Introduction to Organic Chemistry and Biochemistry Instructor Dr. Upali Siriwardane (Ph.D. Ohio State) Office: 311 Carson Taylor Hall ; Phone: ; Office Hours: MTW 8: :00 am; ThF 9: :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

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

Chapter 19: Lipids Silde Structure and Classification of Lipids, Types of Fatty Acids, Physical Properties of Fatty Acids, Energy-Storage Lipids: Triacylglycerols, Dietary Considerations and Triacylglycerols, Chemical Reactions of Triacylglycerols, Membrane Lipids: Phospholipids, Membrane Lipids: Sphingoglycolipids, Membrane Lipids: Cholesterol, Cell Membranes, Emulsification Lipids: Bile Acids, Messenger Lipids: Steroid Hormones, Messenger Lipids: Eicosanoids, Protective-Coating Lipids: Biological Waxes, Saponifiable and Nonsaponifiable Lipids, 697 CHEM 121 Winter 2015

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

Lipid Structures 5CHEM 121 Winter 2015

Eicosanoids: Messenger lipids 6CHEM 121 Winter 2015

Glycolipids based on spingosine 7CHEM 121 Winter 2015

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

Common Names of Carboxylic Acids

Fatty Acids: Lipid Building Blocks 10CHEM 121 Winter 2015

Fatty Acid Names CHEM 121 Winter

Fatty Acids: Lipid Building Blocks 12CHEM 121 Winter 2015

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

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

Physical Properties of Fatty Acids 15CHEM 121 Winter 2015

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

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

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

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

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

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

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

Phospholipids 23CHEM 121 Winter 2015

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

Spingosine and Spingolipids 25CHEM 121 Winter 2015

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

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

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

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

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

Acetaminophen (Tylanol) 31CHEM 121 Winter 2015

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

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

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

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