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Chapter 17
Lipids

Opening Essay

On July 11, 2003, the Food and Drug Administration amended its food labeling regulations to
require that manufacturers list the amount of trans fatty acids on Nutrition Facts labels of foods
and dietary supplements, effective January 1, 2006. This amendment was a response to published
studies demonstrating a link between the consumption of trans fatty acids and an increased risk
of heart disease. Trans fatty acids are produced in the conversion of liquid oils to solid fats, as in
the creation of many commercial margarines and shortenings. They have been shown to increase
the levels of low-density lipoproteins (LDLs)—complexes that are often referred to as bad
cholesterol—in the blood. In this chapter, you will learn about fatty acids and what is meant by a
trans fatty acid, as well as the difference between fats and oils. You will also learn what
cholesterol is and why it is an important molecule in the human body.
 All food products must
display the amount of
trans fatty acids they
contain. A listing of 0 g
means that a serving
contains less than 0.5 g of
trans fatty acids.

© Thinkstock

Fats and oils, found in many of the foods we eat, belong to a class of biomolecules known as lipids.
Gram for gram, they pack more than twice the caloric content of carbohydrates: the oxidation of fats
and oils supplies about 9 kcal of energy for every gram oxidized, whereas the oxidation of
carbohydrates supplies only 4 kcal/g. Although the high caloric content of fats may be bad news for
the dieter, it says something about the efficiency of nature’s designs. Our bodies use carbohydrates,
primarily in the form of glucose, for our immediate energy needs. Our capacity for storing
carbohydrates for later use is limited to tucking away a bit of glycogen in the liver or in muscle tissue.
We store our reserve energy in lipid form, which requires far less space than the same amount of
energy stored in carbohydrate form.

Lipids have other biological functions besides energy storage. They are a major component of the
membranes of the 10 trillion cells in our bodies. They serve as protective padding and insulation for
vital organs. Furthermore, without lipids in our diets, we would be deficient in the fat-soluble
vitamins A, D, E, and K.

Lipids are not defined by the presence of specific functional groups, as carbohydrates are, but by a
physical property—solubility. Compounds isolated from body tissues are classified as lipids if they
are more soluble in organic solvents, such as dichloromethane, than in water. By this criterion, the
lipid category includes not only fats and oils, which are esters of the trihydroxy alcohol glycerol and
fatty acids, but also compounds that incorporate functional groups derived from phosphoric acid,
carbohydrates, or amino alcohols, as well as steroid compounds such as cholesterol. (Figure 17.1
"Lipid Organization Based on Structural Relationships" presents one scheme for classifying the
various kinds of lipids.) We will discuss the various kinds of lipids by considering one subclass at a
time and pointing out structural similarities and differences as we go.

Figure 17.1 Lipid Organization Based on Structural Relationships

17.1 Fatty Acids

LEARNING OBJECTIVE

1. Recognize the structures of common fatty acids and classify them as saturated, monounsaturated,
or polyunsaturated.

Fatty acids are carboxylic acids that are structural components of fats, oils, and all other categories
of lipids, except steroids. More than 70 have been identified in nature. They usually contain an even
number of carbon atoms (typically 12–20), are generally unbranched, and can be classified by the
presence and number of carbon-to-carbon double bonds. Thus, saturated fatty acids contain no
carbon-to-carbon double bonds, monounsaturated fatty acids contain one carbon-to-carbon
double bond, and polyunsaturated fatty acids contain two or more carbon-to-carbon double
bonds. Table 17.1 "Some Common Fatty Acids Found in Natural Fats" lists some common fatty acids
and one important source for each. The atoms or groups around the double bonds in unsaturated
fatty acids can be arranged in either the cis or trans isomeric form. Naturally occurring fatty acids are
generally in the cis configuration. (For more information about cis-trans isomerism, see Chapter 13
"Unsaturated and Aromatic Hydrocarbons", Section 13.2 "Cis-Trans Isomers (Geometric Isomers)".)

Table 17.1 Some Common Fatty Acids Found in Natural Fats

Abbreviated Melting
Name Condensed Structural Formula Source
Structural Formula Point (°C)

palm kernel
lauric acid C11H23COOH CH3(CH2)10COOH 44
oil

oil of
myristic acid C13H27COOH CH3(CH2)12COOH 58
nutmeg

palmitic acid C15H31COOH CH3(CH2)14COOH 63 palm oil

palmitoleic C15H29COOH CH3(CH2)5CH=CH(CH2)7COOH macadamia

0.5
acid oil

stearic acid C17H35COOH CH3(CH2)16COOH 70 cocoa butter

oleic acid C17H33COOH CH3(CH2)7CH=CH(CH2)7COOH 16 olive oil

linoleic acid C17H31COOH CH3(CH2)3(CH2CH=CH)2(CH2)7COOH −5 canola oil

α-linolenic
C17H29COOH CH3(CH2CH=CH)3(CH2)7COOH −11 flaxseed
acid

arachidonic
C19H31COOH CH3(CH2)4(CH2CH=CH)4(CH2)2COOH −50 liver
acid

Two polyunsaturated fatty acids—linoleic and α-linolenic acids—are termed essential fatty acids
because humans must obtain them from their diets. Both substances are required for normal growth
and development, but the human body does not synthesize them. The body uses linoleic acid to
synthesize many of the other unsaturated fatty acids, such as arachidonic acid, a precursor for the
synthesis of prostaglandins. In addition, the essential fatty acids are necessary for the efficient
transport and metabolism of cholesterol. The average daily diet should contain about 4–6 g of the
essential fatty acids.

To Your Health: Prostaglandins

Prostaglandins are chemical messengers synthesized in the cells in which their physiological
activity is expressed. They are unsaturated fatty acids containing 20 carbon atoms and are
synthesized from arachidonic acid—a polyunsaturated fatty acid—when needed by a particular
cell. They are called prostaglandins because they were originally isolated from semen found in
the prostate gland. It is now known that they are synthesized in nearly all mammalian tissues and
affect almost all organs in the body. The five major classes of prostaglandins are designated as
PGA, PGB, PGE, PGF, and PGI. Subscripts are attached at the end of these abbreviations to
denote the number of double bonds outside the five-carbon ring in a given prostaglandin.

