4.5. Lec (4 & 5) BCHM-201

Title: lecture (4&5)
Lipid Chemistry
Present By: Associate

Prof.Ingy Badawy
Outlines
• 1. Lipid classification
• 2. Fatty acids
• 3. Eicosanoids
• 4. Simple lipids
• 5. Complex lipids
• 6. Derived lipids
Lipids
Lipids
Copyright © 2007 by Pearson Education, Inc.

Publishing as Benjamin Cummings
3
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.
4
Types of Lipids
The types of lipids containing fatty acids are
• Waxes.
• Fats and oils (triacylglycerols).
• Glycerophospholipids.
• Prostaglandins.
• Not steroids, as they do not contain fatty acids.
5
Structures of Lipids
Copyright © 2007 by Pearson Education, Inc. 6

15.2 Fatty Acids

7
Fatty Acids
Fatty acids
• Are long-chain carboxylic acids.
• Typically contain 12-18 carbon
atoms.
• Are insoluble in water.
• Can be saturated or
unsaturated.
Copyright © 2007 by Pearson Education, Inc. 8

Fatty Acid Formulas
The formulas for fatty acids are written as
• Condensed formulas.
• Line-bond formulas.
• For example caprylic acid with 8 carbon atoms.
CH3—(CH2)6—COOH
CH3—CH2—CH2—CH2—CH2—CH2—CH2—COOH
O
OH
9
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.
Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 10

Some Saturated Fatty Acids
Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
11
Unsaturated Fatty Acids
Unsaturated fatty acids
• Have one or more double C=C bond
• Typically contain cis double bonds.
12
Properties of Unsaturated Fatty Acids
Unsaturated fatty acids “kinks” in
chain
• Have “kinks” in the fatty
acid chains.
• Do not pack closely.
• Have few attractions
between chains.
• Have low melting points.
• Are liquids at room
temperature.
13
Unsaturated Fatty Acids
14
Comparing Melting Points of Some Fatty Acids
15
Learning Check
Assign the melting points of –17°C, 13°C, and 69°C
to the correct fatty acid. Explain.
stearic acid (18 C) saturated
oleic acid (18 C) one double bond
linoleic acid (18 C) two double bonds
16
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
17
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

18
Prostaglandins in the Body
Prostaglandins are
• Produced by injured
tissues.
• Involved in pain, fever,
and inflammation.
• Not produced when
anti-inflammatory
drugs such as aspirin
inhibit their synthesis.
19
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
Publishing as Benjamin Cummings 20
Some Omega-6 and Omega-3
Fatty Acids
21
Learning Check
Write a fatty acid with 10 carbon atoms that

is:
A. saturated
B. monounsaturated omega-3
C. monounsaturated omega-6
22
Solution
Write a fatty acid with 10 carbon atoms that is:
A. saturated
CH3—CH2—CH2—CH2—CH2—CH2—CH2—CH2—CH2—COOH
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
23
Waxes, Fats, and Oils

24
Waxes
Waxes are
• Esters of saturated fatty acids and long-chain
alcohols.
• Coatings that prevent loss of water by leaves of
TABLE 17.2
plants.
25
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.

26
Triacylglycerols
In a triacylglycerol,
• Glycerol forms ester bonds with three fatty acids.
27
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
28
Olive Oil
Olive oil
• Contains a high
percentage of oleic
acid, which is a
monounsaturated
fatty acid with one cis
double bond.
29
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
30
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
31
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.
A triacylglycerol that is an oil

• Is liquid at room temperature.
• Is prevalent in plants such as olive and safflower.
32
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.
33
Diagram of Triacylglycerol with Unsaturated Fatty
Acids
Unsaturated fatty acid

chains have kinks that
do not allow close
packing.

