Flavor Chemistry and Technology

1-56676-933-7

Table of contents :
FLAVOR CHEMISTRY and TECHNOLOGY, SECOND EDITION……Page 2
Dedication……Page 4
Preface……Page 5
Acknowledgments……Page 7
The Author……Page 8
Contents……Page 9
Table of Contents……Page 0
Part I: Flavor Chemistry……Page 20
1.2 TASTE PERCEPTION……Page 21
1.2.1 ANATOMY OF TASTE……Page 22
1.2.2 SYNOPSES OF TASTES……Page 24
1.3.1 CHEMESTHETIC RESPONSES……Page 28
1.3.2 TACTILE RESPONSE……Page 30
1.4 OLFACTION……Page 31
1.4.2 ODOR RECEPTOR FUNCTIONING……Page 32
1.4.3 SIGNAL ENCODING……Page 33
REFERENCES……Page 36
2.2 HISTORY OF FLAVOR LITERATURE……Page 40
2.3 JOURNALS……Page 41
2.4 PROFESSIONAL SOCIETIES……Page 42
2.5.1 INTERNAL COMMUNICATION……Page 44
2.5.5 INTERNET SEARCHES……Page 45
2.5.6 LITERATURE RETRIEVAL……Page 46
2.5.7 LOCATING MATERIALS AND EQUIPMENT SUPPLIERS……Page 47
REFERENCES……Page 48
3.2.1 INTRODUCTION……Page 50
3.2.2 SAMPLE SELECTION/PREPARATION……Page 52
3.2.3.2 Solubility……Page 53
3.2.3.3 Sorptive Extraction……Page 55
3.2.3.4 Volatility……Page 56
3.2.4.1 Static Headspace……Page 58
3.2.4.2 Headspace Concentration Methods (Dynamic Headspace)……Page 60
3.2.4.3 Distillation Methods……Page 62
3.2.4.4 Solvent Extraction……Page 65
3.2.4.5 Sorptive Extraction……Page 66
3.2.4.6 Concentration for Analysis……Page 68
3.2.4.7 Aroma Isolation Summary……Page 69
3.2.5.1 Prefractionation……Page 70
3.2.5.3 GC/Olfactometry (GC/O) or GC-MS/Olfactometry (GC-MS/O)……Page 71
3.2.5.4 Mass Spectrometry……Page 73
3.2.6.1 Key Components in Foods……Page 75
3.2.6.2 Aroma Release During Eating……Page 78
3.2.7 ELECTRONIC NOSES……Page 80
3.3.1.1 Taste Compounds……Page 81
3.3.2.1 Sweeteners……Page 82
3.3.2.5 Bitter Substances……Page 83
REFERENCES……Page 84
4.1 INTRODUCTION……Page 90
4.2.1 AROMA COMPOUNDS FROM FATTY ACID METABOLISM……Page 91
4.2.2 AROMA COMPOUNDS FROM AMINO ACID METABOLISM……Page 94
4.2.3 AROMA COMPOUNDS FORMED FROM CARBOHYDRATE METABOLISM……Page 97
4.3 BIOGENESIS OF VEGETABLE AROMA……Page 100
4.3.1 THE ROLE OF LIPIDS IN VEGETABLE AROMA FORMATION……Page 102
4.3.2 AROMA COMPOUND FORMATION FROM CYSTEINE SULFOXIDE DERIVATIVES……Page 103
4.4 GLYCOSIDICALLY BOUND AROMA COMPOUNDS……Page 105
4.4.2 FREEING OF GLYCOSIDICALLY BOUND FLAVOR COMPOUNDS……Page 108
4.6 INFLUENCE OF GENETICS, NUTRITION, ENVIRONMENT, MATURITY, AND STORAGE ON DEVELOPMENT OF FLAVOR……Page 109
4.6.1.2.1 Soil Nutrition……Page 110
4.6.1.3.1 Maturity……Page 111
4.6.1.3.2 Postharvest Storage……Page 112
4.8 CONCLUSIONS……Page 114
REFERENCES……Page 115
5.2.1 GENERAL OVERVIEW OF THE MAILLARD REACTION……Page 119
5.2.2 PATHWAYS FOR FLAVOR FORMATION VIA THE MAILLARD REACTION……Page 120
5.2.3 FACTORS INFLUENCING THE MAILLARD REACTION……Page 121
5.2.3.1 Heating Time/Temperature……Page 122
5.2.3.2 Influence of System Composition……Page 124
5.2.3.4 Influence of pH……Page 125
5.2.3.6 Influence of Oxidation/Reduction State……Page 126
5.2.4.1 Pyrazines……Page 127
5.2.4.2 Oxygen-Containing Heterocyclic Compounds……Page 128
5.2.4.4 Miscellaneous Compounds……Page 129
5.2.5 FLAVOR FORMATION VIA THE MAILLARD REACTION……Page 130
