Food Flavorings Third Edition Edited by Philip R Ashurst Dr RR Ashurst & Associates Kingstone, Hereford, United Kingdom ANASPEN PUBLICATION® Aspen Publishers, Inc Gaithersburg, Maryland 1999 The author has made every effort to ensure the accuracy of the information herein However, appropriate information sources should be consulted, especially for new or unfamiliar procedures It is the responsibility of every practitioner to evaluate the appropriateness of a particular opinion in the context of actual clinical situations and with due considerations to new developments The author, editors, and the publisher cannot be held responsible for any typographical or other errors found in this book Aspen Publishers, Inc., is not affiliated with the American Society of Parenteral and Enteral Nutrition Library of Congress Cataloging-in-Publication Data Food flavorings / edited by Philip R Ashurst — 3rd ed p cm ISBN 0-8342-1621-3 Flavoring essences I Ashurst, P R TP450.F66 1999 664'.5—dc21 99-27422 CIP Copyright © 1999 by Aspen Publishers, Inc A Walters Kluwer Company www.aspenpublishers.com All rights reserved Aspen Publishers, Inc grants permission for photocopying for limited personal or internal use This consent does not extend to other kinds of copying, such as copying for general distribution, for advertising or promotional purposes, for creating new collective works, or for resale For information, address Aspen Publishers, Inc., Permissions Department, 200 Orchard Ridge Drive, Suite 200, Gaithersburg, Maryland 20878 Orders: (800) 638-8437 Customer Service: (800) 234-1660 About Aspen Publishers • For more than 35 years, Aspen has been a leading professional publisher in a variety of disciplines Aspen's vast information resources are available in both print and electronic formats We are committed to providing the highest quality information available in the most appropriate format for our customers Visit Aspen's Internet site for more information resources, directories, articles, and a searchable version of Aspen's full catalog, including the most recent publications: http://www.aspenpublishers.com Aspen Publishers, Inc • The hallmark of quality in publishing Member of the worldwide Wolters Kluwer group Editorial Services: Ruth Bloom Library of Congress Catalog Card Number: 99-27422 ISBN: 0-8342-1621-3 Printed in the United States of America Contributors Philip Ashurst, Ph.D Dr RR Ashurst & Associates Kingstone Hereford United Kingdom D.G Ashwood Burtons Gold Medal Biscuits Quality House Blackpool United Kingdom D Bahri Givaudan Aromen GmbH Dortmund Germany Belayet H Choudhury Takasago International Corporation (USA) Rockeigh, New Jersey D.C.F Church D.C Flavours Ltd Clacton-on-Sea Essex United Kingdom H Kuentzel Givaudan Research Company Dubendorf Switzerland D V Lawrence Flavex Ltd Kingstone Hereford United Kingdom Charles H Manley, Ph.D Takasago International Corporation (U.S.A.) Rockeigh, New Jersey Giinter Matheis Dragoco Gerberding & Co AG Holzminden Germany A.C Mathews Net Consultancy Drake House Cinderford United Kingdom Peter Mazeiko Takasago International Corporation (USA) Rockeigh, New Jersey David A Moyler Fuerst Day Lawson Ltd St Katherines Way London United Kingdom Roger N Penn, Ph.D Director Tobacco Business Unit MANE Bar-sur-Loup France Barry Taylor Danisco Flavours Dennington Industrial Estate Wellingborough Northhampton United Kingdom Geoff White The Edlong Company Martlesham Heath Ipswich Suffolk United Kingdom Suzanne White The Edlong Company Martlesham Heath Ipswich Suffolk United Kingdom John Wright Bush Boake Allen Inc Montvale, New Jersey Preface It is almost a decade since the first edition of this volume was produced and nearly years from the second Despite the many organizational changes that have taken place in both the flavor and publishing businesses, it is again gratifying to find that the demand for a third edition remains This is in no small part due to the fact that the flavor industry continues to flourish despite the takeovers and amalgamations that increase the size of the major manufacturers These activities tend inevitably to create a fallout of skilled personnel, a proportion of whom restart in a small