Saturated and Unsaturated Fatty Acids In Fats
and Oils

Chemical Properties of Triacylglycerols

36
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.
37
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.
38
Copyright © 2007 by Pearson Education, Inc Publishing as Benjamin Cummings
Hydrogenation
O
CH2 O C (CH2)5CH CH(CH2)7CH3
O Ni
CH O C (CH2)5CH CH(CH2)7CH3 + 3H2
O O
CH2 O C (CH2)5CH CH(CH2)7CH3 CH2 O C (CH2)14CH3
O
glyceryl tripalmitoleate
CH O C (CH2)14CH3
(tripalmitolean)
O
CH2 O C (CH ) CH
glyceryl tripalmitate 2 14 3
(tripalmitin)
39
Learning Check
What product(s) is obtained from the complete
hydrogenation of glyceryl trioleate?
1. Glycerol and 3 oleic acids

2. Glyceryltristearate
3. Glycerol and 3 stearic acids
40
Solution
What product(s) is obtained from the complete
hydrogenation of glyceryl trioleate?
2. Glyceryltristearate
41
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.
42
Cis and Trans Fatty Acids
Unsaturated fatty acids can be
• Cis with bulky groups on same side of C=C.
CH3─ (CH2)5 (CH2)7─ COOH cis
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
43
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 reported to raise
LDL-cholesterol and lower HDL-cholesterol.
44
Learning Check
(1) True or (2) False
A. There are more unsaturated fats in vegetable oils.

B. Vegetable oils have higher melting points than
fats.
C. Hydrogenation of oils converts some cis-double
bonds to trans- double bonds.
D. Animal fats have more saturated fats.
45
Solution
(1) True or (2) False
A. T There are more unsaturated fats in vegetable

oils.
B. F Vegetable oils have higher melting points than
fats.
C. T Hydrogenation of oils converts some cis-double
bonds to trans- double bonds.
D. T Animal fats have more saturated fats.
46
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
47
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.
48
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”
49
Learning Check
What products are obtained from the complete
hydrolysis of glyceryl trioleate?
2. Glyceryl tristearate
3. Glycerol and 3 stearic acids
50
Solution
What products are obtained from the
complete hydrolysis of glyceryl trioleate?
51
Learning Check
Write the product of the following reaction.
O
O
Ni
CH O C (CH2)5CH CH(CH2)7CH3 + 3 H2
O
52
Solution
O
CH2 O C (CH2)14CH3
O
CH O C (CH2)14CH3
O
CH2 O C (CH2)14CH3
53
Glycerophospholipids
Glycerophospholipids are
• 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
54
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−
serine
55
Structure and Polarity of A
Glycerophospholipid
56
Lecithin and Cephalin
Lecithin and cephalin are glycerophospholipids
• Abundant in brain and nerve tissues.
• Found in egg yolk, wheat germ, and yeast.
Copyright © 2007 by Pearson Education, Inc Publishing as Benjamin Cummings

57
Learning Check
Identify each as a
A. fatty acid B. triacylglycerol
C. amino alcohol D. glycerophospholipid
1. glyceryl trioleate
2. cephalin
3. choline
4. palmitic acid
58
Solution
Identify each as a
A. fatty acid B. triacylglycerol
C. amino alcohol D. glycerophospholipid
1. glyceryl trioleate B. triacylglycerol

2. cephalin D. glycerophospholipid
3. choline C. amino alcohol
4. palmitic acid A. fatty acid
59
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-
60
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
61
Sphingolipids

62
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
63
Sphingosine
Sphingosine is a long-chain unsaturated amino alcohol.
CH3−(CH2)12 −CH=CH−CH−OH
│
CH−NH2
│
CH2−OH
sphingosine
64
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
• Glycosphingolipids
contain
monosaccharides
bonded to the –OH
of sphingosine by a
glycosidic bond.
66
Glycosphingolipids and Cerebrosides
Glycosphingolipids
• Are sphingolipids that contain
monosaccharides.
• Can be a cerebroside with galactose.

