Chapter 15 Lipids 1 15 3 Waxes Fats

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Chapter 15 Lipids 1 15. 3 Waxes, Fats, and Oils Waxes are esters of

Chapter 15 Lipids 1 15. 3 Waxes, Fats, and Oils Waxes are esters of long-chain alcohols and fatty acids. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Waxes 2 Waxes are • esters of saturated fatty acids and long-chain alcohols •

Waxes 2 Waxes are • esters of saturated fatty acids and long-chain alcohols • coatings that prevent loss of water by leaves of plants Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Fats and Oils: Triacylglycerols 3 Fats and oils are • also called triacylglycerols •

Fats and Oils: Triacylglycerols 3 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 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Triacylglycerols 4 In a triacylglycerol, glycerol forms ester bonds with three fatty acids. Chemistry:

Triacylglycerols 4 In a triacylglycerol, glycerol forms ester bonds with three fatty acids. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Formation of a Triacylglycerol 5 In a triacylglycerol, three hydroxyl groups on a glycerol

Formation of a Triacylglycerol 5 In a triacylglycerol, three hydroxyl groups on a glycerol molecule form ester bonds with the carboxyl groups of three fatty acids. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Triacylglycerols 6 Triacylglycerol may contain different fatty acids. Chemistry: An Introduction to General, Organic,

Triacylglycerols 6 Triacylglycerol may contain different fatty acids. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Learning Check 7 What are the fatty acids in the following triacylglycerol? Chemistry: An

Learning Check 7 What are the fatty acids in the following triacylglycerol? Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Solution 8 What are the fatty acids in the following triacylglycerol? Stearic acid Oleic

Solution 8 What are the fatty acids in the following triacylglycerol? Stearic acid Oleic acid Myristic acid Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Melting Points of Fats and Oils 9 A fat • is usually solid at

Melting Points of Fats and Oils 9 A fat • is usually solid at room temperature • is prevalent in meats, whole milk, butter, and cheese An oil • is usually liquid at room temperature • is prevalent in plants such as olive and safflower Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Oils with Unsaturated Fatty Acids 10 Oils • • • have more unsaturated fats

Oils with Unsaturated Fatty Acids 10 Oils • • • have more unsaturated fats have cis double bonds that cause “kinks” in the fatty acid chains with “kinks” in the chains do not allow the triacylglycerol molecules to pack closely have lower melting points than saturated fatty acids are liquids at room temperature Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Diagram of Triacylglycerol with Unsaturated Fatty Acids 11 Unsaturated fatty acid chains with kinks

Diagram of Triacylglycerol with Unsaturated Fatty Acids 11 Unsaturated fatty acid chains with kinks cannot pack closely. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Percent Saturated and Unsaturated Fatty Acids in Fats and Oils 12 Vegetable oils have

Percent Saturated and Unsaturated Fatty Acids in Fats and Oils 12 Vegetable oils have low melting points because they have a higher percentage of unsaturated fatty acids than do animal fats. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Learning Check 13 Draw the condensed structural formula of glyceryl trilinoleate (trilinolein). Chemistry: An

Learning Check 13 Draw the condensed structural formula of glyceryl trilinoleate (trilinolein). Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Solution 14 Draw the condensed structural formula of glyceryl trilinoleate (trilinolein). Chemistry: An Introduction

Solution 14 Draw the condensed structural formula of glyceryl trilinoleate (trilinolein). Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

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