Lipids: Fats, Oils, Waxes, etc.

All Lipids are hydrophobic: thats the one property they have in common. This group of molecules
includes fats and oils, waxes, phospholipids, steroids (like cholesterol), and some other related
compounds.

Fats and oils are made from two kinds of molecules: glycerol (a type of
alcohol with a hydroxyl group on each of its three carbons) and three fatty
acids joined by dehydration synthesis. Since there are three fatty acids
attached, these are known as triglycerides. Bread and pastries from a
bread factory often contain mono- and diglycerides as dough
conditioners. Can you figure out what these molecules would look like?
The main distinction between fats and oils is whether theyre solid or liquid
at room temperature, and this, as well soon see, is based on differences in
the structures of the fatty acids they contain.

Structure of Fatty Acids

The tail of a fatty acid is a long

hydrocarbon chain, making it
hydrophobic. The head of the
molecule is a carboxyl group which is
hydrophilic. Fatty acids are the main
component of soap, where their tails are
soluble in oily dirt and their heads are
soluble in water to emulsify and wash
away the oily dirt. However, when the
head end is attached to glycerol to form
a fat, that whole molecule is
hydrophobic.

The terms saturated, mono-

unsaturated, and poly-
unsaturated refer to the number
of hydrogens attached to the
hydrocarbon tails of the fatty
acids as compared to the number
of double bonds between carbon
atoms in the tail. Fats, which are
mostly from animal sources, have
all single bonds between the
carbons in their fatty acid tails,
thus all the carbons are also
bonded to the maximum number
of hydrogens possible. Since the
fatty acids in these triglycerides
contain the maximum possible amouunt of hydrogens, these would be called saturated fats. The
hydrocarbon chains in these fatty acids are, thus, fairly straight and can pack closely together, making
these fats solid at room temperature. Oils, mostly from plant sources, have some double bonds
between some of the carbons in the hydrocarbon tail, causing bends or kinks in the shape of the
molecules. Because some of the carbons share double bonds, theyre not bonded to as many
hydrogens as they could if they werent double bonded to each other. Therefore these oils are called
unsaturated fats. Because of the kinks in the hydrocarbon tails, unsaturated fats cant pack as closely
together, making them liquid at room temperature. Many people have heard that the unsaturated fats
are healthier than the saturated ones. Hydrogenated vegetable oil (as in shortening and commercial
peanut butters where a solid consistency is sought) started out as good unsaturated oil. However,
this commercial product has had all the double bonds artificially broken and hydrogens artificially
added (in a chemistry lab-type setting) to turn it into saturated fat that bears no resemblance to the
original oil from which it came (so it will be solid at room temperature).

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 you fry an egg, only a few of the bonds do this so its 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-causing. The levels of trans
fatty acids in highly-processed, lipid-containing products such as margarine are quite high, and I have
heard that the government is considering requiring that the amounts of trans fatty acids in such
products be listed on the labels.

We need fats in our bodies and in our diet. Animals in general use fat for energy storage because fat
stores 9 KCal/g of energy. Plants, which dont move around, can afford to store food for energy in a
less compact but more easily accessible form, so they use starch (a carbohydrate, NOT A LIPID) for
energy storage. Carbohydrates and proteins store only 4 KCal/g of energy, so fat stores over twice as
much energy/gram as carbohydrates or proteins. By the way, this is also related to the idea behind
some of the high-carbohydrate weight loss diets. The human body burns carbohydrates and fats for
fuel in a given proportion to each other. The theory behind these diets is that if they supply
carbohydrates but not fats, then it is hoped that the fat needed to balance with the sugar will be taken
from the dieters body stores. Fat is also is used in our bodies to a) cushion vital organs like the
kidneys and b) serve as insulation, especially just beneath the skin.
Phospholipids

Phospholipids are made

from glycerol, two fatty
acids, and (in place of the
third fatty acid) a
phosphate group with
some other molecule
attached to its other end.
The hydrocarbon tails of
the fatty acids are still
hydrophobic, but the
phosphate group end of the
molecule is hydrophilic
because of the oxygens
with all of their pairs of
unshared electrons. This
means that phospholipids
are soluble in both water
and oil.