The prostaglandins are among the most potent biological substances known. Slight structural
differences give them highly distinct biological effects; however, all prostaglandins exhibit some
ability to induce smooth muscle contraction, lower blood pressure, and contribute to the
inflammatory response. Aspirin and other nonsteroidal anti-inflammatory agents, such as
ibuprofen, obstruct the synthesis of prostaglandins by inhibiting cyclooxygenase, the enzyme
needed for the initial step in the conversion of arachidonic acid to prostaglandins.

Their wide range of physiological activity has led to the synthesis of hundreds of prostaglandins
and their analogs. Derivatives of PGE2 are now used in the United States to induce labor. Other

prostaglandins have been employed clinically to lower or increase blood pressure, inhibit stomach
secretions, relieve nasal congestion, relieve asthma, and prevent the formation of blood clots,
which are associated with heart attacks and strokes.
Although we often draw the carbon atoms in a straight line, they actually have more of a zigzag
configuration (part (a) of Figure 17.2 "The Structure of Saturated Fatty Acids"). Viewed as a whole,
however, the saturated fatty acid molecule is relatively straight (part (b) of Figure 17.2 "The Structure
of Saturated Fatty Acids"). Such molecules pack closely together into a crystal lattice, maximizing the
strength of dispersion forces and causing fatty acids and the fats derived from them to have relatively
high melting points. In contrast, each cis carbon-to-carbon double bond in an unsaturated fatty acid
produces a pronounced bend in the molecule, so that these molecules do not stack neatly. As a result,
the intermolecular attractions of unsaturated fatty acids (and unsaturated fats) are weaker, causing
these substances to have lower melting points. Most are liquids at room temperature.

Figure 17.2 The Structure of Saturated Fatty Acids

(a) There is a zigzag pattern formed by the carbon-to-carbon single bonds in the ball-and-stick model of a
palmitic acid molecule. (b) A space-filling model of palmitic acid shows the overall straightness of a saturated
fatty acid molecule.

Waxes are esters formed from long-chain fatty acids and long-chain alcohols. Most natural waxes are
mixtures of such esters. Plant waxes on the surfaces of leaves, stems, flowers, and fruits protect the
plant from dehydration and invasion by harmful microorganisms. Carnauba wax, used extensively in
floor waxes, automobile waxes, and furniture polish, is largely myricyl cerotate, obtained from the
leaves of certain Brazilian palm trees. Animals also produce waxes that serve as protective coatings,
keeping the surfaces of feathers, skin, and hair pliable and water repellent. In fact, if the waxy coating
on the feathers of a water bird is dissolved as a result of the bird swimming in an oil slick, the feathers
become wet and heavy, and the bird, unable to maintain its buoyancy, drowns.
 CONCEPT REVIEW EXERCISES

1. Give an example of each compound.

a. saturated fatty acid

b. polyunsaturated fatty acid
c. monounsaturated fatty acid

2. Why do unsaturated fatty acids have lower melting points than saturated fatty acids?

ANSWERS

1. a. stearic acid (answers will vary)

b. linoleic acid (answers will vary)
c. palmitoleic acid (answers will vary)

2. Unsaturated fatty acids cannot pack as tightly together as saturated fatty acids due to the presence of the
cis double bond that puts a “kink” or bend in the hydrocarbon chain.

K E Y TA K E AWAY S

Fatty acids are carboxylic acids that are the structural components of many lipids. They may be
saturated or unsaturated.
Most fatty acids are unbranched and contain an even number of carbon atoms.
Unsaturated fatty acids have lower melting points than saturated fatty acids containing the same
number of carbon atoms.

EXERCISES
1. Classify each fatty acid as saturated or unsaturated and indicate the number of carbon atoms in each
molecule.

a. palmitoleic acid
b. myristic acid
c. linoleic acid

2. Classify each fatty acid as saturated or unsaturated and indicate the number of carbon atoms in each
molecule.

a. stearic acid
b. oleic acid
c. palmitic acid

3. Write the condensed structural formula for each fatty acid.

a. lauric acid
b. palmitoleic acid
c. linoleic acid

4. Write the condensed structural formulas for each fatty acid.

a. oleic acid
b. α-linolenic acid
c. palmitic acid

5. Arrange these fatty acids (all contain 18 carbon atoms) in order of increasing melting point. Justify your
arrangement.

a.

b.

c.

6. Arrange these fatty acids (all contain 16 carbon atoms) in order of increasing melting point. Justify your
arrangement.

a. CH3(CH2)14COOH
 b.

c.

ANSWERS

1. a. unsaturated; 16 carbon atoms

b. saturated; 14 carbon atoms
c. unsaturated; 18 carbon atoms

3. a. CH3(CH2)10COOH

b. CH3(CH2)5CH=CH(CH2)7COOH

c. CH3(CH2)3(CH2CH=CH)2(CH2)7COOH

5. c < a < b; an increase in the number of double bonds will lower the melting point because it is more
difficult to closely pack the fatty acids together.

17.2 Fats and Oils

LEARNING OBJECTIVES

1. Explain why fats and oils are referred to as triglycerides.

2. Explain how the fatty acid composition of the triglycerides determines whether a substance is a fat
or oil.
3. Describe the importance of key reactions of triglycerides, such as hydrolysis, hydrogenation, and
oxidation.

Fats and oils are the most abundant lipids in nature. They provide energy for living organisms,
insulate body organs, and transport fat-soluble vitamins through the blood.
Structures of Fats and Oils

Fats and oils are called triglycerides (or triacylcylgerols) because they are esters composed of three
fatty acid units joined to glycerol, a trihydroxy alcohol:

If all three OH groups on the glycerol molecule are esterified with the same fatty acid, the resulting
ester is called a simple triglyceride. Although simple triglycerides have been synthesized in the
laboratory, they rarely occur in nature. Instead, a typical triglyceride obtained from naturally
occurring fats and oils contains two or three different fatty acid components and is thus termed a
mixed triglyceride.

A triglyceride is called a fat if it is a solid at 25°C; it is called an oil if it is a liquid at that temperature.
These differences in melting points reflect differences in the degree of unsaturation and number of
carbon atoms in the constituent fatty acids. Triglycerides obtained from animal sources are usually
solids, while those of plant origin are generally oils. Therefore, we commonly speak of animal fats and
vegetable oils.

