Chapter 17 Lipids

17.3
Waxes, Fats, and Oils

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Waxes

Waxes are
 esters of saturated fatty acids and long-chain alcohols
 coatings that prevent loss of water from leaves of plants

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 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

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Triacylglycerols
In a triacylglycerol,
 glycerol forms ester bonds with three fatty acids

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Formation of a Triacylglycerol
Glycerol and three stearic acid molecules form a
triacylglycerol named
 glyceryl tristearate
 tristearin

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Olive Oil
Olive oil
 contains a high
percentage of oleic
acid, which is a
monounsaturated fatty
acid with one cis
double bond

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 Learning Check
What are the fatty acids in the following triacylglycerol?

CH2 O C (CH2)16 CH3

O

CH O C (CH2)7 CH CH (CH2)7 CH3

CH2 O C (CH2)12 CH3

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 Solution
O

CH2 O C (CH2)16 CH3 Stearic acid

O

CH O C (CH2)7 CH CH (CH2)7 CH3 Oleic acid

O

CH2 O C (CH2)12 CH3 Myristic acid

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 Melting Points of Fats and Oils
A triacylglycerol that is usually called a fat
 is solid at room temperature
 is prevalent in meats, whole milk, butter, and cheese

A triacylglycerol that is usually called an oil

 is liquid at room temperature
 is prevalent in plants such as olive and safflower

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 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 do saturated fats
 are liquids at room temperature

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Diagram of Triacylglycerol with
Unsaturated Fatty Acids
Unsaturated fatty
acid chains have
kinks that do not
allow close
packing.

General, Organic, and Biological Chemistry 11

Saturated and Unsaturated Fatty
Acids In Fats and Oils

General, Organic, and Biological Chemistry 12