Chemistry 1506: Allied Health Chemistry 2. Section 8: Lipids. Biochemical Esters and Hydrocarbons. Outline
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1 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 1/21 hemistry 1506: Allied ealth hemistry 2 Section 8: Lipids Biochemical Esters and ydrocarbons utline SETIN 8.1 INTRDUTIN...2 SETIN SETIN SETIN 8.2 LIPIDS MEMBRANES MEMBRANE MPNENTS RELATED T GLYERIDES...15 SETIN 8.5 STERIDS...17
2 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 2/21 Section 8.1 Introduction Lipids Defined by solubility rather than structure Insoluble in water Soluble in low polarity solvents Includes both Esters and ydrocarbon like molecules Uses Energy Storage 9 kcal/g vs. 4 kcal/g for carbohydrates ell Membranes Regulatory
3 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 3/21 Section 8.2 Lipids Triglycerides R R R Glycerol 1,2,3-propanetriol Liquid at room temperature Found in glycerin soap
4 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 4/21 Fatty Acids Strait hain arboxylic Acids R-(=), R to 20 carbons in length Most in our bodies have 16 or 18 carbons All have an even number of carbons They have only - single bonds and = double bonds No other functional groups on chains Types of Triglycerides See Table in Text
5 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 5/21 Saturated Fatty Acids Solids at room temperature Due to excellent packing of tail groups Leads to fatty deposits on arteries 14 example is Myristic Acid Nutmeg 3 -( 2 ) example is Palmitic Acid Palm oil 3 -( 2 ) example is Steric Acid Butter, animal fats 3 -( 2 ) 16-2
6 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 6/21 Unsaturated Fatty Acids Found in Vegetable ils and Fish ils Natural compounds have cis double bonds Thermodynamically disfavored cis double bonds Monounsaturated and Polyunsaturated is bonds in middle of chains, disrupt packing Liquids at room temperature Much more healthful, don t clog arteries leic Acid 18, one cis double bond 3 -( 2 ) 7 -=-( 2 ) 7-2 Linoleic Acids 18, two cis double bonds 3 -( 2 ) 4 -=- 2 -=-( 2 ) 7-2
7 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 7/21 Trans Unsaturated Fatty Acids Man-made materials Made from saturated fatty acids By Dehydrogenation (- 2, uses catalyst) Saturated Fats - 2 (Pt catalyst) trans-unsaturated Fats Produces the thermodynamically favored trans isomers Double bonds at many places in chain ommon ingredients in margarine ave all trans Fatty Acids These groups pack well Solids at room temperature
8 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 8/21 Dietary Fats Vegetable Fats (and Fish ils) is unsaturated and polyunsaturated Fatty Acids Liquids at room temperature Best for you Animal Fats Saturated Fatty Acids Solids at room temperature Moderate-Poor for you Margarine Trans Fatty Acids Solids at room temperature Worst for you????
9 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 9/21 ydrogenation of Unsaturated Fats risco replaces lard in cooking Solid fat produced from vegetable sources Unsaturated Fats + 2 (Pt catalyst) Saturated Fats lestra See Text Produced by Proctor and Gamble Produced from natural ingredients Sucrose (table sugar) Fatty Acids (corn oil or soybean oil) Similar Flavor and Mouth Feel to saturated fats 7-8 Fatty acids join to sucrose by ester linkages
10 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 10/21 Saponification See Text First rganic Synthesis Boil Fat with wood ashes wood ash solution leaning Agents Micelle formation ydrophilic eads and ydrophobic Tails
11 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 11/21 ommercial Soap Fatty Acid salts - R 2 Na + salts are solids K + salts are liquids ther ingredients Enzymes p modifiers water softeners surfactants fragrances, colors Detergents R-S 3 - and/or R-Ar-S 3 - instead of R 2 - Don t react with metal ions in hard water
12 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 12/21 Waxes Produced by Plants, Insects, etc. Box 17D, page 567 Long chain esters R- 2 -R Fatty Acids Alcohols 30 strait chain properties comparable with paraffin wax exterior of molecules looks much like an alkane
13 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 13/21 Section 8.3 Membranes Reminder of Soap Micelles Micelles and Fatty Acids ydrophilic heads ydrophobic tails Dipole-Dipole and ydrogen Bonding Lipid Bilayer typically have two hydrophobic tails ydrophilic heads Fluid Mosaic Model Rapid lateral diffusion Little or no trans-membrane diffusion fluidizers
14 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 14/21 Diagram of ell Membrane See Figure in Text Lipids Proteins arbohydrates
