Food enrichment with omega-3 fatty acids © Woodhead Publishing Limited, 2013 Related titles: Encapsulation technologies and delivery systems for food ingredients and nutraceuticals (ISBN 978-0-85709-124-6) Reducing saturated fats in foods (ISBN 978-1-84569-740-2) Functional foods (ISBN 978-1-84569-690-0) Details of these books and a complete list of titles from Woodhead Publishing can be obtained by: • • • visiting our web site at www.woodheadpublishing.com contacting Customer Services (e-mail: sales@woodheadpublishing.com; fax: +44 (0) 1223 832819; tel.: +44 (0) 1223 499140 ext 130; address: Woodhead Publishing Limited, 80 High Street, Sawston, Cambridge CB22 3HJ, UK) in North America, contacting our US office (e-mail: usmarketing@ woodheadpublishing.com; tel.: (215) 928 9112; address: Woodhead Publishing, 1518 Walnut Street, Suite 1100, Philadelphia, PA 19102-3406, USA) If you would like e-versions of our content, please visit our online platform: www.woodheadpublishingonline.com Please recommend it to your librarian so that everyone in your institution can benefit from the wealth of content on the site We are always happy to receive suggestions for new books from potential editors To enquire about contributing to our Food Science, Technology and Nutrition series, please send your name, contact address and details of the topic/s you are interested in to nell.holden@woodheadpublishing.com We look forward to hearing from you The team responsible for publishing this book: Commissioning Editor: Nell Holden Publications Coordinator: Emily Cole Project Editor: Kate Hardcastle Editorial and Production Manager: Mary Campbell Production Editor: Adam Hooper Copyeditor: Helen MacFadyen Proofreader: Janice Gordon Cover Designer: Terry Callanan © Woodhead Publishing Limited, 2013 Woodhead Publishing Series in Food Science, Technology and Nutrition: Number 252 Food enrichment with omega-3 fatty acids Edited by Charlotte Jacobsen, Nina Skall Nielsen, Anna Frisenfeldt Horn and Ann-Dorit Moltke Sørensen Oxford Cambridge Philadelphia New Delhi © Woodhead Publishing Limited, 2013 Published by Woodhead Publishing Limited, 80 High Street, Sawston, Cambridge CB22 3HJ, UK www.woodheadpublishing.com www.woodheadpublishingonline.com Woodhead Publishing, 1518 Walnut Street, Suite 1100, Philadelphia, PA 19102-3406, USA Woodhead Publishing India Private Limited, 303 Vardaan House, 7/28 Ansari Road, Daryaganj, New Delhi – 110002, India www.woodheadpublishingindia.com First published 2013, Woodhead Publishing Limited © Woodhead Publishing Limited, 2013 The publisher has made every effort to ensure that permission for copyright material has been obtained by authors wishing to use such material The authors and the publisher will be glad to hear from any copyright holder it has not been possible to contact The authors have asserted their moral rights This book contains information obtained from authentic and highly regarded sources Reprinted material is quoted with 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be trademarks or registered trademarks, and are used only for identification and explanation, without intent to infringe British Library Cataloguing in Publication Data A catalogue record for this book is available from the British Library Library of Congress Control Number: 2013936412 ISBN 978-0-85709-428-5 (print) ISBN 978-0-85709-886-3 (online) ISSN 2042-8049 Woodhead Publishing Series in Food Science, Technology and Nutrition (print) ISSN 2042-8057 Woodhead Publishing Series in Food Science, Technology and Nutrition (online) The publisher’s policy is to use permanent paper from mills that operate a sustainable forestry policy, and which has been manufactured from pulp which is processed using acid-free and elemental chlorine-free practices Furthermore, the publisher ensures that the text paper and cover board used have met acceptable environmental accreditation standards Typeset by Toppan Best-set Premedia Limited Printed by MPG Printgroup, UK © Woodhead Publishing Limited, 2013 Contents Contributor contact details Woodhead Publishing Series in Food Science, Technology and Nutrition Preface Part I xi xv xxv Background to omega-3 food enrichment Nutritional benefits of omega-3 fatty acids P C Calder, University of Southampton, UK 1.1 Introduction 1.2 Dietary sources and typical intakes of omega-3 fatty acids 1.3 Marine omega-3 fatty acids 1.4 Health effects of α-linolenic acid 1.5 Future trends 1.6 Conclusion 1.7 Sources of further information and advice 1.8 References 1.9 Appendix: abbreviations Sources of omega-3 fatty acids A P Bimbo, Consultant, USA 2.1 Introduction 2.2 Background 2.3 Marine oils in perspective 2.4 Current and alternative marine oils 2.5 Krill and single-cell marine oils © Woodhead Publishing Limited, 2013 11 18 18 19 20 21 26 27 27 28 34 39 40 vi Contents 2.6 2.7 2.8 2.9 2.10 2.11 Part II Wild fish and other marine oils Species farmed for marine oils Sustainability and certifications Plant sources Conclusion and future trends References 44 69 84 93 98 100 Stabilisation of fish oil and foods enriched with omega-3 fatty acids 109 Impact of extraction, refining and concentration stages on the stability of fish oil Å Oterhals and G Vogt, Nofima, Norway 3.1 Introduction 3.2 Methods for the extraction, refining and concentration of fish oil 3.3 Impact of extraction, refining and concentration stages on oil stability 3.4 Conclusion and future trends 3.5 Sources of further information and advice 3.6 References Stabilization of omega-3 oils and enriched foods using antioxidants C Jacobsen, A.-D M Sørensen and N S Nielsen, Technical University of Denmark, Denmark 4.1 Introduction 4.2 Lipid oxidation and antioxidant reactions 4.3 Antioxidant protection of oils and oil-based products 4.4 Antioxidant protection of other food products 4.5 Future trends 4.6 Conclusion 4.7 References Stabilization of omega-3 oils and enriched foods using emulsifiers C Genot, T.