Chapter 2 - Lipids Part 1

Chapter 19 Chapter 19
19.1 Structure and classification of lipids

19.2 Types of fatty acids
19.3 Physical properties of fatty acids
19.4 Energy-storage lipids: Triacylglycerols
Chapter 2 19.5 Dietary considerations and triacylglycerols
19.6 Chemical reactions of triacylglycerols
19.7 Membrane lipids: Phospholipids
19.8 Membrane lipids: Sphingoglycolipids
19.9 Membrane lipids: Cholesterol
19.10 Cell membranes
19.11 Emulsification lipids: Bile acids
19.12 Messenger lipids: Steroid hormones
19.13 Messenger lipids: Eicosanoids
19.14 Protective-coating lipids: Biological waxes
19.15 Saponifiable and nonsaponifiable lipids
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Lipids Lipids
• Lipid: An organic compound found in living • They are defined by a physical property, and not
organisms that is insoluble (or only sparingly by the presence of a particular functional group.
soluble) in water but soluble in non-polar organic
solvents • They contain many nonpolar C—C and C—H
bonds and few polar bonds resulting in their low
• Unlike other biomolecules, lipids do not have a water solubility.
common structural feature that serves as the
basis for defining such compounds • Classification is based on two methods
– Biochemical function
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– Saponification Return to TOC
Classification based on Biochemical Function Classification Based on Saponification
• For purposes of simplicity of study, lipids are • Saponification reaction - Hydrolysis reaction that
divided into five categories based on their occurs in a basic solution
biochemical function: • Based on saponification reactions, lipids are
– Energy-storage lipids (triacylglycerols) divided into two categories:
– Membrane lipids (phospholipids, sphingoglycolipids, – Saponifiable lipids (triacylglycerols, phospholipids,
and cholesterol) sphingoglycolipids, cholesterol, and biological waxes)
– Emulsification lipids (bile acids) – Nonsaponifiable lipids (bile acids, steroid
– Messenger lipids (steroid hormones and hormones, and eicosanoids)
eicosanoids)
– Protective-coating lipids (biological waxes)
Structural Diversity of Lipids

Lipids can be categorized as:
• Lipids exhibit structural diversity
• Hydrolyzable lipids can be converted into • Some are esters, some are amides, and some
smaller molecules by hydrolysis.
are alcohols (acyclic, cyclic, and polycyclic)
 Or saponifiable
• Nonhydrolyzable lipids cannot be cleaved into

smaller molecules by aqueous hydrolysis.
 Or nonsaponifiable
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Figure 19.1 - Structural Formula of Types of Lipids
A lipid is an organic compound found in living

organisms that is:
a.soluble in water and insoluble in nonpolar organic

solvents.
b.soluble in water and soluble in nonpolar organic solvents.
c.insoluble in water and insoluble in nonpolar organic
solvents.
d.insoluble in water and soluble in nonpolar organic
solvents.
Fatty Acids - An Introduction
A lipid is an organic compound found in living • Fatty acids: Naturally occurring monocarboxylic
organisms that is: acids with linear (unbranched) carbon chain
a.soluble in water and insoluble in nonpolar organic – Nearly always contain even number of carbon atoms
solvents. • Long-chain fatty acids (C12 to C26)
b.soluble in water and soluble in nonpolar organic solvents. • Medium-chain fatty acids (C8 to C10)
c.insoluble in water and insoluble in nonpolar organic • Short-chain fatty acids (C4 to C6)
solvents.
d.insoluble in water and soluble in nonpolar organic • Naturally occurring fatty acids have an even
number of C atoms.
solvents.
Fatty Acids - An Introduction
• Two types:
– Saturated - All C–C bonds are single bonds (SFA)
– Unsaturated
• Monounsaturated (MUFA)
• Polyunsaturated (PUFA)
Saturated Fatty Acids Saturated Fatty Acids

• Saturated fatty acids have no double bonds • Consider the structural notations for palmitic
in their long hydrocarbon chains. acid:
• Numbering starts from the end of –COOH

group
Unsaturated Fatty Acids
• Monounsaturated fatty acid: Fatty acid with a

carbon chain in which one carbon–carbon
double bond is present (generally cis) in their
long hydrocarbon chains.
• There are different ways of depicting the

structure
Stearic acid (mp 𝟕𝟏 ℃) is a saturated fatty acid. Polyunsaturated Fatty Acids (PUFAs)
• Fatty acids with a carbon chain in which two or

more carbon–carbon double bonds are present
Oleic acid (mp 𝟏𝟔 ℃) is an unsaturated fatty acid.

