Trans fat

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Types of fats in food

 Unsaturated fat
o Monounsaturated fat
o Polyunsaturated fat
o Trans fat
o Cis fat
o Omega fatty acids:
 ω−3
 ω−6
 ω−9
 Saturated fat
o Interesterified fat

See also
 Fatty acid
 Essential fatty acid

Trans fat is the common name for unsaturated fat with trans-isomer fatty acid(s). Trans fats
may be monounsaturated or polyunsaturated but never saturated.

Unsaturated fat is a fat molecule containing one or more double bonds between the carbon
atoms. Since the carbons are double-bonded to each other, there are fewer bonds connected to
hydrogen, so there are fewer hydrogen atoms, hence "unsaturated". Cis and trans are terms
that refer to the arrangement of chains of carbon atoms across the double bond. In the cis
arrangement, the chains are on the same side of the double bond, resulting in a kink. In the
trans arrangement, the chains are on opposite sides of the double bond, and the chain is
straight.

The process of hydrogenation adds hydrogen atoms to cis-unsaturated fats, eliminating

double bonds and making them into partially or completely saturated fats. However, partial
hydrogenation converts a part of cis-isomers into trans-unsaturated fats instead of
hydrogenating them completely. Trans fats also occur naturally to a limited extent: Vaccenyl
and conjugated linoleyl (CLA) containing trans fats occur naturally in trace amounts in meat
and dairy products from ruminants, although the latter also constitutes a cis fat.

Unlike other dietary fats, trans fats are not essential, and they do not promote good health.[1]
The consumption of trans fats increases the risk of coronary heart disease[2] by raising levels
of "bad" LDL cholesterol and lowering levels of "good" HDL cholesterol.[3] Health
authorities worldwide recommend that consumption of trans fat be reduced to trace amounts.
Trans fats from partially hydrogenated oils are more harmful than naturally occurring oils.[4]
Contents
[hide]

 1 History
 2 Chemistry
 3 Presence in food
 4 Nutritional guidelines
 5 Health risks
o 5.1 Coronary heart disease
o 5.2 Other effects
 6 Public response and regulation
o 6.1 International
o 6.2 Australia
o 6.3 Brazil
o 6.4 Canada
o 6.5 Denmark
o 6.6 Switzerland
o 6.7 European Union
o 6.8 United Kingdom
o 6.9 United States
 6.9.1 Local regulation in the United States
 7 Food industry response
o 7.1 Manufacturer response
o 7.2 Major users' response
 8 See also
 9 References
 10 Further reading
 11 External links

[edit] History
The examples and perspective in this article may not represent a worldwide view
of the subject. Please improve this article and discuss the issue on the talk page.
Cover of original Crisco cookbook, 1912

Nobel laureate Paul Sabatier worked in the late 1890s to develop the chemistry of
hydrogenation, which enabled the margarine, oil hydrogenation, and synthetic methanol
industries.[5] Whereas Sabatier considered hydrogenation of only vapors, the German chemist
Wilhelm Normann showed in 1901 that liquid oils could be hydrogenated, and patented the
process in 1902.[6][7][8] During the years 1905 – 1910, Normann built a fat-hardening facility in
the Herford company. At the same time, the invention was extended to a large-scale plant in
Warrington, England, at Joseph Crosfield & Sons, Limited. It took only two years until the
hardened fat could be successfully produced in the plant in Warrington, commencing
production in the autumn of 1909. The initial year's production totalled nearly 3,000 tonnes.[9]
In 1909, Procter & Gamble acquired the US rights to the Normann patent;[10] in 1911, they
began marketing the first hydrogenated shortening, Crisco (composed largely of partially
hydrogenated cottonseed oil). Further success came from the marketing technique of giving
away free cookbooks in which every recipe called for Crisco.