-H Kabri and A Meynier, INRA, France 5.1 Introduction 5.2 Reasons for using emulsifiers 5.3 Emulsifiers for omega-3 polyunsaturated fatty acid (PUFA) delivery systems and emulsified foods 5.4 Emulsifiers and lipid oxidation 5.5 The impact of emulsifiers and emulsification on flavour and texture perception © Woodhead Publishing Limited, 2013 111 111 115 121 124 125 126 130 130 131 134 139 146 146 146 150 150 151 159 175 178 Contents 5.6 5.7 5.8 5.9 5.10 180 183 184 185 185 Spray drying and encapsulation of omega-3 oils C J Barrow and B Wang, Deakin University, Australia and B Adhikari and H Liu, University of Ballarat, Australia 6.1 Introduction 6.2 Microencapsulation methods for stabilizing omega-3 oils in food 6.3 Emulsion assemblies for omega-3 oils 6.4 Microencapsulation techniques for stabilizing omega-3 oils 6.5 Characteristics and analysis of microencapsulated omega-3 oil products 6.6 Conclusion and future trends 6.7 References 194 Analysis of omega-3 fatty acids in foods and supplements J M Curtis and B A Black, University of Alberta, Canada 7.1 Introduction 7.2 The analysis of omega-3 oils by gas–liquid chromatography / flame ionization detector (GC/FID) 7.3 The measurement of omega-3 levels in foods 7.4 Methyl esters and other fatty acid derivatives 7.5 ‘One-step’ methods combining extraction, digestion and derivatization 7.6 Examples in literature of the analysis of omega-3 containing foods 7.7 Alternative analytical methods for omega-3 analysis 7.8 Future trends 7.9 Sources of further information and advice 7.10 References 226 Part III Applications of emulsifiers to stabilize delivery systems and foods enriched with omega-3 PUFA Future trends Sources of further information Acknowledgements References vii Food enrichment with omega-3 fatty acids Modification of animal diets for the enrichment of dairy and meat products with omega-3 fatty acids R J Dewhurst and A P Moloney, Teagasc, Animal & Grassland Research and Innovation Centre, Ireland 8.1 Introduction © Woodhead Publishing Limited, 2013 194 197 201 206 214 218 219 226 227 230 237 241 243 245 248 249 249 255 257 257 viii Contents 8.2 8.3 8.4 8.5 8.6 8.7 8.8 10 11 12 Sources of omega-3 fatty acids Feeds that increase omega-3 fatty acids in ruminant milk and meat Increasing omega-3 fatty acids in animal diets Future trends Conclusion Sources of further information and advice References Egg enrichment with omega-3 fatty acids G Cherian, Oregon State University, USA 9.1 Introduction 9.2 Egg lipid composition, formation and deposition 9.3 Modifying egg lipid composition 9.4 Egg omega-3 fatty acid enrichment: consequences and challenges 9.5 Conclusion and future trends 9.6 References Enrichment of meat products with omega-3 fatty acids by methods other than modification of animal diet D Ansorena and I Astiasarán, University of Navarra, Spain 10.1 Introduction 10.2 Enrichment of meat products with omega-3 fatty acids 10.3 Future trends 10.4 Conclusion 10.5 Sources of further information and advice 10.6 References Enrichment of baked goods with omega-3 fatty acids E M Hernandez, Omega Protein Inc., USA 11.1 Introduction 11.2 Omega-3 fatty acids in baked goods 11.3 Omega-3 fatty acids in nutrition bars 11.4 Application techniques for adding omega-3 fatty acids to foods 11.5 Analysis of omega-3 fatty acids 11.6 Conclusion 11.7 References Enrichment of emulsified foods with omega-3 fatty acids C Jacobsen, A F Horn and N S Nielsen, Technical University of Denmark, Denmark 12.1 Introduction © Woodhead Publishing Limited, 2013 258 261 271 276 277 277 277 288 288 288 291 294 296 297 299 299 300 311 312 312 314 319 319 321 326 327 330 332 332 336 336 Contents 12.2 12.3 12.4 12.5 12.6 12.7 12.8 12.9 13 Enrichment of infant formula with omega-3 fatty acids C Kuratko, J R Abril, J P Hoffman and N Salem, Jr, DSM Nutritional Products, USA 13.1 Introduction 13.2 Importance of omega-3 fatty acids during infancy 13.3 Omega-3 fatty acid supplementation in infant formula 13.4 Adding omega-3 fatty acids to infant formula 13.5 Sensory characteristics of omega-3 enriched infant formula 13.6 Future trends 13.7 Conclusion 13.8 Sources of further information and advice 13.9 References Part IV 14 Volatile oxidation products and off-flavor formation in omega-3 enriched food emulsions – using milk as an example Factors affecting lipid oxidation in emulsified omega-3 enriched foods Delivery systems Antioxidative effects of other ingredients in emulsified omega-3 enriched foods Other omega-3 enriched food emulsions Future trends Conclusion References ix 337 338 342 345 347 349 349 350 353 353 356 360 366 373 375 375 376 377 New directions 387 Algal oil as a source of omega-3 fatty acids R J Winwood, DSM Nutritional Products, UK 14.1 Introduction 14.2 Using microalgae to produce food ingredients 14.3 Typical production of docosahexaenoic acid (DHA) algal oils 14.4 DSM DHA intellectual property 14.5 Regulatory approval of algal oil 14.6 A case study: the story of the development of Martek Biosciences Corporation 14.7 Future trends 14.8 Sources of further information and advice 14.9 Acknowledgements 14.10 References 389 © Woodhead Publishing Limited, 2013 389 391 395 398 399 400 402 403 403 403 Labelling and claims in foods containing omega-3 fatty acids 411 to assist in controlling a serious disease or condition by either reducing risk factors or improving health (FSANZ, 2013) With regard to omega-3 fatty acids, the allowed claims fall under the general claims category After review of the published literature on the health benefits of omega-3s, a scientific committee for FSANZ concluded that further evidence was needed to establish an omega-3 intake requirement