15 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 15/21 Section 8.4 Membrane omponents Related to Glycerides Glycerophospholipids Lecithin is common name holine ydrophilic group N( 3 ) 3 Two Fatty Acid hydrophobic groups Glycerol linker Phosphate linker hydrophilic group R R P N 3 3 ften referred to simply as phospholipids
16 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 16/21 Sphingolipids especially rich in Myelin Sphingosine hydrophobic group and linker ne Fatty Acid hydrophobic group Phosphate hydrophilic group holine hydrophilic group 3 ( 2 ) 12 R N 2 P N 3 3 Glycolipids Lipid + carbohydrate
17 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 17/21 Section 8.5 Steroids Basic Steroid Ring Structure Three six membered and one five membered ring D A B holesterol Fluidizers in cell membranes They are rich in animal fats Gall stones are almost pure cholesterol They come from both diet and biosynthesis 3 3 Steroid ormones
18 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 18/21 Regulatory Functions Same basic steroid core structures See figure in text Testosterone Estradiol Progesterone Anabolic Steroids Bile Salts harged steroids with extra groups Used to dissolve fats in the intestines
19 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 19/21 Index of Topics and Vocabulary 1,2,3-propanetriol... 3 Alcohols alkane Anabolic Steroids animal fats... 5, 17 Animal Fats... 8 arteries... 5 Bile Salts biosynthesis Boil Fat with wood ashes Butter... 5 = double bonds... 4 carbohydrates... 2 arbohydrates arboxylic Acids... 4 catalyst single bonds... 4 ell Membrane cell membranes ell Membranes... 2 harged steroids with extra groups holesterol holine holine hydrophilic group cis double bonds... 6 is unsaturated... 8 leaning Agents clog arteries... 6 colors ommercial Soap corn oil... 9 risco... 9 Dehydrogenation...7 Detergents...11 diet...17 Dietary Fats...8 Dipole-Dipole...13 disrupt packing...6 dissolve fats...18 double bond...6 Double bonds...7 Energy Storage...2 Enzymes...11 ester linkages...9 esters...12 Esters...2 Estradiol...18 even number of carbons...4 Fatty Acid...15 Fatty Acid hydrophobic group.16 Fatty Acid salts...11 Fatty Acids...4, 9, 12, 13 fatty deposits...5 Fish ils...6, 8 Flavor...9 Fluid Mosaic Model...13 fluidizers...13 Fluidizers...17 fragrances...11 functional groups...4 Gall stones...17 glycerin soap...3 Glycerol...3 Glycerol linker...15 Glycerophospholipids...15
20 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 20/21 Glycolipids hard water healthful... 6 ydrocarbon like molecules... 2 ydrogen Bonding ydrogenation of Unsaturated Fats... 9 ydrophilic group ydrophilic heads ydrophilic eads hydrophobic groups ydrophobic tails ydrophobic Tails Insects Insoluble in water... 2 intestines Introduction... 2 K + salts are liquids lard... 9 lateral diffusion Lecithin length... 4 Linoleic Acids... 6 Lipid + carbohydrate Lipid Bilayer Lipids... 2, 3, 14 Liquid... 3 Liquids at room temperature. 6, 8 low polarity solvents... 2 Man-made materials... 7 margarine... 7 Margarine... 8 Membrane omponents Related to Glycerides...15 Membranes...13 Micelle...10 Micelles...13 middle of chains...6 Monounsaturated...6 Mouth Feel...9 Myelin...16 Myristic Acid...5 Na + salts are solids...11 natural ingredients...9 Nutmeg...5 leic Acid...6 lestra...9 rganic Synthesis...10 pack well...7 packing of tail groups...5 Palm oil...5 Palmitic Acid...5 paraffin wax...12 p modifiers...11 Phosphate hydrophilic group...16 Phosphate linker hydrophilic group...15 phospholipids...15 Plants...12 Polyunsaturated...6 polyunsaturated Fatty Acids...8 Proctor and Gamble...9 Progesterone...18 Proteins...14 Pt catalyst...9 R-Ar-S
21 hemistry 1506 Dr. unter s lass Section 8 Notes - Page 21/21 R R- 2 -R Regulatory... 2 Regulatory Functions R-S Saponification saturated fatty acids... 7 Saturated Fatty Acids... 5, 8 Skip Soap Micelles Solids at room temperature5, 7, 8 solubility... 2 soybean oil... 9 Sphingolipids Sphingosine hydrophobic group and linker Steric Acid... 5 steroid core structures Steroid ormones Steroid Ring Structure Steroids...17 strait chain...12 Strait hain...4 surfactants...11 table sugar...9 Testosterone...18 Thermodynamically disfavored.6 thermodynamically favored...7 trans Fatty Acids...7 Trans Fatty Acids...8 Trans Unsaturated Fatty Acids..7 trans-membrane diffusion...13 Triglycerides...3, 4 Unsaturated Fatty Acids...6 Vegetable Fats...8 Vegetable ils...6 water softeners...11 Waxes...12 wood ash...10
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