way and start the cycle all over again The industry generally becomes more oriented to high technology operations, although these generally impact more on the control of manufacture, sales and finance than on the actual creation of flavors themselves The heart of a good flavor remains the simple blending of high-quality ingredients to produce a creation that is, to its user, more than the sum of its parts The industry continues to supply traditional demands for flavors in the food industry—soft drinks, baking and confectionery—and at the same time to meet the new challenges of ready-prepared meals and other new developments in products and processing For the first time, however, this third edition acknowledges the important contribution made by flavors to areas other than food Flavors play a vital part in the formulation, acceptability and, therefore, efficacy of most oral medicines—both over-the-counter (OTC) and ethical preparations A chapter on the use of flavors in pharmaceutical applications deals with this subject Similarly, a chapter reflects the major use of flavors in tobacco products Whatever the level of social acceptability of smoking, the subject is of great significance with the flavor industry Other new chapters deal with the important topics of flavor modifiers and the whole realm of flavor quality control Of the remaining contributions, some are unchanged and others updated and amended Overall, it is hoped that readers will again find this to be a useful work Its contributors are widely experienced and I am extremely grateful to them for taking time from busy schedules to prepare and edit manuscripts Any errors and omissions are those of the editor and I accept responsibility for them I hope, however, they will not detract too much from the important contribution this book has made and will continue to make to those seeking knowledge of the flavor industry I would, finally, like to acknowledge the help of my colleague, Sue Bate, for her invaluable help and support in preparing this volume Philip R Ashurst Contents Contributors xv Preface xxvii Essential Oils 1.1 Introduction 1.2 The Production of Essential Oils 1.3 Further Processing of Essential Oils 1.4 The Uses of Essential Oils 1.5 The Composition of Essential Oils Oleoresins, Tinctures and Extracts 39 2.1 Introduction 39 2.2 Plant Materials 40 2.3 Solvents 51 2.4 Tinctures 53 2.5 Oleoresins 55 2.6 Absolutes 57 2.7 Extraction with Carbon Dioxide as a Solvent 61 2.8 Summary 68 Fruit Juices 71 3.1 Introduction 71 3.2 Fruit Processing 72 3.3 Specialized Fruit Processing 77 This page has been reformatted by Knovel to provide easier navigation iii iv Contents 3.4 Products and Packaging 80 3.5 Product Specification(s) 83 3.6 Volatile Components of Fruit Juices 92 3.7 The Use of Fruit Juices in Flavorings 99 3.8 Summary 101 Synthetic Ingredients of Food Flavorings 103 4.1 General Aspects 103 4.2 Synthetic Flavor Ingredients 112 4.3 Synthetic Flavor Ingredients and the Future 145 Quality Control of Flavorings and Their Raw Materials 153 5.1 Introduction 153 5.2 Importance and Complexity of Quality Control 166 5.3 Physico-Chemical Analysis 167 5.4 Biotechnology-Based Analysis 182 5.5 Microbiology Analysis 186 5.6 Sensory Analysis 187 5.7 Conclusions 194 Beverage Flavorings and Their Applications 199 6.1 Introduction 199 6.2 Categories of Beverages 200 6.3 Types of Flavorings for Beverages 201 6.4 Methods of Extraction, Solubilization and Concentration of Flavorings 202 6.5 Beverages Based on Ginger 205 6.6 Formulation of Beverages 213 6.7 Summary 228 This page has been reformatted by Knovel to provide easier navigation Contents v The Flavoring of Confectionery and Bakery Products 229 7.1 Introduction to Confectionery Flavorings 229 7.2 Basic Confectionery Types, Recipes, Inherent Flavors 231 7.3 Flavors from Ingredients 249 7.4 Flavors Developed During Processing 249 7.5 Selection of Flavorings 250 7.6 Ingredients of Bakery Products 254 7.7 Bakery Products 258 7.8 Bakery Fillings 262 7.9 Summary of Flavoring Characteristics 264 Savory Flavors for Snacks and Crisps 267 8.1 Introduction 267 8.2 History of Savory Flavors for Snacks and Crisps (Potato Chips) 267 8.3 Snacks 268 