for reduction in risk of cardiovascular disease (CVD) FSANZ considers that the evidence for a benefit of long-chain omega-3 fatty acids EPA and DHA on CVD morbidity and mortality can be rated as ‘probable’ but cannot be rated as ‘convincing’ Therefore, FSANZ issued an opinion that there is sufficient evidence to support a ‘general’ level health claim based on the diet–disease relationship between long-chain omega-3 fatty acids and cardiovascular health (FSANZ, 2013) Australia’s government National Health and Medical Research Council (NHMRC), on the other hand, recommends 430–570 mg/day from foods, as an amount which might be expected to reduce the risk of CVD in the ANZ population (NHMRC, 2006) Japan’s Ministry of Health Labor and Welfare recommends an intake of 1.8–2.4 g of total omega-3 fatty acids per day (NIH, 2005) 15.5 Implications of omega-3 nutrition and health claims for the global food industry The growing consumer interest in the nutrition content of foods and supplements has resulted in the introduction of a wide variety of more healthoriented products with more specialized bioactive compounds As a result, the information about nutrition and health provided in packaging can be complex and difficult to understand This information has become increasingly important as both the general population and health institutions become more interested in areas such as children’s nutrition, heart, digestive, cognitive and immune health, obesity, and healthy aging The demand for health-oriented foods has also spurred manufacturers to market food products with healthier connotations, such as low in saturated fats, nontrans fats, low in cholesterol, higher protein content, lower in carbohydrates, higher in fiber This has led manufacturers to introduce supplements and fortified foods with ingredients that have disease prevention and, in some cases, pharmaceutic-like properties Omega-3 fatty acids are considered ingredients that have disease prevention properties and, as mentioned before, their use as an ingredient in foods and supplements has grown appreciably in the last few years 15.6 Conclusion and future trends The demand for fortified foods with bioactive compounds will continue to grow and the distinction between some fortified foods and supplements will © Woodhead Publishing Limited, 2013 412 Food enrichment with omega-3 fatty acids become less apparent This new generation of health-oriented food products will require more accurate and better explanatory information to be included in the labels This will also require involvement of official institutions to set labelling guidelines for nutrition or health claims, for example: identifying allowable claims, and implementation and enforcement mechanisms for compliance Technological advances have enabled manufacturers to overcome formulation challenges with omega-3s in regard to shelf-life enhancement and product stability The widely recognized health benefits of omega-3s have translated into these fatty acids becoming integrated not just through supplements but also into the general diet through new products in the areas of wellness nutrition and medical foods New labelling guidelines for omega-3 fatty acids in foods and supplements will allow the consumer to become better informed on the health benefits of omega3s and help distinguish between food and therapeutic-type dietary supplements 15.7 References aha (2013) Frequently Asked Questions About Fish Dallas, TX: American Heart Association, available at: http://www.heart.org/HEARTORG/General/ Frequently-Asked-Questions-About-Fish_UCM_306451_Article.jsp [accessed February 2013] commission regulation (EC) No 1924/2006 of the European Parliament and of the Council of 20 December 2006 on nutrition and health claims made on foods, OJ, L404, 9–25 efsa (2009) Labelling reference intake values for n-3 and n-6 polyunsaturated fatty acids, EFSA Journal, 1176, 1–11 efsa (2010) ‘Scientific opinion on the substantiation of health claims related to eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), docosapentaenoic acid (DPA) and maintenance of normal cardiac function’, EFSA Journal, 8(10): 1796 efsa (2012a) ‘General function’ health claims under article 13 Parma: European Food Safety Authority, available at: http://www.efsa.europa.eu/en/topics/topic/ article13.htm [accessed February 2013] efsa (2012b) Claims on disease risk reduction and child development or health under Article 14 Parma: European Food Safety Authority, available at: http://www.efsa europa.eu/en/topics/topic/article14.htm [accessed February 2013] efsa (2012c) ‘Scientific opinion on the tolerable upper intake level of eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA) and docosapentaenoic acid (DPA)’, EFSA Journal, 10(7), 2815 fda (2003) Claims That Can Be Made for Conventional Foods and Dietary Supplements http://www.fda.gov/Food/LabelingNutrition/LabelClaims/ucm111447.htm [accesed 7/9/2012] fda/cfsan (2004a) Letter Responding to Health Claim Petition dated June 23, 2003 (Wellness petition): Omega-3 Fatty Acids and Reduced Risk of Coronary Heart Disease (Docket No 2003Q-0401), available at: http://www.fda.gov/ Food/LabelingNutrition/LabelClaims/QualifiedHealthClaims/ucm072936.htm [accessed February 2013] © Woodhead Publishing Limited, 2013 Labelling and claims in foods containing omega-3 fatty acids 413 fda/cfsan (2004b) Letter Responding to Health Claim Petition dated November 3, 2003 (Martek Petition): Omega-3 Fatty Acids and Reduced Risk of Coronary Heart Disease (Docket No 2003Q-0401), available at: http://www.fda.gov/Food/ LabelingNutrition/LabelClaims/QualifiedHealthClaims/ucm072932.htm [accessed February 2013] fsanz (2013) Long chain omega-3 fatty acids and cardiovascular disease – FSANZ consideration of a commissioned review Food Standards