Preface ......................................................... v
List of Contributors ......................................... xiii
1 Omega-3 fatty acids - Introduction ........................... 1
Frank D. Gunstone
A What are omega-3 fatty acids? ................................ 1
B How are omega-3 fatty acids formed in plants and animals? .... 3
C Dietary sources of omega-3 fatty acids ....................... 4
1 ALA
2 Stearidonic acid
3 EPA and DHA from fish oils
4 DHA from microbial oils
5 LC-PUFA from animal fats
6 LC-PUFA from plant lipids
7 LC-PUFA in structured lipids
D Omega-3 fatty acids - physiological and medical effects ..... 11
E Omega-3 fatty acids - does chain length matter? ............. 12
F Omega-3 fatty acids - dietary intakes and recommendations ... 14
G Stability ................................................... 18
References .................................................. 19
2 Fish oil sources ............................................ 23
Peter D. Nichols
A Introduction ................................................ 23
1 Definition of fish oil and omega-3 oils
2 History
3 Global production
4 Global trade
5 Usage by region
B Fish oils - fatty acid profiles ............................. 29
C Fish oil resources and other issues ......................... 33
1 Aquaculture
2 Aquaculture versus nutraceutical use
D Other oils .................................................. 37
1 Seal and penguin oils
2 Whale oil
3 Krill oil
E The future .................................................. 39
Acknowledgements
References
3 Microbial oils: production, processing and markets for
specialty long-chain omega-3 polyunsaturated fatty acids .... 43
James P. Wynn and Colin Ratledge
A Introduction ................................................ 43
B Biochemistry of fatty acid biosynthesis and lipid
accumulation in oleaginous microorganisms ................... 46
C Advantages/disadvantages of SCOs versus 'traditional'
omega-3 oils ................................................ 54
D Choice of production organism ............................... 56
E Current production .......................................... 58
F Safety ...................................................... 62
G Current applications for omega-3 LC-PUFA SCO ................ 66
H Future applications of microbial omega-3 LC-PUFA ............ 67
1 DHA-richSCOs
2 Prospects for an EPA-rich SCO?
I Future of omega-3 LC-PUFA SCOs .............................. 71
References .................................................. 72
4 Processing of marine oils ................................... 77
Anthony P. Bimbo
A Introduction ................................................ 77
B World fish statistics ....................................... 77
C Production of crude fish oil ................................ 80
1 Raw materials
2 Cooking process
3 Pressing process
4 Drying process
5 Antioxidant addition
6 Oil-water separation
7 Evaporation process
D Fish oil .................................................... 83
1 Introduction
2 Fish oil statistics
3 Fish oil markets
4 Crude fish oil quality parameters
5 Fish oil pricing
E Nutraceutical fish oils ..................................... 90
1 Introduction
2 Market segments
3 Raw materials
4 Processing beyond crude oil
F Liver oils .................................................. 99
1 Raw materials
2 Processing
G Tuna and bonito oil ........................................ 102
1 Raw materials
2 Processing
H Krill oil .................................................. 102
1 Raw materials
2 Processing
3 Quality
References ................................................. 107
5 Concentrates ............................................... 111
Harald Breivik
A Introduction ............................................... 111
B Fractionation techniques ................................... 114
1 Counter-current extraction of fatty acid salts
2 Fractionation by molecular distillation/short-path
distillation
3 Fractionation by urea complexation
4 Extraction with aqueous silver nitrate
5 Supercritical fluid fractionation
6 Production-scale chromatography
7 Enzymatic reactions
8 Iodolactones
9 Re-esterification to acylglycerols
C By-products and contaminants ............................... 130
1 Compounds naturally occurring in fish oils
2 By-products formed during work-up
3 Contamination during transport and storage; solvent
residues and contamination from reagents
D Stability of concentrates .................................. 135
E Production conforming to GMP regulations ................... 136
F Labelling .................................................. 137
References ................................................. 137
6 Enzymatic processing of omega-3 specialty oils ............. 141
Xuebing Xu, Aran H-Kittikun and Hong Zhang
A Introduction ............................................... 141
B Enzyme-assisted extraction offish oils ..................... 143
1 Traditional production of fish oil
2 Enzyme-assisted production of fish oil
C Enzymatic concentration of omega-3 fatty acids ............. 146
1 Concentration of omega-3 PUFA by hydrolysis with
lipases
2 Enrichment of omega-3 PUFA by lipase-catalysed
alcoholysis
D Enzymatic production of omega-3 ethyl esters 153
E Enzymatic production of structured lipids containing
omega-3 fatty acids ........................................ 155
F Enzymatic production of omega-3 monoacylglycerols .......... 157