No single formula can be written to represent the naturally occurring fats and oils because they are
highly complex mixtures of triglycerides in which many different fatty acids are represented. Table
17.2 "Average Fatty Acid Composition of Some Common Fats and Oils (%)*" shows the fatty acid
compositions of some common fats and oils. The composition of any given fat or oil can vary
depending on the plant or animal species it comes from as well as on dietetic and climatic factors. To
cite just one example, lard from corn-fed hogs is more highly saturated than lard from peanut-fed
hogs. Palmitic acid is the most abundant of the saturated fatty acids, while oleic acid is the most
abundant unsaturated fatty acid.

Table 17.2 Average Fatty Acid Composition of Some Common Fats and Oils (%)*

Lauric Myristic Palmitic Stearic Oleic Linoleic Linolenic

Fats

butter (cow) 3 11 27 12 29 2 1

tallow 3 24 19 43 3 1

lard 2 26 14 44 10

Oils

canola oil 4 2 62 22 10

coconut oil† 47 18 9 3 6 2

corn oil 11 2 28 58 1

olive oil 13 3 71 10 1

peanut oil 11 2 48 32

soybean oil 11 4 24 54 7

*Totals less than 100% indicate the presence of fatty acids with fewer than 12 carbon atoms or more
than 18 carbon atoms.
†Coconut oil is highly saturated. It contains an unusually high percentage of the low-melting C , C , and
8 10
C12 saturated fatty acids.

Terms such as saturated fat or unsaturated oil are often used to describe the fats or oils obtained
from foods. Saturated fats contain a high proportion of saturated fatty acids, while unsaturated oils
contain a high proportion of unsaturated fatty acids. The high consumption of saturated fats is a
factor, along with the high consumption of cholesterol, in increased risks of heart disease. (For more
information about cholesterol, see Section 17.4 "Steroids".)

Physical Properties of Fats and Oils

Contrary to what you might expect, pure fats and oils are colorless, odorless, and tasteless. The
characteristic colors, odors, and flavors that we associate with some of them are imparted by foreign
substances that are lipid soluble and have been absorbed by these lipids. For example, the yellow
color of butter is due to the presence of the pigment carotene; the taste of butter comes from two
compounds—diacetyl and 3-hydroxy-2-butanone—produced by bacteria in the ripening cream from
which the butter is made.
Fats and oils are lighter than water, having densities of about 0.8 g/cm3. They are poor conductors of
heat and electricity and therefore serve as excellent insulators for the body, slowing the loss of heat
through the skin.

Chemical Reactions of Fats and Oils

Fats and oils can participate in a variety of chemical reactions—for example, because triglycerides are
esters, they can be hydrolyzed in the presence of an acid, a base, or specific enzymes known as lipases.
The hydrolysis of fats and oils in the presence of a base is used to make soap and is called
saponification. Today most soaps are prepared through the hydrolysis of triglycerides (often from
tallow, coconut oil, or both) using water under high pressure and temperature [700 lb/in2 (∼50 atm
or 5,000 kPa) and 200°C]. Sodium carbonate or sodium hydroxide is then used to convert the fatty
acids to their sodium salts (soap molecules):

Looking Closer: Soaps

Ordinary soap is a mixture of the sodium salts of various fatty acids, produced in one of the oldest
organic syntheses practiced by humans (second only to the fermentation of sugars to produce
ethyl alcohol). Both the Phoenicians (600 BCE) and the Romans made soap from animal fat and
wood ash. Even so, the widespread production of soap did not begin until the 1700s. Soap was
traditionally made by treating molten lard or tallow with a slight excess of alkali in large open
vats. The mixture was heated, and steam was bubbled through it. After saponification was
completed, the soap was precipitated from the mixture by the addition of sodium chloride (NaCl),
removed by filtration, and washed several times with water. It was then dissolved in water and
reprecipitated by the addition of more NaCl. The glycerol produced in the reaction was also
recovered from the aqueous wash solutions.
 Pumice or sand is added to produce scouring soap, while ingredients such as perfumes or dyes are
added to produce fragrant, colored soaps. Blowing air through molten soap produces a floating
soap. Soft soaps, made with potassium salts, are more expensive but produce a finer lather and
are more soluble. They are used in liquid soaps, shampoos, and shaving creams.

Dirt and grime usually adhere to skin, clothing, and other surfaces by combining with body oils,
cooking fats, lubricating greases, and similar substances that act like glues. Because these
substances are not miscible in water, washing with water alone does little to remove them. Soap
removes them, however, because soap molecules have a dual nature. One end, called the head,
carries an ionic charge (a carboxylate anion) and therefore dissolves in water; the other end, the
tail, has a hydrocarbon structure and dissolves in oils. The hydrocarbon tails dissolve in the soil;
the ionic heads remain in the aqueous phase, and the soap breaks the oil into tiny soap-enclosed
droplets called micelles, which disperse throughout the solution. (For more information about
cell structure, see Section 17.3 "Membranes and Membrane Lipids".) The droplets repel each
other because of their charged surfaces and do not coalesce. With the oil no longer “gluing” the
dirt to the soiled surface (skin, cloth, dish), the soap-enclosed dirt can easily be rinsed away.

The double bonds in fats and oils can undergo hydrogenation and also oxidation. The hydrogenation
of vegetable oils to produce semisolid fats is an important process in the food industry. Chemically, it
is essentially identical to the catalytic hydrogenation reaction described for alkenes in Chapter 13
"Unsaturated and Aromatic Hydrocarbons", Section 13.4 "Chemical Properties of Alkenes".
In commercial processes, the number of double bonds that are hydrogenated is carefully controlled to
produce fats with the desired consistency (soft and pliable). Inexpensive and abundant vegetable oils
(canola, corn, soybean) are thus transformed into margarine and cooking fats. In the preparation of
margarine, for example, partially hydrogenated oils are mixed with water, salt, and nonfat dry milk,
along with flavoring agents, coloring agents, and vitamins A and D, which are added to approximate
the look, taste, and nutrition of butter. (Preservatives and antioxidants are also added.) In most
commercial peanut butter, the peanut oil has been partially hydrogenated to prevent it from
separating out. Consumers could decrease the amount of saturated fat in their diet by using the
original unprocessed oils on their foods, but most people would rather spread margarine on their
toast than pour oil on it.