8.4 Basic Recipes for Crisps and Snack Savory Flavors 270 8.5 Ingredients for Savory Flavors 273 8.6 Major Raw Materials and Ingredients Used in Powder Savory Flavor Blends 273 8.7 New Developments and Trends 281 8.8 Conclusions 281 Thermal Process Flavorings 283 9.1 Introduction 283 9.2 History 284 9.3 The Maillard Reaction 285 9.4 Aromatic Compounds from Precursors 285 This page has been reformatted by Knovel to provide easier navigation vi Contents 9.5 Aroma Components Found in Cooked Foods 295 9.6 Components Used to Create a Process Flavor 302 9.7 Process Techniques 306 9.8 Final Flavor Compounds 309 9.9 Applications of Thermal Flavors 311 9.10 Regulatory Issues 314 9.11 The Safety Question 317 9.12 Conclusions 320 Appendix 9-A: International Organization of the Flavour Industry (IOFI) Guidelines for the Production and Labeling of Process Flavorings 323 10 The Development of Dairy Flavorings 327 10.1 Introduction 327 10.2 Milk and Cream 331 10.3 Yogurt and Fermented Products 337 10.4 Butter 343 10.5 Cheese 348 10.6 Manufacturing Considerations 364 10.7 Conclusions 365 11 Flavor Modifiers 367 11.1 Introduction 367 11.2 Monosodium Glutamate, Purine 5'Ribonucleotides and Related Substances 368 11.3 Maltol and Ethyl Maltol 393 11.4 Furanones and Cyclopentenolones 396 11.5 Vanillin and Ethyl Vanillin 398 11.6 Other Flavor Modifiers 399 11.7 Sodium Chloride 400 11.8 Conclusions 402 This page has been reformatted by Knovel to provide easier navigation 473 Index terms Links Pharmaceutical product flavoring (Continued) dry flavorings 413 examples 416 German market 420 need for 407 pharmacist-flavorist cooperation 415 physical state of flavorings 408 strong inherent taste or odor 419 toning down the inherent taste and odor 408 U.S market 420 volatile flavoring interactions 412 Physical analysis 169 Physico-chemical analysis, quality control 167 examples Pineapple juice, fruit juice Pipe tobacco 418 411 417 168 79 433 Plant material chopping 48 curing 48 drying 48 extract 40 crop to crop variations 41 degradation 43 origin 40 preparation 48 storage 42 yield 43 fermentation 48 grinding 48 oleoresin crop to crop variations 41 degradation 43 This page has been reformatted by Knovel to provide easier navigation 44 418 474 Index terms Links Plant material (Continued) origin 40 preparation 48 storage 42 yield 43 roasting 48 tincture 40 crop to crop variations 41 degradation 43 origin 40 preparation 48 storage 42 yield 43 Polarity, solvent 52 Polyphenol 75 Pork flavor, aroma 297 Pork flavor formulation 310 44 44 Potato chips See Crisps Preservative beverage 226 fruit juice 87 Preserved juice 82 Pressure, solvent 53 Processed cheese 360 Protein hydrolysis process 300 Pulled sugar work 233 Pulp, fruit juice Purine 5'-ribonucleotide disodium salts 87 376 378 distillation methods expression 381 This page has been reformatted by Knovel to provide easier navigation 475 Index terms Links Purine 5'-ribonucleotide (Continued) extraction historical background 368 oil quality processing production production methods 379 rectification steam distillation uses washed oil water distillation Pyrazine 287 Pyridine 291 Pyrrole 290 382 288 292 Q Quality control 153 biotechnology-based analysis 182 complexity 166 importance 166 microbiological analysis 186 physico-chemical analysis 167 examples 168 sensory analysis 187 analytical testing 190 areas 188 classification of sensory evaluation 192 selection and training of panelists 192 test cabin 188 test facility 188 test media 190 193 194 191 This page has been reformatted by Knovel to provide easier navigation 293 476 Index terms Links Quality control (Continued) test methods 190 test panel 187 types of thresholds 190 192 193 192 R Raspberry flavor 253 Recognition threshold 192 Refractive index, measurement 169 170 Regulatory issues autolyzed yeast extract 316 hydrolyzed protein 316 thermal process flavoring 314 tobacco product 430 yeast extract 316 Resin, defined 41 Ringing test 170 Roast beef flavor formulation 310 Roasted nut, aroma 298 Roasted seed, aroma 298 Roasty burnt flavor note 115 Roll Your Own (RYO) Tobacco 438 Rose flavor 253 Rose oil quantitative components Rosemary oil 431 131 30 31 31 S Saccharin, AH/B/X