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General, Organic, and Biological Chemistry:
Structures of Life
Sixth Edition
Chapter 17
Lipids
17.1 Lipids
Lipids are
• biomolecules that contain fatty acids building blocks
• soluble in organic solvents but not in water
• an important component of cell membranes
• are naturally occurring compounds in cells and tissues.
Learning Goal: Describe the classes of lipids.
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Types and General Structure of Lipids
Types of Lipids
Lipids are characterized by their structures:
Lipids such as
• waxes,
• triacylglycerols,
• glycerophospholipids, and
• sphingolipids
are esters that can be hydrolyzed to give fatty acids and other
molecules.
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Lipids Containing Glycerol
Triacylglycerols and glycerophospholipids contain the alcohol glycerol.
Lipids Containing Sphingosine
Sphingolipids contain the amino alcohol sphingosine.
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Steroids
Steroids, which have a completely different structure, do not
contain fatty acids and cannot be hydrolyzed. They are
characterized by the steroid nucleus of four fused carbon rings.
Learning Check 1
Lipids are characterized by presence of fatty acids or a steroid
nucleus. Which type is described by the following?
A. contain a fused four-membered ring system
B. contain long carbon chains
C. include carboxyl groups
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Learning Check 2
Which of the following is Not a characteristic of lipids?
A. may contain a carboxylic acid group
B. may contain a four-ring structure
C. soluble in water
D. mostly nonpolar
17.2 Fatty Acids
Fatty acids are
• long, unbranched carbon chains with a carboxylic acid group at the end.
• typically 12–20 carbon atoms long.
• insoluble in water because of the long carbon chain.
• saturated when they do not contain C=C double bonds in the carbon
chain.
• unsaturated when they contain C=C double bonds in the carbon chain.
Learning Goal: Draw the condensed structural and line-angle formulas for a fatty acid and
identify it as saturated or unsaturated.
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Drawing Fatty Acids
• In a line-angle structural formula of a fatty acid, the ends and bends of
the line are the carbon atoms.
• The structural formula of lauric acid can be drawn in several forms.
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Saturated Fatty Acids
Fatty acids can be saturated, with only C—C single bonds in the
carbon chain
Structures and Melting Points of Common Saturated Fatty Acids.
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Monounsaturated Fatty Acids
Fatty acids can be monounsaturated, with only one double C=C
bond in the carbon chain.
Structures and Melting Points of Common Monounsaturated Fatty Acids
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Polyunsaturated Fatty Acids
Fatty acids can be polyunsaturated, with at least two double C=C bond
in the carbon chain.
Structures and Melting Points of Common Polyunsaturated Fatty Acids
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Cis and Trans Unsaturated Fatty Acids
• Unsaturated fatty acids can be drawn as cis and trans isomers.
• Oleic acid is a monounsaturated fatty acid found in olives, with one
double bond at carbon 9.
• The trans isomer of oleic acid is called elaidic acid.
Almost all naturally occurring unsaturated fatty acids have one or more cis
double bonds.
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Properties of Saturated Fatty Acids (1 of 2)
Saturated fatty acids
• contain only single C—C bonds and fit close together in a regular
pattern, with strong dispersion forces between carbon chains.
• require a significant amount of energy and high temperatures to
separate and melt. Solids at room temperature.
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Properties of Unsaturated Fatty Acids (2 of 2)
In unsaturated fatty acids, cis
double bonds cause the
carbon chain to bend or kink,
giving the molecules an
irregular shape and thus
allowing fewer interactions
between molecules.
The reduced interactions in
fatty acids with cis bonds
reduce the melting point of
the molecules. Liquids at
room temperature.
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Learning Check 2
Label each of the following fatty acids as saturated, monounsaturated,
or polyunsaturated.
A. linolenic acid
B. palmitoleic acid
C. stearic acid
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Learning Check 1
Consider the line-angle formula for vaccenic acid.
A. Why is this substance an acid?
B. How many total carbon atoms are in vaccenic acid?
C. Is this a saturated, monounsaturated, or polyunsaturated fatty acid?
D. Is it likely to be a solid or liquid at room temperature?
E. Would it be soluble in water?
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Essential Fatty Acids
Humans
• are capable of synthesizing some fatty acids from
carbohydrates or other fatty acids.
• cannot synthesize sufficient amounts of polyunsaturated fatty
acids such as linoleic acid, linolenic acid, and arachidonic acid.
Because these polyunsaturated fatty acids must be obtained
from the diet, they are known as essential fatty acids.
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Chemistry Link to Health: Omega-6 Fatty
Acids in Vegetables
• Unsaturated fats such as those in vegetable oils and fish are
recognized as more beneficial to health than saturated fats.
• Vegetables contain omega-6 acids, meaning the first double
bond occurs at carbon 6 counting from the methyl end of the
carbon chain.
