Lipids

• The lipids are a heterogeneous

group of compounds, including
fats, oils, steroids, waxes, and
related compounds, which are
related more by their physical
than by their chemical properties.
• Lipids are a class of compounds
distinguished by their insolubility
in water and solubility in nonpolar
solvents.
 Lipids are important in biological systems because they form the cell
membrane, a mechanical barrier that divides a cell from the external
environment.

• Lipids also provide energy for life • Lipids can be divided in two
and several essential vitamins are major classes, nonsaponifiable
lipids. lipids and saponifiable lipids.
 Each of these categories can be further broken down.

• Nonpolar lipids, such as triglycerides, are used for energy

storage and fuel.
• Polar lipids, which can form a barrier with an external water
environment, are used in membranes.
• Polar lipids include glycerophospholipids and sphingolipids.
• Fatty acids are important components of all of these lipids.
 BIOLOGICAL ROLES OF LIPID
• Lipids have the common property of being relatively insoluble
in water and soluble in nonpolar solvents such as ether and
chloroform.
• They are important dietary constituents not only because of
their high energy value but also because of the fat-soluble
vitamins and the essential fatty acids contained in the fat of
natural foods.
 BIOLOGICAL ROLES OF LIPID
• Fat is stored in adipose tissue,
where it also serves as a
thermal insulator in the
subcutaneous tissues and
around certain organs.
• Nonpolar lipids act as electrical
insulators, allowing rapid
propagation of depolarization
waves along myelinated
nerves.
 BIOLOGICAL ROLES OF LIPID

• Combinations of lipid and • Knowledge of lipid biochemistry

protein (lipoproteins) are is necessary in understanding
important cellular constituents, many important biomedical
occurring both in the cell areas, e.g., obesity, diabetes
membrane and in the mellitus, atherosclerosis, and the
mitochondria, and serving also role of various polyunsaturated
as the means of transporting fatty acids in nutrition and
lipids in the blood. health.
 CLASSIFICATION OF LIPIDS
1. Simple lipids: Esters of fatty acids with various alcohols.

(a) Fats: Esters of fatty acids with glycerol. Oils are fats in
the liquid state.
(b) Waxes: Esters of fatty acids with higher molecular
weight monohydric alcohols.
 CLASSIFICATION OF LIPIDS
2. Complex lipids: Esters of fatty acids containing groups in addition to an
alcohol and a fatty acid.
(a) Phospholipids: Lipids containing, in addition to fatty acids and an alcohol, a phosphoric acid
residue. They frequently have nitrogen containing bases and other substituents, eg, in
glycerophospholipids the alcohol is glycerol and in sphingophospholipids the alcohol is
sphingosine.
(b) Glycolipids (glycosphingolipids): Lipids containing a fatty acid, sphingosine, and
carbohydrate.
(c) Other complex lipids: Lipids such as sulfolipids and aminolipids. Lipoproteins may also be
placed in this category.
 CLASSIFICATION OF LIPIDS
3. Precursor and derived lipids:
These include fatty acids, glycerol, steroids, other alcohols,
fatty aldehydes, and ketone bodies, hydrocarbons, lipid-
soluble vitamins, and hormones.

Because they are uncharged, acylglycerols (glycerides),

cholesterol, and cholesteryl esters are termed neutral
lipids.
• Lipids are composed of C, H, O
– long hydrocarbon chains (H-C)
• Do not form polymers
– big molecules made of smaller
subunits
– not a continuing chain
 Fatty Acids
A fatty acid is a molecule characterized by the presence of a
carboxyl group attached to a long hydrocarbon chain.

Therefore these are molecules with a formula R–COOH where R

is a hydrocarbon chain.

