CHEM 1152 Dr. Sheppard Spring 2015

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CHEM 1152 Dr. Sheppard Spring 2015 Chapter 18: Lipids CHEM 1152 Dr. Sheppard Spring 2015

Lipids One of 4 major classes of compounds found in living tissue Nucleic acids, proteins, carbohydrates, lipids Specific types differ in structure Includes fats, oils, cholesterol Insoluble in water (large nonpolar section) Soluble in organic solvents Energy storage Cell membranes Insulation Hormones/messengers Some vitamins

18.1 Classification of lipids Saponifiable = esters Simple = two components (fatty acid and alcohol) Complex = more than two components

Some example lipid structures

18.2 Fatty acids (FAs) Simplest type of lipid Component of other more complex lipids Carboxylic acid with long (10-20) carbon chain Even number of carbons Typically unbranched

Fatty acids and micelle formation

Saturated vs. unsaturated fatty acids Saturated (“bad” fat) Only C─C Highly flexible Pack together Unsaturated (“good” fat) Contains C═C Cis double bonds “Kink” in chain reduces possibility of heart disease Don’t stick to walls of blood vessels Promote blood flow Monounsaturated Polyunsaturated

Essential fatty acids Not synthesized by the body Needed as precursors for essential molecules Must be obtained from the diet Plant and fish oils Linoleic acid (18 carbons, 2 double bonds) Linolenic acid (18 carbons, 3 double bonds)

Some important unsaturated fatty acids Oleic acid (18:1) Olives 18 carbons, C=C at C9 Linoleic (18:2) Corn, soybean oil Essential FA Omega-6 FA Linolenic acid (18:3) Corn, fish oil Omega-3 FA

Physical properties of fatty acids Solubility Insoluble in water Soluble in organic solvents (ether, chloroform) Melting point Saturated = solid at room temperature MP increases with longer chains MP decreases with number of unsaturations

18.3 Structure of Fats and oils Triglycerides/triacylglycerols (TAGs) Most abundant class of lipids in animals Fatty acid triesters of glycerol Formed from esterification

Triglycerides Function Stored in adipocytes throughout the body Energy reserves Insulation Stored in adipocytes throughout the body Hydrolyzed as needed by enzymes called lipases

Triglycerides Mixed vs. simple mp determined by degree of unsaturation More unsaturation in plants than in animals “Fat” = mostly saturated Solid at room temperature Meat, butter (animal sources other than fish) “Oil” = mostly unsaturated Liquid at room temperature Olive oil, peanut oil (fish and plants)

Triglycerides

Mixed or simple? Fat or oil?