• Examples of omega-6 acids are linoleic and arachidonic acids.
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Chemistry Link to Health: Omega-3 Fatty Acids
Fish have high levels of omega-3 acids, meaning the first double
bond occurs at carbon 3, counting from the methyl end of the chain.
Examples of omega-3 acids include linolenic acid.
Cold-water fish are a source of omega-3 fatty acids.
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17.3 Waxes and Triacylglycerols
Natural waxes are found on the surface of fruits and on the leaves and
stems of plants, where they help prevent loss of water and damage
from pests.
A wax is an ester of a long chain fatty acid and a long chain alcohol,
each containing from 14 to 30 carbon atoms.
Learning Goal: Draw the condensed structural and line-angle formulas for a wax or triacylglycerol
produced by the reaction of a fatty acid and an alcohol or glycerol.
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Typical Waxes
Type Condensed Structural Formula Source Uses
Candles, shoe
Beeswax CHsub3,singlebondCHsub2,14,singlebondCdoublebondOsinglebondOsinglebondCHsub2,29,CHsub3.
Honeycomb polish, wax
paper
Waxes for
Carnauba CHsub3,singlebondCHsub2,24,singlebondCdoublebondOsinglebondOsinglebondCHsub2,29,CHsub3.
Brazilian furniture, cars,
wax palm tree floors, shoes
Candles,
Jojoba CHsub3,singlebondCHsub2,18,singlebondCdoublebondOsinglebondOsinglebondCHsub2,19,CHsub3.
Jojoba bush soaps,
wax cosmetics
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Triacylglycerols
• Glycerol has three hydroxyl groups which form ester bonds with the
carboxyl groups of three fatty acids.
• Glycerol and three molecules of stearic acid form a triacylglycerol.
• glycerol is named glyceryl and the fatty acids are named as
carboxylates.
• The product name is glyceryl tristearate.
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Triacylglycerols: glyceryl tristearate
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Mixed Triacylglycerols
Triacylglycerol may contain different fatty acids, such as the
triacylglycerol made from stearic, oleic, and palmitic acids.
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Learning Check 1
What are the fatty acids in the following triacylglycerol?
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Learning Check 2
Write the equation with the condensed structural formulas for the
reaction of triacylglycerol with three molecules of palmitoleic acid to form
glyceryl tripalmitoleate
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Learning Check 2
Draw the condensed structural formula for the triacylglycerol
containing three molecules of myristic acid.
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Melting Points of Fats and Oils
A fat
• is usually solid at room temperature.
• usually comes from animal sources such as meat, whole milk,
butter, and cheese.
An oil
• is usually liquid at room temperature.
• is usually obtained from a plant source such as corn and olive.
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Oils with Unsaturated Fatty Acids (1 of 2)
Oils from
• olive and peanut are monounsaturated because they contain
large amounts of oleic acid.
• corn, cottonseed, safflower seed, and sunflower seed are
polyunsaturated because they contain fatty acids with two or
more double bonds.
• palm and coconut are solids at room temperature because
they consist mostly of saturated fatty acids.
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Oils with Unsaturated Fatty Acids (2 of 2)
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Saturated and Unsaturated Melting Points
Saturated fatty acids
• have higher melting points than do unsaturated fatty acids
because they pack together more tightly.
• are usually found in animal fats, coconut oil, and palm oil.
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Percent Saturated and Unsaturated Fatty
Acids in Fats and Oils
Vegetable oils have low melting points because they have a
higher percentage of unsaturated fatty acids than do animal fats.
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17.4 Chemical Properties of Triacylglycerols
Many soft margarines,
stick margarines, and solid
shortenings are produced
by the partial
hydrogenation of
vegetable oils.
Learning Goal: Draw the condensed structural and line-angle formulas for the products of
a triacylglycerol that undergoes hydrogenation, hydrolysis, or saponification.
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Triacylglycerols, Hydrogenation
In hydrogenation reactions,
• double bonds in unsaturated fatty acids react with hydrogen gas to
produce carbon–carbon single bonds.
• hydrogen gas is bubbled through the heated oil typically in the
presence of a nickel catalyst.
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Hydrogenation Reactions
In commercial hydrogenation,
• the addition of hydrogen is
stopped before all the double
bonds in a liquid vegetable oil
become completely saturated.
• the partial hydrogenation of a
liquid vegetable oil changes it
to a soft, semisolid, or solid
fats. No cholesterol.
• the more saturated product
has a higher melting point.
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Learning Check 1
What product or products are obtained from the complete
hydrogenation of glyceryltrioleate?
A. glycerol and three oleic acids
B. glyceryltristearate
C. glycerol and three stearic acids
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Learning Check 2
Draw the condensed structural formula for the product of a
glyceryl tripalmitoleate that undergoes hydrogenation.
