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Flavor chemistry and technology

PART I Flavor Chemistry

Chapter 1 An Overview of Flavor Perception
1.1 Flavor Perception
1.2 Taste Perception
1.2.1 Anatomy of Taste
1.2.2 Synopses of Tastes
1.3 Chemesthesis
1.3.1 Chemesthetic Responses
1.3.2 Tactile Response
1.4 Olfaction
1.4.1 Anatomy of Olfaction
1.4.2 Odor Receptor Functioning
1.4.3 Signal Encoding

Chapter 2 Flavor and the Information Age
2.2 History of Flavor Literature
2.3 Journals
2.4 Professional Societies
2.5 Internet


Chapter 3 Flavor Analysis
3.1 Introduction
3.2 Aroma Compounds
3.2.1 Introduction
3.2.2 Sample Selection/Preparation
3.2.3 Principles of Aroma Isolation
3.2.3.1 Introduction
3.2.3.2 Solubility
3.2.3.3 Sorptive Extraction
3.2.3.4 Volatility
3.2.4 Methods of Aroma Isolation
3.2.4.1 Static Headspace
3.2.4.2 Headspace Concentration Methods (Dynamic Headspace
3.2.4.3 Distillation Methods
3.2.4.4 Solvent Extraction
3.2.4.5 Sorptive Extraction
3.2.4.6 Concentration for Analysis
3.2.4.7 Aroma Isolation Summary
3.2.5 Analysis of Aroma Isolates
3.2.5.1 Prefractionation
3.2.5.2 Gas Chromatography
3.2.5.3 GC/Olfactometry (GC/O) or GC-MS/Olfactometry (GC-MS/O)
3.2.5.4 Mass Spectrometry
3.2.6 Specific Analysis
3.2.6.1 Key Components in Foods
3.2.6.2 Aroma Release During Eating
3.2.7 Electronic Noses

3.3 Taste Compounds (Nonvolatiles
3.3.1 Introduction
3.3.1.1 Taste Compounds
3.3.1.2 Other Nonvolatile Components of Foods
3.3.2 The Analysis of Taste Substances
3.3.2.1 Sweeteners
3.3.2.2 Salt
3.3.2.3 Acidulants
3.3.2.4 Umami
3.3.2.5 Bitter Substances


Chapter 4 Flavor Formation in Fruits and Vegetables
4.1 Introduction
4.2 Biogenesis of Fruit Aroma
4.2.1 Aroma Compounds from Fatty Acid Metabolism
4.2.2 Aroma Compounds from Amino Acid Metabolism..........................77
4.2.3 Aroma Compounds Formed from Carbohydrate Metabolism ..........80
4.3 Biogenesis of Vegetable Aroma.....................................................................83
4.3.1 The Role of Lipids in Vegetable Aroma Formation..........................85
4.3.2 Aroma Compound Formation from Cysteine Sulfoxide Derivatives
4.3.3 Glucosinolates as Aroma Precursors in Vegetables...........................88
4.3.4 Additional Pathway for Vegetable Flavor Formation........................88
4.4 Glycosidically Bound Aroma Compounds....................................................88
4.4.1 Glycoside Structure............................................................................91
4.4.2 Freeing of Glycosidically Bound Flavor Compounds ......................91
4.5 Location of Flavor in Plant............................................................................92
4.6 Influence of Genetics, Nutrition, Environment, Maturity, and Storage on Development of Flavor
4.6.1 Plant Products ....................................................................................93
4.6.1.1 Genetics...............................................................................93
4.6.1.2 Environmental and Cultural Effects on Flavor Development on the Plant
4.6.1.3 Influence of Maturity and Postharvest Storage on Flavor Development off the Plant
4.7 Animal Products.............................................................................................97
4.8 Conclusions ....................................................................................................97


