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Not since "Sugar Chemistry" by Shallenberger and Birch (1975) has a text clearly presented and applied basic carbohydrate chemistry to the quality attributes and functional properties of foods. Now in Food Carbohydrate Chemistry, author Wrolstad emphasizes the application of carbohydrate chemistry to understanding the chemistry, physical and functional properties of food carbohydrates. Structure and nomenclature of sugars and sugar derivatives are covered, focusing on those derivatives that exist naturally in foods or are used as food additives. Chemical reactions emphasize those that have an…mehr
Not since "Sugar Chemistry" by Shallenberger and Birch (1975) has a text clearly presented and applied basic carbohydrate chemistry to the quality attributes and functional properties of foods. Now in Food Carbohydrate Chemistry, author Wrolstad emphasizes the application of carbohydrate chemistry to understanding the chemistry, physical and functional properties of food carbohydrates. Structure and nomenclature of sugars and sugar derivatives are covered, focusing on those derivatives that exist naturally in foods or are used as food additives. Chemical reactions emphasize those that have an impact on food quality and occur under processing and storage conditions. Coverage includes: how chemical and physical properties of sugars and polysaccharides affect the functional properties of foods; taste properties and non-enzymic browning reactions; the nutritional roles of carbohydrates from a food chemist's perspective; basic principles, advantages, and limitations of selected carbohydrate analytical methods. An appendix includes descriptions of proven laboratory exercises and demonstrations. Applications are emphasized, and anecdotal examples and case studies are presented. Laboratory units, homework exercises, and lecture demonstrations are included in the appendix. In addition to a complete list of cited references, a listing of key references is included with brief annotations describing their important features. Students and professionals alike will benefit from this latest addition to the IFT Press book series. In Food Carbohydrate Chemistry, upper undergraduate and graduate students will find a clear explanation of how basic principles of carbohydrate chemistry can account for and predict functional properties such as sweetness, browning potential, and solubility properties. Professionals working in product development and technical sales will value Food Carbohydrate Chemistry as a needed resource to help them understand the functionality of carbohydrate ingredients. And persons in research and quality assurance will rely upon Food Carbohydrate Chemistry for understanding the principles of carbohydrate analytical methods and the physical and chemical properties of sugars and polysaccharides.
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RONALD E. WROLSTAD, Ph.D. is Distinguished Professor of Food Science & Technology, Emeritus in the Department of Food Science & Technology, Oregon State University, Corvallis, OR. Dr. Wrolstad has authored over 150 professional publications, including 115 papers in refereed journals and 17 books or book chapters. He has served on the editorial boards of numerous scientific journals including Food Chemistry, Journal of Food Processing and Preservation, and Journal of Food Science Education, and has served as chair of the Food Chemistry Division and Fruit & Vegetable Division of the Institute of Food Technologists.
Inhaltsangabe
