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Outline
Chapter 28
Lipids
Polar bears
have a large
reserve
of lipids.
Course Outline
1. Introduction
2. Classification of Lipids
• Simple lipids
• Complex lipids
• Derived lipids
3. Edible fats & oil
4. Industrial application
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Classification of Lipids
Lipids molecules are relatively large and nonpolar. Yet,
within this broad description, lipid structures vary
markedly. Lipids can be classified in four categories
which recognize major structural similarities.
• Simple lipids
• Complex lipids
• Derived lipids
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Simple Lipids
The simple lipids include fats, oils, and waxes. These
simple lipids are derivatives of lipid-like substances call
fatty acids.
Simple Lipids
Fats and waxes are solids due to a higher composition of
saturated fatty acids while oils are liquids due to a
higher composition of unsaturated fatty acids.
Simple Lipids
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Simple Lipids
Unsaturated fatty acids exist as cis and trans isomers. The
cis isomer is more prevalent in nature.
The cis and trans isomers of oleic acid are shown on the
next slide.
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Simple Lipids
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Your Turn!
Draw the cis and trans isomers of palmitoleic acid.
CH3(CH2)5CH=CH(CH2)7COOH.
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Your Turn!
Draw the cis and trans isomers of palmitoleic acid.
CH3(CH2)5CH=CH(CH2)7COOH.
H
C
C
trans-isomer
H
H
C
H
C
cis-isomer
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Simple Lipids
Certain fatty acids, as well as other lipids, are biochemical
precursors of several classes of hormones.
For example, ω-6 (omega-6) and ω-3 fatty acids are used
to make hormones, the most common of which are the
eicosanoids.
Simple Lipids
Omega (ω) is the last letter in the Greek alphabet.
Correspondingly, the last carbon atom in a carbon chain
of a compound is often referred to as the omega carbon.
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Simple Lipids
So for example arachidonic acid is an ω-6 fatty acid
because the first double bond from the last carbon atom
is on the sixth carbon atom.
arachidonic acid
COOH
CH3
5 3 1
6 4 2
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Outline
Your Turn!
What is the correct classification of the fatty acid shown
below?
CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH
• ω-3
• ω-6
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Outline
Your Turn!
What is the correct classification of the fatty acid shown
below?
CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH
• ω-3
• ω-6
Simple Lipids
Examples of eicosanoids are:
• Thromboxanes
• Prostacyclins
• Prostaglandins
• Leukotrienenes
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Simple Lipids
Eicosanoids are hormones and coordinate various cellular
responses.
Simple Lipids
• Some eicosanoids stimulate and attract white cells,
while other eicosanoids cause the white cells to
disperse.
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Simple Lipids
Many drugs control one or more of the physiological
effects produced by the eicosanoids.
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Simple Lipids
Fats and oils are triester derivatives of glycerol and three
fatty acid molecules as shown below.
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Simple Lipids
Triglycerides are prepared by the reaction of a glycerol
molecule and three fatty acid molecules. The fatty acid
molecules can be saturated or unsaturated.
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Simple Lipids
Waxes are esters of high-molar-mass fatty acids and high-
molar-mass alcohols.
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Outline
Simple Lipids
Waxes are very large molecules with almost no polar
groups. They represent one of the most hydrophobic
classes of lipids.
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Simple Lipids
An important biological function of a wax is to act as a
protective coating. The “shine” on these leaves is due
to a thick protective wax coating.
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Outline
Your Turn!
Write the formula for a wax formed from palmitic acid
[CH3(CH2)14COOH] and 1-hexacosanol
[CH3(CH2)24CH2OH].
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Outline
Your Turn!
Write the formula for a wax formed from palmitic acid
[CH3(CH2)14COOH] and 1-hexacosanol
[CH3(CH2)24CH2OH].
O
palmitic acid portion
1-hexacosanol portion
Fats in Metabolism
Fats are an important food source for humans and
normally account for about 25–50% of our caloric
intake. Fats are an especially good source of metabolic
energy.
Fats in Metabolism
Fats are what our bodies prefer when storing energy
reserves. These reserves are in the form of
triacylglycereols in fatty tissue.
