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17.1
Lipids
1
Lipids
Lipids are
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.”
Extracted from cells using organic solvents.
2
Types of Lipids
The types of lipids containing fatty acids are
Waxes.
Fats and oils (triacylglycerols).
Glycerophospholipids.
Prostaglandins.
Steroids do not contain fatty acids.
3
Structures of Lipids
4
Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
Chapter 17 Lipids
17.2 Fatty Acids
6
Copyright © 2007 by Pearson Education, Inc.
Publishing as Benjamin Cummings
Fatty Acid Formulas
CH3—CH2—CH2—CH2—CH2—CH2—CH2—COOH
OH
7
Saturated Fatty Acids
Saturated fatty acids have
Single C–C bonds.
Molecules that fit closely together
in a regular pattern.
Strong attractions between fatty
acid chains.
High melting points that make
them solids at room temperature.
8
Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
Some Saturated Fatty Acids
TABLE 17.1
10
Properties of Unsaturated Fatty
Acids
Unsaturated fatty acids “kinks” in
Have “kinks” in the fatty chain
acid chains.
Do not pack closely.
13
Learning Check
14
Solution
Stearic acid is saturated and would have a higher
melting point than the unsaturated fatty acids.
Because linoleic has two double bonds, it would have
a lower mp than oleic acid, which has one double
bond.
stearic acid mp 69°C saturated
oleic acid mp 13°C
linoleic acid mp -17°C most unsaturated
15
Prostaglandins
Prostaglandins have
20 carbon atoms in their fatty acid chains.
An OH on carbon 11 and 15.
A trans double bond at carbon 13.
C 11
C 13 C 15
17
Omega-6 and Omega 3- Fatty
Acids
Fatty acids
In vegetable oils are mostly omega-6 with
the first C=C at C6.
linoleic acid
CH3─(CH2)4─CH=CH─CH2─CH=CH─(CH2)7─COOH
6
In fish oils are mostly omega-3 with the
first C=C at C3.
linolenic acid
CH3─CH2─(CH=CH─CH2)3─(CH2)6─COOH
3
Copyright © 2007 by Pearson Education, Inc. 18
Publishing as Benjamin Cummings
Some Omega-6 and Omega-3
Fatty Acids
19
Learning Check
B. monounsaturated omega-3
C. monounsaturated omega-6
20
Solution
B. monounsaturated omega-3
CH3—CH2—CH=CH—CH2—CH2—CH2—CH2—CH2—COOH
C. monounsaturated omega-6
CH3—CH2—CH2—CH2—CH2—CH=CH—CH2—CH2—COOH
21
Chapter 17 Lipids
17.3
Waxes, Fats, and Oils
22
Waxes
Waxes are
Esters of saturated fatty acids and long-chain alcohols.
Coatings that prevent loss of water by leaves of plants.
TABLE 17.2
23
Fats and Oils: Triacylglycerols
Fats and oils are
Also called triacylglycerols.
Esters of glycerol.
Produced by esterification.
Formed when the hydroxyl
groups of glycerol react with the
carboxyl groups of fatty acids.
In a triacylglycerol,
Glycerol forms ester bonds with three fatty acids.
25
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
26
Olive Oil
Olive oil
Contains a high
percentage of oleic
acid, which is a
monounsaturated fatty
acid with one cis
double bond.
27
Learning Check
What are the fatty acids in the following triacylglycerol?
O
CH2 O C (CH2)16CH3
O
CH O C (CH2)7CH CH(CH2)7CH3
O
CH2 O C (CH2)12CH3
28
Solution
O
CH2 O C (CH2)16CH3 Stearic acid
O
CH O C (CH2)7CH CH(CH2)7CH3 Oleic acid
O
CH2 O C (CH2)12CH3 Myristic acid
29
Melting Points of Fats and Oils
A triacylglycerol that is a fat
Is solid at room temperature.
Is prevalent in meats, whole milk, butter, and cheese.
30
Oils with Unsaturated Fatty Acids
Oils
Have more unsaturated fats.
Have cis double bonds that cause “kinks” in the
fatty acid chains.
Cannot pack triacylglycerol molecules as close
together as in fats.
Have lower melting points than saturated fats.
Are liquids at room temperature.
31
Diagram of Triacylglycerol with
Unsaturated Fatty Acids
33
Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
Chapter 17 Lipids
17.4
Chemical Properties of
Triacylglycerols
34
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.
35
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.
36
38
Solution
What product(s) is obtained from the complete
hydrogenation of glyceryl trioleate?
2. Glyceryltristearate
39
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.
C=C
H H
Trans have bulky groups on opposite sides of C=C.
CH3─ (CH2)5 H
C=C trans
H (CH2)7─ COOH
41
Trans Fatty Acids and
Hydrogenation
Trans fatty acids
Are formed during hydrogenation when cis double
bonds are converted to trans double bonds.
In the body behave like saturated fatty acids.
Are estimated to make up 2-4% of our total
Calories.
Are reported in several studies to raise LDL-
cholesterol and lower HDL-cholesterol.
42
Learning Check
(1) True or (2) False
43
Solution
(1) True or (2) False
44
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 +3H2O
O
CH2 O C (CH2)14CH3 CH2 OH
O
CH OH + 3 HO C (CH2)14CH3
CH2 OH
45
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.
46
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
CH2 OH “soap”
47
Learning Check
48
Solution
What products are obtained from the complete
hydrolysis of glyceryl trioleate?
1. Glycerol and 3 oleic acids
49
Learning Check
Write the product of the following reaction.