Many people have switched from butter to margarine or vegetable shortening because of concerns
that saturated animal fats can raise blood cholesterol levels and result in clogged arteries. However,
during the hydrogenation of vegetable oils, an isomerization reaction occurs that produces the trans
fatty acids mentioned in the opening essay. However, studies have shown that trans fatty acids also
raise cholesterol levels and increase the incidence of heart disease. Trans fatty acids do not have the
bend in their structures, which occurs in cis fatty acids and thus pack closely together in the same way
that the saturated fatty acids do. Consumers are now being advised to use polyunsaturated oils and
soft or liquid margarine and reduce their total fat consumption to less than 30% of their total calorie
intake each day.

Fats and oils that are in contact with moist air at room temperature eventually undergo oxidation and
hydrolysis reactions that cause them to turn rancid, acquiring a characteristic disagreeable odor. One
cause of the odor is the release of volatile fatty acids by hydrolysis of the ester bonds. Butter, for
example, releases foul-smelling butyric, caprylic, and capric acids. Microorganisms present in the air
furnish lipases that catalyze this process. Hydrolytic rancidity can easily be prevented by covering the
fat or oil and keeping it in a refrigerator.

Another cause of volatile, odorous compounds is the oxidation of the unsaturated fatty acid
components, particularly the readily oxidized structural unit

in polyunsaturated fatty acids, such as linoleic and linolenic acids. One particularly offensive product,
formed by the oxidative cleavage of both double bonds in this unit, is a compound called
malonaldehyde.
Rancidity is a major concern of the food industry, which is why food chemists are always seeking new
and better antioxidants, substances added in very small amounts (0.001%–0.01%) to prevent
oxidation and thus suppress rancidity. Antioxidants are compounds whose affinity for oxygen is
greater than that of the lipids in the food; thus they function by preferentially depleting the supply of
oxygen absorbed into the product. Because vitamin E has antioxidant properties, it helps reduce
damage to lipids in the body, particularly to unsaturated fatty acids found in cell membrane lipids.

CONCEPT REVIEW EXERCISES

1. What functions does fat serve in the body?

2. Which of these triglycerides would you expect to find in higher amounts in oils? In fats? Justify your
choice.

ANSWERS

1. Fats provide energy for living organisms. They also provide insulation for body organs and transport fat-
soluble vitamins.

2. The triglyceride on the left is expected to be present in higher amounts in fats because it is composed of
a greater number of saturated fatty acids. The triglyceride on the right is expected to be present in higher
amounts in oils because it is composed of a greater number of unsaturated fatty acids.
 K E Y TA K E AWAY S

Fats and oils are composed of molecules known as triglycerides, which are esters composed of
three fatty acid units linked to glycerol.
An increase in the percentage of shorter-chain fatty acids and/or unsaturated fatty acids lowers
the melting point of a fat or oil.
The hydrolysis of fats and oils in the presence of a base makes soap and is known as
saponification.
Double bonds present in unsaturated triglycerides can be hydrogenated to convert oils (liquid) into
margarine (solid).
The oxidation of fatty acids can form compounds with disagreeable odors. This oxidation can be
minimized by the addition of antioxidants.

EXERCISES

1. Draw the structure for each compound.

a. trimyristin
b. a triglyceride likely to be found in peanut oil

2. Draw the structure for each compound.

a. tripalmitin
b. a triglyceride likely to be found in butter

3. Draw structures to write the reaction for the complete hydrogenation of tripalmitolein (see Table 17.1
"Some Common Fatty Acids Found in Natural Fats" for the condensed structure of palmitoleic acid).
Name the product formed.

4. Draw structures to write the reaction for the complete hydrogenation of trilinolein (see Table 17.1 "Some
Common Fatty Acids Found in Natural Fats" for the condensed structure of linoleic acid). Name the
product formed.

5. Draw structures to write the reaction for the hydrolysis of trilaurin in a basic solution (see Table 17.1
"Some Common Fatty Acids Found in Natural Fats" for the condensed structure of lauric acid).

6. Draw structures to write the reaction for the hydrolysis of tristearin in a basic solution (see Table 17.1
"Some Common Fatty Acids Found in Natural Fats" for the condensed structure of stearic acid).

7.

a. What compounds with a disagreeable odor are formed when butter becomes rancid?
 b. How are these compounds formed?
c. How can rancidity be prevented?

8.

a. What compound with a disagreeable odor is formed when unsaturated fatty acids react with oxygen
in the atmosphere?
b. How can this process be prevented?

ANSWERS

1.

3.

5.

7. a. smaller carboxylic acids, such as butyric, caprylic, and capric acids

b. These compounds are formed by the hydrolysis of the triglycerides found in butter.
 c. Rancidity can be prevented by covering the butter (to keep out moisture) and storing it in a
refrigerator. (Cold temperatures slow down hydrolysis reactions.)

17.3 Membranes and Membrane Lipids

LEARNING OBJECTIVES

1. Identify the distinguishing characteristics of membrane lipids.

2. Describe membrane components and how they are arranged.

All living cells are surrounded by a cell membrane. Plant cells (Figure 17.3 "An Idealized Plant Cell")
and animal cells (Figure 17.4 "An Idealized Animal Cell") contain a cell nucleus that is also
surrounded by a membrane and holds the genetic information for the cell. (For more information
about genetics and DNA, see Chapter 19 "Nucleic Acids".) Everything between the cell membrane and
the nuclear membrane—including intracellular fluids and various subcellular components such as the
mitochondria and ribosomes—is called the cytoplasm. The membranes of all cells have a
fundamentally similar structure, but membrane function varies tremendously from one organism to
another and even from one cell to another within a single organism. This diversity arises mainly from
the presence of different proteins and lipids in the membrane.

Figure 17.3 An Idealized Plant Cell

Not all the structures shown here occur in every type of plant cell.

Figure 17.4 An Idealized Animal Cell

The structures shown here will seldom all be found in a single animal cell.
The lipids in cell membranes are highly polar but have dual characteristics: part of the lipid is ionic
and therefore dissolves in water, whereas the rest has a hydrocarbon structure and therefore dissolves
in nonpolar substances. Often, the ionic part is referred to as hydrophilic, meaning “water loving,”
and the nonpolar part as hydrophobic, meaning “water fearing” (repelled by water). When allowed
to float freely in water, polar lipids spontaneously cluster together in any one of three arrangements:
micelles, monolayers, and bilayers (Figure 17.5 "Spontaneously Formed Polar Lipid Structures in
Water: Monolayer, Micelle, and Bilayer"). Micelles are aggregations in which the lipids’ hydrocarbon
tails—being hydrophobic—are directed toward the center of the assemblage and away from the
surrounding water while the hydrophilic heads are directed outward, in contact with the water. Each
micelle may contain thousands of lipid molecules. Polar lipids may also form a monolayer, a layer one
molecule thick on the surface of the water. The polar heads face into water, and the nonpolar tails
stick up into the air. Bilayers are double layers of lipids arranged so that the hydrophobic tails are
sandwiched between an inner surface and an outer surface consisting of hydrophilic heads. The
hydrophilic heads are in contact with water on either side of the bilayer, whereas the tails,
sequestered inside the bilayer, are prevented from having contact with the water. Bilayers like this
make up every cell membrane (Figure 17.6 "Schematic Diagram of a Cell Membrane").