Fatty acids can be said to be carboxylic acids, and come in two

major varieties.
 Fatty acid
• Structure:
– glycerol (3C alcohol) +fatty acid
• fatty acid =
long HC “tail” with carboxyl (COOH) group “head”

enzyme
H2O

dehydration synthesis
 Building Fats
• Triacylglycerol
– 3 fatty acids linked to glycerol
– ester linkage = between OH & COOH
hydroxyl carboxyl
 Dehydration synthesis

H2O

dehydration synthesis

enzyme
H2O

enzyme
H2O

enzyme
HO
 Fats store energy
• Long HC chain
– polar or non-polar?
– hydrophilic or hydrophobic?
• Function:
– energy storage
• concentrated
– all H-C!
• 2x carbohydrates
– cushion organs
– insulates body
 Fatty Acids

• Saturated fatty acids do not have • Saturated fatty acids are solids at
any double bonds. room temperature.
• A fatty acid is saturated when • Animal fats are a source of
every carbon atom in the saturated fatty acids.
hydrocarbon chain is bonded to • In addition, fatty acids pack easily
as many hydrogen atoms as and form rigid structures (e.g.,
possible (the carbon atoms are fatty acids are found in
saturated with hydrogen). membranes).
 Fatty Acids
• Unsaturated fatty acids can have one • The melting point of a fatty acid is
or more double bonds along its influenced by the number of double
hydrocarbon chain. bonds that the molecule contains and
by the length of the hydrocarbon tail.
• A fatty acid with one double bond is • The more double bonds it contains, the
called monounsaturated. lower the melting point.
• As the length of the tail increases, the
• If it contains two or more double melting point increases.
bonds, we say that the fatty acid is • Plants are the source of unsaturated
polyunsaturated. fatty acids
Fatty Acids
 CLASSIFICATION OF FATTY ACIDS
Naturally occurring fatty acids have cis bonds.
Trans-fatty acids are created artificially using a process called
hydrogenation.
A trans-fatty acid has a trans configuration rather than cis configuration
at each double bond. This causes the molecule to straighten. These two
stereoisomers can be distinguished in the following way:
– In a cis stereoisomer, two similar groups attached to the carbon double bond are found on the same side.
– In a trans stereoisomer, two similar groups attached to the carbon double bond are found on opposite sides.
 ESSENTIAL AND NONESSENTIAL FATTY ACIDS
• If a fatty acid can only be obtained from the diet (for humans) then the
fatty acid is an essential fatty acid.
• Two fatty acids cannot be synthesized in the human body and are
therefore essential.
– These are linoleic and linolenic fatty acids, which are both unsaturated.
Nonessential fatty acids can be made by the human body and so
do not need to be obtained from diet alone.
• These are made from carbohydrates and proteins or from
other fatty acids.
• Fatty acids are an important source of energy.
• While carbohydrates or proteins only provide 4 kcal/g of
energy, fatty acids provide more than twice the energy per unit
weight of 9 kcal/g. This is one reason why a high-fat diet can
lead to obesity.
https://chem.libretexts.org/Bookshelves/Introductory_Chemistry/The_Basics_of_GOB_Chemistry_(Ball_et_al.)/17%3A_Lipids/17.01%3A_Fatty_Acids
 Fatty acids are aliphatic carboxylic acids
• Fatty acids occur mainly as esters in natural fats and oils but do
occur in the unesterified form as free fatty acids, a transport
form found in the plasma.
• Fatty acids that occur in natural fats are usually straight-chain
derivatives containing an even number of carbon atoms.
• The chain may be saturated (containing no double bonds) or
unsaturated (containing one or more double bonds).
 Most naturally occurring unsaturated fatty
acids have cis double bonds
• The carbon chains of saturated fatty acids form a zigzag pattern
when extended, as at low temperatures.
• At higher temperatures, some bonds rotate, causing chain
shortening, which explains why biomembranes become
thinner with increases in temperature.
• A type of geometric isomerism occurs in unsaturated fatty
acids, depending on the orientation of atoms or groups around
the axes of double bonds, which do not allow rotation.

• If the acyl chains are on the same side of the bond, it is cis-, as
in oleic acid; if on opposite sides, it is trans-, as in elaidic acid,
the trans isomer of oleic acid.
 Most naturally occurring unsaturated fatty acids have
cis double bonds
• Naturally occurring unsaturated long-chain fatty acids are nearly all of cis
configuration.
• Thus, oleic acid has an L shape, whereas elaidic acid remains “straight.”

