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Chemistry and Technology of Flavours and Fragrances

De
352 pages
Modern flavours and fragrances are complex formulated products, containing blends of aroma compounds with auxiliary materials, enabling desirable flavours or fragrances to be added to a huge range of products. From the identification and synthesis of materials such as cinnamaldehyde and vanillin in the 19th Century to the current application of advanced analytical techniques for identification of trace aroma compounds present in natural materials, the flavour and fragrance industry has developed as a key part of the worldwide specialty chemicals industry.


With contributions mainly coming from industry based experts, Chemistry & Technology of Flavours and Fragrances provides a detailed overview of the synthesis, chemistry and application technology of the major classes aroma compounds. With separate chapters covering important technical aspects such as the stability of aroma compounds, structure – odour relationships and identification of aroma compounds, this book will be essential reading for both experienced and graduate level entrants to the flavour & fragrance industry. It will also serve as an important introduction to the subject for chemists and technologists in those industries that use flavours and fragrances, eg food, cosmetics & toiletries, and household products.


David Rowe is Technical Manager at De Monchy Aromatics Ltd., Poole UK

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Contents
Contributors
Preface
1
2
IntroductionDavid J. Rowe 1.1 History: in the beginning 1.2 The classical world 1.3 The mediaeval world 1.4 From the Renaissance to the Enlightment 1.5 The industrial age 1.6 The post-war world 1.6.1 Technical factors 1.6.2 Social factors 1.7 The future 1.8 The structure of the flavour and fragrance industry 1.9 A note on regulations 1.10 A note on quality References
Identification of Aroma ChemicalsNeil C. Da Costa and Sanja Eri 2.1 Introduction 2.2 Isolation of aroma chemicals 2.2.1 Solvent extraction 2.2.2 Steam distillation methods 2.2.3 Headspace techniques 2.2.4 Direct thermal desorption (DTD) 2.2.5 Sorptive techniques 2.3 Gas chromatography-olfactometry 2.4 Techniques for identification of aroma compounds 2.5 A case study: Generessence® 2.5.1 Sample preparation 2.5.2 Valencia orange 2.5.3 Roast chicken
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1 1 1 2 3 3 5 5 5 7 7 8 9 11
12 12 12 13 18 20 22 23 25 26 27 27 28 29
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2.5.4 2.5.5 References
Narcissus Post-analysis work
Contents
Flavor Generation in FoodLiam O’Hare and John Grigor 3.1 Introduction 3.2 Taste and aroma 3.3 Cooked meat 3.3.1 Flavour precursors 3.3.2 Influence of method of cooking 3.4 Cheese 3.4.1 Lactose and citrate fermentation 3.4.2 Protein degradation 3.4.3 Lipid degradation Acknowledgements References
Aroma Chemicals I: C, H, O CompoundsDavid J. Rowe Introduction Alcohols 4.2.1 Saturated alkyl alcohols 4.2.2 Unsaturated alkyl alcohols 4.2.3 Complex fragrance alcohols 4.2.4 Aromatic and aralkyl alcohols 4.2.5 Phenolics Acids 4.3.1 Saturated aliphatic acids 4.3.2 Unsaturated acids 4.3.3 Aromatic acids Esters 4.4.1 Saturated esters 4.4.2 Unsaturated esters 4.4.3 Aromatic esters 4.4.4 Lactones – gamma and delta 4.4.5 Synthesis of esters Aldehydes 4.5.1 Aliphatic aldehydes 4.5.2 Unsaturated aldehydes 4.5.3 Acetals 4.5.4 Aromatics 4.5.5 Nitriles Ketones 4.6.1 Carotenoids, ionones, irones, damascones and related compounds Hydrocarbons
4.1 4.2 4.3 4.4 4.5 4.6 4.7
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35 35 35 35 36 42 44 45 47 50 52 52
56 56 56 56 57 58 59 60 61 61 62 62 63 63 64 65 66 68 69 69 70 72 73 78 78
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Acknowledgements References
Contents
Aroma Chemicals II: HeterocyclesMichael Zviely 5.1 Introduction 5.2 Introduction to heterocyclic compounds 5.2.1 Terminology of heterocycles 5.2.2 Non-aromatic heterocyclic compounds 5.3 Oxygen-containing heterocyclic aroma chemicals 5.4 Heterocyclic compounds containing nitrogen and/or sulfur References
