Introduction

We sometimes talk about fat as if it were a malevolent substance bent on our dietary destruction. In
reality, fats are elegant little molecules, each one made of three long hydrocarbon tails attached to a
little coathanger-like molecule called glycerol. Like the other large biological molecules, they play
essential roles in the biology of humans and other organisms. (Also, many recent dietary studies see
sugar as causing a lot more health problems than fat!)

Fats are just one type of lipid, a category of molecules united by their inability to mix well with water.
Lipids tend to be hydrophobic, nonpolar, and made up mostly of hydrocarbon chains, though there are
some variations on this, which we'll explore below. The different varieties of lipids have different
structures, and correspondingly diverse roles in organisms. For instance, lipids store energy, provide
insulation, make up cell membranes, form water-repellent layers on leaves, and provide building blocks
for hormones like testosterone.

Here, well look in greater detail at some of the most important types of lipids, including fats and oils,
waxes, phospholipids, and steroids.

Fats and oils

A fat molecule consists of two kinds of parts: a glycerol backbone and three fatty acid tails. Glycerol is a
small organic molecule with three hydroxyl (OH) groups, while a fatty acid consists of a long hydrocarbon
chain attached to a carboxyl group. A typical fatty acid contains 1218 carbons, though some may have
as few as 4 or as many as 36.

To make a fat molecule, the hydroxyl groups on the glycerol backbone react with the carboxyl groups of
fatty acids in a dehydration synthesis reaction. This yields a fat molecule with three fatty acid tails bound
to the glycerol backbone via ester linkages (linkages containing an oxygen atom next to a carbonyl, or
C=O, group). Triglycerides may contain three identical fatty acid tails, or three different fatty acid tails
(with different lengths or patterns of double bonds).

Fat molecules are also called triacylglycerols, or, in bloodwork done by your doctor,
triglycerides. In the human body, triglycerides are primarily stored in specialized fat cells, called
adipocytes, which make up a tissue known as adipose tissue1^11start superscript, 1, end
superscript. While many fatty acids are found in fat molecules, some are also free in the body,
and they are considered a type of lipid in their own right.

Saturated and unsaturated fatty acids

As shown in the example above, the three fatty acid tails of a triglyceride need not be identical to
each other. Fatty acid chains may differ in length, as well as in their degree of unsaturation.

If there are only single bonds between neighboring carbons in the hydrocarbon chain, a
fatty acid is said to be saturated. (The thing that fatty acids are saturated with is
hydrogen; in a saturated fat, as many hydrogen atoms as possible are attached to the
carbon skeleton.)
 When the hydrocarbon chain h a double bond, the fatty acid is said to be unsaturated, as
it now has fewer hydrogens. If there is just one double bond in a fatty acid, its
monounsaturated, while if there are multiple double bonds, its polyunsaturated.

The double bonds in unsaturated fatty acids, like other types of double bonds, can exist in either
a cis or a trans configuration. In the cis configuration, the two hydrogens associated with the
bond are on the same side, while in a trans configuration, they are on opposite sides (see below).
A cis double bond generates a kink or bend in the fatty acid, a feature that has important
consequences for the behavior of fats.

Saturated fatty acids tails are straight, so fat molecules with fully saturated tails can pack tightly against
one another. This tight packing results in fats that are solid at room temperature (have a relatively high
melting point). For instance, most of the fat in butter is saturated fat2^22start superscript, 2, end
superscript.

In contrast, cis-unsaturated fatty acid tails are bent due to the cis double bond. This makes it hard for fat
molecules with one or more cis-unsaturated fatty acid tails to pack tightly. So, fats with unsaturated tails
tend to be liquid at room temperature (have a relatively low melting point) they are what we
commonly call oils. For instance, olive oil is mostly made up of unsaturated fats2^22start superscript, 2,
end superscript.

Trans fats
At this point, you may be noticing that Ive left something out: I didnt say anything about unsaturated
fats with trans double bonds in their fatty acid tails, or trans fats. Trans fats are rare in nature, but are
readily produced in an industrial procedure called partial hydrogenation.

In this process, hydrogen gas is passed through oils (made mostly of cis-unsaturated fats), converting
some but not all of the double bonds to single bonds. The goal of partial hydrogenation is to give the
oils some of the desirable properties of saturated fats, such as solidity at room temperature, but an
unintended consequence is that some of the cis double bonds change configuration and become trans
double bonds3^33start superscript, 3, end superscript. Trans-unsaturated fatty acids can pack more
tightly and are more likely to be solid at room temperature. Some types of shortening, for example,
contain a high fraction of trans fats3^33start superscript, 3, end superscript.

Partial hydrogenation and trans fats might seem like a good way to get a butter-like substance at oil-like
prices. Unfortunately, trans fats have turned out to have very negative effects on human health. Because
of a strong link between trans fats and coronary heart disease, the U.S. Food and Drug Administration
(FDA) recently issued a ban on trans fats in foods, with a three-year deadline for companies to remove
trans fats from their products4^44start superscript, 4, end superscript.

Omega fatty acids

Another class of fatty acids that deserves mention includes the omega-3 and omega-6 fatty acids. There
are different types of omega-3 and omega-6 fatty acids, but all of them are made from two basic
precursor forms: alpha-linoleic acid (ALA) for omega-3s and linoleic acid (LA) for omega-6s. The human
body needs these molecules (and their derivatives), but can't synthesize either ALA or LA itself5^55start
superscript, 5, end superscript. Accordingly, ALA and LA are classified as essential fatty acids and must
be obtained from a persons diet. Some fish, such as salmon, and some seeds, such as chia and flax, are
good sources of omega-3 fatty acids.

