THE CHEMISTRY OF

LIPIDS

MARVIN N. BUSTAMANTE
BSED IV – SCIENCE
Saint Joseph College of Cavite
1ST Semester 2017 - 2018
CONCEPT MAP
Lipids
• Lipids are family of biomolecules that have
common property of being soluble in organic
solvents but not in water.
• The word "lipid" comes from the greek word "lipos”
meaning fat or lard.
• The lipid content of a cell can be extracted using an
organic solvent.
• Lipids are important feature in cell membranes, fat-
soluble vitamins, and steroid hormones.
Properties of Lipids
1. Insoluble in water, but soluble in
organic solvent.
2. Actually or potentially related to
fatty acids
3. It can be used as sourced of
energy by animals
Types of Lipids
• Within the lipid family, there are distinct structures
that distinguish the different types of lipids. Lipids
such as waxes,fats,oils and glycerophospholipids
are esters that can be hydrolyzed to give fatty acids
along with other products including an alcohol.
• Steriods are characterized by the steroid nucleus of
four fused carbon rings. They do not contain fatty
acids and cannot be hydrolyzed.
Question #1

What type of lipid does

not contain fatty acids?

The steroids are a group of

lipids with no fatty acids.
Function of Lipids
1. They are rich source of energy
2. Protect and insulate internal organs
3. Other type of lipids are found in nerve fibers and
in hormones , which acts as chemical messenger.
4. Provide polyunsaturated fatty acids.
5. A major function of lipids is to build the cell
membranes that separate the internal contents
of the cells from the surrounding aqueous
environment.
Question #2

Lipids are NOT soluble in water.

Are Lipids polar or non polar
molecules?

Lipids are non-polar molecules

Fatty Acids
• It is the simplest type of lipid and are found as
components in more complex lipids.
• It contains a long carbon chain attached to
carboxylic acid group at one end.
• Although the carboxylic acid is hydrophilic, the long
hydrophobic carbon chain makes long-chain fatty
acids insoluble in water.
• Fatty acids have even number of carbon atoms,
usually between 10-20.
Example
• Lauric Acid – a 12-carbon acid found in coconut oil.
Fatty Acids
Saturated Fatty Acids such as lauric acid
contain only single bonds between
carbons.
Monounsaturated Fatty Acids have one
double bond in the carbon chain.
Polyunsaturated Fatty Acids have two or
more double bonds.
Structures and Common Melt Points of
Fatty Acids
Structures and Common Melt Points of
Fatty Acids
Fatty Acids
• The human body is capable of synthesizing most
fatty acids from carbohydrates or other fatty acids.
However human do not synthesize sufficient
amounts of fatty acids that have more than one
doubled bond. (Polyunsaturated fatty acids)
• These fatty acids are called essential fatty acids
because they must be provided by diet.
• A deficiency of essential fatty acids can cause skin
dermatitis in infants.
Physical Property of Fatty Acids
• The saturated fatty acids fit close together in a
regular pattern, which allows strong attraction to
occur between the carbon chains. As a result , a
significant amount of energy and high
temperatures are required to separate the fatty
acids and melt the fat. As the length of the carbon
chain increases, the more interaction occur
between the carbon chains, requiring higher
melting points.
Physical Property of Saturated Fatty
Acids

COOH
COOH
COOH
Physical Properties of Fatty Acids
• In unsaturated fatty acids, the cis double bond
cause the carbon chain to bend, which gives the
molecules an irregular shape. As a result, fewer
interaction occur between carbon chains.
Consequently, the melting points of unsaturated
fats are lower than those of saturated fats.
Physical Property of Unsaturated
Fatty Acids
HOOC
H
COOH
H C
C

