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Fatty Acids This Page Intentionally Left Blank Fatty Acids Chemistry, Synthesis, and Applications Fatty Acids This page intentionally left blank Fatty Acids Chemistry, Synthesis, and Applications Edited by Moghis U. Ahmad Jina Pharmaceuticals, Inc., Libertyville, IL, United States Academic Press and AOCS Press Academic Press is an imprint of Elsevier 125 London Wall, London EC2Y 5AS, United Kingdom 525 B Street, Suite 1800, San Diego, CA 92101-4495, United States 50 Hampshire Street, 5th Floor, Cambridge, MA 02139, United States The Boulevard, Langford Lane, Kidlington, Oxford OX5 1GB, United Kingdom Copyright r 2017 AOCS Press. Published by Elsevier Inc. All rights reserved. Published in cooperation with American Oil Chemists’ Society www.aocs.org Director, Content Development: Janet Brown. No part of this publication may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, recording, or any information storage and retrieval system, without permission in writing from the publisher. Details on how to seek permission, further information about the Publisher’s permissions policies and our arrangements with organizations such as the Copyright Clearance Center and the Copyright Licensing Agency, can be found at our website: www.elsevier.com/permissions. This book and the individual contributions contained in it are protected under copyright by the Publisher (other than as may be noted herein). Notices Knowledge and best practice in this field are constantly changing. As new research and experience broaden our understanding, changes in research methods, professional practices, or medical treatment may become necessary. Practitioners and researchers must always rely on their own experience and knowledge in evaluating and using any information, methods, compounds, or experiments described herein. In using such information or methods they should be mindful of their own safety and the safety of others, including parties for whom they have a professional responsibility. To the fullest extent of the law, neither the Publisher nor the authors, contributors, or editors, assume any liability for any injury and/or damage to persons or property as a matter of products liability, negligence or otherwise, or from any use or operation of any methods, products, instructions, or ideas contained in the material herein. British Library Cataloguing-in-Publication Data A catalogue record for this book is available from the British Library Library of Congress Cataloging-in-Publication Data A catalog record for this book is available from the Library of Congress ISBN: 978-0-12-809521-8 For Information on all Academic Press publications visit our website at https://www.elsevier.com/books-and-journals Publisher: Andre´ G. Wolff Acquisition Editor: Nancy Maragioglio Editorial Project Manager: Billie Jean Fernandez Production Project Manager: Lisa Jones Cover Designer: Victoria Pearson Typeset by MPS Limited, Chennai, India Contents List of Contributors xvii Meet the Editor xix Preface xxi 1. History of Fatty Acids Chemistry Gary R. List, James A. Kenar and Bryan R. Moser 1.1 Introduction 2 1.2 Early Fatty Acid History 2 1.3 Major Developments in the