Figure 17.5 Spontaneously Formed Polar Lipid Structures in Water: Monolayer, Micelle, and Bilayer

Figure 17.6 Schematic Diagram of a Cell Membrane

The membrane enclosing a typical animal cell is a phospholipid bilayer with embedded cholesterol and protein
molecules. Short oligosaccharide chains are attached to the outer surface.

In the bilayer interior, the hydrophobic tails (that is, the fatty acid portions of lipid molecules)
interact by means of dispersion forces. The interactions are weakened by the presence of unsaturated
fatty acids. As a result, the membrane components are free to mill about to some extent, and the
membrane is described as fluid.

The lipids found in cell membranes can be categorized in various ways. Phospholipids are lipids
containing phosphorus. Glycolipids are sugar-containing lipids. The latter are found exclusively on
the outer surface of the cell membrane, acting as distinguishing surface markers for the cell and thus
serving in cellular recognition and cell-to-cell communication. Sphingolipids are phospholipids or
glycolipids that contain the unsaturated amino alcohol sphingosine rather than glycerol.
Diagrammatic structures of representative membrane lipids are presented in Figure 17.7 "Component
Structures of Some Important Membrane Lipids".

Figure 17.7 Component Structures of Some Important Membrane Lipids

Phosphoglycerides (also known as glycerophospholipids) are the most abundant phospholipids in cell
membranes. They consist of a glycerol unit with fatty acids attached to the first two carbon atoms,
while a phosphoric acid unit, esterified with an alcohol molecule (usually an amino alcohol, as in part
(a) of Figure 17.8 "Phosphoglycerides") is attached to the third carbon atom of glycerol (part (b) of
Figure 17.8 "Phosphoglycerides"). Notice that the phosphoglyceride molecule is identical to a
triglyceride up to the phosphoric acid unit (part (b) of Figure 17.8 "Phosphoglycerides").

Figure 17.8 Phosphoglycerides

(a) Amino alcohols are commonly found in phosphoglycerides, which are evident in its structural formula (b).

There are two common types of phosphoglycerides. Phosphoglycerides containing ethanolamine as

the amino alcohol are called phosphatidylethanolamines or cephalins. Cephalins are found in brain
tissue and nerves and also have a role in blood clotting. Phosphoglycerides containing choline as the
amino alcohol unit are called phosphatidylcholines or lecithins. Lecithins occur in all living
organisms. Like cephalins, they are important constituents of nerve and brain tissue. Egg yolks are
especially rich in lecithins. Commercial-grade lecithins isolated from soybeans are widely used in
foods as emulsifying agents. An emulsifying agent is used to stabilize an emulsion—a dispersion of
two liquids that do not normally mix, such as oil and water. Many foods are emulsions. Milk is an
emulsion of butterfat in water. The emulsifying agent in milk is a protein called casein. Mayonnaise is
an emulsion of salad oil in water, stabilized by lecithins present in egg yolk.
Sphingomyelins, the simplest sphingolipids, each contain a fatty acid, a phosphoric acid,
sphingosine, and choline (Figure 17.9 "Sphingolipids"). Because they contain phosphoric acid, they
are also classified as phospholipids. Sphingomyelins are important constituents of the myelin sheath
surrounding the axon of a nerve cell. Multiple sclerosis is one of several diseases resulting from
damage to the myelin sheath.

Figure 17.9 Sphingolipids

(a) Sphingosine, an amino alcohol, is found in all sphingolipids. (b) A sphingomyelin is also known as a
phospholipid, as evidenced by the phosphoric acid unit in its structure.

Most animal cells contain sphingolipids called cerebrosides (Figure 17.10 "Cerebrosides").
Cerebrosides are composed of sphingosine, a fatty acid, and galactose or glucose. They therefore
resemble sphingomyelins but have a sugar unit in place of the choline phosphate group. Cerebrosides
are important constituents of the membranes of nerve and brain cells.

Figure 17.10 Cerebrosides

Cerebrosides are sphingolipids that contain a sugar unit.

The sphingolipids called gangliosides are more complex, usually containing a branched chain of
three to eight monosaccharides and/or substituted sugars. Because of considerable variation in their
sugar components, about 130 varieties of gangliosides have been identified. Most cell-to-cell
recognition and communication processes (e.g., blood group antigens) depend on differences in the
sequences of sugars in these compounds. Gangliosides are most prevalent in the outer membranes of
nerve cells, although they also occur in smaller quantities in the outer membranes of most other cells.
Because cerebrosides and gangliosides contain sugar groups, they are also classified as glycolipids.

Membrane Proteins

If membranes were composed only of lipids, very few ions or polar molecules could pass through their
hydrophobic “sandwich filling” to enter or leave any cell. However, certain charged and polar species
do cross the membrane, aided by proteins that move about in the lipid bilayer. The two major classes
of proteins in the cell membrane are integral proteins, which span the hydrophobic interior of the
bilayer, and peripheral proteins, which are more loosely associated with the surface of the lipid
bilayer (Figure 17.6 "Schematic Diagram of a Cell Membrane"). Peripheral proteins may be attached
to integral proteins, to the polar head groups of phospholipids, or to both by hydrogen bonding and
electrostatic forces.

Small ions and molecules soluble in water enter and leave the cell by way of channels through the
integral proteins. Some proteins, called carrier proteins, facilitate the passage of certain molecules,
such as hormones and neurotransmitters, by specific interactions between the protein and the
molecule being transported.
 CONCEPT REVIEW EXERCISES

1. Name the structural unit that must be present for a molecule to be classified as a

a. phospholipid.
b. glycolipid.
c. sphingolipid.