• Increase in the number of cis double bonds in a fatty acid leads to a variety of
possible spatial configurations of the molecule – e.g., arachidonic acid, with four cis
double bonds, has “kinks” or a U shape. This has profound significance on molecular
packing in membranes and on the positions occupied by fatty acids in more complex
molecules such as phospholipids.
• Trans double bonds alter these • An additional small contribution
spatial relationships. comes from the ingestion of
ruminant fat that contains trans
• Trans fatty acids are present in fatty acids arising from the action
certain foods, arising as a by- of microorganisms in the rumen.
product of the saturation of fatty
acids during hydrogenation, or
“hardening,” of natural oils in the
manufacture of margarine.
 COMMON LIPIDS AND THEIR FUNCTIONS
Triglycerides

• A triglyceride (often called • Fatty acids can be attached at these

triacylgycerol) is a fatty acid trimester three sites forming a triglyceride.
of glycerol. • One important characteristic of a
• Triglycerides are important for human tryglycerol is its state at room
health in that they provide most of the temperature.
lipids in our diet. • The degree of saturation and the
• Glycerol has three hydroxyl groups. length of their chains attached to the
glycerol backbone both determine
their state at room temperature.
• Short-chain unsaturated • Animal fats (lard) contain a high
triglycerides are liquid at room amount of saturated triglycerides
temperature. while plant oils (vegetable oil)
contain a high amount of
• Long-chain saturated unsaturated triglycerides.
triglycerides are solid at room
temperature. • While neither is healthy when
consumed in excess, vegetable
oils are far healthier than lard.
 Triglycerides are the main storage forms of fatty acids

• The triglycerides are esters of the trihydric

alcohol glycerol and fatty acids.
• Mono- and diacylglycerols wherein one or
two fatty acids are esterified with glycerol
are also found in the tissues.
• These are of particular significance in the
synthesis and hydrolysis of triacylglycerols.
 The role of triglycerides in health

While fat may seem bad, triglycerides play many important roles in the body.

• For example, triglycerides can be used for energy storage in animals.

• This food reserve can be called upon during periods of starvation, with the high-
calorie content of the fatty acids adding to the value of storing fat and providing
much needed energy.

In addition, triglycerides can provide insulation for animals in the form of body fat, which allows them to survive in
colder temperatures. These two roles played by fat in the body, which arose over eons of evolution, are now
deemed undesirable in modern industrialized society where humans no longer face starvation or have to deal
directly with cold weather.
 Phospholipids are the main lipid constituents
of membranes
• Phospholipids may be regarded as derivatives of phosphatidic
acid, in which the phosphate is esterified with the OH of a
suitable alcohol.
• Phosphatidic acid is important as an intermediate in the
synthesis of triacylglycerols as well as phosphoglycerols but is
not found in any great quantity in tissues.
• Amphipathic lipids self-orient at oil:water interfaces.
– They form Membranes, Micelles, Liposomes, & Emulsions .
In general, lipids are insoluble in water since they contain a
predominance of nonpolar (hydrocarbon) groups.

• However, fatty acids, phospholipids, sphingolipids, bile salts,

and, to a lesser extent, cholesterol contain polar groups.
– Therefore, part of the molecule is hydrophobic, or water-insoluble;
and part is hydrophilic, or water-soluble.
– Such molecules are described as amphipathic.
– They become oriented at oil:water interfaces with the polar group in
the water phase and the nonpolar group in the oil phase.
 CHOLESTEROL AND ITS IMPORTANCE
• Cholesterol is an important lipid found
in the cell membrane.
• It is a sterol, which means that
cholesterol is a combination of a
steroid and an alcohol.

It is an important component of cell

membranes and is also the basis for the
synthesis of other steroids, including the sex
hormones estradiol and testosterone, as well
as other steroids such as cortisone and
vitamin D.
 CHOLESTEROL AND ITS IMPORTANCE
• In the cell membrane, the steroid
ring structure of cholesterol
provides a rigid hydrophobic
structure that helps boost the
rigidity of the cell membrane.
• Without cholesterol the cell
membrane would be too fluid. In
the human body, cholesterol is
synthesized in the liver.
Cholesterol is insoluble in the blood, so when it is released into the blood
stream it forms complexes with lipoproteins.

Cholesterol can bind to two types Therefore, when cholesterol is

of lipoprotein, called high-density bound to a lipoprotein, it becomes
lipoprotein (HDL) and low-density blood soluble and can be
lipoprotein (LDL). transported throughout the body.

A lipoprotein is a spherical HDL cholesterol is transported back

molecule with water soluble to the liver. If HDL levels are low,
proteins on the exterior. then the blood level of cholesterol
will increase.