Fatty Acid and Lipid Chemistry

This book has a pedigree. It has developed from earlier publications by the author and from his experience over 50 years in reading, writing, thinking, and working with lipids and fatty acids. The earlier publications are: (i) An Introduction to the Chemistry of Fats and Fatty Acids, Chapman and Hall, 1958. (ii) An Introduction to the Chemistry and Biochemistry of Fatty Acids and their Glycerides, Chapman and Hall, 1967. (iii) Lipids in Foods: Chemistry, Biochemistry, and Technology (with F. A. Norris), Pergamon Press, 1983. (iv) The Lipid Handbook (with J. L. Harwood and F. B. Padley), Chapman and Hall, first edition 1986, second edition 1994. (v) A Lipid Glossary (with B. G. Herslof), The Oily Press, Dundee, 1992. (vi) Lecture notes for a course on Fatty Acids and Lipids designed for those entering the oil and fat industry and given on over 20 occasions since 1977. The book is dedicated to the next generation of lipid scientists. The study of lipids now involves many disciplines, all of which require a basic knowledge of the chemical nature and properties of these molecules, which is what this book is about. It is written particularly for those who, with some knowledge of chemistry or biochemistry, need to know more about the nature of lipids and fatty acids.

Fatty acids — Nomenclature, structure, isolation and structure-determination, biosynthesis, and chemical synthesis.- 1.1 Fatty acid nomenclature.- 1.2 Fatty acids — main structural features.- 1.3 Saturated acids.- 1.4 Monoene acids.- 1.5 Methylene-interrupted polyene acids.- 1.6 Conjugated polyene acids.- 1.7 Other polyene acids.- 1.8 Acetylenic and allenic acids.- 1.9 Acids with trans-olefinic unsaturation.- 1.10 Branched-chain acids.- 1.11 Cyclic acids.- 1.12 Oxygenated acids.- 1.13 Other acids.- 1.14 Fatty acids — isolation and identification.- 1.15 Fatty acid biosynthesis.- 1.16 Fatty acids — chemical synthesis.- Lipids — Nomenclature, structure, biosynthesis, and chemical synthesis.- 2.1 Introduction.- 2.2 Acylglycerols.- 2.3 Glycosyldiacylglycerols.- 2.4 Phosphoglycerides.- 2.5 Ether lipids.- 2.6 Acyl derivatives of other alcohols.- 2.7 Sphingolipids.- 2.8 Lipid biosynthesis.- 2.9 Chemical synthesis of acylglycerols and phospholipids.- The major sources of oils, fats, and other lipids.- 3.1 Fats and oils in the marketplace.- 3.2 The major vegetable oils and fats.- 3.3 Fats of animal origin.- 3.4 Fatty acid composition.- 3.5 Triacylglycerol composition.- 3.6 Interchangeability of oils and fats.- 3.7 New oilseed crops.- 3.8 Phospholipids: sources and composition.- 3.9 Minor components.- 3.10 Waxes.- Processing: Extraction, refining, fractionation, hydrogénation, interesterification.- 4.1 Extraction.- 4.2 Refining.- 4.3 Hydrogenation.- 4.4 Fractionation.- 4.5 Interesterification.- Analytical procedures.- 5.1 Standard procedures.- 5.2 Lipid analysis.- Physical properties.- 6.1 Polymorphism, crystal structure, and melting point.- 6.2 Ultraviolet spectroscopy.- 6.3 Infrared spectroscopy.- 6.4 Electron spin resonance (ESR) spectroscopy.- 6.5 1HNMRspectroscopy.- 6.6 13CNMR spectroscopy.- 6.7 Mass spectrometry.- Reactions associated with double bonds.- 7.1 Catalytic hydrogenation, chemical reduction, biohydrogenation.- 7.2 Autoxidation and photo-oxygenation.- 7.3 Antioxidants.- 7.4 Biological oxidation.- 7.5 Other oxidation reactions.- 7.6 Halogenation.- 7.7 Oxymercuration.- 7.8 Stereomutation.- 7.9 Metathesis.- 7.10 Double bond migration and cyclization.- 7.11 Dimerization.- 7.12 Other double bond reactions.- Reactions of the carboxy 1 group.- 8.1 Introduction.- 8.2 Hydrolysis.- 8.3 Esterification.- 8.4 Acid chlorides, anhydrides, and ketene dimers.- 8.5 Peroxy acids and esters.- 8.6 Alcohols.- 8.7 Nitrogen-containing compounds.- 8.8 Other reactions of the carboxyl group.- Dietary fats and nutrition.- 9.1 Storage and structural fats.- 9.2 Digestion, absorption, and transport.- 9.3 The role of fats in health and disease.- Practical applications of oils and fats.- 10.1 Introduction.- 10.2 Butter.- 10.3 Margarine.- 10.4 Other food uses.- 10.5 Food-grade surfactants and emulsifiers.- 10.6 Non-food uses of fatty acids and their derivatives.