Normann's hydrogenation process made it possible to stabilize affordable whale oil or fish oil
for human consumption, a practice kept secret to avoid consumer distaste.[11]

Prior to 1910, dietary fats consisted primarily of butterfat, beef tallow, and lard. During
Napoleon’s reign in France in the early 1800s, a type of margarine was invented to feed the
troops using tallow and buttermilk; it did not gain acceptance in the U.S. In the early 1900s,
soybeans began to be imported into the U.S. as a source of protein; soybean oil was a by-
product. What to do with that oil became an issue. At the same time, there was not enough
butterfat available for consumers. The method of hydrogenating fat and turning a liquid fat
into a solid one had been discovered, and now the ingredients (soybeans) and the “need”
(shortage of butter) were there. Later, the means for storage, the refrigerator, was a factor in
trans fat development. The fat industry found that hydrogenated fats provided some special
features to margarines, which, unlike butter, allowed margarine to be taken out of the
refrigerator and immediately spread on a slice of bread. By some minor changes to the
chemical composition of hydrogenated fat, such hydrogenated fat was found to provide
superior baking properties compared to lard. Margarine made from hydrogenated soybean oil
began to replace butterfat. Hydrogenated fat such as Crisco and Spry, sold in England, began
to replace lard in the baking of bread, pies, cookies, and cakes in 1920.[12]

In the 1940s, Dr Catherine Kousmine researched the effects of trans fats on cancer.

Production of hydrogenated fats increased steadily until the 1960s, as processed vegetable
fats replaced animal fats in the US and other western countries. At first, the argument was a
financial one due to lower costs; however, advocates also said that the unsaturated trans fats
of margarine are healthier than the saturated fats of butter.[13]

There were suggestions in the scientific literature as early as 1988 that trans fats could be a
cause of the large increase in coronary artery disease.[13][14] In 1994, it was estimated that trans
fats caused 20,000 deaths annually in the US from heart disease.[15]

In January 2007, faced with the prospect of an outright ban on the sale of their product,
Crisco was reformulated to meet the United States Food and Drug Administration definition
of "zero grams trans fats per serving" (that is less than one gram per tablespoon, or up to 7%
by weight)[16][17][18][19] by boosting the saturation and then cutting the resulting solid with oils.
A University of Guelph research group has found a way to mix oils (such as olive, soybean
and Canola--an alias for rapeseed oil), water, monoglycerides and fatty acids to form a
"cooking fat" that acts the same way as trans and saturated fats.[20][21]

[edit] Chemistry
In chemical terms, trans fat refers to a lipid molecule that contains one or more double bonds
in trans geometric configuration. A double bond may exhibit one of two possible
configurations: trans or cis. In trans configuration, the carbon chain extends from opposite
sides of the double bond, rendering a straighter molecule, whereas, in cis configuration, the
carbon chain extends from the same side of the double bond, rendering a bent molecule.

Trans (Elaidic acid) Cis (Oleic acid) Saturated (Stearic acid)

Stearic acid is a saturated fatty
Elaidic acid is the principal acid found in animal fats and is
Oleic acid is a cis unsaturated
trans unsaturated fatty acid the intended product in full
fatty acid that comprises 55–
often found in partially hydrogenation. Stearic acid is
80% of olive oil.[23]
hydrogenated vegetable oils.[22] neither cis nor trans because it
has no double bonds.
 This fatty acid contains no
These fatty acids are geometric isomers (structurally identical double bond and is not
except for the arrangement of the double bond). isomeric with the previous
two.

Fatty acids are characterized as either saturated or unsaturated based on the presence of
double bonds in its structure. If the molecule contains no double bonds, it is said to be
saturated; otherwise, it is unsaturated to some degree.[24][25]

Only unsaturated fats can be trans fats. Saturated fatty acids are never trans fats because they
have no double bonds, and, therefore, cannot display a trans- configuration. Moreover, lipids
containing a triple bond (but no double bonds) cannot be trans fats because a triple bond can
assume only one configuration.