Australia New Zealand, available at: http://www.foodstandards.gov.au/_srcfiles/FSANZ%20consideration %20of%20omega-3%20review1.pdf [accessed February 2013] iom (Institutes of Medicine) (2002) Dietary Reference Intakes for Energy, Carbohydrate, Fiber, Fat, Fatty Acids, Cholesterol, Protein, and Amino Acids Washington DC: National Academies Press nih (2005) Dietary Reference Intakes for Japanese Tokyo: Ministry of Health, Labour and Welfare, available at: http://www0.nih.go.jp/eiken/english/research/ pdf/dris2005_eng.pdf [accessed February 2013] © Woodhead Publishing Limited, 2013 Index α-linolenic acid (ALA), 258–9, 355–6, 406–7 health effects, 18 plant sources, α–tocopheryl acetate, 294–5 accelerated-solvent extraction (ASE), 236–7 acid catalysed esterification method, 243 activated carbon, 123 Alaska pollock, 60 10-year average landings, 65 omega-3 fatty acid content of oils and lipids, 65 algal oil, 8, 308, 310 DSM DHA intellectual property, 398 microalgae in production of food ingredients, 391–4 extraction/downstream processing of microbial oil, 394 extraction methods, 393 industrial production of oils, 393–4 lipids from microalgae, 392 marine-sourced omega-3 LC PUFA, 391 rationale, 392 suitability for industrial production, 393 omega-3 fatty acids, 389–403 future trends, 402–3 LC-PUFAs source, 390 production of DHA algal oils, 395–8 extraction, 396–7 fermentation, 395–6 purification, 397–8 storage conditions, 398 regulatory approval of algal oil, 399–400 European Union, 399 USA, 399–400 alkoxyl lipid radical, 132 Alpine herbages, 268–9 effects of Alpine pasture on 18:3 as a percentage of total milk fatty acids, 269 American Oil Chemists Society Method (Ce 1b-89), 331 anchovy, 44, 46–7 10-year average landings, 46 omega-3 fatty acid content of oils and lipids, 47 animal diet modification dairy and meat products enrichment with omega-3 fatty acids, 257–77 feeds that increase omega-3 fatty acids in ruminant milk and meat, 261–71 future trends, 276 increasing omega-3 fatty acids in animal diets, 271–6 sources, 258–61 antioxidant radicals, 132 © Woodhead Publishing Limited, 2013 416 Index antioxidants, 294–5, 310, 328 future trends, 146 lipid oxidation and reactions, 131–4 factors affecting efficacy, 133–4 omega-3 oils stabilisation and enriched foods, 130–46 protection of oils and oil-based products, 134–9 protection of other food products, 139–45 AOAC 996.06, 244 AOCS methods Celi-07, 229 apolipoproteins, 289 arachidonic acid (ARA), 355–6, 361, 407 area percent method, 330 ascorbyl palmitate, 140 Asia, 410–11 ASTM D6751-1b, 31 Atlantic cod, 53, 60 10-year average landings, 61 omega-3 fatty acid content of oils and lipids, 62 Australia, 410–11 authorised health claims, 408 autotrophic, 391 baked goods omega-3 fatty acids, 321–6 analysis, 330–2 application techniques for adding in foods, 327–30 examples of baked products fortified with omega-3 fats, 323 nutritious bars, 326–7 Bayley Scales of Infant Development (BSID), 360, 365 bioavailability, 217–18 biohydrogenation, 261 biosurfactants, 173–4 Bligh and Dyer method, 231 blue grenadier, 69 10-year average landings, 70 omega-3 fatty acid content of oils and lipids, 71 bologna typed sausages, 307–8 bonito, 69 10-year average landings, 74 omega-3 fatty acid content of oils and lipids, 75 botanical herbages, 268–9 brain development, 356, 358 bread, 143–4, 322 breast milk effect of milk lipids on omega-3 status and development, 359–60 factors infuencing composition of breast milk, 359 omega-3 fatty acid composition, 359 Cambrian explosion, 391 capelin, 69 10-year average landings, 72 omega-3 fatty acid content of oils and lipids, 73 capillary gas chromatography, 248 Carbowax, 240 casein, 344 chicken meat patties, 306–7 chilling, 208 cholesterol, 291–2 clover silages, 266–7 effects of clover silages vs grass silages on 18:3 n-3, 266 effects of replacing grass silage with red clover silage on 18:3 n-3 proportion, 267 clupeoids, 48 10-year average landings, 49 omega-3 fatty acid content of oils and lipids, 50 coalescence, 156, 158 Code of Conduct for Responsible Fisheries, 84 Commission Regulation (EC) No 853/2004, 112 Commission Regulation (EC) No 1022/2008, 112, 113 Commission Regulation (EC) No 1881/2006, 113 Commission Regulation (EC) No 1924/2006, 406 Commission Regulation (EU) No 1259/2011, 113 complex co-acervation, 209–12 formation of hydrogel particles, 210 confocal laser scanning microscopy (CLSM), 342 cooked meat products, 307–9 creaming, 156 © Woodhead Publishing Limited, 2013 Index crude oil quality influencing factors, 116–18 quality standards, 113–14 guidelines, 113 specifications given in selected fish oil monographs, 114 Crypthecodinium, 401 Crypthecodinium cohnii, 394 Crythecodiniacea, 393 dairy products analysis of omega-3, 243–4 enrichment with omega-3 fatty acids in animal diet modification, 257–77 feeds that increase omega-3 fatty acids in ruminant milk and meat, 261–71 future trends, 276 increasing omega-3 fatty acids in animal diet, 271–6 sources, 258–61 decontamination, 118–21 degumming, 118–19 delivery system emulsified foods, 342–5 intensity of fishy odour and flavour of milk, 343 deodorisation, 120 dewaxing, 397 DHASCO, 394, 399 DIAMOND study, 364, 365 diglycerides, 172 DINO study, 362 docosahexaenoic acid (DHA), 3–4, 6–7, 27, 355–6, 389–90, 394, 399, 400–1, 406–7 breast milk, 359–60 evolutionary origins, 391 increase concentration in plasma lipid, cells and tissues in human, 8, 10–11 time course of changes in human blood mononuclear cells, 11 safety of supplementation in infant formula, 361 supplementation in preterm infant formula, 361–3 neurocognitive development, 363 visual development, 362 417 supplementation in term infant formula, 363–6 neurocognitive function, 365–6 visual acuity, 363–5 docosapentaenoic acid (DPA), 6–7 dressing, 138–9 drinking