• Up to six double bonds are found in
biochemically important PUFAs
19
Double-Bond Position in Unsaturated Fatty Acids Types of Unsaturated Fatty Acids

• Numbering starts at –COOH end • Omega (ω)-3 fatty acid: Unsaturated fatty acid
• Structural notation indicates number of C atoms with its endmost double bond three carbon
• Example: atoms away from its methyl end
– 18:3 signifies that a fatty acid has 18 carbons with 3
double bonds
– 18:3 (9,12,15)signifies that a fatty acid has 18 carbons
with 3 double bonds with location between C9 and
C10, C12 and C13, and between C15 and C16
Types of Unsaturated Fatty Acids
• Omega (ω)-6 fatty acid: Unsaturated fatty acid

with its endmost double bond six carbon atoms
away from its methyl end
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24
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A fatty acid is a naturally occurring _____ acid that A fatty acid is a naturally occurring _____ acid that
nearly always contains an _____ number of nearly always contains an _____ number of
carbon atoms with a carbon chain that is _____. carbon atoms with a carbon chain that is _____.
a.monocarboxylic; even; branched a.monocarboxylic; even; branched

b.dicarboxylic; odd; unbranched b.dicarboxylic; odd; unbranched
c.monocarboxylic; even; unbranched c.monocarboxylic; even; unbranched
d.dicarboxylic; even; branched d.dicarboxylic; even; branched
Which of the following statements is true about the Which of the following statements is true about the
classification of fatty acids? classification of fatty acids?
a.They are classified as saturated, monounsaturated, or a.They are classified as saturated, monounsaturated, or
polyunsaturated fatty acids. polyunsaturated fatty acids.
b.They are classified as saturated or branched unsaturated b.They are classified as saturated or branched unsaturated
fatty acids. fatty acids.
c.They are classified as saturated or polyunsaturated fatty c.They are classified as saturated or polyunsaturated fatty
acids. acids.
d.None of the above. d.None of the above.
Water Solubility Melting Point
• Short-chain fatty acids have some solubility, • Depends upon the

whereas long-chain fatty acids are insoluble following:
• Short-chain fatty acids are sparingly soluble – Length of carbon
because of the presence of carboxylic group chain
– Degree of
unsaturation (number
of double bonds in a
molecule)
As the number of double bonds in the fatty

acid increases, the melting point decreases.
• Number of “bends” in Which of the following best describe the physical

a fatty acid chain properties of fatty acids?
increases as the
number of double a.Melting points of fatty acids are influenced by the carbon
bonds increases chain length.
• Less packing occurs b.Melting points of fatty acids are influenced by their
• Melting point is lower degree of unsaturation.
• Tend to be liquid at c.All physical properties of fatty acids are influenced by the
room temperature length and degree of unsaturation of their carbon chain.
d.All the above.
Energy-Storage Materials
Which of the following best describe the physical • With the notable exception of nerve cells, human
properties of fatty acids? cells store small amounts of energy-providing
materials
a.Melting points of fatty acids are influenced by the carbon – Carbohydrate glycogen - Most widespread energy
chain length. storage material present in small amounts
b.Melting points of fatty acids are influenced by their • Major energy-storage material is triacylglycerol
degree of unsaturation. – Concentrated primarily in special cells (adipocytes)
c.All physical properties of fatty acids are influenced by the which are nearly filled with triacylglycerols
length and degree of unsaturation of their carbon chain.
d.All the above.
Triacylglycerols (triglycerides) are three esters The general reaction for the formation of a
formed from glycerol and three molecules of fatty triacylglycerol is:
acids.
Below is a generalized block diagram of a

triacylglycerol:
35
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36
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Two Types of Triacylglycerols

Simple triacylglycerols have three identical fatty
• Simple triacylglycerol: Triester formed from the acid side chains.
esterification if glycerol with three identical fatty
acid molecules
– Naturally occurring simple triacylglycerols are rare
• Mixed triacylglycerol: Triester formed from the
esterification of glycerol with more than one kind
of fatty acid molecule
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38
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Fats and Oils

Mixed triacylglycerols have two or three different
fatty acids. • Fats:
– Predominantly Saturated
– Solids or semisolids at room temperature
– Source: Animals
• Oils:
– Predominantly unsaturated
– Liquids at room temperature
– Sources: Plants and fish oil
• Pure oils and fats are colorless, odorless, and
tasteless
39
Triacylglycerols are _____ in their ability to store Triacylglycerols are _____ in their ability to store
energy when compared to glycogen, the energy energy when compared to glycogen, the energy
storing form of glucose in the human body. storing form of glucose in the human body.
a.less efficient a.less efficient

b.more efficient b.more efficient
c.equally efficient c.equally efficient
d.insignificant d.insignificant
Studies Concerning Role of Dietary Factors as a Cause of