Contributors xv Acknowledgments xvii Introduction xix 1 Classifying, Identifying, Naming, and Drawing Sugars and Sugar Derivatives 1 Structure and Nomenclature of Monosaccharides 2 Aldoses and Ketoses 2 Configurations of Aldose Sugars 3 D- vs. L-Sugars 3 Different Ways of Depicting Sugar Structures 5 Fischer, Haworth, Mills, and Conformational Structures 5 Classifying Sugars by Compound Class--Hemiacetals, Hemiketals, Acetals, and Ketals 7 Structure and Nomenclature of Disacchaarides 8 Structure and Optical Activity 10 A Systematic Procedure for Determining Conformation (C-1 or 1-C), Chiral Family (D or L), and Anomeric Form (or ) of Sugar Pyranoid Ring Structures 13 Structure and Nomenclature of Sugar Derivatives with Relevance to Food Chemistry 14 Glycols (Alditols) 14 Glyconic, Glycuronic, and Glycaric Acids 15 Deoxy Sugars 17 Amino Sugars and Glycosyl Amines 17 Glycosides 18 Sugar Ethers and Sugar Esters 19 Vocabulary 20 References 21 2 Sugar Composition of Foods 23 Introduction 23 Sugar Content of Foods 24 Composition of Sweeteners 24 Cane and Beet Sugar 24 Honey 26 Starch-Derived Sweeteners 27 Inulin Syrup 28 Sugar Composition of Fruits and Fruit Juices 28 Vocabulary 31 References 31 3 Reactions of Sugars 35 Introduction 35 Mutarotation 35 Oxidation of Sugars 39 Glycoside Formation 40 Acid Catalyzed Sugar Reactions 42 Alkaline-Catalyzed Sugar Reactions 43 Summary 45 Vocabulary 47 References 47 4 Browning Reactions 49 Introduction 50 Key Reactions in Maillard Browning 51 Introductory Comments 51 Sugar-Amino Condensation 51 The Amadori and Heyn's Rearrangements 53 Dehydration, Enolization, and Rearrangement Reactions 54 The Strecker Degradation 55 Final Stages: Condensation and Polymerization 58 An Alternate Free-Radical Mechanism for Nonenzymatic Browning 58 Measurement of Maillard Browning 59 Control of Maillard Browning 60 Introductory Comments 60 Water Activity 60 The Importance of pH 61 Nature of Reactants 62 Temperature 65 Oxygen 68 Chemical Inhibitors 68 Other Browning Reactions 68 Caramelization 68 Ascorbic Acid Browning 69 Enzymatic Browning 69 Assessing Contributing Factors to Nonenzymatic Browning 70 Vocabulary 72 References 72 5 Functional Properties of Sugars 77 Introduction 77 Taste Properties of Sugars 78 The Shallenberger-Acree Theory for Sweetness Perception 80 Sugar Solubility 83 Crystallinity of Sugars 85 Hygroscopicity 86 Humectancy 87 Viscosity 87 Freezing Point Depression and Boiling Point Elevation 87 Osmotic Effects 88 Vocabulary 88 References 88 6 Analytical Methods 91 Introduction 91 Physical Methods 92 Refractometry 92 Density 94 Polarimetry 95 Colorimetric Methods 95 Total Sugars by Phenol-Sulfuric Acid 95 Reducing Sugar Methods 96 Chromatographic Methods 96 Paper and Thin-Layer Chromatography 96 Gas-Liquid Chromatography 97 HPLC 100 Enzymic Methods 102 Carbon Stable-Isotopic Ratio Analysis (SIRA) 103 References 104 7 Starch in Foods 107 Introduction 108 Sources of Starch 108 Molecular Structure of Starch 109 Starch Granules 112 Gelatinization and Pasting: The Cooking of Starch 113 Retrogradation and Gelation: The Cooling of Cooked Starch 115 Monitoring Starch Transitions 118 Microscopy 118 Viscometric Methods 118 Differential Scanning Calorimetry 119 Starch Hydrolytic Enzymes 120 -Amylase 121 -Amylase 122 Modified Starches 122 Physical Modifications 123 Chemical Modifications 125 Resistant Starch 127 Concluding Remarks 129 Vocabulary 129 References 131 8 Plant CellWall Polysaccharides 135 Introduction: Why Plant Cell Walls are Important 135 Cellulose 137 Hemicelluloses 139 Xyloglucans 139 Heteroxylans 140 (1-->3),(1-->4)--D-Glucans 140 Mannans 141 Pectic Polysaccharides 141 Interactions Between Polysaccharides and Cellulose 143 The Plant Cell Wall Structure 144 Vocabulary 145 References 145 9 Nutritional Roles of Carbohydrates 147 Introduction 147 The Digestive Process: From the Bucchal Cavity through the Small Intestine 148 Absorption of Sugars 149 Sugar Metabolism 152 The Large Intestine and the Digestive Process 153 The Colon 153 Intestinal Microflora 153 Fate of Nonabsorbed Monosaccharides, Sugar Derivatives, and Oligosaccharides 155 Dietary Fiber 158 Carbohydrate Nutrition and Human Health 159 Vocabulary 162 References 163 Appendices 165 Unit 1. Laboratory/Homework Exercise--Building Molecular Models of Sugar Molecules 167 Unit 2. Homework Exercise--Recognizing Hemiacetal, Hemiketal, Acetal, and Ketal