“kinks” in
chain
H
C
C
H
Waxes, Fats, and
Oils
Waxes, Fats, and Oils
• A wax is an ester of unsaturated fatty acid and long-
chain alcohol, each containing from 14-30 carbon
atoms.
• Bees wax obtained from honey combs and carnauba
wax obtained from palm trees are used to give a
protective coating to furniture, car and floors.
• Jojoba wax is used in making candles and cosmetics
such as lipstick.
• Lanolin, a mixture of waxes obtained from wool, is used
in hand and facial lotions to aid retention of water,
which softens the skin.
Some Typical Waxes
Fats and Oils: Triacylglycerols
• In the body, fatty acids are stored as fats and oils
known as triacylglycerols.
• These substances, also called triglycerides, are
triesters of glycerol and fatty acids.
Triacylglycerols
• A triacylglycerol is produced by esterfication, a
reaction in which the hydroxylgroups of glycerol
form ester bonds with carboxyl groups of fatty
acids.
Triacylglycerols
• A triacylglycerol are the major form of energy storage
for animals.
• Animals that hibernate eat large quantities of
plants,seeds and nuts that contain large amount of fats
and oils.
• They gain as much 14 Kg a week. As the external
temperature drops, the animal goes into hibernation.
The body temperature drops to nearly freezing and
there is a dramatic reduction in cellular activity,
respiration and heart rate.
• Animals who live in extremely cold climates will
hibernate for 4-7 months.
Triacylglycerols
• However, most fats and oils are mixed
triacyglycerols that contain two or three different
fatty acids.
• For example a mix tricylglycerol might be made
from lauric acid,myristic acid and palmitic acid.
Melting Points of Fats and Oils.
• A fat is a triacylglycerol that is solid at room
temperature, such as fats in meat, whole milk, butter
and cheese. Most fats come from animal sources.
• An oil is a triacylglycerol that is liquid at room
temperature. The most commonly used oils come from
plant sources. Olive oil and peanut oil are
monounsaturated because they contain large amounts
of oleic acid.
• Oils from corn,cotton seed, safflower and sunflower are
polyunsaturated because they contain large amounts of
fatty acids with two or more double bonds.
Diagram of Triacylglycerol with
Unsaturated Fatty Acids

Unsaturated
fatty acid chains
with kinks
cannot pack
closely.
Melting Points of Fats and Oils.
• A few oils such as palm oil and coconut oil are solid
at room temperature because they consist mostly
of saturated fatty acids.
Melting Points of Fats and Oils.
• Saturated fatty acids have higher melting points
than unsaturated fatty acids because they pack
together more tightly.

• Vegetable oils have low melting points because they

have a higher percentage of unsaturated fatty acids
than do animal fats.
Chemical Properties
of Triacylglycerols
Chemical Properties of
Triacylglycerols
The chemical reactions of triacylglycerols are similar
to those of alkenes and esters.

• In hydrogenation, double bonds in unsaturated

fatty acids react with H2 in the presence of a Ni or
Pt catalyst.
• In hydrolysis, ester bonds are split by water in the
presence of an acid, a base, or an enzyme.
Hydrogenation of Oils
The hydrogenation of oils

• adds hydrogen (H2) to

the carbon atoms of
double bonds.
• converts double bonds
to single bonds.
• increases the melting point.
• produces solids such as margarine
and shortening.
Hydrogenation
O
O
CH2 O C (CH2)5CH CH(CH2)7CH3 CH2 O C (CH2)14CH3
O O
CH O C (CH2)5CH CH(CH2)7CH3 Ni
+ 3H2 CH O C (CH2)14CH3
O O
CH2 O C (CH2)5CH CH(CH2)7CH3
CH2 O C (CH2)14CH3
glyceryl tripalmitoleate glyceryl tripalmitate
(tripalmitolean) (tripalmitin)
Olestra a Fat Substitute
Olestra is
• used in foods as an artificial fat.
• sucrose linked by ester bonds to several long-
chain fatty chains.
• not broken down in the intestinal tract.
Hydrolysis
In hydrolysis,
• triacylglycerols split into glycerol and three fatty
acids.
• an acid or enzyme catalyst is required.
O
CH2 O C (CH2)14CH3
O
H+
CH O C (CH2)14CH3 H2O
O
CH2 O C (CH2)14CH3 CH2 OH O
CH OH HO C (CH2)14CH3

CH2 OH
Saponification and Soap
Saponification
• is the reaction of a fat with a strong base.
• splits triacylglycerols into glycerol and the salts of
fatty acids.
• is the process of forming “soaps” (salts of fatty
acids).
• with KOH gives softer soaps.
 Saponification
O
CH2 OH
CH2 O C (CH2)14CH3
O O
CH O C (CH2)14CH3 + 3NaOH CH OH + Na+ -O C (CH2)14CH3
O
CH2 O C (CH2)14CH3
CH2 OH
3 sodium
Glyceryl Glycerol palmitate
tripalmitate
Glycerophospholipids