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Hydrolysis (1 of 2)
Triacylglycerols are hydrolyzed (split by water) in the presence
of strong acids such as HCl or H2SO4 or digestive enzymes
called lipases.
• The products of ester hydrolysis are glycerol and three fatty
acids.
• The polar glycerol is soluble in water, but the fatty acids with
their long hydrocarbon chains are not.
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Hydrolysis (2 of 2)
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Saponification and Soap (1 of 2)
Saponification
• is the reaction of fat with a strong base such as NaOH in the
presence of heat.
• splits triacylglycerols into glycerol and the salts of fatty acids.
• is the process of forming “soaps” (salts of fatty acids).
• gives solid soaps that can be molded into different shapes
when mixed with NaOH.
• gives softer, liquid soaps when mixed with KOH.
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Saponification and Soap (2 of 2)
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Lipid Reactions
Table 17.3 Summary of Lipid Reactions
Reaction Reactants and Products
Hydrogenation Unsaturated fat (double bonds) + hydrogen ¾¾
Ni
® saturated fat (single bonds)
Unsaturatedfat,doublebonds,+hydrogen,inthepresenceofNi,yieldsaturatedfat,singlebonds.
Hydrolysis Triacylglycerol (fat) + 3 water ¾¾¾¾
Enzyme
® 3 fatty acids + glycerol
Triacylglycerol,fat+3water,inthepresenceofenzyme,yields3fattyacids+glycerol.
Saponification Triacylglycerol (fat) + 3 sodium hydroxide ¾¾¾ ® 3 sodium salts of fatty acid (soap) + glycerol
Triacylglycerol,fat,+3sodiumhydroxide,inthepresenceofheat,yields3sodiumsaltsoffattyacid,soap,+glycerol.
Heat
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Learning Check 3
Write the balanced chemical equation for the reaction catalyzed
by the enzyme lipase that hydrolyzes glyceryltrilaurate during the
digestion process.
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17.5 Phospholipids
Phospholipids are a family of
lipids similar in structure to
triacylglycerols
They include
glycerophospholipids and
sphingomyelin.
Learning Goal: Draw the structure of a phospholipid that contains glycerol or sphingosine.
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Glycerophospholipids
Glycerophospholipids contain
• two fatty acids that form ester
bonds with the first and
second hydroxyl groups of
glycerol.
• a hydroxyl group that forms
phosphoester bond with
phosphoric acid, which forms
another phosphoester bond
with an amino alcohol.
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Sphingomyelin
Sphingomyelin
• contains sphingosine
instead of glycerol.
• contains a fatty acid,
phosphate, and an amino
alcohol.
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Amino Alcohols
Amino alcohols found in glycerophospholipids
• are choline and ethanolamine.
• are ionized at pH of 7.4.
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Lecithin and Cephalin
Lecithin and cephalin are two types of glycerophospholipids that are
• abundant in brain and nerve tissues.
• found in egg yolk, wheat germ, and yeast.
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Structure and Polarity of Glycerophospholipid
Glycerophospholipids
• contain both polar and nonpolar regions that allow them to interact
with polar and nonpolar substances.
• have a polar head containing the ionized amino alcohol and
phosphate portion, which is strongly attracted to water.
• have a nonpolar hydrocarbon tail portion soluble only in nonpolar
substances such as lipids.
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Structure and Polarity of a Glycerophospholipid
(a) The components of a typical
glycerophospholipid: an amino alcohol,
phosphoric acid, glycerol, and two fatty
acids.
(b) In a glycerophospholipid, a polar “head”
contains the ionized amino alcohol and
phosphate, while the hydrocarbon
chains of two fatty acids make up the
nonpolar “tails.”
(c) A simplified drawing indicates the polar
region and the nonpolar region.
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Learning Check 1
Draw the condensed structural formula for the cephalin that
contains two stearic acids, phosphate, and ethanolamine.
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Learning Check 2
Identify each of the following as a fatty acid, triacylglycerol, amino
alcohol, or glycerophospholipid:
A. glyceryl trioleate
B. cephalin
C. choline
D. palmitic acid
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Sphingomyelin (1 of 2)
Sphingomyelins are abundant in a coating surrounding the nerve
cells that increases the speed of nerve impulses and insulates
and protects the nerve cells.
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Sphingomyelin (2 of 2)
Sphingomyelin contains
• sphingosine, a long-chain amino alcohol that replaces glycerol.
• an amide bond formed by the amine group on sphingosine to a fatty acid.
• a hydroxyl group that forms a phosphoester bond with phosphate, which
forms another phosphoester bond to choline or ethanolamine.
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Learning Check 3
Palmitic acid, the 16-carbon saturated fatty acid, is the most
common fatty acid found along with the ionized amino alcohol
choline in the sphingomyelin of eggs.
Draw the condensed structural formula for this sphingomyelin.
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