Oleochemical Industry 9 1.3.1 Fat Splitting 9 1.3.2 Catalytic Hydrogenation 10 1.3.3 Fatty Acid Distillation 11 1.3.4 Fatty Alcohols 11 1.3.5 Estolides 12 1.3.6 Dimer and Trimer Cyclic Fatty Acids 13 1.3.7 Hydroformylation of Fatty Acids 14 1.3.8 Ozonolysis of Fatty Acids and Triglycerides 14 1.4 Contributions of Analytical Chemistry to Fatty Acids 15 1.5 Recent Developments in Fatty Acids 16 1.6 Conclusion 17 References 18 2. Naturally Occurring Fatty Acids: Source, Chemistry, and Uses James A. Kenar, Bryan R. Moser and Gary R. List 2.1 Introduction 24 2.2 Production of Naturally Occurring Fatty Acids 28 2.2.1 Chemical Splitting 29 2.2.2 Lipase Splitting 30 2.3 Purification of Fatty Acids 31 2.3.1 Simple Distillation 31 2.3.2 Fractional Distillation 32 2.3.3 Molecular Distillation 35 2.3.4 Crystallization 35 2.3.5 Urea Fractionation 36 v vi Contents 2.4 Sources and Types of Naturally Occurring Fatty Acids 37 2.4.1 Saturated Fatty Acids 38 2.4.2 Unsaturated Fatty Acids 39 2.4.3 Hydroxy Fatty Acids 43 2.4.4 Acetylenic Fatty Acids 45 2.4.5 Allenic and Cumulenic Fatty Acids 47 2.5 Chemistry of Naturally Occurring Fatty Acids 49 2.5.1 Reactions at the Carboxylic Acid Group 50 2.5.2 Reactions at Unsaturated Sites 57 2.6 Conclusion 71 References 71 3. Epoxy Fatty Acids: Chemistry and Biological Effects Arnis Kuksis and Waldemar Pruzanski 3.1 Introduction 83 3.2 Natural Occurrence and Structure of Epoxy Fatty Acids 84 3.2.1 Oleic and Linoleic Acid Monoepoxides and Hydroxides 84 3.2.2 Arachidonic Acid Monoepoxides 85 3.2.3 Eicosapentaenoic Acid and Docosahexaenoic Acid Monoepoxides 85 3.3 Chemical Synthesis 88 3.3.1 Direct Epoxidation 88 3.3.2 Chemo-Enzymatic Perhydrolysis 89 3.3.3 Other Chemo-Enzymatic Epoxidations 90 3.4 Biosynthesis of Epoxy Fatty Acids 90 3.4.1 Oxygenases and Lipoxygenases 91 3.4.2 Peroxygenases 91 3.4.3 Cytochrome P450-Like Oxygenases 92 3.5 Analysis of Epoxy Fatty Acids 94 3.5.1 Resolution of Regioisomers 95 3.5.2 Resolution of Enantiomers 97 3.5.3 GC/MS and LC/MS Identification of Lipid Epoxides 103 3.6 Biological Effects 104 3.6.1 Lipid Signaling 104 3.6.2 Cellular Effects 105 3.6.3 Systemic Effects 107 3.7 Pathological Effects 108 3.7.1 Toxicity 108 3.7.2 Inflammation and Pain 108 3.7.3 Angiogenesis and Cardiovascular Disease 110 3.7.4 Cancer 111 3.8 Conclusion 112 Abbreviations 112 References 113 Contents vii 4. Acetylenic Epoxy Fatty Acids: Chemistry, Synthesis, and Their Pharmaceutical Applications Valery M. Dembitsky and Dmitry V. Kuklev 4.1 Introduction 121 4.2 Occurrence Epoxy Acetylenic Fatty Acids in Nature 122 4.3 Lipids Containing Epoxy Acetylenic Fatty Acids 125 4.4 Epoxy Acetylenic Furanoid and Thiophene Fatty Acid and Derivatives 128 4.5 Pyranone and Macrocyclic Epoxides 129 4.6 Acetylenic Cyclohexanoid Epoxy Fatty Acids 130 4.7 Determination or Epoxy Acetylenic Lipids 131 4.8 Synthesis of Epoxy Acetylenic Lipids 136 4.9 Concluding Remarks 141 References 142 Further Reading 146 5. Carbocyclic Fatty Acids: Chemistry and Biological Properties Moghis U. Ahmad, Shoukath M. Ali, Ateeq Ahmad, Saifuddin Sheikh and Imran Ahmad 5.1 Introduction 148 5.2 Naturally Occurring Cyclopropene Fatty Acids 150 5.2.1 The Halphen Test 151 5.2.2 Isolation of Cyclopropene Fatty