structure 156 157 Safety hydrolyzed protein 319 This page has been reformatted by Knovel to provide easier navigation 133 477 Index terms Links Safety (Continued) thermal process flavoring 317 Salt bakery product 257 savory flavor 280 Salt and vinegar flavor 270 Salty taste 155 three dimensional model for stimuli 386 Sauce, thermal process flavoring 313 Savory biscuit 268 Savory flavor acid 273 acidity regulator 273 anti-caking agent 273 carrier 278 color 278 crisps 267 history 267 recipes 270 U.K top ten flavors 269 dairy powder 278 extruded maize snack 269 fat powder 279 filler 278 flavor enhancer 279 flavoring 279 fried snack 270 herb 279 hydrolyzed vegetable protein 279 ingredients 273 production methods 273 274 This page has been reformatted by Knovel to provide easier navigation 478 Index terms Links Savory flavor (Continued) quality systems 273 new developments 281 nut 270 pre-extrusion flavors 281 raw materials 273 salt 280 snack 267 history 267 recipes 270 snack biscuit 270 spice 279 sweetener 280 tortilla snack 270 vegetable powder 280 vitamin 280 yeast 280 yeast extract 280 Self-preserved juice 82 Sense, number 153 Sensogram 153 Sensory analysis, quality control 187 275 analytical testing 190 193 areas 188 classification of sensory evaluation 192 selection and training of panelists 192 test cabin 188 test facility 188 test media 190 191 test methods 190 192 test panel 187 types of thresholds 190 194 192 This page has been reformatted by Knovel to provide easier navigation 193 479 Index terms Separation, fruit juice Sidestream smoke, tobacco product Links 88 439 aroma 440 irritation 440 tobacco heated not burned 440 Skimmed milk 333 Smoky bacon flavor 271 Snack 268 history 268 market separation 268 savory flavor 267 history 267 recipes 270 thermal process flavoring 313 Snack biscuit, savory flavor 270 Snuff 437 Sodium chloride 400 Solubility, oleoresin 440 56 Solubilization, beverage flavoring 202 Soluble solids content, fruit juice 83 Solvent 51 absolute 57 allowable residues in foodstuffs 51 boiling point 52 85 carbon dioxide advantages 61 commercial carbon dioxide extracts 67 comparison with traditional forms of extraction 61 modes of extraction 61 comparison 52 latent heat of evaporation 53 This page has been reformatted by Knovel to provide easier navigation 62 480 Index terms Links Solvent (Continued) oleoresin commercial solvent extraction system 56 54 polarity 52 pressure 53 temperature 53 viscosity 52 Solvent extraction plant 313 Sour taste 154 386 Soured cream 335 Sparkling lemonade 221 Spearmint oil 32 Specific gravity, measurement 169 170 Specific natural isotope fractionation NMRS 176 181 Spectroscopy 173 174 Spice, savory flavor 279 Spicy herbaceous flavor note 115 Stable isotope ratio analysis 180 Star anise oil 127 33 Sterilized cream 335 Sterilized milk 333 Strawberry flavor 253 Strawberry natural flavoring extract 213 217 Strecker degradation 105 214 Sugar bakery product 255 thermal process flavoring 303 Sulfur containing substance, umami 58 54 Soup, thermal process flavoring three-dimensional model for stimuli 56 258 385 This page has been reformatted by Knovel to provide easier navigation 216 481 Index terms Sulfurous alliaceous flavor note examples Sweet basil oil Sweet cream butter Links 114 33 343 34 Sweet marjoram oil 34 Sweet orange oil 34 Sweet taste 35 155 AH/B/X structure 156 three-dimensional model for stimuli 386 Sweetened condensed milk 146 144 Sweet fennel oil quantitative components 144 334 Sweetener beverage 219 savory flavor 280 Synergism taste threshold 387 umami 385 Synthetic flavor ingredient 112 classification 112 composition 112 development 145 documentation systems 104 formulation 112 future directions 145 Tangerine oil 113 113 36 quantitative components 36 Tar reduction, tobacco product 439 Taste 153 See also Specific type defined 390 165 167 409 This page has been reformatted by Knovel to provide easier navigation 407 482 Index terms Links Taste receptor 153 Taste threshold, synergism 387 Temperature, solvent 53 Terminal threshold 192 Terpenoid, biosynthesis 106 Thaumatin 402 Thermal process flavoring 283 amino acid 303 application 311 aromatic compound 304 carbohydrate 303 components 