Organic chemistry II Zdeněk Friedl Chapter 26 Lipids Solomons & Fryhle: Organic Chemistry 8th Ed., Wiley 2004 Lipids • • • • • • triacylglycerols terpenes and terpenoids steroids prostaglandins phospholipids, phosphatides waxes 2 Basic types of lipids 3 Triacylglycerols I structure 4 Triacylglycerols II common fatty acids 5 Triacylglycerols III hydrogenation of unsaturated triacylglycerols (partially hydrogenated fat) 6 Triacylglycerols IV common polyunsaturated fatty acids 7 Triacylglycerols V alkaline hydrolysis (saponification) 8 Triacylglycerols VI dispersal of oil-coated dirt particles by a soap 9 Terpenes I acyclic monoterpenes, sesquiterpenes 10 Terpenes II cyclic monoterpenes; containing OXYGEN a TERPENOIDS 11 Terpenes III tetraterpenes a CAROTENES 12 Steroids I male and female sex hormones 13 Steroids II perhydrocyclopentanophenanthrene ring system GONANE 14 Steroids III the basic ring system of steroids ANDROSTANE 15 Steroids IV names of steroid hydrocarbons 16 Steroids V CHOLESTEROL 17 Steroids VI the photochemical reaction of ergosterol to vitamin D2 18 Prostaglandins I C20 carboxylic acids (5-membered ring, at least one C=C bond and several oxygen groups) 19 Prostaglandins II the biosynthesis of prostaglandins 20 Phospholipids I basic structure: PHOSPHATIDIC acid 21 Phospholipids II aminoesters of phosphatidic acid: PHOSPHATIDES 22 Phospholipids III PHOSPHATIDES 23 Waxes esters of long-chain fatty acids and long-chain alcohols 24
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