2. Why is it important that membrane lipids have dual character—part of the molecule is hydrophilic and
part of the molecule is hydrophobic?

3. Why do you suppose lecithins (phosphatidylcholines) are often added to processed foods such as hot
cocoa mix?

ANSWERS

1. a. a phosphate group
b. a saccharide unit (monosaccharide or more complex)
c. sphingosine

2. The dual character is critical for the formation of the lipid bilayer. The hydrophilic portions of the
molecule are in contact with the aqueous environment of the cell, while the hydrophobic portion of the
lipids is in the interior of the bilayer and provides a barrier to the passive diffusion of most molecules.

3. Lecithin acts as an emulsifying agent that aids in the mixing of the hot cocoa mix with water and keeps
the cocoa mix evenly distributed after stirring.

K E Y TA K E AWAY S

Lipids are important components of biological membranes. These lipids have dual characteristics:
part of the molecule is hydrophilic, and part of the molecule is hydrophobic.
Membrane lipids may be classified as phospholipids, glycolipids, and/or sphingolipids.
Proteins are another important component of biological membranes. Integral proteins span the
lipid bilayer, while peripheral proteins are more loosely associated with the surface of the
membrane.

EXERCISES
1. Classify each as a phospholipid, a glycolipid, and/or a sphingolipid. (Some lipids can be given more than
one classification.)

a.

b.

2. Classify each as a phospholipid, a glycolipid, and/or a sphingolipid. (Some lipids can be given more than
one classification.)

a.

b.

3. Draw the structure of the sphingomyelin that has lauric acid as its fatty acid and ethanolamine as its
amino alcohol.

4. Draw the structure of the cerebroside that has myristic acid as its fatty acid and galactose as its sugar.

5.

a. Distinguish between an integral protein and a peripheral protein.

b. What is one key function of integral proteins?
 ANSWERS

1. a. phospholipid
b. sphingolipid and glycolipid

3.

5. a. Integral proteins span the lipid bilayer, while peripheral proteins associate with the surfaces of the
lipid bilayer.
b. aid in the movement of charged and polar species across the membrane

17.4 Steroids

LEARNING OBJECTIVE

1. Identify the functions of steroids produced in mammals.

All the lipids discussed so far are saponifiable, reacting with aqueous alkali to yield simpler
components, such as glycerol, fatty acids, amino alcohols, and sugars. (For more information about
saponification, see Section 17.2 "Fats and Oils".) Lipid samples extracted from cellular material,
however, also contain a small but important fraction that does not react with alkali. The most
important nonsaponifiable lipids are the steroids. These compounds include the bile salts,
cholesterol and related compounds, and certain hormones (such as cortisone and the sex hormones).

Figure 17.11 Steroids

(a) The four-fused-ring steroid skeleton uses letter designations for each ring and the numbering of the carbon
atoms. (b) The cholesterol molecule follows this pattern.

Steroids occur in plants, animals, yeasts, and molds but not in bacteria. They may exist in free form or
combined with fatty acids or carbohydrates. All steroids have a characteristic structural component
consisting of four fused rings. Chemists identify the rings by capital letters and number the carbon
atoms as shown in part (a) of Figure 17.11 "Steroids". Slight variations in this structure or in the atoms
or groups attached to it produce profound differences in biological activity.

Cholesterol

Cholesterol (part (b) of Figure 17.11 "Steroids") does not occur in plants, but it is the most abundant
steroid in the human body (240 g is a typical amount). Excess cholesterol is believed to be a primary
factor in the development of atherosclerosis and heart disease, which are major health problems in
the United States today. About half of the body’s cholesterol is interspersed in the lipid bilayer of cell
membranes (Figure 17.6 "Schematic Diagram of a Cell Membrane"). Much of the rest is converted to
cholic acid, which is used in the formation of bile salts. Cholesterol is also a precursor in the synthesis
of sex hormones, adrenal hormones, and vitamin D. Excess cholesterol not metabolized by the body is
released from the liver and transported by the blood to the gallbladder. Normally, it stays in solution
there until being secreted into the intestine (as a component of bile) to be eliminated. Sometimes,
however, cholesterol in the gallbladder precipitates in the form of gallstones. Indeed, the name
cholesterol is derived from the Greek chole, meaning “bile,” and stereos, meaning “solid.”

To Your Health: Cholesterol and Heart Disease

Heart disease is the leading cause of death in the United States for both men and women. The
Centers for Disease Control and Prevention reported that heart disease claimed 631,636 lives in
the United States (26% of all reported deaths) in 2006.
Scientists agree that elevated cholesterol levels in the blood, as well as high blood pressure,
obesity, diabetes, and cigarette smoking, are associated with an increased risk of heart disease. A
long-term investigation by the National Institutes of Health showed that among men ages 30 to
49, the incidence of heart disease was five times greater for those whose cholesterol levels were
above 260 mg/100 mL of serum than for those with cholesterol levels of 200 mg/100 mL or less.
The cholesterol content of blood varies considerably with age, diet, and sex. Young adults average
about 170 mg of cholesterol per 100 mL of blood, whereas males at age 55 may have cholesterol
levels at 250 mg/100 mL or higher because the rate of cholesterol breakdown decreases with age.
Females tend to have lower blood cholesterol levels than males.

To understand the link between heart disease and cholesterol levels, it is important to understand
how cholesterol and other lipids are transported in the body. Lipids, such as cholesterol, are not
soluble in water and therefore cannot be transported in the blood (an aqueous medium) unless
they are complexed with proteins that are soluble in water, forming assemblages called
lipoproteins. Lipoproteins are classified according to their density, which is dependent on the
relative amounts of protein and lipid they contain. Lipids are less dense than proteins, so
lipoproteins containing a greater proportion of lipid are less dense than those containing a
greater proportion of protein.

Research on cholesterol and its role in heart disease has focused on serum levels of low-density
lipoproteins (LDLs) and high-density lipoproteins (HDLs). One of the most fascinating
discoveries is that high levels of HDLs reduce a person’s risk of developing heart disease, whereas
high levels of LDLs increase that risk. Thus the serum LDL:HDL ratio is a better predictor of
heart disease risk than the overall level of serum cholesterol. Persons who, because of hereditary
 or dietary factors, have high LDL:HDL ratios in their blood have a higher incidence of heart
disease.