An emulsifying agent is a
substance which is soluble
in both oil and water, thus
enabling the two to mix. A
famous phospholipid is
lecithin which is found in
egg yolk and soybeans.
Egg yolk is mostly water
but has a lot of lipids,
especially cholesterol,
which are needed by the
developing chick. Lecithin
is used to emulsify the
lipids and hold them in the
water as an emulsion.
Lecithin is the basis of the
classic emulsion known as
mayonnaise.

Our cell membranes are made mostly of

phospholipids arranged in a double layer with the
tails from both layers inside (facing toward each
other) and the heads facing out (toward the
watery environment) on both surfaces.
Steroids

The general structure of cholesterol consists of

two six-membered rings side-by-side and sharing
one side in common, a third six-membered ring off
the top corner of the right ring, and a five-
membered ring attached to the right side of that.
The central core of this molecule, consisting of
four fused rings, is shared by all steroids,
including estrogen (estradiol), progesterone,
corticosteroids such as cortisol (cortisone),
aldosterone, testosterone, and Vitamin D. In the
various types of steroids, various other
groups/molecules are attached around the edges. Know how to draw the four rings that make up the
central structure.

Cholesterol is not a bad guy! Our bodies make about 2 g of cholesterol per day, and that makes up
about 85% of blood cholesterol, while only about 15% comes from dietary sources. Cholesterol is the
precursor to our sex hormones and Vitamin D. Vitamin D is formed by the action of UV light in
sunlight on cholesterol molecules that have risen to near the surface of the skin. At least one source
I read suggested that people not shower immediately after being in the sun, but wait at least hour
for the new Vitamin D to be absorbed deeper into the skin. Our cell membranes contain a lot of
cholesterol (in between the phospholipids) to help keep them fluid even when our cells are exposed
to cooler temperatures.

Many people have hear the claims that egg yolk contains too much cholesterol, thus should not be
eaten. An interesting study was done at Purdue University a number of years ago to test this. Men in
one group each ate an egg a day, while men in another group were not allowed to eat eggs. Each of
these groups was further subdivided such that half the men got lots of exercise while the other half
were couch potatoes. The results of this experiment showed no significant difference in blood
cholesterol levels between egg-eaters and non-egg-eaters while there was a very significant difference
between the men who got exercise and those who didnt.

Lipoproteins are clusters of proteins and lipids all tangled up together. These act as a means of
carrying lipids, including cholesterol, around in our blood. There are two main categories of
lipoproteins distinguished by how compact/dense they are. LDL or low density lipoprotein is the
bad guy, being associated with deposition of cholesterol on the walls of someones arteries. HDL
or high density lipoprotein is the good guy, being associated with carrying cholesterol out of the
blood system, and is more dense/more compact than LDL.

What are lipids??

Lipids are molecules that contain hydrocarbons and make up the building blocks of the structure and
function of living cells. Examples of lipids include fats, oils, waxes, certain vitamins, hormones and
most of the non-protein membrane of cells.

What are lipids soluble in?

Lipids are not soluble in water. They are non-polar and are thus soluble in nonpolar environments like
in choloroform but not soluble in polar environments like water.
What do lipids consist of?

Lipids have mainly hydrocarbons in their composition and are highly reduced forms of carbon. When
metabolized, lipids are oxidized to release large amounts of energy and thus are useful to living
organisms.

Where do lipids come from?

Lipids are molecules that can be extracted from plants and animals using nonpolar solvents such as
ether, chloroform and acetone. Fats (and the fatty acids from which they are made) belong to this
group as do other steroids, phospholipids forming cell membrane components etc.