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
50
Solution
O
CH2 O C (CH2)14CH3
O
CH O C (CH2)14CH3
O
CH2 O C (CH2)14CH3
51
Chapter 17 Lipids
17.5
Glycerophospholipids
Fatty acid
Fatty acid
Glycerol
Amino
PO4
alcohol
Fatty acid
Fatty acid
Glycerol
Amino
PO4
alcohol
53
Glycerophospholipids Are Polar
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− 54
serine
Structure and Polarity of A
Glycerophospholipid
1. glyceryl trioleate
2. cephalin
3. choline
4. palmitic acid
57
Solution
Identify each as a
A. fatty acid B. triacylglycerol
C. amino alcohol D. glycerophospholipid
58
Learning Check
Identify the components and type of glycerophospholipid
O
║
CH2−O −C −(CH2)16 −CH3
O
║
CH2−O −C −(CH2)16 −CH3
+
O NH3
║ │
CH2−O −P −O − CH2−CH−COO-
│
O- 59
Solution
Identify the components and type of glycerophospholipid
O
║
CH2−O −C −(CH2)16 −CH3
O 2 stearic acids
║
CH2−O −C −(CH2)16 −CH3
+
O NH3
║ │ type = cephalin
CH2−O −P −O − CH2−CH−COO-
│ serine
O-
phosphate amino alcohol
60
Chapter 17 Lipids
17.6
Sphingolipids
61
Sphingolipids
Sphingolipids
Are similar to phospholipids.
Contain sphingosine (a long-chain amino alcohol), a
fatty acid, phosphate, and a small amino alcohol.
Have polar and nonpolar regions.
fatty acid
sphingosine
amino
PO4
alcohol 62
Sphingosine
CH3−(CH2)12 −CH=CH−CH−OH
│
CH−NH2
│
CH2−OH
sphingosine
63
Sphingolipids
In sphingomyelin, a sphingolipid found in nerve cells
There is an amide bond between a fatty acid and
sphingosine, an 18-carbon alcohol.
65
Glycosphingolipids and
Cerebrosides
Glycosphingolipids
Are sphingolipids that contain
monosaccharides.
Can be a cerebroside with galactose.
66
Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
Gangliosides
Gangliosides
Are similar to cerebrosides, but contain two or
more monosaccharides.
Are important in neurons.
Act as receptor for hormones and viruses.
Can accumulate and cause genetic diseases.
67
Gangliosides
GM2 is a ganglioside
That accumulates in Tay-Sachs disease.
TABLE 17.3
69
Learning Check
Identify each as a
1) Fatty acid 2) Triacylglycerol
3) Amino alcohol 4) Glycerophospholipid
5) Glycosphingolipid
A. Glyceryl trioleate
B. Cephalin
C. Choline
D. Galactocerebroside
E. Palmitic acid
70
Solution
71
Chapter 17 Lipids
17.7
Steroids: Cholesterol, Bile Salts,
and Steroid Hormones
CH3 CH3
CH3
CH3
CH3
HO
Copyright © 2007 by Pearson Education, Inc.
Publishing as Benjamin Cummings 72
Steroid Nucleus
A steroid nucleus consists of
3 cyclohexane rings.
1 cyclopentane ring.
No fatty acids.
steroid nucleus
73
Cholesterol
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
74
Cholesterol in the Body
A normal, open artery.
Cholesterol in the body
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
Copyright © 2007 by Pearson Education, Inc. 75
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Cholesterol in Foods
76
Learning Check
D
CH3 CH3
CH3
B CH3
CH3
A
C
HO 77
Solution
Match the components of the cholesterol molecule with
the following:
D carbon chain A hydroxyl group
C steroid nucleus B methyl group
D
CH3 CH3
CH3
B CH3
CH3
A
C
HO 78
Bile Salts
Bile salts
Are synthesized in the liver from cholesterol.
Are stored in the gallbladder.
Are secreted into the small intestine.
Have a polar and a nonpolar region
Mix with fats to break them part.
Emulsify fat particles to provide large surface area.
79
Bile Salts
O
CH3 CH2
OH C
N COO- Na+
CH3
H Polar region
CH3
HO OH
Nonpolar region
80
Lipoproteins
Lipoproteins
• Combine lipids with proteins and phospholipids.
• Are soluble in water because the surface consists of
polar lipids.
81
TABLE 17.5
82
Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
Transport of Lipoproteins in
the Body
83
Steroid Hormones
Steroid hormones
Are chemical
messengers in cells.
Are produced from
cholesterol.
Include sex hormones
such as androgens
(testosterone) in
males and estrogens
(estradiol) in females.
84
85
Adrenal Corticosteroids
86
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.
87
Learning Check
Identify each as a
1. fatty acid 2. steroid 3. triacylglycerol
4. phospholipid 5. sphingolipid
A. cholesterol
B. glycerol, 2 fatty acids, phosphate, and choline
C. glyceryl tristearate
D. sphingosine, fatty acid, phosphate, and choline
E. estradiol
F. bile salts
G. lipids in plasma membranes
88
Solution
A. cholesterol 2 steroid
B. glycerol, 2 fatty acids, phosphate, and choline
4 phospholipid
C. glyceryl tristearate 3 triacylglycerol
D. sphingosine, fatty acid, phosphate, and choline
5 sphingolipid
E. estradiol 2 steroid
F. bile salts 2 steroid
G. lipids in plasma membranes
4 phospholipid, 5 sphingolipid
.
89