Omega-3 and omega-6 fatty acids have at least two cis-unsaturated bonds, which gives them a curved
shape. ALA, shown below, is quite bent but isnt the most extreme example DHA, an omega-3 fatty acid
made from ALA by the formation of additional double bonds, has six cis-unsaturated bonds and is curled
up almost in a circle!

Omega-3 and omega-6 fatty acids play a number of different roles in the body. They are precursors
(starting material) for the synthesis of a number of important signaling molecules, including ones that
regulate inflammation and mood. Omega-3 fatty acids in particular may reduce the risk of sudden death
from heart attacks, decrease triglycerides in the blood, lower blood pressure, and prevent the formation
of blood clots.

Role of fats
Fats have received a lot of bad publicity, and its true that eating large amounts of fried foods and other
fatty foods can lead to weight gain and cause health problems. However, fats are essential to the body
and have a number of important functions.

For instance, many vitamins are fat-soluble, meaning that they must be associated with fat molecules in
order to be effectively absorbed by the body. Fats also provide an efficient way to store energy over long
time periods, since they contain over twice as much energy per gram as carbohydrates, and they
additionally provide insulation for the body. Like all the other large biological molecules, fats in the right
amounts are necessary to keep your body (and the bodies of other organisms) functioning correctly.

Waxes
Waxes are another biologically important category of lipids. Wax covers the feathers of some aquatic
birds and the leaf surfaces of some plants, where its hydrophobic (water-repelling) properties prevent
water from sticking to, or soaking into, the surface. This is why water beads up on the leaves of many
plants, and why birds dont get soaked through when it rains.

Structurally speaking, waxes typically contain long fatty acid chains connected to alcohols by ester
linkages, although waxes produced by plants often have plain hydrocarbons mixed in as well6^66start
superscript, 6, end superscript.

Phospholipids
What keeps the watery goo (cytoplasm) inside of your cells from spilling out? Cells are surrounded by a
structure called the plasma membrane, which serves as a barrier between the inside of the cell and its
surroundings.

Specialized lipids called phospholipids are major components of the plasma membrane. Like fats, they
are typically composed of fatty acid chains attached to a backbone of glycerol. Instead having three fatty
acid tails, however, phospholipids generally have just two, and the third carbon of the glycerol backbone
is occupied by a modified phosphate group. Different phospholipids have different modifiers on the
phosphate group, with choline (a nitrogen-containing compound) and serine (an amino acid) being
common examples. Different modifiers give phospholipids different properties and roles in a cell.

A phospholipid is an amphipathic molecule, meaning it has a hydrophobic part and a hydrophilic part.
The fatty acid chains are hydrophobic and do not interact with water, whereas the phosphate-containing
group is hydrophilic (because of its charge) and interacts readily with water. In a membrane,
phospholipids are arranged into a structure called a bilayer, with their phosphate heads facing the water
and their tails pointing towards the inside (above). This organization prevents the hydrophobic tails from
coming into contact with the water, making it a low-energy, stable arrangement.

If a drop of phospholipids is placed in water, it may spontaneously form a sphere-shaped structure

known as a micelle, in which the hydrophilic phosphate heads face the outside and the fatty acids face
the interior of this structure. Formation of micelle is an energetically favored because it sequesters the
hydrophobic fatty acid tails, allowing the hydrophilic phosphate head group to instead interact with the
surrounding water7,8^{7,8}7,8start superscript, 7, comma, 8, end superscript.

[More details]

A micelle is an ordered structure, but its formation actually increases the entropy (disorder, or number of
microstates) of the system, as compared to having the phospholipids distributed among the water
molecules. That's because the fatty acid tails of the phospholipids limit the number of microstates
available to the water molecules they touch, in that the water molecules must form a sort of cavity
surrounding each phospholipid tails. Sequestering the fatty acid tails on the inside of a micelle frees up
the water molecules, allowing the system to take on a greater number of microstates (that is, increasing
its entropy)7,8^{7,8}7,8start superscript, 7, comma, 8, end superscript.

Steroids
Steroids are another class of lipid molecules, identifiable by their structure of four fused rings. Although
they do not resemble the other lipids structurally, steroids are included in lipid category because they
are also hydrophobic and insoluble in water. All steroids have four linked carbon rings and several of
them, like cholesterol, also have a short tail. Many steroids also have an OH functional group attached
at a particular site, as shown for cholesterol below; such steroids are also classified as alcohols, and are
thus called sterols.
Cholesterol, the most common steroid, is mainly synthesized in the liver and is the precursor to
many steroid hormones. These include the sex hormones testosterone and estradiol, which are
secreted by the gonads (testes and ovaries). Cholesterol also serves as the starting material for
other important molecules in the body, including vitamin D and bile acids, which aid in the
digestion and absorption of fats from dietary sources. Its also a key component of cell
membranes, altering their fluidity and dynamics.
Of course, cholesterol is also found in the bloodstream, and blood levels of cholesterol are what
we often hear about at the doctors office or in news reports. Cholesterol in the blood can have
both protective effects (in its high-density, or HDL, form) and negative effects (in its low-
density, or LDL, form) on cardiovascular health.