Hydrolyzable/Non-hydrolyzable lipids

Lipids that contain a functional group ester are hydrolysable in water. These include neutral fats,
waxes, phospholipids, and glycolipids.
Nonhydrolyzable lipids lack such functional groups and include steroids and fat-soluble vitamins (e.g.
A, D, E, and K). Fats and oils are composed of triacylglycerols or triglycerides. These are composed
of glycerol (1,2,3-trihydroxypropane) and 3 fatty acids to form a triester. Triglycerides are found in
blood tests. Complete hydrolysis of triacylglycerols yields three fatty acids and a glycerol molecule.

Fatty acids

Fatty acids are long chain carboxylic acids (typically 16 or more carbon atoms) which may or may not
contain carbon-carbon double bonds. The number of carbon atoms are almost always an even number
and are usually unbranched. Oleic acid is the most abundant fatty acid in nature.

The membrane that surrounds a cell is made up of proteins and lipids. Depending on the membranes
location and role in the body, lipids can make up anywhere from 20 to 80 percent of the membrane,
with the remainder being proteins. Cholesterol, which is not found in plant cells, is a type of lipid that
helps stiffen the membrane. Image Credit: National Institute of General Medical Sciences
Waxes/fats and oils

These are esters with long-chain carboxylic acids and long-alcohols. Fat is the name given to a class
of triglycerides that appear as solid or semisolid at room temperature, fats are mainly present in
animals. Oils are triglycerides that appear as a liquid at room temperature, oils are mainly present in
plants and sometimes in fish.

Mono/poly unsaturated and saturated

Those fatty acids with no carbon-carbon double bonds are called saturated. Those that have two or
more double bonds are called polyunsaturated. Oleic acid is monounsaturated.

Saturated fats are typically solids and are derived from animals, while unsaturated fats are liquids and
usually extracted from plants.

Unsaturated fats assume a particular geometry that prevents the molecules from packing as efficiently
as they do in saturated molecules. Thus the boiling points of unsaturated fats is lower.

Synthesis and function of lipids in the body

Lipids are utilized or synthesized from the dietary fats. There are in addition numerous biosynthetic
pathways to both break down and synthesize lipids in the body.

There are, however, some essential lipids that need to be obtained from the diet. The main biological
functions of lipids include storing energy as lipids may be broken down to yield large amounts of
energy. Lipids also form the structural components of cell membranes and form various messengers
and signalling molecules within the body.
Reviewed by April Cashin-Garbutt, BA Hons (Cantab)

What is a lipid profile?

The lipid profile is a group of tests that are often ordered together to determine risk of coronary heart
disease. They are tests that have been shown to be good indicators of whether someone is likely to
have a heart attack or stroke caused by blockage of blood vessels or hardening of the arteries
(atherosclerois). The lipid profile typically includes:

Total cholesterol
High density lipoprotein cholesterol (HDL-C) often called good cholesterol
Low density lipoprotein cholesterol (LDL-C) often called bad cholesterol
Triglycerides

An extended profile may also include:

Very low density lipoprotein cholesterol (VLDL-C)

Non-HDL-C

Sometimes the report will include additional calculated values such as the Cholesterol/HDL ratio or a
risk score based on lipid profile results, age, sex, and other risk factors. Talk to your doctor about
what these other reported values may mean for you.

How is the sample collected for testing?

A blood sample is obtained by inserting a needle into a vein in the arm. Sometimes a drop of blood is
collected by puncturing the skin on a fingertip. This fingerstick sample is typically used when a lipid
profile is being measured on a portable testing device, for example, at a health fair. You need to fast
for 9-12 hours before having your blood drawn; only water is permitted.

How is a lipid profile used?

The lipid profile is used to help determine your risk of heart disease and to help guide you and your
health care provider in deciding what treatment may be best for you if you have borderline or high
risk. The results of the lipid profile are considered along with other known risk factors of heart disease
to develop a plan of treatment and follow-up. Depending on your results and other risk factors,
treatment options may involve life-style changes such as diet and exercise or lipid-lowering
medications such as statins.