Chapter 5 Changes in Food Flavor Due to Processing ....................................103
5.1 Introduction ..................................................................................................103
5.2 The Maillard Reaction .................................................................................103
5.2.1 General Overview of the Maillard Reaction ...................................103
5.2.2 Pathways for Flavor Formation via the Maillard Reaction.............104
5.2.3 Factors Influencing the Maillard Reaction ......................................105
5.2.3.1 Heating Time/Temperature ...............................................106
5.2.3.2 Influence of System Composition ....................................108
5.2.3.3 Influence of Water Activity ..............................................109
5.2.3.4 Influence of pH.................................................................109
5.2.3.5 Influence of Buffer/Salts...................................................110
5.2.3.6 Influence of Oxidation/Reduction State ...........................110
5.2.4 Kinetics of the Maillard Reaction and Flavor.................................111
5.2.4.1 Pyrazines ...........................................................................111
5.2.4.2 Oxygen-Containing Heterocyclic Compounds.................112
5.2.4.3 Sulfur-Containing Compounds.........................................113
5.2.4.4 Miscellaneous Compounds...............................................113
5.2.4.5 Summary...........................................................................114
5.2.5 Flavor Formation via the Maillard Reaction ...................................114
5.2.5.1 Carbonyl Compounds .......................................................115
5.2.5.2 Nitrogen-Containing Heterocyclic Compounds ...............115
5.2.5.3 Oxygen-Containing Heterocyclic Compounds.................117
5.2.5.4 Sulfur-Containing Heterocyclic Compounds ...................118
5.2.5.5 Oxygen-Containing Compounds ......................................119
5.3 Flavors from Lipids......................................................................................119
5.3.1 Deep Fat Fried Flavor ......................................................................119
5.3.2 Lactones ...........................................................................................121
5.3.3 Secondary Reactions ........................................................................121
5.4 Flavors Formed via Fermentation................................................................123
5.4.1 Esters ................................................................................................123
5.4.2 Acids.................................................................................................124
5.4.3 Carbonyls..........................................................................................125
5.4.4 Alcohols ...........................................................................................127
5.4.5 Terpenes............................................................................................128
5.4.6 Lactones ...........................................................................................129
5.4.7 Pyrazines ..........................................................................................129
5.4.8 Sulfur Compounds ...........................................................................130
5.4.9 Conclusions ......................................................................................130

Chapter 6 Flavor Release from Foods..............................................................139
6.1 Introduction ..................................................................................................139
6.2 Lipid/Flavor Interactions..............................................................................140
6.2.1 Effect of Fat: Flavor Interactions on Aroma ...................................141
6.2.1.1 Equilibrium Conditions ....................................................141
6.2.1.2 Dynamic Conditions .........................................................143
6.2.2 Effect of Fat: Flavor Interactions on Taste......................................144
6.3 Carbohydrate: Flavor Interactions ...............................................................145
6.3.1 Simple Sugars: Aroma Interactions .................................................145
6.3.2 High Potency Sweeteners: Aroma Interactions ...............................146
6.3.3 Complex Carbohydrate (Polysaccharide): Aroma Interactions.......148
6.3.3.1 Chemical Interactions .......................................................149
6.3.3.2 Resistance to Mass Transfer.............................................151
6.3.4 Carbohydrate: Taste Interactions .....................................................152
6.4 Protein: Flavor Interactions..........................................................................153
6.4.1 Protein: Aroma Interactions .............................................................153
6.4.1.1 Chemical Interactions .......................................................153
6.4.1.2 Resistance to Mass Transfer.............................................155
6.4.2 Protein Hydrolysate: Aroma Interactions ........................................155
6.4.3 Protein: Taste Interactions................................................................155
6.5 Minor Food Components: Aroma Interactions............................................155
6.5.1 Melanoidin: Flavor Interaction ........................................................156
6.5.2 Hydrogen Ion Effects (pH effects) ..................................................156

Chapter 7 Off-Flavors and Taints in Foods
7.1 Introduction
7.2 Sensory Aspects of Off-Flavor Testing
7.3 Taints in Foods
7.3.1 Airborne Sources
7.3.2 Waterborne Sources
7.3.3 Disinfectants, Pesticides, and Detergents
7.3.4 Packaging Sources
7.4 Off-Flavors Due to Genetics or Diet
7.4.1 Genetics
7.4.2 Diet
7.5 Off-Flavors Due to Chemical Changes in the Food
7.5.1 Lipid Oxidation
7.5.2 Nonenzymatic Browning
7.5.3 Photo-Induced Off-Flavors
7.5.4 Enzymatic Flavor Changes
7.6 Microbial Off-Flavors