Carbon atoms are tetravalent, forming four covalent bonds with other atoms, whereas
hydrogen atoms bond with only one other atom. In saturated fatty acids, each carbon atom is
connected to its two neighbour carbon atoms as well as two hydrogen atoms. In unsaturated
fatty acids, the carbon atoms that are missing a hydrogen atom are joined by double bonds
rather than single bonds so that each carbon atom participates in four bonds.

Wilhelm Normann patented the hydrogenation of liquid oils in 1902

Hydrogenation of an unsaturated fatty acid refers to the addition of hydrogen atoms to the
acid, causing double bonds to become single ones, as carbon atoms acquire new hydrogen
partners (to maintain four bonds per carbon atom). Full hydrogenation results in a molecule
containing the maximum amount of hydrogen (in other words, the conversion of an
unsaturated fatty acid into a saturated one). Partial hydrogenation results in the addition of
hydrogen atoms at some of the empty positions, with a corresponding reduction in the
number of double bonds. Typical commercial hydrogenation is partial in order to obtain a
malleable mixture of fats that is solid at room temperature, but melts upon baking (or
consumption).

In most naturally occurring unsaturated fatty acids, the hydrogen atoms are on the same side
of the double bonds of the carbon chain (cis configuration — from the Latin, meaning "on the
same side"). However, partial hydrogenation reconfigures most of the double bonds that do
not become chemically saturated, twisting them so that the hydrogen atoms end up on
different sides of the chain. This type of configuration is called trans, from the Latin,
meaning "across."[26] The trans conformation is the lower energy form, and is favored when
catalytically equilibriated as a side reaction in hydrogenation.

The same molecule, containing the same number of atoms, with a double bond in the same
location, can be either a trans or a cis fatty acid depending on the conformation of the double
bond. For example, oleic acid and elaidic acid are both unsaturated fatty acids with the
chemical formula C9H17C9H17O2.[27] They both have a double bond located midway along the
carbon chain. It is the conformation of this bond that sets them apart. The conformation has
implications for the physical-chemical properties of the molecule. The trans configuration is
straighter, while the cis configuration is noticeably kinked as can be seen from the three-
dimensional representation shown above.

The trans fatty acid elaidic acid has different chemical and physical properties, owing to the
slightly different bond configuration. It can be noted that it has a much higher melting point,
45 °C, than oleic acid, 13.4 °C, due to the ability of the trans molecules to pack more tightly,
forming a solid that is more difficult to break apart.[27] This notably means that it is a solid at
human body temperatures.

In food production, the goal is not to simply change the configuration of double bonds while
maintaining the same ratios of hydrogen to carbon. Instead, the goal is to decrease the
number of double bonds and increase the amount of hydrogen in the fatty acid. This changes
the consistency of the fatty acid and makes it less prone to rancidity (in which free radicals
attack double bonds). Production of trans fatty acids is therefore a side effect of partial
hydrogenation.

Catalytic partial hydrogenation necessarily produces trans-fats, because of the reaction

mechanism. In the first reaction step, one hydrogen is added, with the other, coordinatively
unsaturated, carbon being attached to the catalyst. The second step is the addition of
hydrogen to the remaining carbon, producing a saturated fatty acid. The first step is
reversible, such that the hydrogen is readsorbed on the catalyst and the double bond is re-
formed. The intermediate with only one hydrogen added contains no double bond and can
freely rotate. Thus, the double bond can re-form as either cis or trans, of which trans is
favored, regardless the starting material. Complete hydrogenation also hydrogenates any
produced trans fats to give saturated fats.

Researchers at the United States Department of Agriculture have investigated whether

hydrogenation can be achieved without the side effect of trans fat production. They varied the
pressure under which the chemical reaction was conducted — applying 1400 kPa (200 psi) of
pressure to soybean oil in a 2-liter vessel while heating it to between 140 °C and 170 °C. The
standard 140 kPa (20 psi) process of hydrogenation produces a product of about 40% trans
fatty acid by weight, compared to about 17% using the high-pressure method. Blended with
unhydrogenated liquid soybean oil, the high-pressure-processed oil produced margarine
containing 5 to 6% trans fat. Based on current U.S. labeling requirements (see below), the
manufacturer could claim the product was free of trans fat.[28] The level of trans fat may also
be altered by modification of the temperature and the length of time during hydrogenation.

