Preparation of Ester Derivatives of Fatty Acids for Chromatographic Analysis

A. Introduction B. Acid-Catalysed Esterification and Transesterification 1. General mechanism 2. Methanolic hydrogen chloride 3. Methanolic sulfuric acid 4. Boron trifluoride-methanol 5. Other acidic catalysts C. Base-Catalysed Transesterification 1. General mechanism 2. Sodium and potassium methoxide catalysts 3. Organic base catalysis D. Diazomethane and Related Reagents 1. Diazomethane and methyl ester preparation 2. Preparation of UV-absorbing and other derivatives E. Pyrolysis of Tetramethylammonium Salts of Fatty acids for the Preparation of Methyl Esters F. Preparation of Esters and Amides via Activated Fatty Acids 1. Acid halides 2. Fatty acid anhydrides 3. Imidazolides 4. Other coupling reagents G. Reaction of Alkyl or Aryl Halides with a Base 1. Derivatives for gas chromatography 2. Phenacyl esters and other derivatives for high-performance liquid chromatography H. Alternative Methods for the Preparation of Esters, Amides and Other Fatty Acid Derivatives 1. Dimethylsulfate with dicyclohexylamine 2. Preparation of esters with alkyl formamide derivatives 3. Trimethylsilyl esters 4. Preparation of pyrrolidides from esters 5. Preparation of hydroxamic acid and related derivatives 6. Reaction with Grignard reagents I. Special Cases 1. Short-chain fatty acids 2. Fatty acids with unusual structures 3. Sphingolipids and other N-acyl lipids 4. Sterol esters 5. Selective esterification of free fatty acids in the presence of other lipids J. Preparation of Esters in the Presence of Adsorbents for Thin-Layer Chromatography K. Simultaneous Extraction from Tissues and Transesterification L. Artefacts of Esterification Procedures M. The Choice of Reagents a Summary