5.2.5.2 Nitrogen-Containing Heterocyclic Compounds……Page 131
5.2.5.3 Oxygen-Containing Heterocyclic Compounds……Page 133
5.2.5.4 Sulfur-Containing Heterocyclic Compounds……Page 134
5.3.1 DEEP FAT FRIED FLAVOR……Page 135
5.3.3 SECONDARY REACTIONS……Page 137
5.4.1 ESTERS……Page 139
5.4.2 ACIDS……Page 140
5.4.3 CARBONYLS……Page 141
5.4.4 ALCOHOLS……Page 143
5.4.5 TERPENES……Page 144
5.4.7 PYRAZINES……Page 145
5.4.9 CONCLUSIONS……Page 146
REFERENCES……Page 148
6.1 INTRODUCTION……Page 154
6.2 LIPID/FLAVOR INTERACTIONS……Page 155
6.2.1.1 Equilibrium Conditions……Page 156
6.2.1.2 Dynamic Conditions……Page 158
6.2.2 EFFECT OF FAT: FLAVOR INTERACTIONS ON TASTE……Page 159
6.3.1 SIMPLE SUGARS: AROMA INTERACTIONS……Page 160
6.3.2 HIGH POTENCY SWEETENERS: AROMA INTERACTIONS……Page 161
6.3.3 COMPLEX CARBOHYDRATE (POLYSACCHARIDE): AROMA INTERACTIONS……Page 163
6.3.3.1 Chemical Interactions……Page 164
6.3.3.2 Resistance to Mass Transfer……Page 166
6.3.4 CARBOHYDRATE: TASTE INTERACTIONS……Page 167
6.4.1.1 Chemical Interactions……Page 168
6.5 MINOR FOOD COMPONENTS: AROMA INTERACTIONS……Page 170
6.5.2 HYDROGEN ION EFFECTS (PH EFFECTS)……Page 171
REFERENCES……Page 172
7.2 SENSORY ASPECTS OF OFF-FLAVOR TESTING……Page 175
7.3 TAINTS IN FOODS……Page 177
7.3.1 AIRBORNE SOURCES……Page 178
7.3.2 WATERBORNE SOURCES……Page 180
7.3.3 DISINFECTANTS, PESTICIDES, AND DETERGENTS……Page 181
7.3.4 PACKAGING SOURCES……Page 182
7.4.2 DIET……Page 188
7.5.1 LIPID OXIDATION……Page 190
7.5.2 NONENZYMATIC BROWNING……Page 197
7.5.3 PHOTO-INDUCED OFF-FLAVORS……Page 198
7.5.4 ENZYMATIC FLAVOR CHANGES……Page 199
7.6 MICROBIAL OFF-FLAVORS……Page 203
7.7 SUMMARY……Page 206
REFERENCES……Page 207
Part II: Flavor Technology……Page 215
8.1.1.2 Natural Flavoring……Page 216
8.2 NATURAL FLAVORING MATERIALS (PLANT SOURCES)……Page 217
8.2.1.1 Definitions and Markets……Page 218
8.2.1.2 Historical Associations……Page 219
8.2.1.3 Classification of Herbs and Spices……Page 222
8.2.1.4 Flavor Character of Herbs……Page 224
8.2.1.5 Preparation of Herbs for Market……Page 225
8.2.1.6 Introduction to Spices……Page 226
8.2.1.6.1 Milling of Spices……Page 227
8.2.1.6.2 Microbiology of Spices……Page 228
8.2.2.1 Essential Oils (Distillation)……Page 229
8.2.2.1.1 Manufacture of Spice Essential Oils……Page 230
8.2.2.1.2 Use of Spice Essential Oils……Page 232
8.2.2.2 Oleoresins (Solvent Extraction)……Page 233
8.2.2.2.1 Solvents……Page 234
8.2.2.2.2 Manufacture of Oleoresins……Page 235
8.2.2.2.4 Oleoresins and Related Products……Page 236
8.2.2.3.1 Citrus Fruits……Page 237
8.2.2.3.2 Citrus Essential Oils……Page 238
8.2.2.3.4 Processed Citrus Oils……Page 240
8.2.2.2.5 Methods of Deterpenation……Page 241
8.2.2.4.2 Peppermint……Page 243
8.2.2.4.3 Cornmint……Page 246
8.2.2.4.6 Composition of Mint Oils……Page 247
8.2.2.4.7 Other Commercially Important Sources……Page 248
8.2.2.5 Fruit, Fruit Juices, and Concentrates……Page 249
8.2.2.5.1 Fruit Juices……Page 250
8.2.2.5.2 Fruit Juice Concentrates……Page 251
8.2.2.5.5 Dehydrated Fruit Juices……Page 253
8.2.2.6 Vanilla……Page 254