Trans fat levels may be measured. Measurement techniques include chromatography (by
silver ion chromatography on thin layer chromatography plates, or small high-performance
liquid chromatography columns of silica gel with bonded phenylsulfonic acid groups whose
hydrogen atoms have been exchanged for silver ions). The role of silver lies in its ability to
form complexes with unsaturated compounds. Gas chromatography and mid-infrared
spectroscopy are other methods in use.

[edit] Presence in food

Salers Cow. Milk and meat from cows and other ruminants contains naturally occurring trans
fats in small quantities

A type of trans fat occurs naturally in the milk and body fat of ruminants (such as cattle and
sheep) at a level of 2–5% of total fat.[29] Natural trans fats, which include conjugated linoleic
acid (CLA) and vaccenic acid, originate in the rumen of these animals. CLA has two double
bonds, one in the cis configuration and one in trans, which makes it simultaneously a cis- and
a trans-fatty acid.

Animal-based fats were once the only trans fats consumed, but by far the largest amount of
trans fat consumed today is created by the processed food industry as a side effect of partially
hydrogenating unsaturated plant fats (generally vegetable oils). These partially-hydrogenated
fats have displaced natural solid fats and liquid oils in many areas, the most notable ones
being in the fast food, snack food, fried food, and baked goods industries.

Partially hydrogenated oils have been used in food for many reasons. Partial hydrogenation
increases product shelf life and decreases refrigeration requirements. Many baked foods
require semi-solid fats to suspend solids at room temperature; partially hydrogenated oils
have the right consistency to replace animal fats such as butter and lard at lower cost. They
are also an inexpensive alternative to other semi-solid oils such as palm oil.

Partially-hydrogenated plant oils, and also non-hydrogenated plant shortenings made from
naturally saturated palm oil, coconut oil and palm kernel oil, can be used to replace animal
fats in foodstuffs for adherents to the dietary rules of Kashrut (kosher) and Halal, and for all
vegetarians and vegans.

Foods containing artificial trans fats formed by partially hydrogenating plant fats may contain
up to 45% trans fat compared to their total fat.[29] Baking shortenings, in general, contain 30%
trans fats compared to their total fats, whereas animal fats from ruminants such as butter
contain up to 4%. Margarines not reformulated to reduce trans fats may contain up to 15%
trans fat by weight.[30]

It has been established that trans fats in human milk fluctuate with maternal consumption of
trans fat, and that the amount of trans fats in the bloodstream of breastfed infants fluctuates
with the amounts found in their milk. Reported percentages of trans fats (compared to total
fats) in human milk range from 1% in Spain, 2% in France, 4% in Germany, and 7% in
Canada.[31]

Trans fats are used in shortenings for deep-frying in restaurants, as they can be used for
longer than most conventional oils before becoming rancid. In the early twenty-first century,
non-hydrogenated vegetable oils that have lifespans exceeding that of the frying shortenings
became available.[32] As fast-food chains routinely use different fats in different locations,
trans fat levels in fast food can have large variations. For example, an analysis of samples of
McDonald's french fries collected in 2004 and 2005 found that fries served in New York City
contained twice as much trans fat as in Hungary, and 28 times as much as in Denmark (where
trans fats are restricted). At KFC, the pattern was reversed with Hungary's product containing
twice the trans fat of the New York product. Even within the US there was variation, with
fries in New York containing 30% more trans fat than those from Atlanta.[33]

[edit] Nutritional guidelines

The examples and perspective in this article deal primarily with the United States
and do not represent a worldwide view of the subject. Please improve this article
and discuss the issue on the talk page.

The National Academy of Sciences (NAS) advises the United States and Canadian
governments on nutritional science for use in Public policy and product labeling programs.
Their 2002 Dietary Reference Intakes for Energy, Carbohydrate, Fiber, Fat, Fatty Acids,
Cholesterol, Protein, and Amino Acids[34] contains their findings and recommendations
regarding consumption of trans fat (summary).