302 defined 315 extrusion 307 final flavor compounds 309 gravy 313 history 283 hydrolysate 302 label 323 liquid reactions (kettle with water, oil or both) 306 meat extract 302 paste reactions (higher temperature and high solids) 307 peptide 303 from precursors 285 process techniques 306 reactions involved 286 regulatory issues 314 roller dryer (lower moisture reactions) 307 safety 317 sauce 313 soup 313 287 This page has been reformatted by Knovel to provide easier navigation 483 Index terms Links Thermal process flavoring (Continued) spray drying 308 sugar 303 tray drying 309 yeast product 303 Thialdine, synthesis 136 137 Thiazole 287 289 290 Thiazolidine 287 289 290 Thiazoline 287 289 290 Thiophene 288 Thyme oil 37 Tincture 39 carbon dioxide 61 applications 66 commercial carbon dioxide extracts 67 modes of extraction 61 plant material 53 40 crop to crop variations 41 degradation 43 origin 40 preparation 48 storage 42 yield 43 44 preparation 39 41 costs 39 processes 40 raw materials 40 Titratable acidity, fruit juice 85 Tobacco basic smoke chemistry 432 carotenoid 427 428 This page has been reformatted by Knovel to provide easier navigation 484 Index terms Links Tobacco (Continued) chemically functional group structures 429 deterpenoid 427 428 isoprenoid flavor component 427 428 types 425 Tobacco flavoring 423 history 423 tobacco flavor volatile systems 429 types of flavor systems 427 Tobacco product developments 438 flavor system characteristics 431 history 423 nicotine reduction 439 regulatory issues 430 431 sidestream smoke 439 440 aroma 440 irritation 440 tobacco heated not burned 440 tar reduction 439 trends 438 types of flavor systems 427 Toffee 236 Tomato, fruit juice, processes requiring heat 80 Tongue 155 Tortilla snack, savory flavor 270 Trans-2-nonenal, synthesis 139 Trigeminal nerve 157 Trigeminal perception 157 Turbidity, fruit juice 140 88 This page has been reformatted by Knovel to provide easier navigation 485 Index terms Links U UHT cream 335 UHT milk 334 Ultraviolet/visible spectroscopy 174 Umami 154 382 amino acid 385 common structural element 384 157 390 159 389 effect of selected substances relative to monosodium glutamate 390 monosodium glutamate 391 peptide 385 sulfur containing substance 385 synergism 385 three-dimensional model for the stimuli 386 usage levels 377 Vanilla bean, curing 48 390 V Vanilla flavor 254 Vanillin 180 181 historical background 398 synthesis from guaiacol 398 400 synthesis from lingnin 398 400 Vegetable powder, savory flavor 280 Vegetarian product, cheese flavoring 362 Violet leaf absolute 37 Viscosity fruit juice 88 solvent 52 This page has been reformatted by Knovel to provide easier navigation 398 486 Index terms Links Vitamin beverage 225 savory flavor 280 volatile, fruit juice 90 aldehyde 90 ester content of volatile fractions 92 optical rotation 91 organoleptic quality 91 peroxide value 91 refractive index 91 residue on evaporation 91 Volatile Compounds in Food 104 Volatile flavor component 103 W Washed oil Water 199 beverage 222 Water infusion 53 Water pipe 435 Wet analysis 171 Whey 335 Whole cow's milk 331 Whole milk powder 333 Wine, history 199 Winter flavor 254 Woody smoky flavor note 115 55 129 Y Yeast, savory flavor 280 This page has been reformatted by Knovel to provide easier navigation 487 Index terms Yeast autolysate ribonucleotide content Links 390 390 Yeast extract 390 defined 316 regulatory issues 316 savory flavor 280 Yeast product, thermal process flavoring 303 Yogurt 337 bacteria 337 flavor components 339 preparation 338 Yogurt flavoring 341 392 Z Ziziphin 401 This page has been reformatted by Knovel to provide easier navigation ... Components of Fruit Juices 92 3.7 The Use of Fruit Juices in Flavorings 99 3.8 Summary 101 Synthetic Ingredients of Food Flavorings 103 4.1 General Aspects 103 4.2 Synthetic... Society of Parenteral and Enteral Nutrition Library of Congress Cataloging-in-Publication Data Food flavorings / edited by Philip R Ashurst — 3rd ed p cm ISBN 0-8342-1621-3 Flavoring essences I... 5.7 Conclusions 194 Beverage Flavorings and Their Applications 199 6.1 Introduction 199 6.2 Categories of Beverages 200 6.3 Types of Flavorings for Beverages 201 6.4