When is it ordered?
It is recommended that healthy adults with no other risk factors for heart disease be tested with a
fasting lipid profile once every five years. You may be screened using only a cholesterol test and not a
full lipid profile. However, if the cholesterol test result is high, you may have follow-up testing with a
lipid profile.

If you have other risk factors or have had a high cholesterol level in the past, you should be tested
more regularly and you should have a full lipid profile.

For children and adolescents at low risk, lipid testing is usually not ordered routinely. However,
screening with a lipid profile is recommended for children and youths who are at an increased risk of
developing heart disease as adults. Some of the risk factors are similar to those in adults and include a
family history of heart disease or health problems such as diabetes, high blood pressure
(hypertension), or being overweight. High-risk children should have their first lipid profile between 2
and 10 years old, according to the American Academy of Pediatrics. Children younger than 2 years
old are too young to be tested.

A lipid profile may also be ordered at regular intervals to evaluate the success of lipid-lowering
lifestyle changes such as diet and exercise or to determine the effectiveness of drug therapy such as
statins.

What are risk factors (in addition to high LDL-C) for coronary heart disease?

Risk factors include:

Cigarette smoking
Age (if you are a male 45 years or older or a female 55 years or older)
Low HDL cholesterol (less than 40 mg/dL (1.04 mmol/L))
Hypertension (Blood Pressure of 140/90 or higher or taking high blood pressure medications)
Family history of premature heart disease (heart disease in a first degree male relative under
age 55 or a first degree female relative under age 65)
Diabetes

Note: High HDL (60 mg/dL or above) is considered a "negative risk factor" and its presence allows
the removal of one risk factor from the total.

What do the results mean?

In general, your doctor will take into consideration the results of each component of a lipid profile
plus other risk factorsto determine whether treatment is necessary and, if so, which treatment will best
help you to lower your risk of heart disease. The National Cholesterol Education Program offers the
following guidelines for adults for classifying results of the tests:
LDL Cholesterol
Optimal: Less than 100 mg/dL (2.59 mmol/L)
Near/above optimal: 100-129 mg/dL (2.59-3.34 mmol/L)
Borderline high: 130-159 mg/dL (3.37-4.12 mmol/L)
High: 160-189 mg/dL (4.15-4.90 mmol/L)
Very high: Greater than 190 mg/dL (4.90 mmol/L)

Total Cholesterol
Desirable: Less than 200 mg/dL (5.18 mmol/L)
Borderline high: 200-239 mg/dL (5.18 to 6.18 mmol/L)
High: 240 mg/dL (6.22 mmol/L) or higher

HDL Cholesterol
Low level, increased risk: Less than 40 mg/dL (1.0 mmol/L) for men and less than 50 mg/dL (1.3
mmol/L) for women
Average level, average risk: 40-50 mg/dL (1.0-1.3 mmol/L) for men and between 50-59 mg/dl (1.3-
1.5 mmol/L) for women
High level, less than average risk: 60 mg/dL (1.55 mmol/L) or higher for both men and women

Fasting Triglycerides
Desirable: Less than 150 mg/dL (1.70 mmol/L)
Borderline high: 150-199 mg/dL(1.7-2.2 mmol/L)
High: 200-499 mg/dL (2.3-5.6 mmol/L)
Very high: Greater than 500 mg/dL (5.6 mmol/L)

The risk categories for children and adolescents are different than adults. Talk to your child's
pediatrician about your childs results.

How is treatment determined?

Treatment is determined by your overall risk of coronary heart disease. Based on the results of lipid
tests and other major risk factors, your target LDL cholesterolis identified. If your LDL-C is above the
target value, you will be treated.