Their recommendations are based on two key facts. First, "trans fatty acids are not essential
and provide no known benefit to human health",[1] whether of animal or plant origin.[35]
Second, while both saturated and trans fats increase levels of LDL cholesterol (so-called bad
cholesterol), trans fats also lower levels of HDL cholesterol (good cholesterol);[2] thus
increasing the risk of coronary heart disease. The NAS is concerned "that dietary trans fatty
acids are more deleterious with respect to coronary heart disease than saturated fatty acids".[2]
This analysis is supported by a 2006 New England Journal of Medicine (NEJM) scientific
review that states "from a nutritional standpoint, the consumption of trans fatty acids results
in considerable potential harm but no apparent benefit."[4]

Because of these facts and concerns, the NAS has concluded there is no safe level of trans fat
consumption. There is no adequate level, recommended daily amount or tolerable upper limit
for trans fats. This is because any incremental increase in trans fat intake increases the risk of
coronary heart disease.[2]

Despite this concern, the NAS dietary recommendations have not recommended the
elimination of trans fat from the diet. This is because trans fat is naturally present in many
animal foods in trace quantities, and therefore its removal from ordinary diets might
introduce undesirable side effects and nutritional imbalances if proper nutritional planning is
not undertaken. The NAS has, therefore, "recommended that trans fatty acid consumption be
as low as possible while consuming a nutritionally adequate diet".[36] Like the NAS, the
World Health Organization has tried to balance public health goals with a practical level of
trans fat consumption, recommending in 2003 that trans fats be limited to less than 1% of
overall energy intake.[29]

The US National Dairy Council has asserted that the trans fats present in animal foods are of
a different type than those in partially hydrogenated oils, and do not appear to exhibit the
same negative effects.[37] While a recent scientific review agrees with the conclusion (stating
that "the sum of the current evidence suggests that the Public health implications of
consuming trans fats from ruminant products are relatively limited"), it cautions that this may
be due to the low consumption of trans fats from animal sources compared to artificial ones.[4]

[edit] Health risks

Partially hydrogenated vegetable oils have been an increasingly significant part of the human
diet for about 100 years (in particular, since the latter half of the 20th century and where more
processed foods are consumed), and some deleterious effects of trans fat consumption are
scientifically accepted, forming the basis of the health guidelines discussed above.

The exact biochemical methods by which trans fats produce specific health problems are a
topic of continuing research. The most prevalent theory is that the human lipase enzyme is
specific to the cis configuration, rendering the human body unable to metabolize or remove
trans fat. A lipase is a water-soluble enzyme that catalyzes the hydrolysis of ester bonds in
water-insoluble, lipid substrates. Lipases, thus, comprise a subclass of the esterases. Lipases
perform essential roles in the digestion, transport, and processing of dietary lipids (e.g.
triglycerides, fats, oils) in most – if not all – living organisms. The human lipase enzyme is
ineffective with the trans configuration, so trans fat remains in the blood stream for a much
longer period of time and is more prone to arterial deposition and subsequent plaque
formation. While the mechanisms through which trans fats contribute to coronary heart
disease are fairly well understood, the mechanism for trans fat's effect on diabetes is still
under investigation.

[edit] Coronary heart disease

The primary health risk identified for trans fat consumption is an elevated risk of coronary
heart disease (CHD).[38] A comprehensive review of studies of trans fats was published in
2006 in the New England Journal of Medicine reports a strong and reliable connection
between trans fat consumption and CHD, concluding that "On a per-calorie basis, trans fats
appear to increase the risk of CHD more than any other macronutrient, conferring a
substantially increased risk at low levels of consumption (1 to 3% of total energy intake)".[4]
This study estimates that between 30,000 and 100,000 cardiac deaths per year in the United
States are attributable to the consumption of trans fats.[39]