Acids From Seed Oils 152 5.2.3 Chemical Characterization 152 5.3 Synthesis and Characterization of Sterculic Acid 156 5.3.1 Characterization of Dihydrosterculic Acid 158 5.3.2 Total Synthesis of cis-Cyclopropane Fatty Acids 160 5.3.3 Deuterated Cyclopropene Fatty Acids 161 5.4 Biosynthesis of Cyclopropane and Cyclopropene Fatty Acids 163 5.5 Mass Spectrometry of Cyclopropene Fatty Acids 165 5.5.1 Gas Chromatography-Mass Spectrometry Analysis of Cyclopropene Fatty Acids 166 5.5.2 Gas Chromatography-Mass Spectrometry Analysis of Cyclopropane Fatty Acids 171 5.6 Physiological Properties of Cyclopropene Fatty Acids 171 5.7 Cyclopropaneoctanoic Acid 2-Hexyl in Human Adipose Tissue and Serum 173 5.7.1 Cyclopropaneoctanoic Acid 2-Hexyl in Patients With Hypertriglyceridemia 175 5.8 Leishmania Cyclopropane Fatty Acid Synthetase 176 5.8.1 Leishmania: A Fungal Infection 177 5.9 Conclusion 178 References 179 Further Reading 185 viii Contents 6. Modification of Oil Crops to Produce Fatty Acids for Industrial Applications John L. Harwood, Helen K. Woodfield, Guanqun Chen and Randall J. Weselake 6.1 Introduction 188 6.2 Key Aspects of Plant Oil Biosynthesis 189 6.3 Major Oil Crops 194 6.3.1 Oil Palm (Elaeis guineensis) 194 6.3.2 Soybean (Glycine max) 197 6.3.3 Brassica Oilseed Species (Brassica napus, Brassica rapa, Brassica oleracea, Brassica carinata) 201 6.3.4 Sunflower (Helianthus annuus) 206 6.4 Minor Oil Crops 208 6.4.1 Alfalfa (Medicago sativa, Medicago falcata) 209 6.4.2 Almond (Prunus dulcis, Prunus amygdalus, Amygdalus communis) 209 6.4.3 Avocado (Persea americana, Persea gratissima) 209 6.4.4 Blackcurrant (Ribes niger) 209 6.4.5 Borage (Borago officinalis) 209 6.4.6 Borneo Tallow (Shorea stenoptera) 209 6.4.7 Camelina (Camelina sativa)(Section 6.5 Also) 211 6.4.8 Castor (Ricinus communis) 211 6.4.9 Cocoa (Theobroma cacao) 211 6.4.10 Coconut (Cocos nucifera) 212 6.4.11 Coriander (Coriandrum sativum) 212 6.4.12 Cottonseed (Gossypium hirsutum, Gossypium barbadense) 212 6.4.13 Crambe (Crambe abyssinica, Crambe hispanica) (Section 6.5 Also) 212 6.4.14 Cuphea spp. 212 6.4.15 Dimorphotheca (Dimorphotheca pluvialis) 213 6.4.16 Echium (Echium plantagineum) 213 6.4.17 Flax (Linum usitatissimum) 213 6.4.18 Hazelnut (Corylus avellana) 213 6.4.19 Jatropha curcas (See Section 6.5) 213 6.4.20 Jojoba (Simmondsia chinensis) 214 6.4.21 Lesquerella (Lesquerella fendleri) (See Section 6.5) 214 6.4.22 Maize (Corn; Zea mays) 215 6.4.23 Meadowfoam (Limnanthes alba) 215 6.4.24 Mustard (Brassica alba, Brassica carinata, Brassica hirta, Brassica juncea, Brassica nigra) 215 6.4.25 Oats (Avena sativa) 215 6.4.26 Olive (Olea europaea) 215 6.4.27 Peanut (Ground Nut, Arachis hypogaea) 216 6.4.28 Pine Nuts (Pinus spp.) 216 6.4.29 Poppy (Papaver somniferum) 216 Contents ix 6.4.30 Rice (Oryza sativa) Bran Oil 216 6.4.31 Safflower (Carthamus tinctorius) 217 6.4.32 Shea (Butyrospermum parkii, Shea Butter, Karate Butter) 217 6.4.33 Tall 217 6.4.34 Tung (Aleurites fordii) 217 6.4.35 Vernonia Oils 218 6.5 Emerging Industrial Oil Crops 218 6.6 Prospects for Production of Industrial Oils in Vegetative Tissue 222 Acknowledgments 223 References 223 Further Reading 236 7.
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