Each 2% increase in the intake of energy from trans
unsaturated fats, as opposed to that from carbohydrates, was associated with a 73%
greater risk of ovulatory infertility…”

TRANS FATTY ACID IN PALM AND PALM KERNEL OIL PRODUCT

Malaysia produced around 50% of world’s palm and palm kernel oil product last year.
According to Journal of Oil Palm Research Vol. 14 No. 1, June 2002; trans-fatty acids were
generally absent in crude palm and palm kernel oils. However, they were present at 0.01%-
0.06% in refined palm kernel products and 0%-0.61% in refined palm products, all well below
the 1.0% level stipulated by some importers such as United Kingdom and United States.
These trans-fatty acids were formed from their natural cis-isomers as a result of the high
temperature used during deodorization. In cooking oil, the trans-fatty acid contents of palm-
based products were 0.25%-0.67%, again well below 1%. However, in the non-palm-based

7
Some of the example are Omega-6 and Omega-3
8
Published in journal from Institute of Nutrition, Friedrich Schiller University Jena, Dornburger Street
25-29, 07743, Jena, Germany (2003) and American Journal of Clinical Nutrition, Vol 42, 1201-1205,
The American Society for Clinical Nutrition, Inc.
 Biochemistry of Fatty Acids

cooking oils, the contents ranged from 0.43%-3.83%. The higher contents in the non-palm-
based oils were expected as they had high contents of unsaturated fatty acids, which are
more prone to isomerisation at elevated temperatures.

In the nutshell, this provides us with further evidence that palm and palm kernel oil products
are excellent9 hard-stocks for trans-free formulation of texturized fatty products such as
margarines, shortenings, confectionery fats, and vanaspati (a hydrogenated vegetable oil
commonly used in South Asian cooking instead of butter). These products can
advantageously replace hydrogenated fats which contain not only trans-fatty acids, but also
possibly a host of other unnatural and polymerized fatty acids formed during hydrogenation
to reduce their unsaturation.

9
Center of Science of Public Interest, USA, made up a controversy and false statement that
"Consumers and food processors should realize, though, that palm oil still promotes heart disease and
that producing palm oil has a devastating impact on rainforest and endangered wildlife". CSPI
executive director Michael F. Jacobson also said "We applaud food manufacturers for moving away
from trans-fat-laden partially hydrogenated oils, and happily, many companies are switching to such
heart-healthy oils as soybean, corn, or canola"