PART II Flavor Technology

Chapter 8 Flavoring Materials
8.1 Introduction
8.1.1 Definitions
8.1.1.1 Flavoring
8.1.1.2 Natural Flavoring
8.1.1.3 Artificial Flavoring
8.2 Natural Flavoring Materials (Plant Sources)
8.2.1 Herbs and Spices
8.2.1.1 Definitions and Markets
8.2.1.2 Historical Associations
8.2.1.3 Classification of Herbs and Spices
8.2.1.4 Flavor Character of Herbs
8.2.1.5 Preparation of Herbs for Market
8.2.1.6 Introduction to Spices
8.2.2 Derivatives of Spices
8.2.2.1 Essential Oils (Distillation)
8.2.2.2 Oleoresins (Solvent Extraction)
8.2.2.3 Expressed ¡°Essential¡± Oils (Citrus Oils)
8.2.2.4 Mint Oils
8.2.2.5 Fruit, Fruit Juices, and Concentrates
8.2.2.6 Vanilla
8.2.2.7 Cocoa, Coffee, and Tea Flavorings
8.2.2.8 Aromatic Vegetables


Chapter 9 Flavoring Materials Made by Processing ........................................261
9.1 Introduction ..................................................................................................261
9.2 Natural Products Made by Roasting: Cocoa/Chocolate..............................261
9.2.1 Production of Cocoa Powder...........................................................262
9.2.2 The Dutch Process ...........................................................................262
9.2.3 Chocolate..........................................................................................262
9.3 Process Flavors: Meat-Like Flavors ............................................................263
9.3.1 The Evolution of Process Meat-Like Flavorings ............................264
9.3.2 The Creation of Process Flavorings ................................................265
9.3.2.1 Reaction System Composition .........................................265
9.3.2.2 Reaction Conditions..........................................................271
9.3.2.3 Final Flavor.......................................................................272
9.3.3 Hydrolyzed Vegetable Proteins (HVP) ............................................273
9.3.4 Autolyzed Yeast Extracts (AYE)......................................................273
9.4 Enzymatically Derived Flavorings...............................................................274
9.4.1 Introduction ......................................................................................274
9.4.2 Properties of Enzyme Catalyzed Reactions ....................................275
9.4.3 Enzyme Modified Butter/Butter Oil ................................................278
9.4.4 Enzyme-Modified Cheese (EMC) ...................................................279
9.4.4.1 Enzymes Used ..................................................................280
9.4.4.2 General Processes Employed ...........................................281
9.4.5 Further Processed EM Dairy Products ............................................282
9.5 Flavors Made by Fermentation....................................................................283
9.5.1 Yeasts................................................................................................283
9.5.2 Vinegar/Acetic Acid .........................................................................283
9.5.3 Dried Inactive Yeast Powder............................................................285
9.6 Flavors Made by Pyrolysis: Smoke Flavors................................................285
9.6.1 The Smoking of Foods ....................................................................285
9.6.2 Natural Liquid Smoke Flavorings ...................................................286
9.6.3 Pyroligneous Acid ............................................................................286
9.6.4 Smoke Condensates .........................................................................286
9.7 Biotechnology to Produce Flavoring Materials...........................................287
9.7.1 Introduction ......................................................................................287
9.7.2 Production of Natural Flavoring Materials by Enzymatic Action ...287
9.7.2.1 Ester Formation ................................................................288
9.7.2.2 Resolution of Racemic Mixtures......................................290
9.7.3 Production of Natural Flavoring Materials by MicrobialAction 290
9.7.3.1 Fermentation to Produce Flavoring Materials...............291
9.7.3.2 Bioconversions Via Microorganisms .............................293
9.7.3.3 Resolution of Racemic Mixtures...................................293
9.7.4 Economics of Biotechnology .........................................................294