8.2.2.6.1 The Vanilla Plant……Page 255
8.2.2.6.2 The Curing Process……Page 256
8.2.2.6.3 Classification and Grading of Vanilla Beans……Page 257
8.2.2.6.5 The Chemistry of Vanilla Flavor……Page 258
8.2.2.6.6 Vanilla Flavorings……Page 260
8.2.2.6.8 Imitation Vanilla Flavorings……Page 261
8.2.2.7.1 Cocoa/Chocolate Plant and Processing……Page 262
8.2.2.7.4 Coffee Flavor……Page 264
8.2.2.7.5 Tea……Page 265
8.2.2.8.1 Onion……Page 266
8.2.2.8.2 Onion Flavor……Page 267
8.2.2.8.4 Garlic Flavor……Page 268
REFERENCES……Page 269
9.2 NATURAL PRODUCTS MADE BY ROASTING: COCOA/CHOCOLATE……Page 273
9.2.3 CHOCOLATE……Page 274
9.3 PROCESS FLAVORS: MEAT-LIKE FLAVORS……Page 275
9.3.1 THE EVOLUTION OF PROCESS MEAT-LIKE FLAVORINGS……Page 276
9.2.2.1.1 Sulfur Sources……Page 277
9.3.2.1.2 Reducing Sugars……Page 279
9.3.2.1.4 Lipids……Page 280
9.3.2.1.6 Hydrolyzed Vegetable Proteins (HVP), Savory Enhancers (MSG and 5′-Nucleotides), and Autolyzed Yeast Extracts (AYE)……Page 281
9.3.2.1.7 Miscellaneous Components……Page 282
9.3.2.2 Reaction Conditions……Page 283
9.3.2.3 Final Flavor……Page 284
9.3.4 AUTOLYZED YEAST EXTRACTS (AYE)……Page 285
9.4.1 INTRODUCTION……Page 286
9.4.2 PROPERTIES OF ENZYME CATALYZED REACTIONS……Page 287
9.4.3 ENZYME MODIFIED BUTTER/BUTTER OIL……Page 290
9.4.4 ENZYME-MODIFIED CHEESE (EMC)……Page 291
9.4.4.1 Enzymes Used……Page 292
9.4.4.2 General Processes Employed……Page 293
9.4.5 FURTHER PROCESSED EM DAIRY PRODUCTS……Page 294
9.5.2 VINEGAR/ACETIC ACID……Page 295
9.6.1 THE SMOKING OF FOODS……Page 297
9.6.4 SMOKE CONDENSATES……Page 298
9.7.2 PRODUCTION OF NATURAL FLAVORING MATERIALS BY ENZYMATIC ACTION……Page 299
9.7.2.1 Ester Formation……Page 300
9.7.3 PRODUCTION OF NATURAL FLAVORING MATERIALS BY MICROBIAL ACTION……Page 302
9.7.3.1 Fermentation to Produce Flavoring Materials……Page 303
9.7.3.3 Resolution of Racemic Mixtures……Page 305
REFERENCES……Page 306
10.2.1 INTRODUCTION……Page 311
10.3 CLASSIFICATION OF AROMA COMPOUNDS BY MOLECULAR STRUCTURE……Page 312
10.4 SENSORY THRESHOLD VALUES……Page 315
10.5 SENSORY CHARACTERS OF ODOR COMPOUNDS……Page 317
10.5.1 HYDROCARBONS……Page 318
10.5.3 ACETALS……Page 319
10.5.5 CARBONYLS……Page 320
10.5.6 ESTERS……Page 321
10.5.8 HETEROCYCLIC COMPOUNDS……Page 322
10.5.10.2 Amides……Page 323
10.5.12 SULFUR-CONTAINING COMPOUNDS……Page 324
REFERENCES……Page 325
11.1 INTRODUCTION……Page 328
11.2.1 STRUCTURES……Page 329
11.2.2 STABILITY……Page 330
11.3.1 INFLUENCE OF MSG AND 5′-NUCLEOTIDES ON TASTE……Page 331
11.3.2 INFLUENCE OF MSG AND 5′-NUCLEOTIDES ON AROMA……Page 332
11.4.1 MSG AND 5′-NUCLEOTIDES IN FOODS……Page 333
11.4.1.1 Yeast Extracts……Page 334
11.4.1.2 Hydrolyzed Vegetable Proteins (HVP)……Page 335
11.4.2 MSG AND 5′-NUCLEOTIDES ADDED TO FOODS……Page 336
11.4.3 SOURCES OF MSG AND 5′-NUCLEOTIDES……Page 337
11.5.1 MONOSODIUM GLUTAMATE……Page 340
11.6.1 BEEFY MEATY PEPTIDE……Page 341
11.6.3 ALAPYRIDAINE……Page 342
REFERENCES……Page 343
12.2.1 SELECTION OF INDIVIDUALS TO BECOME FLAVORISTS……Page 347
12.3 WORKING ENVIRONMENT……Page 348
12.4.1 IMITATION FLAVORINGS……Page 350