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.
68
Gangliosides
GM2 is a ganglioside
• That accumulates in Tay-Sachs disease.
69
Lipid Diseases (Lipidoses)
• In many lipid diseases, the deficiency of an enzyme
causes the accumulation of glycolipids.
TABLE 17.3
70
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
71
Solution
A. Glyceryl trioleate 2) Triacylglycerol

B. Cephalin 4) Glycerophospholipid
C. Choline 3) Amino alcohol
D. Galactocerebroside 5) Glycosphingolipid
E. Palmitic acid 1) Fatty acid
72
Steroids: Cholesterol, Bile Salts, and
Steroid Hormones
CH3 CH3
CH3
CH3
CH3
HO
73
Steroid Nucleus
A steroid nucleus consists
of
• 3 cyclohexane rings.
• 1 cyclopentane ring.
• No fatty acids.
steroid nucleus
74
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
75
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
Publishing as Benjamin Cummings 76
Cholesterol in Foods
Cholesterol is TABLE 17.4
• Synthesized in
the liver.
• Obtained from
foods.
• Considered
elevated if
plasma
cholesterol
exceeds 200
mg/dL. Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
77
Learning Check
Match the components of the cholesterol molecule

with
the following:
___ carbon chain ___hydroxyl group
___ steroid nucleus D ___methyl group
CH3 CH3
CH3
B
CH3
CH3
A
C
HO
78
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
79
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.
80
Bile Salts
cholic acid, a bile acid glycine, an amino acid
O
CH3 CH2
OH C
N COO- Na+
CH3
H Polar region
CH3
HO OH
Nonpolar region
sodium glycocholate, a bile salt
81
Lipoproteins
Lipoproteins
• Combine lipids with proteins and phospholipids.
• Are soluble in water because the surface consists
of polar lipids.
82
Types of Lipoproteins
Lipoproteins
• Differ in density, composition, and function.
• Include low-density lipoprotein (LDLs) and high-
density lipoprotein (HDLs).
TABLE 17.5

Transport of Lipoproteins in the
Body
84
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.
85
Adrenal Corticosteroids
Adrenal corticosteroids are steroid hormones
that
• 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.
86
Adrenal Corticosteroids
87
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.
88
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
89
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
.
90
Cell Membranes

91
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.
92
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.
93
Fluid Mosaic Model

94
Transport Through Cell Membranes
The transport of substances through cell
Membranes involves
• 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.
95
Transport Pathways Through Cell Membranes

96
Learning Check
The transport of particles across a cell membrane from
high concentration to low concentration is called
1. Facilitated transport
2. Diffusion
3. Active transport
97
Solution
The transport of particles across a cell membrane from
high concentration to low concentration is called
2. Diffusion
98

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4.5. Lec (4 & 5) BCHM-201

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Title: lecture (4&5)

Present By: Associate

Copyright © 2007 by Pearson Education, Inc.

Copyright © 2007 by Pearson Education, Inc. 6

Copyright © 2007 by Pearson Education, Inc.

Copyright © 2007 by Pearson Education, Inc. 8

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 10

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

 In fish oils are mostly omega-3 with the

Write a fatty acid with 10 carbon atoms that

Copyright © 2007 by Pearson Education, Inc.

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

Copyright © 2007 by Pearson Education, Inc.

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

A triacylglycerol that is an oil

Unsaturated fatty acid

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 34

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 35

Copyright © 2007 by Pearson Education, Inc.

1. Glycerol and 3 oleic acids

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

A. There are more unsaturated fats in vegetable oils.

A. T There are more unsaturated fats in vegetable

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

Copyright © 2007 by Pearson Education, Inc Publishing as Benjamin Cummings

1. glyceryl trioleate B. triacylglycerol

Copyright © 2007 by Pearson Education, Inc.

Sphingosine is a long-chain unsaturated amino alcohol.

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

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Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

A. Glyceryl trioleate 2) Triacylglycerol

Match the components of the cholesterol molecule

sodium glycocholate, a bile salt

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 83

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

Copyright © 2007 by Pearson Education, Inc.

Copyright © 2007 by Pearson Education, Inc.

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

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