yoghurt, 142–3 droplet size, 215 dry blending, 367 echium oil, 269–70 egg consequences and challenges, 294–6 consumption and reported health effects, 296 human studies, 295–6 lipid oxidation products in eggs, 295 sensory characteristics and consumer acceptance, 295 egg yolk lipid formation and deposition, 289–91 physiological factors, 289–90 lipid composition, formation and deposition, 288–91 composition, 288–9 modifying egg lipid composition, 291–4 effect o fatty acid content of chicken eggs of feeding flax seeds or fish oil, 293 egg and cholesterol controversy, 291–2 egg omega-3 fatty acid enrichment through hen’s diet, 292–3 hen production performance and egg quality aspects, 293–4 omega-3 fatty acid content in feed sources, 293 reasons for increasing omega-3 fatty acids in chicken eggs, 292 omega-3 fatty acids, 288–97 future trends, 296–7 role of hen diet, 290–1 omega-6 and omega-3 fatty acids and concentrations o chicken egg, 291 egg yolk, 339 © Woodhead Publishing Limited, 2013 418 Index eicosapentaenoic acid (EPA), 3–4, 5–6, 6–7, 27, 389–90, 406–7 increase concentration in plasma lipid, cells and tissues in human, 8, 10–11 dose-dependent incorporation into human plasma and blood mononuclear cell phospholipids, 10 time course of changes in human blood mononuclear cells, 11 emulsification, 154–5 impact on flavour and texture perception, 178–80 microencapsulation, 206–12 emulsified foods antioxidative effects of other ingredients, 345–7 1-pentene-3-ol (ng/g emulsion) and hexanal (ng/g emulsion) in milk emulsions, 346 delivery system, 342–5 enrichment with omega-3 fatty acids, 336–50 factors affecting lipid oxidation, 338–42 choice of other ingredients, 340 effect of emulsification conditions and oil droplet size, 340–42 emulsifiers and pH, 339–40 omega-3 oil quality, 338–9 future trends, 349 other food emulsions, 347–9 overall flavour scores, 348 volatile oxidation and off-flavour formation in milk, 337–8 emulsifiers, 339–40 applications to stabilise delivery systems, 180–3 delivery systems and emulsified foods, 159–75 adsorption at the oil-in-water (o/w) interface and emulsion stabilisation, 160–1 emulsification impact on flavour and texture perception, 178–80 future trends, 183–4 lipid oxidation, 175–8 omega-3 stabilisation and enriched foods, 150–84 uses, 151–9 emulsification process, 154–5 emulsion and other delivery systems, 152–4 emulsion destabilisation, 155–7 omega-3 polyunsaturated fatty acid (PUFA) oils characteristics, 151–2 role in emulsion stabilisation, 157–9 emulsion and other delivery systems, 152–4 representation of various oil and water dispersions, 153 assemblies for omega-3 oils, 201–6 encapsulation systems utilised to encapsulate omega-3 fatty acids, 202 destabilisation, 155–7 mechanism, 156 emulsifier role in stabilisation, 157–9 partition of emulsifiers between interface, oil and water phase, 157 encapsulated fish oil, 243 encapsulated fish oil, 325 encapsulated flaxseed oil, 325 encapsulation emulsion assemblies, 201–6 future trends, 218–19 microencapsulated products characteristics and analysis, 214–18 microencapsulation methods for stabilizing omega-3, 197–201 microencapsulation techniques, 206–14 omega-3 oils, 194–219 overview, 194–7 food products fortified with omega-3 fatty acids, 196 health benefits of dietary omega-3 oils, 194–6 oxidative instability of omega-3 oils, 196–7 enzyme-mediated antioxidant systems, 121 EPA, 402 essential fats infant formula, 354–5 ethylenediaminetetra acetic acid (EDTA), 133, 136–7, 141 © Woodhead Publishing Limited, 2013 Index Europe, 406–7 European Food Safety Authority (EFSA), 406–7 European Pharmacopeia methods, 229 European Union, 275 extraction, 396–7 extrusion-based microencapsulation, 213 Famewax, 240 farmed catfish, 78 10-year average production, 82 omega-3 fatty acid content of oils and lipids, 83 farmed fish, 78, 84 aquaculture production, 5-year vs 10-year average, 86 Chinese farmed carp 10-year average production, 84 omega-3 fatty acid content of oils and lipids, 85 farmed river eels, 78 10-year average production, 80 omega-3 fatty acid content of oils and lipids, 81 fatty acid methyl esters (FAME), 227–8, 231, 237–8 fatty acids composition in milk, 273 derivatives, 237–41 fermentation algal oil, 395–6 production process for infant formula, 395 fermented products, 309–11 fish oils, 7, 270, 325, 327, 340 extraction, refining and concentration methods, 115–21 decontamination, 118–21 factors influencing crude oil quality, 116–18 fishmeal and oil process, 115–16 main unit operations in oil manufacturing process, 115 processing steps in the production of edible grade fish oil and ethyl ester, 119 extraction, refining and concentration stages, 111–25 impact on oil stability, 121–4 419 future trends, 124–5 overview, 111–14 crude and refined oil quality standards, 113–14 raw materials and quality regulations, 112–13 rumen protected, 271 fish product, 144–5 fitness bar, 143–4 flame ionisation detector (FID), 227–30 flavour perception, 179 flavour release, 179 flavour volatile analysis, 275 flaxseed, 322–3 flour, 324 oil, 324 flocculation, 155 fluidised-based microencapsulation, 213–14 characteristics of the techniques for microencapsulation, 214 industrialisation characters of different microencapsulation techniques, 215 fluidised bed coating, 213 Folch method, 234 food labelling foods with omega-3 fatty acids, 405–12 Food Standards Australia New Zealand (FSANZ), 410–11 foods analysis of omega-3 fatty acids, 226–49 alternative analytical methods, 245–8 examples in literature containing foods, 243–5 future trends, 248–9 gas–liquid chromatography / flame ionisation detector (GC/FID), 227–30 measurement in foods, 230–7 methyl esters ad other fatty acids derivatives, 237–41 one-step methods combining extraction, digestion and derivatisation, 241–3 fortification, 