12.4.2 BLENDING OF SEASONINGS (CULINARY PRODUCTS)……Page 355
12.5 SENSORY ASSESSMENT……Page 356
12.5.1 SAMPLE EVALUATION……Page 357
REFERENCES……Page 358
13.2 LIQUID FLAVORINGS……Page 360
13.3 EMULSIONS……Page 361
13.3.1 BEVERAGE EMULSIONS……Page 362
13.4.1 EXTENDED OR PLATED FLAVORS……Page 369
13.4.2.1 Cyclodextrins……Page 371
13.4.3 PHASE SEPARATION/COACERVATION PROCESSES……Page 373
13.4.4 DEHYDRATION PROCESSES……Page 375
13.4.4.1.1 Encapsulation Matrices……Page 376
13.4.4.1.2 Flavor Retention During Drying……Page 377
13.4.4.1.3 Flavor Stability……Page 382
13.4.4.2.1 Dryer Descriptions……Page 384
13.4.4.2.2 Flavor Retention During Drying……Page 385
13.4.5.1 Traditional Processes and Formulations……Page 386
13.4.5.2 Modern Extrusion Processes……Page 389
13.4.5.3 Shear Form Process……Page 391
13.6 SUMMARY……Page 392
REFERENCES……Page 393
14.2 THE PEOPLE……Page 399
14.4 SPECIFIC FLAVORING APPLICATIONS……Page 400
14.4.1 CULINARY AND MEAT PRODUCTS……Page 401
14.4.1.1.2 Dry Soups……Page 402
14.4.1.2 Sauces, Seasonings, and Marinades……Page 403
14.4.1.3 Meat Products……Page 404
14.4.2 BAKED GOODS AND BAKERY PRODUCTS……Page 405
14.4.2.2 Flavoring Baked Goods……Page 406
14.4.2.3 Heat Resistant Flavorings……Page 407
14.4.3 SNACK FOODS……Page 408
14.4.3.2 Snack Flavorings……Page 409
14.4.3.3 Flavoring Materials……Page 410
14.4.3.4.1 Topical Flavoring……Page 413
14.4.4.1 Hard Candies……Page 414
14.4.4.2 Caramels (Toffees)……Page 415
14.4.4.4 Starch-Deposited Chews……Page 416
14.4.4.5 Chewing Gum……Page 417
14.4.5.1 Flavored Milks……Page 418
14.4.5.2 Flavored Yogurts……Page 419
14.4.5.3 Flavored Dairy Desserts……Page 420
14.4.6.1 Introduction……Page 422
14.4.6.2.2 Flavoring……Page 423
14.5 SUMMARY……Page 424
REFERENCES……Page 425
15.2 LEGISLATION LIMITING THE USE OF FLAVOR COMPOUNDS……Page 427
15.2.1 U.S. FLAVOR-RELATED LEGISLATION……Page 428
15.3 RELIGIOUS DIETARY RULES……Page 429
15.3.1 KOSHER DIETARY LAWS……Page 430
15.3.2 HALAL RULES……Page 431
15.4.2 LABELING FOR THE CONSUMER……Page 432
15.5 SUMMARY……Page 438
REFERENCES……Page 439
16.2.1.1 Natural Plant Materials……Page 440
16.2.1.2 Essential Oils……Page 441
16.2.1.2.6 Specific Tests and Procedures……Page 442
16.2.1.5 Synthetic Chemicals……Page 443
16.2.1.6.2 General Tests: Emulsions……Page 444
16.2.1.8.1 General Tests……Page 445
16.2.2.1 Density/Specific Gravity……Page 446
16.2.2.5 Residual Solvent……Page 447
16.2.2.6 Particle Size of Emulsions……Page 448
16.2.2.7 Volatile Oil……Page 451
16.2.2.9 Moisture Content……Page 452
16.2.2.10.1 Incoming Ingredients……Page 454
16.2.2.10.3 Flavor Duplication……Page 455
16.2.2.11 Spectroscopic Analysis……Page 456
16.3.1 INCOMING RAW INGREDIENTS……Page 457
16.3.2.1 Sensory Evaluation……Page 458
16.3.2.2 Changes in Finished Flavors with Age……Page 460
16.3.2.3 Sample Rejection……Page 461
16.3.5 SUMMARY……Page 462
16.4.1 GAS CHROMATOGRAPHY/MASS SPECTROMETRY……Page 463
16.4.2 CHIRAL COMPOUNDS……Page 465
16.4.3 HPLC……Page 466
16.4.4 CARBON 14 DATING……Page 467
16.4.5 STABLE ISOTOPE RATIO ANALYSIS……Page 468
REFERENCES……Page 470