1. Introduction to Organic Chemistry and Biochemistry Instructor Dr. Upali Siriwardane (Ph.D. Ohio State) E-mail: upali@latech.edu Office: 311 Carson Taylor Hall ; Phone: 318-257-4941; Office Hours: MTW 8:00 - 10:00 am; ThF 9:00 - 10:00 am 1:00 - 2:00 pm. December 18, 2015: Test 1 (Chapters 12-13) January 25, 2016: Test 2 (Chapters 14-16) February 17, 2016: Test 3 (Chapters 17-19) February 29, 2016: Test 4 (Chapters 20-22) March 1, 2016: Make Up Exam: Chapters 12-22) Bring Scantron Sheet 882-E Chemistry 121 Winter 2016 1

2. Chapter 19 and GHW#9 Questions and Slides Lipids 2CHEM 121 Winter 2015

3. Chapter 19: Lipids Silde 3 19.1 Structure and Classification of Lipids, 654 19.2 Types of Fatty Acids, 656 19.3 Physical Properties of Fatty Acids, 659 19.4 Energy-Storage Lipids: Triacylglycerols, 661 19.5 Dietary Considerations and Triacylglycerols, 664 19.6 Chemical Reactions of Triacylglycerols, 669 19.7 Membrane Lipids: Phospholipids, 674 19.8 Membrane Lipids: Sphingoglycolipids, 681 19.9 Membrane Lipids: Cholesterol, 682 19.10 Cell Membranes, 684 19.11 Emulsification Lipids: Bile Acids, 687 19.12 Messenger Lipids: Steroid Hormones, 689 19.13 Messenger Lipids: Eicosanoids, 692 19.14 Protective-Coating Lipids: Biological Waxes, 694 19.15 Saponifiable and Nonsaponifiable Lipids, 697 CHEM 121 Winter 2015

4. Lipids A wide variety of naturally occurring organic compounds classified together on the basis of common solubility properties: insolubility in water insoluble in water Lipids include a)Waxes: Esters of long chain fatty acids and alcohols b)Triglycerides: Fatty acid esters of glycerol c)Phospholipids: Fatty acid and phosphate esters of glycerol d)Prostaglandins: structures based on Eicosanoids e)Glycolipids: structures based on Spingosine f)cholesterol, steroid hormones, and bile acids g)fat-soluble vitamins 4CHEM 121 Winter 2015

5. Lipid Structures 5CHEM 121 Winter 2015

6. Eicosanoids: Messenger lipids 6CHEM 121 Winter 2015

7. Glycolipids based on spingosine 7CHEM 121 Winter 2015

8. Lipid classification by function Energy-storage lipids – A fat, triacylglycerols or triglycerides.  Membrane lipids - phospholipids, sphingoglycolipids, and cholesterol  Emulsification lipids - bile acids, soaps and detergents  Chemical messenger lipids - steroid hormones, eicosanoids, and prostaglandins  Protective-coating lipids - biological waxes  Fat-soluble vitamins – E.g. Vitamin A 8CHEM 121 Winter 2015

9. Common Names of Carboxylic Acids

10. Fatty Acids: Lipid Building Blocks 10CHEM 121 Winter 2015

11. Fatty Acid Names CHEM 121 Winter 201511

12. Fatty Acids: Lipid Building Blocks 12CHEM 121 Winter 2015

13. Polyunsaturated fatty acids: omega-3 and omega-6 fatty acids 13CHEM 121 Winter 2015

14. Essential Fatty Acids (EFA). Fatty acids that cannot be produced by the body and are necessary for proper metabolism. The OMEGA 6 and OMEGA 3 fatty acids are referred to as Essential Fatty Acids (EFA). 14CHEM 121 Winter 2015

15. Physical Properties of Fatty Acids 15CHEM 121 Winter 2015

16. 1) Give names of the following types of lipids. a) Name:____________ b) Name:____________ c) ) Name:____________ d) Name:____________ 16 CHEM 121 Winter 2015

17. 1) Give names of the following types of lipids. e) Name:____________ f) Name:____________ g) Name:____________ h) Name:____________ 17 CHEM 121 Winter 2015

18. 1) Give names of the following types of lipids. i) Name:____________ j) Name:____________ k) Name:____________ 18CHEM 121 Winter 2015

19. 2) Give the type, structure notation and names of the following fatty acids. 19CHEM 121 Winter 2015

20. a. Decanoic acid b. Stearic acid c. trans-5-Decenoic acid d. cis-5-Decenoic acid 3) Draw the condensed structures of each of the following fatty acids: 20CHEM 121 Winter 2015

21. 4) Write an equation for each of the following reactions: a)Esterification of glycerol with three molecules of myristic acid b)Base (NaOH) hydrolysis or saponification of glyceryl tristearate 21CHEM 121 Winter 2015

22. 4) Write an equation for each of the following reactions: c) Reaction of decanoic acid with KOH d) Hydrogenation of linoleic acid 22CHEM 121 Winter 2015

23. Phospholipids 23CHEM 121 Winter 2015

24. 5) What are the structural differences between triglycerides (triacylglycerols) and phospholipids? Where they are found in living organisms? 24CHEM 121 Winter 2015

25. Spingosine and Spingolipids 25CHEM 121 Winter 2015

26. 6) What is a sphingolipid? Draw an example. 26CHEM 121 Winter 2015

27. Steroids four cycloalkane rings Contains a characteristic arrangement of four cycloalkane rings that are joined to each other. Examples of steroids include the dietary fat cholesterol: 27CHEM 121 Winter 2015

28. 7) What is a steroid? What are their applications? 28CHEM 121 Winter 2015

29. 8) What are the two major types of fat substitutes and how they work 29CHEM 121 Winter 2015

30. How aspirin relieves pain and inflammation? Aspirin inhibits the production of prostaglandins COX enzyme Concept of COX enzyme inhibition 30CHEM 121 Winter 2015

31. Acetaminophen (Tylanol) 31CHEM 121 Winter 2015

32. Triglycerides and lipoproteins: high-density (HDL)or (LDL) lipoproteins Lipoprotein particles: chylomicrons Triglycerides transportation in the blood stream 32CHEM 121 Winter 2015

33. Four major groups of plasma lipoproteins. 1. Chylomicrons 2. Very low-density lipoproteins (VLDL) 3. Low-density lipoproteins (LDL) 4. High-density lipoproteins (HDL) 33CHEM 121 Winter 2015

34. Triglycerides and lipoproteins: high-density (HDL)or (LDL) lipoproteins Lipoprotein particles: chylomicrons Triglycerides transportation in the blood stream chylomicron remnant 34CHEM 121 Winter 2015

35. The roles of HDL, LDL, and cholesterol. Cholesterollipoproteins Cholesterol and lipoproteins are related plaque that causes heart attacks and most strokes. LDL levels When LDL levels are low, atherosclerosis and heart attacks are almost unknown. HDL levels High HDL levels are associated with a reduced risk of heart disease: "good" cholesterol 35CHEM 121 Winter 2015