How do HDLs reduce the risk of developing heart disease? No one knows for sure, but one role of
HDLs appears to be the transport of excess cholesterol to the liver, where it can be metabolized.
Therefore, HDLs aid in removing cholesterol from blood and from the smooth muscle cells of the
arterial wall.

Dietary modifications and increased physical activity can help lower total cholesterol and improve
the LDL:HDL ratio. The average American consumes about 600 mg of cholesterol from animal
products each day and also synthesizes approximately 1 g of cholesterol each day, mostly in the
liver. The amount of cholesterol synthesized is controlled by the cholesterol level in the blood;
when the blood cholesterol level exceeds 150 mg/100 mL, the rate of cholesterol biosynthesis is
halved. Hence, if cholesterol is present in the diet, a feedback mechanism suppresses its synthesis
in the liver. However, the ratio of suppression is not a 1:1 ratio; the reduction in biosynthesis does
not equal the amount of cholesterol ingested. Thus, dietary substitutions of unsaturated fat for
saturated fat, as well as a reduction in consumption of trans fatty acids, is recommended to help
lower serum cholesterol and the risk of heart disease.

Steroid Hormones

Hormones are chemical messengers that are released in one tissue and transported through the
circulatory system to one or more other tissues. One group of hormones is known as steroid
hormones because these hormones are synthesized from cholesterol, which is also a steroid. There are
two main groups of steroid hormones: adrenocortical hormones and sex hormones.

The adrenocortical hormones, such as aldosterone and cortisol (Table 17.3 "Representative Steroid
Hormones and Their Physiological Effects"), are produced by the adrenal gland, which is located
adjacent to each kidney. Aldosterone acts on most cells in the body, but it is particularly effective at
enhancing the rate of reabsorption of sodium ions in the kidney tubules and increasing the secretion
of potassium ions and/or hydrogen ions by the tubules. Because the concentration of sodium ions is
the major factor influencing water retention in tissues, aldosterone promotes water retention and
reduces urine output. Cortisol regulates several key metabolic reactions (for example, increasing
glucose production and mobilizing fatty acids and amino acids). It also inhibits the inflammatory
response of tissue to injury or stress. Cortisol and its analogs are therefore used pharmacologically as
immunosuppressants after transplant operations and in the treatment of severe skin allergies and
autoimmune diseases, such as rheumatoid arthritis.
Table 17.3 Representative Steroid Hormones and Their Physiological Effects

Hormone Effect

regulates salt metabolism; stimulates kidneys to retain sodium and excrete

potassium

stimulates the conversion of proteins to carbohydrates

regulates the menstrual cycle; maintains pregnancy

stimulates female sex characteristics; regulates changes during the

menstrual cycle

stimulates and maintains male sex characteristics

The sex hormones are a class of steroid hormones secreted by the gonads (ovaries or testes), the
placenta, and the adrenal glands. Testosterone and androstenedione are the primary male sex
hormones, or androgens, controlling the primary sexual characteristics of males, or the development
of the male genital organs and the continuous production of sperm. Androgens are also responsible
for the development of secondary male characteristics, such as facial hair, deep voice, and muscle
strength. Two kinds of sex hormones are of particular importance in females: progesterone, which
prepares the uterus for pregnancy and prevents the further release of eggs from the ovaries during
pregnancy, and the estrogens, which are mainly responsible for the development of female secondary
sexual characteristics, such as breast development and increased deposition of fat tissue in the
breasts, the buttocks, and the thighs. Both males and females produce androgens and estrogens,
differing in the amounts of secreted hormones rather than in the presence or absence of one or the
other.

Sex hormones, both natural and synthetic, are sometimes used therapeutically. For example, a
woman who has had her ovaries removed may be given female hormones to compensate. Some of the
earliest chemical compounds employed in cancer chemotherapy were sex hormones. For example,
estrogens are one treatment option for prostate cancer because they block the release and activity of
testosterone. Testosterone enhances prostate cancer growth. Sex hormones are also administered in
preparation for sex-change operations, to promote the development of the proper secondary sexual
characteristics. Oral contraceptives are synthetic derivatives of the female sex hormones; they work
by preventing ovulation.

Bile Salts

Bile is a yellowish green liquid (pH 7.8–8.6) produced in the liver. The most important constituents
of bile are bile salts, which are sodium salts of amidelike combinations of bile acids, such as cholic
acid (part (a) of Figure 17.12 "Bile Acids") and an amine such as the amino acid glycine (part (b) of
Figure 17.12 "Bile Acids"). They are synthesized from cholesterol in the liver, stored in the gallbladder,
and then secreted in bile into the small intestine. In the gallbladder, the composition of bile gradually
changes as water is absorbed and the other components become more concentrated.

Figure 17.12 Bile Acids

(a) Cholic acid is an example of a bile acid. (b) Sodium glycocholate is a bile salt synthesized from cholic acid
and glycine.

Because they contain both hydrophobic and hydrophilic groups, bile salts are highly effective
detergents and emulsifying agents; they break down large fat globules into smaller ones and keep
those smaller globules suspended in the aqueous digestive environment. Enzymes can then hydrolyze
fat molecules more efficiently. Thus, the major function of bile salts is to aid in the digestion of dietary
lipids.

Note

Surgical removal is often advised for a gallbladder that becomes infected, inflamed, or perforated.
This surgery does not seriously affect digestion because bile is still produced by the liver, but the
liver’s bile is more dilute and its secretion into the small intestine is not as closely tied to the
arrival of food.

CONCEPT REVIEW EXERCISES

1. Distinguish between a saponifiable lipid and a nonsaponifiable lipid.

2. Identify a key function for each steroid.

a. bile salt
b. cholesterol
c. estradiol

ANSWERS

1. A saponifiable lipid reacts with aqueous alkali to yield simpler components, while a nonsaponifiable lipid
does not react with alkali to yield simpler components.

2. a. acts as an emulsifying agent to break down large fat globules and keep these globules suspended in
the aqueous digestive environment
b. a key component of mammalian cell membranes (answers will vary)
c. stimulates female sex characteristics and regulates changes during the menstrual cycle

K E Y TA K E AWAY S

Steroids have a four-fused-ring structure and have a variety of functions.

Cholesterol is a steroid found in mammals that is needed for the formation of cell membranes, bile
acids, and several hormones.
Bile salts are secreted into the small intestine to aid in the digestion of fats.