Aroma Chemicals III: Sulfur CompoundsSimon B. Jameson 6.1 Thiols and thioesters 6.2 Acyclic sulfides and polysulfides 6.3 Saturated heterocyclic sulfur compounds 6.4 Quality and stability Acknowledgements References Bibliography Websites
Aroma Chemicals IV: MusksPhilip Kraft 7.1 Introduction 7.2 Natural musks 7.3 Nitro musks 7.4 PCM – Polycyclic aromatic musks 7.5 Evolution of the industrial synthesis of macrocycles 7.6 Modern macrocyclic musks 7.7 New musk structures Acknowledgements References
Aroma Chemicals V: Natural Aroma ChemicalsJohn Margetts 8.1 Introduction 8.2 The natural concept 8.3 Chirality 8.4 Isolation from natural sources such as essential oils 8.5 Biotechnology 8.6 Total flavour enhancement 8.7 Individual flavour chemicals 8.7.1 Alcohols 8.7.2 Carbonyls 8.7.3 Acids
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85 85 85 86 87 88 99 114
116 120 128 131 135 140 140 141 142
143 143 145 150 152 155 159 162 165 165
169 169 169 171 171 177 178 179 179 180 182
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Contents
8.7.4 Lactones 8.7.5 Esters 8.7.6 Green notes 8.7.7 Pyrazines 8.7.8 Sulfur compounds 8.7.9 Terpenoid and related compounds 8.7.10 Vanillin 8.7.11 Precursors 8.8 Soft chemistry 8.9 Conclusion References
Molecules of Taste and SensationMark L. Dewis Introduction The trigeminal nerve system, taste and oral receptors 9.2.1 The trigeminal nerve 9.2.2 Gustation 9.2.3 Oral receptors Chemesthesis ‘Sensates’ – compounds which provide a sensory effect 9.4.1 Tingle compounds 9.4.2 Cooling compounds 9.4.3 Pungent, warming and hot irritants 9.4.4 Astringency 9.4.5 Synergies 9.4.6 Closing comments on compounds which provide a sensory effect Taste-active compounds 9.5.1 Sweeteners 9.5.2 Salt and enhancers 9.5.3 Sour agents 9.5.4 Bitter agents 9.5.5 Umami the fifth taste quality Conclusions References
9.1 9.2 9.3 9.4 9.5 9.6
Stability of Aroma ChemicalsChris Winkel 10.1 Introduction 10.2 Flavour stability 10.3 Flavour precursors 10.4 Encapsulation 10.5 Analogues 10.6 Case study 1: citral and vanillin stability in milk-based products
183 184 186 186 187 189 192 192 193 196 197
199 199 200 200 202 202 204 204 205 212 223 227 227
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Contents
10.7 Case study 2: stability of thiols in an aqueous process flavouring 10.8 Stability and fragrance applications 10.9 Conclusion References
Rational Odorant DesignLuca Turin 11.1 Introduction 11.2 Theories of olfaction 11.2.1 For shape 11.2.2 Against shape 11.2.3 For vibration 11.2.4 Against vibration 11.3 Rational design by shape 11.3.1 Rational design by vibration 11.4 Replacement molecules 11.4.1 Acitral® 11.4.2 Lioral® 11.5 Prospects for the future Acknowledgements References
Applications I: FlavorsDavid Baines and Jack Knights 12.1 Introduction 12.1.1 The early days of flavour analysis 12.1.2 The role of the flavourist 12.2 Liquid flavourings 12.2.1 Water-soluble liquid flavourings 12.2.2 Solvents for special uses 12.2.3 Oil-soluble liquid flavourings 12.2.4 Emulsion liquid flavourings 12.3 Powder flavours 12.3.1 Plating 12.3.2 Spray drying 12.3.3 Spray cooling 12.3.4 Yeast encapsulation 12.3.5 Coacervation 12.3.6 Melt extrusion 12.3.7 Molecular encapsulation 12.4 Formulation issues for the flavourist 12.4.1 Flavour creation 12.4.2 Influence of foodstuff to be flavoured 12.4.3 Influence of legislation 12.4.4 Influence of customer requirements References
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252 258 259 259
261 261 262 263 263 265 267 267 268 269 269 270 271 271 271
274 274 274 275 276 276 278 279 280 280 281 282 290 291 294 296 298 300 300 301 301 302 303
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Contents
Applications II: FragranceStephen J. Herman 13.1 Introduction 13.2 The basic structure of fragrances 13.3 The simplest case: hydroalcoholics 13.4 Personal care applications: emulsions 13.5 Personal care applications: surfactants 13.6 Air fresheners 13.7 Candles 13.8 Reactive hair care 13.9 Depilatories 13.10 Dyes and perms 13.11 Bleach 13.12 Malodor counteractants 13.13 Stability testing 13.14 Conclusion References
Appendix
Index
Common names
David J. Rowe
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