Fatty acid

Fatty acid
Glycerol

PO4 Amino
alcohol
Glycerophospholipids
Glycerophospholipids are
• the most abundant lipids in cell membranes.
• composed of glycerol, two fatty acids, phosphate,
and an amino alcohol
Fatty acid

Glycerol Fatty acid

Amino
PO4
alcohol
Polarity of Glycerophospholipids
A glycerophospholipid has
• two nonpolar fatty acid chains.
• a phosphate group and a polar amino alcohol.
CH3
│+ +
HO−CH2−CH2−N−CH3 HO−CH2−CH2−NH3
│
Choline CH3 Ethanolamine
+
NH3
│ Amino alcohols
HO−CH2−CH−COO− Serine
Structure and Polarity of a
Glycerophospholipid
Lecithin and Cephalin
Lecithin and cephalin are glycerophospholipids
• abundant in brain and nerve tissues.
• found in egg yolk, wheat germ, and yeast.
 Steroids: Cholesterol and
Steroid Hormones
CH3 CH3
CH3
CH3
CH3

HO
Steroid Nucleus
A steroid nucleus consists of
• 3 cyclohexane rings.
• 1 cyclopentane ring.
• no fatty acids.

steroid nucleus
Cholesterol in the Body
A normal, open artery.
Cholesterol
• is obtained from meats, milk,
and eggs.
• is synthesized in the liver.
• is needed for cell membranes,
brain and nerve tissue, steroid
hormones, and vitamin D.
• clogs arteries when high levels
form plaque.
An artery clogged by
cholesterol plaque
Cholesterol in Foods
Cholesterol
• is considered elevated if plasma cholesterol
exceeds 200 mg/dL.
• is synthesized in the liver and obtained from foods.
Lipoproteins
Lipoproteins
• combine lipids
with proteins
and
phospholipids.
• are soluble in
water because
the surface
consists of polar
lipids.
Types of Lipoproteins
Lipoproteins
• differ in density, composition, and function.
• include low-density lipoproteins (LDLs) and high-
density lipoproteins (HDLs).
Steroid Hormones
Steroid hormones are
• chemical messengers in cells.
• sex hormones.
- androgens in males (testosterone)
- estrogens in females (estradiol)
• Adrenocortical hormones from adrenal glands.
- mineralocorticoids (electrolyte balance)
- glucocorticoids (regulate glucose level)
Steroid Hormones
Steroid hormones
• are produced from
cholesterol.
• include sex hormones
such as androgens
(testosterone) in
males and estrogens
(estradiol) in females.
Anabolic Steroids
Anabolic steroids
• are derivatives of testosterone.
• are used illegally to increase muscle mass.
• have side effects including fluid retention, hair
growth, sleep disturbance, and liver damage.
Adrenal Corticosteroids
Steroid hormones called adrenal corticosteroids
• are produced by the adrenal glands located on the
top of each kidney.
• include aldosterone, which regulates electrolytes
and water balance by the kidneys.
• include cortisone, a glucocorticoid, which increases
blood glucose level and stimulates the synthesis of
glycogen in the liver.
Adrenal Corticosteroids
Cell Membranes
Cell Membranes
Cell membranes
• separate cellular contents from the external
environment.
• consist of a lipid bilayer made of two rows of
phospholipids.
• have an inner portion made of the nonpolar tails of
phospholipids with the polar heads at the outer
and inner surfaces.
Fluid Mosaic Model of Cell
Membranes
The lipid bilayer
• contains proteins, carbohydrates, and cholesterol.
• has unsaturated fatty acids that make cell
membranes fluid-like rather than rigid.
• has proteins and carbohydrates on the surface that
communicate with hormones and
neurotransmitters.
Fluid Mosaic Model of Cell
Membranes
Transport Through Cell
Membranes
The transport of substances through cell membranes
involves
• simple diffusion (passive transport), which moves
particles from a higher to a lower concentration.
• facilitated transport, which uses protein channels
to increase the rate of diffusion.
• active transport, which moves ions against a
concentration gradient.
Transport Pathways Through Cell
Membranes
Thank You!