“Good Fats” Versus “Bad Fats”
Disease
• Nations whose citizens have high dietary intakes • Studies indicate that type of dietary fat and
of fats and oils tend to have higher incidences of amount of dietary fat are important to determine
heart disease and certain types of cancers body responses to dietary fat
• Typical American diet contains too much fat • Current recommended amount for total fat
– Americans are being asked to reduce their total intake in calories:
dietary fat intake – 15% - Monounsaturated fat
• Other studies show that risk factors involve more – 10% - Polyunsaturated
than simply the total amount of triacylglycerols – <10% - Saturated fats
consumed
“Good Fats” Versus “Bad Fats” Omega-6 and Omega-3 Fatty Acids in American Diet
• Studies also indicate that: • American diet is high in omega-6 fatty acids and
– Saturated fats are considered “bad fats” deficient in omega-3 fatty acids
– Monounsaturated fats are considered “good fats” – Fish are a good source for omega-3 fatty acids
– Polyunsaturated fats can be both “good fats” and
“bad fats”
• Omega fats are important
Essential Fatty Acids Deficiency of Linoleic and Linoleic Acid
• Fatty acids that must be obtained from dietary • Results in:

sources because they cannot be synthesized – Skin redness
within the body – Infections and dehydration
• Two most important essential fatty acids are: – Liver abnormalities
– Linoleic acid (18:2) - Omega 6
– Linolenic acid (18:3) - Omega 3
• Needed for proper membrane structure
• Serve as starting materials for the production of
several nutritionally important longer-chain omega-6
and omega-3 fatty acids
Fat and Fatty Acid Composition of Nuts

Considerable research in the past two decades
• Numerous studies now indicate that eating nuts
has shown that high intake of dietary
can have a strong protective effect against
triacylglycerols causes diseases such as obesity,
coronary heart disease
cancer, hypertension, and atherosclerosis. This is
– Low amounts of saturated fatty acids
not true for the Inuit people of Greenland because
– Also contain valuable antioxidant vitamins, minerals,
their diet is high in _____ fatty acids.
and plant fiber protein
a.saturated
b.Omega-3
c.Omega-6
d.Omega-9
Considerable research in the past two decades

has shown that high intake of dietary
triacylglycerols causes diseases such as obesity, God loves you!
cancer, hypertension, and atherosclerosis. This is
not true for the Inuit people of Greenland because Be a blessing and pray for
their diet is high in _____ fatty acids.
somebody today!
a.saturated
b.Omega-3
c.Omega-6
d.Omega-9

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Chapter 19 Chapter 19

19.1 Structure and classification of lipids

Return to TOC Return to TOC

Classification based on Biochemical Function Classification Based on Saponification

Structural Diversity of Lipids

• Nonhydrolyzable lipids cannot be cleaved into

Copyright ©2016 Cengage Learning. All Rights Reserved. 8

Figure 19.1 - Structural Formula of Types of Lipids

A lipid is an organic compound found in living

a.soluble in water and insoluble in nonpolar organic

Fatty Acids - An Introduction

Fatty Acids - An Introduction

Return to TOC Return to TOC

Saturated Fatty Acids Saturated Fatty Acids

• Numbering starts from the end of –COOH

Return to TOC Return to TOC

Unsaturated Fatty Acids

• Monounsaturated fatty acid: Fatty acid with a

• There are different ways of depicting the

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• Fatty acids with a carbon chain in which two or

Oleic acid (mp 𝟏𝟔 ℃) is an unsaturated fatty acid.

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Double-Bond Position in Unsaturated Fatty Acids Types of Unsaturated Fatty Acids

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Types of Unsaturated Fatty Acids

• Omega (ω)-6 fatty acid: Unsaturated fatty acid

Copyright ©2016 Cengage Learning. All Rights Reserved. 23

a.monocarboxylic; even; branched a.monocarboxylic; even; branched

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Water Solubility Melting Point

• Short-chain fatty acids have some solubility, • Depends upon the

As the number of double bonds in the fatty

• Number of “bends” in Which of the following best describe the physical

Below is a generalized block diagram of a

Two Types of Triacylglycerols

Copyright ©2016 Cengage Learning. All Rights Reserved. 37

Fats and Oils

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a.less efficient a.less efficient

Return to TOC Return to TOC

Studies Concerning Role of Dietary Factors as a Cause of

Return to TOC Return to TOC

Return to TOC Return to TOC

Essential Fatty Acids Deficiency of Linoleic and Linoleic Acid

• Fatty acids that must be obtained from dietary • Results in:

Return to TOC Return to TOC

Fat and Fatty Acid Composition of Nuts

Considerable research in the past two decades

Copyright ©2016 Cengage Learning. All Rights Reserved. 51

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