Created By Prof. Gary F. Porter, Ph.D.

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Created By Prof. Gary F. Porter, Ph.D. Lipids Created By Prof. Gary F. Porter, Ph.D. © 2014 by John Wiley & Sons, Inc. All rights reserved.

Table of Contents (hyperlinked) Introduction Fatty Acids and Triacylglycerols Terpenes and Terpenoids Steroids Prostaglandins Phospholipids and Cell Membranes Waxes © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 1. Introduction Lipids dissolve in non-polar solvents include a variety of structural types © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 2. Fatty Acids and Triacylglycerols Fatty Acids are long chain (>14 carbons) carboxylic acids, have an even number of carbons, are saturated (no double bonds), and unsaturated (contain double bonds). All double bonds are cis. Double bonds have weakened intermolecular forces because of a molecular bend. They have lower melting points. © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 2. Fatty Acids and Triacylglycerols Triacylglycerol are 3 Fatty Acids & Glycerol, and produce monomeric units by hydrolysis. © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 2. Fatty Acids and Triacylglycerols 2A. Hydrogenation of Triacylglycerols Increases M.P. © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 2. Fatty Acids and Triacylglycerols 2B. Biological Functions of Triacylglycerols include: long term storage of energy, and helping us survive starvation conditions. Fat and health Saturated fats are linked to heart disease. Too much fat in the diet is a health concern. Physical properties Fat is a solid. (saturated) Oil is a liquid. (unsaturated) © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 2. Fatty Acids and Triacylglycerols 2C. Saponification of Triacylglycerol Involves the basic hydrolysis of a triacylglycerol. © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 2. Fatty Acids and Triacylglycerols Soap is a monovalent anion, dissolves dirt, and dirt remover. Multivalent Cations – Ca2+ Fe2+ Fe3+ Mg2+ Soap scum (precipitated soap) is caused by multivalent cations. © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 2. Fatty Acids and Triacylglycerols Detergent is a multivalent anion, keeps multivalent metals solvated, and prevents soap scum. © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 2. Fatty Acids and Triacylglycerols 2F. Reactions of the Carboxyl Group of Fatty Acids © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 2. Fatty Acids and Triacylglycerols 2E. Reactions of the Alkenyl Chain Group of Unsaturated Fatty Acids © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 3. Terpenes and Terpenoids The monomeric unit is isoprene, and 5 carbons. Polymeric Molecules © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 3. Terpenes and Terpenoids See how to find the terpene monomers in the polymers below. © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 3. Terpenes and Terpenoids Practice Problem 23.2 Show the isoprene units in each of the following terpenes. Classify each as a monoterpene, diterpene, sesquiterpene, and so on. © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 3. Terpenes and Terpenoids Carotenes contain two tetraterpenes Vitamin A is a precursor of a carotene, and - is a tetraterpene. © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 3. Terpenes and Terpenoids 3A. Natural Rubber Vulcanization creates disulfide linkages between chains. © 2014 by John Wiley & Sons, Inc. All rights reserved.

Prepared by Dr. Khalid Shadid 4. Steroids 4A. Structure and Systematic Nomenclature Cyclopentophenanthrenes α substitution – Group is trans to C-18 methyl β substitution – Group is cis to C-18 methyl © 2014 by John Wiley & Sons, Inc. All rights reserved.

4A. Structure and Systematic Nomenclature 4. Steroids 4A. Structure and Systematic Nomenclature © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 4. Steroids 4B. Cholesterol Dietary Cholesterol is a mixture of lipids, one of which is cholesterol. HDL – High Density Lipoproteins travel from tissues to liver, and are an indicator of good health. LDL – Low Density Lipoproteins travel from liver to tissues, and are an indicator of poor health. © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 4. Steroids 4C. Sex Hormones Estrogens – female hormone Androgens – male hormone Progestins – pregnancy hormone Suppress ovulation. © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 4. Steroids The Enzyme Aromatase and its Chemistry converts a male hormone into a female hormone. The Chemistry: Estrogen in brain effects male behavior. Testosterone is converted to estrogen by aromatase in the brain. An aromatase deficiency causes a deficit in male sexual behavior (in the brain). After menopause, aromatase produces estrogen for women. Aromatase inhibitors block estrogen synthesis to control estrogen activated breast cancer. © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 4. Steroids 4D. Adrenocortical Hormones are 28 different Hormones, are produced in the adrenal cortex located in adrenal glands found on top of the kidneys, and drive numerous biological regulation activities including the inflammatory response. © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 4. Steroids 4E. D Vitamins Sunlight is needed to produce Vitamin D3. VitaminD3 is needed for health and facilitates the process by which calcium is absorbed to allow proper bone growth. © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 4. Steroids 1. 2. 3. 4. 4F. Other Steroids are isolated from digitalis and strengthen heart muscle, are isolated from bile and emulsify lipids by acting as a soap and aiding in the digestive process, are isolated from soybean oil and inhibit dietary cholesterol absorption, and are isolated from plant sources and are used to synthesize cortisone and sex hormones. © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 4. Steroids 4G. Reactions of Steroids (Cholesterol) involves the double bond © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 4. Steroids 4G. Reactions of Steroids (Cholestane) Reactivity of equatorial vs. axial hydroxyls © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 5. Prostaglandins Structure Includes twenty carbons and a Five membered ring. Synthesized from Arachidonic Acid © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 6. Phospholipids and Cell Membranes Three Components are Glycerol, 2 Fatty Acids, and Phosphate. Phosphatide Has another group, typically bonds to phosphate. © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 6. Phospholipids and Cell Membranes 6A. Phosphatide Has four important classes as shown on the right. © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 6. Phospholipids and Cell Membranes 6A. Phosphatide - Is a soap-like molecule. © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 6. Phospholipids and Cell Membranes 6A. Phosphatide Is found in cell walls © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 6. Phospholipids and Cell Membranes 6B. Derivatives of Sphingosine (Parent Molecule) Sphingomyelin is a component of myelin found in nerve cell membranes (sheaths). Cerebroside is a brain cell membrane component. © 2014 by John Wiley & Sons, Inc. All rights reserved.

© 2014 by John Wiley & Sons, Inc. All rights reserved. 7. Waxes -Most waxes are esters of long-chain fatty acids and long-chain alcohols. -Act as a water resistant coat -Waxes are found as protective coatings on the skin, fur, and feathers of animals and on the leaves and fruits of plants. -Several esters isolated from waxes are the following: © 2014 by John Wiley & Sons, Inc. All rights reserved.