329 bread, 326 © Woodhead Publishing Limited, 2013 420 Index Fourier transform -NIR (FT-NIR), 247–8 Fourier transform-infrared (FT-IR), 248 Frankfurter-type sausages, 308–9 free lipid radicals, 131 freeze-dried emulsions, 207–8 fresh herbage, 262, 264–6 fresh pasture effects vs conserved forages, 264 grazed glass influence on fatty acid composition, 265 fresh meat products, 301, 306–7 Friend of the Sea (FOS), 87 gas chromatography (GC), 326 gas–liquid chromatography (GC), 227–30 gas–liquid chromatography with flame ionisation detector (GC-FID), 227–30 response factors, 228–30 review papers and book chapters related to analysis of omega-3 fatty acids, 228 gas–liquid chromatography with mass spectrometry (GC-MS), 227–8, 245–6 generally recognised as safe (GRAS), 321 grass silage, 268 green tea, 141 hays, 268 health claims, 405–12 herbage fatty acids, 259 heterotrophic, 391 high molecular weight emulsifiers, 174–5 high pressure valve homogenisers, 154 high speed blenders, 154 hoki, 69 10-year average landings, 70 omega-3 fatty acid content of oils and lipids, 71 horse mackerels, 53 10-year average landings, 56 omega-3 fatty acid content of oils and lipids, 57 hydrogenated oils, 320 hydrophilic-lipophilic balance (HLB), 162–3, 198 in situ derivatisation methods, 241–3 infant formula addition to infant formula, 366–73 diagram of production, 370 methods for adding omega-3 fatty acids, 367, 369 nutrients in a marketed newborn infant formula, 368 preventing oxidation during processing, 369–73 typical ingredients, 367 enrichment with omega-3 fatty acids, 353–77 history of essential fats in infant formula, 354–5 omega-3 fatty acid deficiency in infants, 355–6 future trends, 374 importance of omega-3 fatty acids during infancy, 356, 358–60 brain development, 356, 358 breast milk, 359–60 retinal physiology, 358–9 sensory characteristics, 373–4 flavour scores for grading milk, 374 supplementation in infant formula, 360–6 DHA supplementation in preterm infant formula, 361–3 DHA supplementation in term infant formula, 363–6 safety of DHA supplementation, 361 infrared (IR) spectroscopy, 247–8 ISO-IDF, 244 jack mackerels, 53 10-year average landings, 56 omega-3 fatty acid content of oils and lipids, 57 ketones, 337 krill, 40–1 fatty acid content, 42 Antarctic krill catch, 41 Antarctic krill landings, 40 lecithin, 164, 169–72, 176, 177, 182–3 chemical structures of surfactants, 169, 170–1 limit of quatitation (LOQ), 244–5 © Woodhead Publishing Limited, 2013 Index linolenic acid (LA), 407 linseed, 259 linseed oil, 310 lipid hydroperoxide, 131–2, 339 lipid oxidation, 131–4, 175–8 factors, 338–42 sensory attributes determined by descriptive profiling, 341 oxidation of mechanism of polyunsaturated lipids, 131 lipid peroxyl radicals (LOO), 131–2 lipids, 234, 392 fractionation, 245 synthesis, 260–1 lipophilised antioxidants, 141 liposome entrapment, 208–9 liposome formed by phospholipids in an aqueous solution, 209 liquid chromatography mass spectrometry (LC/MS), 245–6 long chain polyunsaturated fatty acid (LC PUFA), 274, 353, 355, 363–5, 369–73, 389, 406–7 marine algae, 391 low molecular weight emulsifiers, 161–74 molecular geometry, 161–2 effect of the molecular geometry of surfactant on o/w interface, 162 o/w interface characteristics, 163–4 classification and characteristics of low molecular weight surfactants used in food industry, 165–8 lyophilisation, 242 mackerels, 48 10-year average landings, 51 omega-3 fatty acid content of oils and lipids, 52 macroemulsion, 152 Maillard reaction, 274 margarine, 139 marine oils, 34–9 current and alternative, 39 fish oil production in other countries, 35 global fish oil production in major countries, 34 global production, 35 421 market, 37–9 prices of crude fish oil, 38 structure change for fish oil, 37 production, 36–7 raw material sources, 36 species farmed, 69, 76–84 farmed salmonids, 10-year average production, 77 major aquaculture-producing countries, 76 marine omega-3 fatty acids, 11–17 increased intake health benefits, 14–16 physiological roles and potential clinical benefits of omega-3 fatty acids, 15 mechanism which influence cell function, 11–14 alterations in membrane structure and function, 11–12 interacting mechanisms that influence cell function, 12 lipid mediators, 12–13 receptor-mediated effects, 13–14 recommended intake, 16–17 Marine Stewardship Council (MSC), 87 Martek Biosciences Corporation, 390–1, 400–2 mayonnaise-based salads, 138 meat, 244–5 meat products, 144–5 enrichment with omega-3 fatty acids in animal diet modification, 257–77 feeds that increase omega-3 fatty acids in ruminant milk and meat, 261–71 future trends, 276 increasing omega-3 fatty acids in animal diet, 271–6 sources, 258–61 methods of enrichment with omega-3 fatty acids, 299–313 future trends, 311–12 omega-3 fatty acids, 300–11 amounts of omega-3 and omega-6, 302–4 cooked meat products, 307–9 fermented products, 309–11 fresh meat products, 301, 306–7 summary of use of synthetic and natural antioxidants, 305 © Woodhead Publishing Limited, 2013 422 Index sources of further information and advice, 312–13 commercial meat products enriched in omega-3 fatty acids, 313 MEG-3, 241 membrane homogenisers, 155 methyl esters, 237–41 methylation, 242–3 microemulsion, 154 microencapsulation, 328–9 products characteristics and analysis, 214–18 systems in food, 197–201 carbohydrate-based systems, 199–200 hydrophile-lipophile balance (HLB), 198 lipid-based systems, 198–9 protein and carbohydrate mixed systems, 200–1 protein-based systems, 199 shell materials, 198 microwave-assisted extraction (MAE), 236 mid-infrared region, 248 milk, 139–42 antioxidant effect, 142 volatile oxidation and off-flavour formation, 337–8 monoglycerides, 172 monoglycerides esters, 172 monounsaturated fatty acid (MUFA), 260–1 multilayer emulsion, 