Chapter 10 Artificial Flavoring Materials ..........................................................299
10.1 Artificial Flavorings .....................................................................................299
10.2 Synthetic Flavoring Materials......................................................................299
10.2.1 Introduction ......................................................................................299
10.2.2 Consumer Attitudes Toward Synthetic Chemicals ..........................300
10.3 Classification of Aroma Compounds by Molecular Structure ....................300
10.4 Sensory Threshold Values............................................................................303
10.5 Sensory Characters of Odor Compounds ....................................................305
10.5.1 Hydrocarbons..................................................................................306
10.5.2 Carboxylic Acids ............................................................................307
10.5.3 Acetals ............................................................................................307
10.5.4 Alcohols..........................................................................................308
10.5.5 Carbonyls........................................................................................308
10.5.5.1 Aldehydes.......................................................................309
10.5.5.2 Ketones...........................................................................309
10.5.6 Esters ..............................................................................................309
10.5.7 Ethers ..............................................................................................310
10.5.8 Heterocyclic Compounds ...............................................................310
10.5.9 Lactones..........................................................................................311
10.5.10 Nitrogen-Containing Compounds ..................................................311
10.5.10.1 Amines ...........................................................................311
10.5.10.2 Amides ...........................................................................311
10.5.10.3 Imines.............................................................................312
10.5.10.4 Amino Acids ..................................................................312
10.5.10.5 Isothiocyanates...............................................................312
10.5.11 Phenols............................................................................................312
10.5.12 Sulfur-Containing Compounds.......................................................312
10.6 Nomenclature of Organic Chemicals ..........................................................313


Chapter 11 Flavor Potentiators ...........................................................................317
11.1 Introduction ..................................................................................................317
11.2 Chemical Properties of L-Amino acids and 5-Nucleotides .......................318
11.2.1 Structures ........................................................................................318
11.2.2 Stability...........................................................................................319
11.3 Sensory Properties of MSG and 5-Nucleotides .........................................320
11.3.1 Influence of MSG and 5-Nucleotides on Taste ..............................320
11.3.2 Influence of MSG and 5-Nucleotides on Aroma ...........................321
11.3.3 Synergism Between MSG and the 5-Nucleotides..........................322
11.4 Traditional Flavor Potentiators in Foods .....................................................322
11.4.1 MSG and 5-Nucleotides in Foods ..................................................322
11.4.1.1 Yeast Extracts ...................................................................323
11.4.1.2 Hydrolyzed Vegetable Proteins (HVP).............................324
11.4.2 MSG and 5-Nucleotides Added to Foods.......................................325
11.4.3 Sources of MSG and 5-Nucleotides ...............................................326
11.4.4 Table Salt as a Flavor Potentiator....................................................329
11.5 Toxicity of MSG and 5-Nucleotides ..........................................................329
11.5.1 Monosodium Glutamate...................................................................329
11.5.2 5-Nucleotides ..................................................................................330
11.6 Other Potentiators ........................................................................................330
11.6.1 Beefy Meaty Peptide........................................................................330
11.6.2 Umami Tasting Glutamate Conjugates ............................................331
11.6.3 Alapyridaine .....................................................................................331
11.6.4 Sweetness Potentiators.....................................................................332
11.6.4.1 Maltol and Ethyl Maltol ...................................................332
11.6.4.2 Cyclic Enolones ................................................................332
11.6.5 Other Potentiators ............................................................................332

Chapter 12 Flavorists and Flavor Creation.........................................................337
12.1 Introduction ..................................................................................................337
12.2 The Flavorist ................................................................................................337
12.2.1 Selection of Individuals to Become Flavorists................................337
12.2.2 Training of Flavorists.......................................................................338
12.3 Working Environment ..................................................................................338
12.4 Flavor Creation.............................................................................................340
12.4.1 Imitation Flavorings .........................................................................340
12.4.2 Blending of Seasonings (Culinary Products) ..................................345
12.5 Sensory Assessment .....................................................................................346
12.5.1 Sample Evaluation ...........................................................................347
12.6 Conclusions ..................................................................................................348


Chapter 13 Flavor Production.............................................................................351
13.1 Introduction ..................................................................................................351
13.2 Liquid Flavorings .........................................................................................351
13.3 Emulsions .....................................................................................................352
13.3.1 Beverage Emulsions.........................................................................353
13.3.2 Baker¡¯s Emulsions............................................................................360
13.4 Dry Flavorings .............................................................................................360
13.4.1 Extended or Plated Flavors..............................................................360
13.4.2 Inclusion Complexes (Cyclodextrins and Starches)........................362
13.4.2.1 Cyclodextrins ....................................................................362
13.4.2.2 Starch ................................................................................364
13.4.3 Phase Separation/Coacervation Processes .......................................364
13.4.4 Dehydration Processes .....................................................................366
13.4.4.1 Spray Drying.....................................................................367
13.4.4.2 Freeze, Drum, and Tray Drying .......................................375
13.4.5 Extrusion ..........................................................................................377
13.4.5.1 Traditional Processes and Formulations...........................377
13.4.5.2 Modern Extrusion Processes ............................................380
13.4.5.3 Shear Form Process ..........................................................382
13.5 Controlled Release .......................................................................................383
13.6 Summary ......................................................................................................383