The major evidence for the effect of trans fat on CHD comes from the Nurses' Health
Study — a cohort study that has been following 120,000 female nurses since its inception in
1976. In this study, Hu and colleagues analyzed data from 900 coronary events from the
study's population during 14 years of followup. He determined that a nurse's CHD risk
roughly doubled (relative risk of 1.94, CI: 1.43 to 2.61) for each 2% increase in trans fat
calories consumed (instead of carbohydrate calories). By contrast, it takes more than a 15%
increase in saturated fat calories (instead of carbohydrate calories) to produce a similar
increase in risk. "The replacement of saturated fat or trans unsaturated fat by cis
(unhydrogenated) unsaturated fats was associated with larger reductions in risk than an
isocaloric replacement by carbohydrates."[40] Hu also reports on the benefits of reducing trans
fat consumption. Replacing 2% of food energy from trans fat with non-trans unsaturated fats
more than halves the risk of CHD (53%). By comparison, replacing a larger 5% of food
energy from saturated fat with non-trans unsaturated fats reduces the risk of CHD by 43%.[40]

Another study considered deaths due to CHD, with consumption of trans fats being linked to
an increase in mortality, and consumption of polyunsaturated fats being linked to a decrease
in mortality.[38][41]

There are two accepted tests that measure an individual's risk for coronary heart disease, both
blood tests. The first considers ratios of two types of cholesterol, the other the amount of a
cell-signalling cytokine called C-reactive protein. The ratio test is more accepted, while the
cytokine test may be more powerful but is still being studied.[38] The effect of trans fat
consumption has been documented on each as follows:

 Cholesterol ratio: This ratio compares the levels of LDL (so-called "bad" cholesterol)
to HDL (so-called "good" cholesterol). Trans fat behaves like saturated fat by raising
the level of LDL, but, unlike saturated fat, it has the additional effect of decreasing
levels of HDL. The net increase in LDL/HDL ratio with trans fat is approximately
double that due to saturated fat.[42] (Higher ratios are worse.) One randomized
crossover study published in 2003 comparing the effect of eating a meal on blood
lipids of (relatively) cis and trans fat rich meals showed that cholesteryl ester transfer
(CET) was 28% higher after the trans meal than after the cis meal and that lipoprotein
concentrations were enriched in apolipoprotein(a) after the trans meals.[43]
 C-reactive protein (CRP): A study of over 700 nurses showed that those in the highest
quartile of trans fat consumption had blood levels of CRP that were 73% higher than
those in the lowest quartile.[44]

[edit] Other effects

There are suggestions that the negative consequences of trans fat consumption go beyond the
cardiovascular risk. In general, there is much less scientific consensus asserting that eating
trans fat specifically increases the risk of other chronic health problems:

 Alzheimer's Disease: A study published in Archives of Neurology in February 2003

suggested that the intake of both trans fats and saturated fats promote the development
of Alzheimer disease.[45]
 Cancer: There is no scientific consensus that consumption of trans fats significantly
increases cancer risks across the board.[38] The American Cancer Society states that a
relationship between trans fats and cancer "has not been determined."[46] However,
one recent study has found connections between trans fat and prostate cancer.[47] An
increased intake of trans-fatty acids may raise the risk of breast cancer by 75%,
suggest the results from the French part of the European Prospective Investigation
into Cancer and Nutrition.[48][49]
 Diabetes: There is a growing concern that the risk of type 2 diabetes increases with
trans fat consumption.[38] However, consensus has not been reached.[4] For example,
one study found that risk is higher for those in the highest quartile of trans fat
consumption.[50] Another study has found no diabetes risk once other factors such as
total fat intake and BMI were accounted for.[51]
 Obesity: Research indicates that trans fat may increase weight gain and abdominal fat,
despite a similar caloric intake.[52] 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.[53][54] Although obesity is frequently linked to trans fat in
the popular media,[55] this is generally in the context of eating too many calories; there
is no scientific consensus connecting trans fat and obesity.
 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.[56]
 Infertility in women: 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...".[57]