154 multilayered o/w emulsions, 203–5 double-layered o/w emulsion formation, 204 multiple emulsions, 205–6 formation, 205 Nannochloropsis, 402 nanoemulsion, 152, 154 National Health and Medical Research Council (NHMRC), 411 near-infrared region, 248 neat fish oils, 134–6 totox value ultrahigh omega-3 concentrates as ethyl esters or triacylglycerides, 136 neuroprotectins, 358 Nitzchia, 402 non-emulsification-based microencapsulation, 213–14 North America status of health and nutrition claims, 407–10 adequate intake (A1) for omega-3 fatty acids, 410 omega-3 health claims in baked foods, 409 Norway pout, 60 10-year average landings, 67 omega-3 fatty acid content of oils and lipids, 68 nuclear magnetic resonance (NMR), 246–7 nutrition omega-3 fatty acids benefits, 3–20 α-linolenic acid health effects, 18 dietary sources and intake, 6–11 future trends, 18–19 marine source, 11–17 overview, 3–6 Nutrition Labelling of Pre-packaged Food Regulation, 410 nutritious bars, 326–7 O’Fallon method, 245 omega-3 enriched mayonnaise, 136–8 omega-3 fatty acid deficiency infants, 355–6 recommendations/regulatory requirements of LC-PUFA content, 357 omega-3 fatty acids α-linolenic acid health effects, 18 algal oil, 389–403 development of Martek Biosciences Corporation, 400–2 DSM DHA intellectual property, 398 future trends, 402–3 microalgae in production of food ingredients, 391–4 production of DHA algal oils, 395–8 regulatory approval of algal oil, 399–400 alternative analytical methods, 245–8 GC/MS and LC/MS, 245–6 © Woodhead Publishing Limited, 2013 Index infrared (IR) spectroscopy, 247–8 nuclear magnetic resonance (NMR), 246–7 analysis, 330–2 analytical methods for quality parameters, 331 animal diet modification for enrichment of dairy and meat products, 257–77 feeds that increase omega-3 fatty acids in ruminant milk and meat, 261–71 future trends, 276 application techniques for adding in foods, 327–30 quality parameters for fish oils, 329 quality parameters of vegetable oils and shortenings, 329 baked goods enrichment, 319–32 approximate composition of omega-3 oils used in food, 322 fatty acid composition of major vegetable oils used in bakery goods, 321 nutritious bars, 326–7 current and alternative marine oils, 39 dietary sources and intake, 6–11 handling and distribution, increase EPA and DHA in plasma lipid, cells and tissues in human, 8, 10–11 marine omega-3 fatty acid content, whole-body handling of dietary fatty acids, egg enrichment, 288–97 consequences and challenges, 294–6 egg lipid composition, formation and deposition, 288–91 future trends, 296–7 modifying egg lipid composition, 291–4 enrichment of emulsified foods, 336–50 antioxidative effects of other ingredients, 345–7 delivery system, 342–5 factors affecting lipid oxidation, 338–42 423 future trends, 349 other food emulsions, 347–9 volatile oxidation and off-flavour formation in milk, 337–8 enrichment of infant formula, 353–77 addition to infant formula, 366–73 future trends, 374 importance of omega-3 fatty acids during infancy, 356, 358–60 sensory characteristics, 373–4 supplementation in infant formula, 360–6 food enrichment nutritional benefits, 3–20 foods and supplements, 226–49 examples in literature containing foods, 243–5 future trends, 248–9 gas liquid chromatography / flame ionisation detector (GC/FID), 227–30 one-step methods combining extraction, digestion and derivatisation, 241–3 future trends, 18–19, 98–100 increased in animal diet, 271–6 chain elongation and desaturation to increase longer-chain omega-3 fatty acids, 271 characteristics of omega-3 PUFA enriched products, 272–6 effects on animals receiving diets designed to increase in milk and meat, 272 krill and single-cell marine oils, 40–4 labelling and claims in foods, 405–12 future trends, 411–12 implications for global food industry, 411 status of health and nutrition claims in Asia and Australia, 410–11 status of health and nutrition claims in Europe, 406–7 status of health and nutrition claims in North America, 407–10 marine oils, 34–9 marine source, 11–17 measurement in foods, 230–7 general process for preparation of FAME derivatives, 232 © Woodhead Publishing Limited, 2013 424 Index less conventional extraction methods, 235–7 overview of methods, 233–5 selected official methods, 233 methods of meat products enrichment, 299–313 future trends, 311–12 methyl esters ad other fatty acids derivatives, 237–41 comparison for GC and GC/MS analyses, 238 GC columns to resolve omega-3 FAME, 239–41 overview, 3–6, 28–34 anchovy and sardines raw materials domination, 29 conversion of linoleic acid to α– linolenic acid and of α–linolenic to longer chain, crude fish oil price and Peru and Chile fish oil production, 31 global fisheries capture and aquaculture production, 29 percent yield from the starting oil through a 90% omega-3 ethyl ester, 33 prices of feed grade menhaden fish oil and B100 biodiesel, 33 sales of omega products all categories and crude fish oil, 30 structure, structure, naming and metabolic relationships, 4–6 supply chain, 32 omega-3 polyunsaturated fatty acid family, plant sources, 93–8 development of transgenic plants with long chain omega-3 fatty acids in seeds, 96–7 omega-3 and omega-6 fatty acid content of seed oil, 98 omega-3 fatty acid content, 95 sources, 27–100, 258–61 ruminant feedstuffs, 258–60 synthesis of lipids in muscle and milk, 260–1 species farmed for marine oils, 69, 76–84 sustainability and certifications, 84, 86–93 Friend of the Sea (FOS) approved fisheries, 88 Friend of the Sea (FOS) certified fish oil, krill and omega-3 products, 89 Marine Stewardship Council (MSC) list of certified fisheries, 90–1 Marine Stewardship Council (MSC) list of fisheries in assessment, 91 Marine Stewardship Council (MSC) list of labelled fish oil and krill product, 92–3 wild fish and other marine