Chapter 14 Flavor Applications ..........................................................................391
14.1 Introduction ..................................................................................................391
14.2 The People....................................................................................................391
14.3 The Laboratory.............................................................................................392
14.4 Specific Flavoring Applications...................................................................392
14.4.1 Culinary and Meat Products ............................................................393
14.4.1.1 Soups and Stocks..............................................................394
14.4.1.2 Sauces, Seasonings, and Marinades .................................395
14.4.1.3 Meat Products ...................................................................396
14.4.2 Baked Goods and Bakery Products .................................................397
14.4.2.1 Problems in Flavoring Baked Goods ...............................398
14.4.2.2 Flavoring Baked Goods ....................................................398
14.4.2.3 Heat Resistant Flavorings.................................................399
14.4.3 Snack Foods .....................................................................................400
14.4.3.1 Problems in Flavoring Snack Foods ................................401
14.4.3.2 Snack Flavorings...............................................................401
14.4.3.3 Flavoring Materials...........................................................402
14.4.3.4 Means of Applying Flavorings .........................................405
14.4.4 Sugar-Based Confectionery Products and Chewing Gum ..............406
14.4.4.1 Hard Candies ....................................................................406
14.4.4.2 Caramels (Toffees)............................................................407
14.4.4.3 Pressed Tablets..................................................................408
14.4.4.4 Starch-Deposited Chews...................................................408
14.4.4.5 Chewing Gum...................................................................409
14.4.5 Dairy Products
14.4.5.1 Flavored Milks
14.4.5.2 Flavored Yogurts
14.4.5.3 Flavored Dairy Desserts
14.4.6 Soft Drinks
14.4.6.1 Introduction
14.4.6.2 Carbonated Beverages


Chapter 15 Flavor Legislation and Religious Dietary Rules
15.1 Introduction
15.2 Legislation Limiting the Use of Flavor Compounds
15.2.1 U.S. Flavor-Related Legislation
15.3 Religious Dietary Rules
15.3.1 Kosher Dietary Laws
15.3.2 Halal Rules
15.4 Labeling of Food Flavorings
15.4.1 Bulk Labeling Requirements
15.4.2 Labeling for the Consumer

Chapter 16 Quality Control
16.1 Introduction
16.2 Analytical Tests
16.2.1 Overview of Physicochemical Tests
16.2.1.1 Natural Plant Materials
16.2.1.2 Essential Oils
16.2.1.3 Oleoresins
16.2.1.4 Plated or Dispersed Spices
16.2.1.5 Synthetic Chemicals
16.2.1.6 Finished Flavorings
16.2.1.7 Vanilla Extract
16.2.1.8 Fruit-Based Products
16.2.2 Generally Used Analytical Testing Methods
16.2.2.1 Density/Specific Gravity
16.2.2.2 Refractive Index
16.2.2.3 Optical Rotation
16.2.2.4 Alcohol Content
16.2.2.5 Residual Solvent
16.2.2.6 Particle Size of Emulsions
16.2.2.7 Volatile Oil
16.2.2.8 Surface Oil
16.2.2.9 Moisture Content
16.2.2.10 Gas Chromatography
16.2.2.11 Spectroscopic Analysis
16.2.2.12 Microbiological Analysis
16.2.2.13 Electronic Noses
16.3 Sensory Analysis
16.3.1 Incoming Raw Ingredients
16.3.2 Finished Flavors
16.3.2.1 Sensory Evaluation
16.3.2.2 Changes in Finished Flavors with Age
16.3.2.3 Sample Rejection
16.3.3 Colorings
16.3.4 Scoville Heat Units
16.3.5 Summary
16.4 Adulteration Testing
16.4.1 Gas Chromatography/Mass Spectrometry
16.4.2 Chiral Compounds
16.4.3 HPLC
16.4.4 Carbon 14 Dating
16.4.5 Stable Isotope Ratio Analysis
16.4.6 Comments on Adulteration



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