EXERCISES

1. Which of these compounds are steroids—tripalmitin, cephalin, or cholesterol?

2. Which of these compounds are steroids—vitamin D, cholic acid, or lecithin?

3. Draw the basic steroid skeleton and label each ring with the appropriate letter designation.

4. Identify each compound as an adrenocortical hormone, a female sex hormone, or a male sex hormone.

a. progesterone
b. aldosterone
c. testosterone
d. cortisol
 ANSWERS

1. cholesterol

3.

17.5 End-of-Chapter Material

Chapter Summary

To ensure that you understand the material in this chapter, you should review the meanings of
the bold terms in the following summary and ask yourself how they relate to the topics in the
chapter.

Lipids, found in the body tissues of all organisms, are compounds that are more soluble in
organic solvents than in water. Many of them contain fatty acids, which are carboxylic acids that
generally contain an even number of 4–20 carbon atoms in an unbranched chain. Saturated
fatty acids have no carbon-to-carbon double bonds. Monounsaturated fatty acids have a
single carbon-to-carbon double bond, while polyunsaturated fatty acids have more than one
carbon-to-carbon double bond. Linoleic and linolenic acid are known as essential fatty acids
because the human body cannot synthesize these polyunsaturated fatty acids. The lipids known as
fats and oils are triacylglycerols, more commonly called triglycerides—esters composed of
three fatty acids joined to the trihydroxy alcohol glycerol. Fats are triglycerides that are solid at
room temperature, and oils are triglycerides that are liquid at room temperature. Fats are found
mainly in animals, and oils found mainly in plants. Saturated triglycerides are those containing a
higher proportion of saturated fatty acid chains (fewer carbon-to-carbon double bonds);
unsaturated triglycerides contain a higher proportion of unsaturated fatty acid chains.

Saponification is the hydrolysis of a triglyceride in a basic solution to form glycerol and three
carboxylate anions or soap molecules. Other important reactions are the hydrogenation and
oxidation of double bonds in unsaturated fats and oils.

Phospholipids are lipids containing phosphorus. In phosphoglycerides, the phosphorus is

joined to an amino alcohol unit. Some phosphoglycerides, like lecithins, are used to stabilize an
emulsion—a dispersion of two liquids that do not normally mix, such as oil and water.
Sphingolipids are lipids for which the precursor is the amino alcohol sphingosine, rather than
glycerol. A glycolipid has a sugar substituted at one of the OH groups of either glycerol or
sphingosine. All are highly polar lipids found in cell membranes.

Polar lipids have dual characteristics: one part of the molecule is ionic and dissolves in water; the
rest has a hydrocarbon structure and dissolves in nonpolar substances. Often, the ionic part is
referred to as hydrophilic (literally, “water loving”) and the nonpolar part as hydrophobic
(“water fearing”). When placed in water, polar lipids disperse into any one of three arrangements:
micelles, monolayers, and bilayers. Micelles are aggregations of molecules in which the
hydrocarbon tails of the lipids, being hydrophobic, are directed inward (away from the
surrounding water), and the hydrophilic heads that are directed outward into the water. Bilayers
are double layers arranged so that the hydrophobic tails are sandwiched between the two layers of
hydrophilic heads, which remain in contact with the water.

Every living cell is enclosed by a cell membrane composed of a lipid bilayer. In animal cells, the
bilayer consists mainly of phospholipids, glycolipids, and the steroid cholesterol. Embedded in
the bilayer are integral proteins, and peripheral proteins are loosely associated with the
surface of the bilayer. Everything between the cell membrane and the membrane of the cell
nucleus is called the cytoplasm.

Most lipids can be saponified, but some, such as steroids, cannot be saponified. The steroid
cholesterol is found in animal cells but never in plant cells. It is a main component of all cell
membranes and a precursor for hormones, vitamin D, and bile salts. Bile salts are the most
important constituents of bile, which is a yellowish-green liquid secreted by the gallbladder into
the small intestine and is needed for the proper digestion of lipids.

ADDITIONAL EXERCISES
1. The melting point of elaidic acid is 52°C.

a. What trend is observed when comparing the melting points of elaidic acid, oleic acid, and stearic
acid? Explain.

b. Would you expect the melting point of palmitelaidic acid to be lower or higher than that of elaidic
acid? Explain.

2. Examine the labels on two brands of margarine and two brands of shortening and list the oils used in the
various brands.

3. Draw a typical lecithin molecule that incorporates glycerol, palmitic acid, oleic acid, phosphoric acid, and
choline. Circle all the ester bonds.

4. In cerebrosides, is the linkage between the fatty acid and sphingosine an amide bond or an ester bond?
Justify your answer.

5. Serine is an amino acid that has the following structure. Draw the structure for a phosphatidylserine that
contains a palmitic acid and a palmitoleic acid unit.

6. Explain whether each compound would be expected to diffuse through the lipid bilayer of a cell
membrane.

a. potassium chloride
b. CH3CH2CH2CH2CH2CH3

c. fructose

7. Identify the role of each steroid hormone in the body.

a. progesterone
b. aldosterone
c. testosterone
d. cortisol

8. How does the structure of cholic acid differ from that of cholesterol? Which compound would you expect
to be more polar? Why?
 9.

a. What fatty acid is the precursor for the prostaglandins?

b. Identify three biological effects of prostaglandins.

10. Why is it important to determine the ratio of LDLs to HDLs, rather than just the concentration of serum
cholesterol?

ANSWERS

1. a. Stearic acid has the highest melting point, followed by elaidic acid, and then oleic acid with the
lowest melting point. Elaidic acid is a trans fatty acid, and the carbon chains can pack together almost
as tightly as those of the saturated stearic acid. Oleic acid is a cis fatty acid, and the bend in the
hydrocarbon chain keeps these carbon chains from packing as closely together; fewer interactions
lead to a much lower melting point.
b. The melting point of palmitelaidic acid should be lower than that of elaidic acid because it has a
shorter carbon chain (16, as compared to 18 for elaidic acid). The shorter the carbon chain, the lower
the melting point due to a decrease in intermolecular interactions.

3.

5.

7. a. regulates the menstrual cycle and maintains pregnancy

b. regulates salt metabolism by stimulating the kidneys to retain sodium and excrete potassium
c. stimulates and maintains male sex characteristics
d. stimulates the conversion of proteins to carbohydrates
9. a. arachidonic acid
b. induce smooth muscle contraction, lower blood pressure, and contribute to the inflammatory
response

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