oils, 44, 46–69 omega-3 oils spray drying and encapsulation, 194–219 emulsion assemblies, 201–6 future trends, 218–19 microencapsulated products characteristics and analysis, 214–18 microencapsulation system in food, 197–201 microencapsulation techniques, 206–14 overview, 194–7 stabilisation and enriched foods using antioxidants, 130–46 future trends, 146 lipid oxidation and reactions, 131–4 protection of oils and oil-based products, 134–9 protection of other food products, 139–45 stabilisation and enriched foods using emulsifiers, 150–84 applications to stabilise delivery systems, 180–3 delivery systems and emulsified foods, 159–75 emulsification impact on flavour and texture perception, 178–80 future trends, 183–4 lipid oxidation, 175–8 reason for using emulsifiers, 151–9 Omegawax, 240 one-step extraction (OSE) methods see in situ derivatisation methods © Woodhead Publishing Limited, 2013 Index oregano, 141 organic production systems, 269 n-3 PUFA as a percentage of total milk fatty acids in organic vs conventional milk, 270 oxidation prevention during processing, 369–73 addition of PUFA-containing oil blend, 371 air vs nitrogen in head space of a reactor, 372 oxidative stability, 215–16 Pacific cod, 53, 60 10-year average landings, 61 omega-3 fatty acid content of oils and lipids, 62 partial least square regression, 338 particle size, 215 payload, 216–17 peroxide value (PV), 339 pH, 339–40 Phaedodactylum tricornutum, 402 photobioreactor (PBR), 43 pilchard, 48 10-year average landings, 49 omega-3 fatty acid content of oils and lipids, 50 plants, 258 plastic shortenings, 330 polysorbates, 173 polyunsaturated fatty acid (PUFA), 4, 229, 260, 322, 336–7, 349 pork sausages, 306 progesterone, 272 prostaglandin, 272 protein emulsifiers, 178 protein-polysaccharides mixtures, 175 protein-surfactant mixtures, 175 proteins, 174–5, 182 purification, 397–8 qualified health claims, 308, 408 quercetin, 135 quercetin glycosides, 135 rapeseed oil, 140 refined oil quality standards, 113–14 guidelines, 113 425 specifications given in selected fish oil monographs, 114 resolvins, 358 retina physiology, 358–9 rosemary, 141 rumen-protected linseed products, 261–2 effects of supplementary linseed products on 18:3 proportions, 264 effects of supplementary linseed products on n-3 PUFA proportions, 263 ruminant feedstuffs, 258–60 sand eels, 53 10-year average landings, 58 omega-3 fatty acid content of oils and lipids, 59 saponification, 243 sardine, 48 10-year average landings, 49 omega-3 fatty acid content of oils and lipids, 50 saturated fats, 320 saturated fatty acid (SFA), 260–1 Schizochytrium sp., 402 selected ion monitoring (SIM) mode, 246 sensory analysis, 217, 275 silver ion chromatography, 240 silver ion solid phase extraction, 240 single-cell oils, 41, 43–4, 99 omega-3 fatty acid content, 45 photo bioreactors and open ponds comparison, 43 single-layered oil-in-water (o/w) emulsions, 201, 203 formation, 203 sodium dodecyl sulphate polyacrylamide gel electrophoresis (SDS-PAGE), 342 sorbitan esters, 173 Soxhlet method, 235–6 soya oil, 340 soybean oil, 324 spray cooling, 208 spray-dried emulsions, 206–7 © Woodhead Publishing Limited, 2013 426 Index spray drying, 369 characteristics and analysis of microencapsulated products, 214–18 emulsion assemblies, 201–6 future trends, 218–19 microencapsulation system in food, 197–201 microencapsulation techniques, 206–14 omega-3 oils, 194–219 overview, 194–7 food products fortified with omega-3 fatty acids, 196 health benefits of dietary omega-3 oils, 194–6 oxidative instability of omega-3 oils, 196–7 squid, 48, 53 10-year average landings, 54 omega-3 fatty acid content of oils and lipids, 55 standard reference material (SRM), 236–7 steroyl CoA desaturase, 290 sucrose esters, 172–3 sucuk, 310 Supelcowax, 240 supercritical fluid extraction (SFE), 235–6 supplements analysis of omega-3 fatty acids, 226–49 alternative analytical methods, 245–8 examples in literature containing foods, 243–5 future trends, 248–9 gas–liquid chromatography / flame ionisation detector (GC/FID), 227–30 measurement in foods, 230–7 methyl esters ad other fatty acids derivatives, 237–41 one-step methods combining extraction, digestion and derivatisation, 241–3 surface-active hydrocolloids, 175 surface oil, 216 Tanniniferous herbages, 268–9 texture perception, 180 thin-layer chromatography, 245 thiobarbituric acid reactive substances (TBARS), 117 Thraustochytrids, 393 tocopherols, 122–3 total acceptable catch (TAC), 40 transglutaminase, 212, 301 triacylglycerol, 289–90 tuna, 69 10-year average landings, 74 omega-3 fatty acid content of oils and lipids, 75 ultrasonic homogenisers, 154–5 ultrasound-assisted extraction (UAE), 236 upper intake level (UL), 407 Vascepa, 39 vegetable oils, 320 visual acuity, 358, 363–5 visual evoked potential (VEP), 362 vitellogenin, 289 walleye pollock, 60 10-year average landings, 65 omega-3 fatty acid content of oils and lipids, 65 walnut paste, 308 weight percent method, 330–1 wet blending, 367, 369 whey protein, 343 wild fish, 44, 46–69 wild Pacific salmon, 60 10-year average landings, 63 omega-3 fatty acid content of oils and lipids, 64 winterisation see dewaxing yoghurt, 142–3 © Woodhead Publishing Limited, 2013 ... References ix 33 7 33 8 34 2 34 5 34 7 34 9 34 9 35 0 35 3 35 3 35 6 36 0 36 6 37 3 37 5 37 5 37 6 37 7 New directions 38 7 Algal oil as a source of omega- 3 fatty acids R J Winwood, DSM... Limited, 20 13 258 261 271 276 277 277 277 288 288 288 291 294 296 297 299 299 30 0 31 1 31 2 31 2 31 4 31 9 31 9 32 1 32 6 32 7 33 0 33 2 33 2 33 6 33 6 Contents 12.2 12 .3 12.4 12.5 12.6 12.7 12.8 12.9 13 Enrichment. .. Enrichment of baked goods with omega- 3 fatty acids E M Hernandez, Omega Protein Inc., USA 11.1 Introduction 11.2 Omega- 3 fatty acids in baked goods 11 .3 Omega- 3 fatty acids