G Enzymatic synthesis of omega-3 triacylglycerols ............ 158
H Concluding remarks ......................................... 159
Acknowledgements ........................................... 160
References ................................................. 160
7 Applications in food products .............................. 165
Reto Muggli
A Introduction ............................................... 165
B Intake recommendations and meeting the requirements of
omega-3 long-chain PUFA intakes ............................ 166
C Foods fortified with long-chain omega-3 fatty acids - the
fishy taste and smell problem .............................. 170
D The origin of fishy taste and smell molecules .............. 171
E Solving the fishy taste and smell problem - precautions
and general approaches ..................................... 173
1 Choosing the raw material
2 Refining of the EPA/DHA oils
3 Stabilization by antioxidants and metal inactivators
4 Stabilization by protection from oxygen, heat and light
F Food manufacturing - technical challenges and solutions .... 178
1 General handling rules
2 Multiphase systems
3 Precautions and possible pitfalls
4 Model recipes for selected food items
G Do EPA/DHA-fortified foods work? ........................... 185
H The challenge of developing and marketing mainstream
foods fortified with EPA/DHA ............................... 186
References ................................................. 190
8 Optimization of oxidative stability of omega-3 enriched
foods ...................................................... 197
Charlotte Jacobsen and Nina Skall Nielsen
A Introduction ............................................... 197
B Lipid oxidation and antioxidant processes .................. 197
1 Oxidation processes
2 Volatile oxidation products and sensory properties
3 Antioxidant processes
C Prevention of lipid oxidation in omega-3 enriched foods .... 200
1 Lipid oxidation in emulsions
2 The influence of the omega-3 oil quality
3 The influence of emulsifiers and pH
4 The effect of the emulsification conditions
5 Antioxidant efficacy in omega-3 enriched food emulsions
6 Optimizing oxidative stability by mixing the omega-3
oil with vegetable oils
7 Optimizing oxidative stability by microencapsulation
D Conclusions and recommendations ............................ 213
References ................................................. 214
9 Analysis of oils and concentrates .......................... 219
Jonathan M. Curtis
A Introduction ............................................... 219
B Principles used in the analysis of the fatty acid content
of omega-3 oils as fatty acid methyl esters (FAME)
using gas chromatography (GC) .............................. 220
1 Methods for forming FAME from oils
2 Official methods for FAME analysis
3 Quantification in FAME analysis
4 Other approaches to the quantification of fatty acids
C Fish oil quantification, authenticity and triacylglycerol
positional analysis by nuclear magnetic resonance
(NMR) spectroscopy ......................................... 229
1 Quantification of DHA by high-resolution 'H NMR
2 Positional distribution by high-resolution "C NMR
D Measurement of oxidation products in refined fish oils ..... 231
1 Peroxide value
2 Conjugated diene test
3 Anisidine value (AV)
4 Measurement of lipid oligomers by size exclusion
chromatography
5 Traits isomers
6 Free fatty acids and unsaponifiable matter
E Measurement of contaminants and impurities in refined
fish oils .................................................. 237
References ................................................. 239
10 The regulation of fish oils and omega-3 fatty acids in
the European Union ......................................... 243
Peter Berry Ottaway
A Introduction ............................................... 243
B The regulation of fish oils in foods and supplements ....... 244
C European Union (EU) ........................................ 244
D General food law ........................................... 245
E Chemical contaminants ...................................... 246
1 Dioxins, furans and PCBs
2 Polycyclic aromatic hydrocarbons
3 Mercury
F Novel ingredients .......................................... 247
1 Scope
2 Safety assessments
3 Applicability to oils
4 Genetically modified organisms (GMOs)
G Food additives ............................................. 251
H Labelling and claims ....................................... 252
1 Fatty acid claims
2 Health claims
3 Types of claims
4 Article 13 claims
5 Substantiation of claims
I Conclusions ................................................ 260
References ................................................. 260
11 Markets for fish oils and fish oil concentrates ............ 263
Baldur Hjaltason And Gudmundur G. Haraldsson
A Introduction ............................................... 263
B Food ingredients and functional foods ...................... 266
1 Europe
2 North America
3 Japan
4 Rest of the world
C Dietary supplements ........................................ 280
1 USA
2 Europe
3 Rest of the world
D Pharmaceuticals ............................................ 285
E Future trends .............................................. 286
References ................................................. 287
Index ......................................................... 291
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