Your target LDL-C value is:

Less than 100 mg/dL (2.59 mmol/L) if you have heart disease or diabetes.
Less than 130 mg/dL (3.37 mmol/L) if you have 2 or more risk factors.
Less than 160 mg/dL (4.14 mmol/L) if you have 0 or 1 risk factor.

The first step in treating high LDL-C is targeted at changes in lifestyle - specifically, adopting diets
low in cholesterol, saturated fat and trans unsaturated fats (trans fats) and participating in moderate
exercise. You may be referred to a dietician for advice in making dietary changes.

If low-fat diets and exercise are not adequate to lower LDL cholesterol to the target value, drug
therapy would be the next step. There are several classes of drugs that are effective in lowering LDL.
You may be prescribed one of these. Your LDL will be checked at regular intervals to assure that the
drug is working. If the drug does not result in reaching your target LDL-cholesterol, your doctor may
increase the amount of drug or possibly add a second drug.

Common Questions
1. I had a screening test for cholesterol. It was less than 200 mg/dL (5.18 mmol/L). Do I need a
lipid profile?
If your total cholesterol is below 200 (5.18 mmol/L) and you have no family history of heart disease
or other risk factors, a full lipid profile is probably not necessary. However, an HDL-cholesterol
measurement would be advisable to assure that you do not have a low HDL. Many screening
programs now offer both cholesterol and HDL.

2. My lipid profile results came back with high triglycerides and no results for LDL-cholesterol.
Why?
In most screening lipid profiles, LDL-cholesterol is calculated from the other lipid measurements.
However, the calculation is not valid if triglycerides are over 400 mg/dL (4.52 mmol/L). To determine
LDL-cholesterol when triglycerides are over 400 mg/dL (4.52 mmol/L) requires special testing
techniques such as a direct LDL-C test or a lipid ultracentrifugation test (sometimes called a beta-
quantification test).

3. What is VLDL?
Very Low Density Lipoprotein (VLDL) is one of three major lipoprotein particles. The other two are
high density lipoprotein (HDL) and low density lipoprotein (LDL). Each one of these particles
contains a mixture of cholesterol, protein, and triglyceride, but in varying amounts unique to each
type of particle. LDL contains the highest amount of cholesterol. HDL contains the highest amount of
protein. VLDL contains the highest amount of triglyceride. Since VLDL contains most of the
circulating triglyceride and since the composition of the different particles is relatively constant, it is
possible to estimate the amount of VLDL cholesterol by dividing the triglyceride value (in mg/dL) by
5. At present, there is no simple, direct way of measuring VLDL-cholesterol, so the estimate
calculated from triglyceride is used in most settings. This calculation is not valid when the triglyceride
is greater than 400 mg/dl (see question 2 above). Increased levels of VLDL-cholesterol have been
found to be associated with increased risk of heart disease and stroke.

4. What is non-HDL-cholesterol?
Non-HDL-cholesterol (non-HDL-C) is calculated by subtracting your HDL-C result from your total
cholesterol result. It represents the atherogenic cholesterol the cholesterol that can build up in the
arteries, form plaques, and cause narrowing of the vessels and blockages. Unlike calculation of
VLDL-C (see question 3 above), this calculation is not affected by high levels of triglycerides. Your
non-HDL-C result may be used to assess your risk for CVD, especially if you have high triglycerides
since high non-HDL-C is associated with increased risk. As recommended by the National
Cholesterol Education Program, Adult Treatment Plan III, if you have high triglycerides (greater than
200 mg/dL), the non-HDL-C result can be used as a secondary target of treatments such as lifestyle
changes and drugs that aim to lower lipid levels.

Is there anything else I should know?

There is increasing interest in measuring triglycerides in people who have not fasted. The reason is
that a non-fasting sample may be more representative of the usual circulating level of triglyceride
since most of the day blood lipid levels reflect post-meal (post-prandial) levels rather than fasting
levels. However, it is not yet certain how to interpret non-fasting levels for evaluating risk, so at
present there is no change in the current recommendations for fasting prior to tests for lipid levels.