Chapter 15 Lipids

• biomolecules that contain fatty acids or a steroid

nucleus.
• soluble in organic solvents, but not in water.
• named for the Greek word lipos, which means
“fat.”
• Provide energy, insulation, hormones

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 Types of Lipids

The types of lipids containing fatty acids are

• waxes
• fats and oils (triacylglycerols or triglycerides)
• glycerophospholipids
• prostaglandins

Lipids that do not contain fatty acids are

• steroids

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 Natural Fatty Acids

• long-chain carboxylic acids,

typically 12-18 carbon atoms.

• typically have even numbers

of C atoms.
Olive oil: 84% unsaturated
• insoluble in water.
16% saturated

• saturated or unsaturated,
unsaturated C=C are cis.

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Saturated and Unsaturated Fatty
Acids
Fatty acids are
• saturated with all single C–C bonds.
• unsaturated with one or more double C=C bonds.

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Properties of Saturated Fatty Acids

contain only single C–C bonds.

are closely packed.
have strong attractions between chains.
have high melting points.
are solids at room temperature = FATS

COOH
COOH
COOH

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 Unsaturated Fatty Acids

contain one or more cis double C=C

bonds.

HOOC
have “kinks” in the fatty acid chains. H
COOH
H C C
do not pack closely.
“kinks” in
have few attractions between chains. chain
H
C
have low melting points. C
H

are liquids at room temperature = OIL

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Melting Points

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Melting Points

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 Melting Points of Fats and Oils

A fat
• is usually solid at room temperature.
• Higher percentage of saturated fatty acids
• is prevalent in meats, whole milk, butter, and cheese.
An oil
• is usually liquid at room temperature.
• Higher percentage of unsaturated fatty acids
• is prevalent in plants such as olive and safflower.

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Percent Saturated and Unsaturated
Fatty Acids

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 Prostaglandins

• Derived from a fatty acid with 20 carbons = icosanoic

acid
• CH3(CH2)18COOH
• Body’s response to injury (causes swelling)
• Smooth muscle contraction, mucus secretion, inhibits
acid production in stomach

Also related are

leukotrienes and
thromboxanes

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 Prostaglandins

increase/decrease blood pressure mucus secretion

smooth muscle contraction stomach acid

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 Prostaglandins: NSAIDs
When tissues are injured, arachidonic acid is converted
to prostaglandins such as PGE and PGF that produce
inflammation and pain in the area.

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 Waxes
• esters = saturated fatty acids + long-chain alcohols.
• coatings that prevent loss of water by leaves of plants.

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 Triacylglycerols or Triglycerides

In a triacylglycerol, glycerol forms ester bonds with

three fatty acids.

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 Formation of a Triacylglycerol

Glycerol + three fatty acids triacylglycerol

O
CH2 OH HO C (CH2)14CH3
O
CH OH + HO C (CH2)14CH3
O
O
CH2 OH HO C (CH2)14CH3 CH2 O C (CH2)14CH3
O
CH O C (CH2)14CH3 + 3H2O

O
CH2 O C (CH2)14CH3

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 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.

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Hydrogenation of Unsaturated Fats

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 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

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 Saponification

O
CH2 O C (CH2)14CH3
O
CH O C (CH2)14CH3 + 3NaOH

O CH2 OH
CH2 O C (CH2)14CH3

CH OH
O
+ 3 Na+ -O C (CH2)14CH3
“soap”
CH2 OH
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Base Hydrolysis of Fatty Acids Produces
Soaps

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 Cleaning Action of Soap
A soap
• contains a nonpolar end
that dissolves in nonpolar
fats and oils, and a polar
end that dissolves in
water.

• forms groups of soap

molecules called
micelles that dissolve in
water and are washed
away.
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 What is the product?
O
CH2 O C (CH2)5CH CH(CH2)7CH3
O
Ni
CH O C (CH2)5CH CH(CH2)7CH3 + 3 H2
O
CH2 O C (CH2)5CH CH(CH2)7CH3

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

Fatty acid

Fatty acid
Glycerol

Amino
PO4
alcohol
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Structure and Polarity of a
Glycerophospholipid

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 Lecithin and Cephalin
glycerophospholipids
• abundant in brain and nerve tissues.
• found in egg yolk, wheat germ, and yeast.

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 Steroid Nucleus

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

steroid nucleus

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 Cholesterol

• is the most abundant steroid in the body.

• has methyl CH3- groups, alkyl chain, and -OH
attached to the steroid nucleus.

CH3 CH3
CH3
CH3
CH3

HO

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 Lipoproteins

Lipoproteins
• combine lipids
with proteins
and
phospholipids.

• are soluble in
water because
the surface
consists of
polar lipids.

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 Lipoproteins

• differ in density, composition, and function.

• include low-density lipoproteins (LDLs) and high-
density lipoproteins (HDLs).

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 Steroid Hormones

• 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)

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Steroid Hormones

• are produced from

cholesterol.

• include sex
hormones such as
androgens
(testosterone) in
males and estrogens
(estradiol) in
females.

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Adrenal Corticosteroids

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 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.

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 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.

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 Transport Pathways

Copyright © 2009 by Pearson Education, Inc.

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