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Complex Lipids
There are three broad categories of complex lipids.
• Phospholipids
• Sphingolipids
• Glycolipids
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Complex Lipids
The phospholipids are a group of compounds that yield
one or more fatty acid molecules, a phosphate group,
and usually a nitrogenous base upon hydrolysis.
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Complex Lipids
Phospholipids are one of the most important membrane
components.
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Complex Lipids
Phosphatidic acids are glyceryl esters of fatty acids and
phosphoric acid. The phosphatidic acids are important
intermediates in the synthesis of triacylglycerols and
other phospholipids.
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Complex Lipids
Phosphatidylcholines (lecithins) are glyceryl esters of fatty
acids, phosphoric acid, and choline.
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Complex Lipids
The single most important biological function for
phosphatidylcholine is as a membrane component which
makes up between 10 and 20% of many membranes.
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Complex Lipids
Another important constituent of biological membranes is
the phosphatidylethanolamines (cephalins). These
lipids are glycerol esters of fatty acids, phosphoric acid,
and ethanolamine (HOCH2CH2NH2).
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Complex Lipids
Sphingolipids are another type of compound lipid that,
when hydrolyzed, yield:
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Complex Lipids
The similarities between sphingosine and glycerol are
shown in the structures below.
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Complex Lipids
Sphingolipids are common membrane components because
they have both hydrophobic and hydrophilic character.
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Complex Lipids
Glycolipids are a third type of compound lipid. These
compounds that contain a carbohydrate group.
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Complex Lipids
A cerebroside may contain either D-galactose or D-
glucose. The following formula of a galactocerebroside
shows the typical structure of cerebrosides.
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Your Turn!
What is the classification of the following lipid?
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Your Turn!
What is the classification of the following lipid?
Your Turn!
What is the classification of the following lipid?
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Your Turn!
What is the classification of the following lipid?
This molecule
is a
glycolipid.
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Derived Lipids
Steroids are compounds that have the steroid nucleus,
which consists of four fused carbocyclic rings. This
nucleus contains 17 carbon atoms in one five-membered
ring and three six-membered rings.
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Derived Lipids
Modifications of this nucleus that occur in the various
steroid compounds include, for example, added side
alkyl chains, hydroxyl groups, carbonyl groups, and ring
double bonds.
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Derived Lipids
For example:
Derived Lipids
• Digitalis and related substances called cardiac glycosides
are potent heart drugs.
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Derived Lipids
Cholesterol is the parent steroid compound from which the
steroid hormones are synthesized. In this process
cholesterol is converted to progesterone, a compound
that helps control the menstrual cycle and pregnancy.
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Derived Lipids
Cholesterol is also used to build cell membranes, many of
which contain about 25% by mass of this steroid.
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Your Turn!
Identify the functional groups in cortisone.
CH2OH
C O
CH3
O
CH3
O 55
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Outline
Your Turn!
Identify the functional groups in cortisone.
hydroxyl group
CH2OH
CH3
O
carbonyl group carbon-carbon 56
double bond
Chapter
Outline
Chapter 28 Summary
• Lipids are water-insoluble, oily, or greasy biochemicals.
All lipids are relatively large and nonpolar, yet lipid
structures may differ markedly.
Chapter 28 Summary
• Compound lipids are composed of fatty acid esters and
other components.
Chapter 28 Summary
• Glycolipids yield sphingosine and a carbohydrate as well
as a fatty acid upon hydrolysis.
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Chapter 28 Summary
• Fatty acids, which form part of most lipids, are
carboxylic acids with long, hydrophobic carbon chains.
Chapter 28 Summary
• Fats and oils are esters of glycerol and long carbon chain
fatty acids.
Chapter 28 Summary
• The phospholipids are a group of compounds that yield
one or more fatty acid molecules, a phosphate group,
and a nitrogenous base upon hydrolysis.
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Chapter 28 Summary
• Glycolipids are sphingolipids that contain carbohydrates.
Chapter 28 Summary
• Improper transport of cholesterol through the blood
system contributes to atherosclerosis. Lipoproteins
(specific protein-lipid aggregates) transport lipids
through the blood.
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