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Chapter 18 18 Lipids Study Goals • • • • • • Describe the properties and types of lipids. Write the structures of triacylglycerols obtained from glycerol and fatty acids. Draw the structure of the product from hydrogenation, hydrolysis, and saponification of triacylglycerols. Distinguish between phospholipids, glycolipids, and sphingolipids. Describe steroids and their role in bile salts, vitamins, and hormones. Describe the lipid bilayer in a cell. Chapter Outline 18.1 18.2 18.3 18.4 18.5 18.6 18.7 18.8 Lipids Explore Your World: Solubility of Fats and Oils Fatty Acids Health Note: Omega-3 Fatty Acids in Fish Oils Waxes, Fats, and Oils Explore Your World: Fats and Oils Chemical Properties of Triacylglycerols Health Note Olestra: A Fat Substitute Environmental Note: Trans Fatty Acids and Hydrogenation Explore Your World: Types of Fats Glycerophospholipids Sphingolipids Health Note: Lipid Diseases Steroids: Cholesterol, Bile Salts, and Steroid Hormones Health Note: Anabolic Steroids Plasma (Cell) Membranes Chapter Summary and Demonstrations 1. Types of Lipids Lipids are discussed in terms of their components and solubility in various solvents. Saturated and unsaturated fatty acids are described along with a comparison of their melting points. Demonstration: I introduce this chapter with examples of lipids such as margarine, butter, lard, cooking oils (corn, olive, safflower), gallstones, and vitamin A and oil of lemon. Demonstration: Read the labels on some vegetable oils, margarines, or peanut butter. Ask students what they know about saturated fat, unsaturated fats, and polyunsaturated fats. What process occurred if the label states that the product is partially hydrogenated? 2. Fatty Acids and Triglycerides The formation of the ester linkage between alcohols and fatty acids in waxes or glycerol and fatty acids in triglycerides is shown. Several reactions of the triglycerides including hydrogenation, acid and enzyme hydrolysis, saponification and oxidation are described. Lipids Demonstration: A discussion of hydrogenation of vegetable oils in the production of margarine is an eye opener for many students. I place bottles of oil on the table along with a tub and cube of margarine, and perhaps some Crisco. I ask the students how the oils in the bottles become the solid products in front of them. This leads into a practical discussion of hydrogenation and the terms associated with lipids such as unsaturated and saturated fats. 3. Phospholipids The phospholipids are discussed along with their dual polarity and function in cell membranes. Students are asked to look at the difference in properties for each of the components in cell membranes. The chapter concludes with the coverage of steroids and steroid hormones with a discussion of high- and low-density lipoproteins. Demonstration: Bring in samples of lecithin, a phospholipid, and perhaps some cholesterol (if you have gallstones). A discussion of anabolic steroids (see health note) is interesting to students who are athletes or lift weights. Laboratory Suggestions Lab 30 Lipids Students observe the physical and chemical properties of some common lipids and draw the structure of a typical triacylglycerol. Chemical tests are used to distinguish between saturated and unsaturated fats. A sample of hand lotion is prepared, which illustrates the physical properties of various types of lipids. A. Triacylglycerols B. Physical Properties of Some Lipids and Fatty Acids C. Bromine Test for Unsaturation D. Preparation of Hand Lotion Laboratory Skills to Demonstrate Remind students of the change in color with bromine adds to a double bond. Lab 31 Glycerophospholipids and Steroids Students isolate cholesterol and lecithin from egg yolk using extraction techniques. The differences in solubility of cholesterol and lecithin in acetone and ether is used to separate the steroid from the glycerophospholipid. A. Isolating Cholesterol in Egg Yolk B. Isolating Lecithin in Egg Yolk Laboratory Skills to Demonstrate Caution in use of flammable solvents Proper disposal techniques for organic compounds Lab 32 Saponification and Soaps Soap is prepared by the saponification of a triglyceride and collected. The behavior of soap with soft water, oil and CaCl2 is observed. A. Saponification: Preparation of Soap B Properties of Soap and Detergents Laboratory Skills to Demonstrate Caution in the saponification procedure using NaOH to form soap. Use of the Büchner filtration apparatus.