Functional Groups 171 Unit 3. Laboratory/Homework Exercise--Specification of Conformation (C-1 or 1-C), Chiral Family (D or L), and Anomeric Form (or ) of Sugar Pyranoid Ring Structures 175 Unit 4. Demonstration of the Existence of Plane-Polarized Light and the Ability of Sugar Solutions to Rotate Plane-Polarized Light 181 Unit 5. Laboratory Exercise--Sugar Polarimetry 183 Unit 6. Laboratory Exercise or Lecture Demonstration--The Fehling's Test for Reducing Sugars 187 Unit 7. Laboratory Exercise--Student-Designed Maillard Browning Experiments 189 Unit 8. Laboratory Exercise or Lecture Demonstration--Microscopic Examination of Starch 193 Unit 9. Names and Structures of Oligosaccharides 197 Index 211
Contributors xv Acknowledgments xvii Introduction xix 1 Classifying, Identifying, Naming, and Drawing Sugars and Sugar Derivatives 1 Structure and Nomenclature of Monosaccharides 2 Aldoses and Ketoses 2 Configurations of Aldose Sugars 3 D- vs. L-Sugars 3 Different Ways of Depicting Sugar Structures 5 Fischer, Haworth, Mills, and Conformational Structures 5 Classifying Sugars by Compound Class--Hemiacetals, Hemiketals, Acetals, and Ketals 7 Structure and Nomenclature of Disacchaarides 8 Structure and Optical Activity 10 A Systematic Procedure for Determining Conformation (C-1 or 1-C), Chiral Family (D or L), and Anomeric Form (or ) of Sugar Pyranoid Ring Structures 13 Structure and Nomenclature of Sugar Derivatives with Relevance to Food Chemistry 14 Glycols (Alditols) 14 Glyconic, Glycuronic, and Glycaric Acids 15 Deoxy Sugars 17 Amino Sugars and Glycosyl Amines 17 Glycosides 18 Sugar Ethers and Sugar Esters 19 Vocabulary 20 References 21 2 Sugar Composition of Foods 23 Introduction 23 Sugar Content of Foods 24 Composition of Sweeteners 24 Cane and Beet Sugar 24 Honey 26 Starch-Derived Sweeteners 27 Inulin Syrup 28 Sugar Composition of Fruits and Fruit Juices 28 Vocabulary 31 References 31 3 Reactions of Sugars 35 Introduction 35 Mutarotation 35 Oxidation of Sugars 39 Glycoside Formation 40 Acid Catalyzed Sugar Reactions 42 Alkaline-Catalyzed Sugar Reactions 43 Summary 45 Vocabulary 47 References 47 4 Browning Reactions 49 Introduction 50 Key Reactions in Maillard Browning 51 Introductory Comments 51 Sugar-Amino Condensation 51 The Amadori and Heyn's Rearrangements 53 Dehydration, Enolization, and Rearrangement Reactions 54 The Strecker Degradation 55 Final Stages: Condensation and Polymerization 58 An Alternate Free-Radical Mechanism for Nonenzymatic Browning 58 Measurement of Maillard Browning 59 Control of Maillard Browning 60 Introductory Comments 60 Water Activity 60 The Importance of pH 61 Nature of Reactants 62 Temperature 65 Oxygen 68 Chemical Inhibitors 68 Other Browning Reactions 68 Caramelization 68 Ascorbic Acid Browning 69 Enzymatic Browning 69 Assessing Contributing Factors to Nonenzymatic Browning 70 Vocabulary 72 References 72 5 Functional Properties of Sugars 77 Introduction 77 Taste Properties of Sugars 78 The Shallenberger-Acree Theory for Sweetness Perception 80 Sugar Solubility 83 Crystallinity of Sugars 85 Hygroscopicity 86 Humectancy 87 Viscosity 87 Freezing Point Depression and Boiling Point Elevation 87 Osmotic Effects 88 Vocabulary 88 References 88 6 Analytical Methods 91 Introduction 91 Physical Methods 92 Refractometry 92 Density 94 Polarimetry 95 Colorimetric Methods 95 Total Sugars by Phenol-Sulfuric Acid 95 Reducing Sugar Methods 96 Chromatographic Methods 96 Paper and Thin-Layer Chromatography 96 Gas-Liquid Chromatography 97 HPLC 100 Enzymic Methods 102 Carbon Stable-Isotopic Ratio Analysis (SIRA) 103 References 104 7 Starch in Foods 107 Introduction 108 Sources of Starch 108 Molecular Structure of Starch 109 Starch Granules 112 Gelatinization and Pasting: The Cooking of Starch 113 Retrogradation and Gelation: The Cooling of Cooked Starch 115 Monitoring Starch Transitions 118 Microscopy 118 Viscometric Methods 118 Differential Scanning Calorimetry 119 Starch Hydrolytic Enzymes 120 -Amylase 121 -Amylase 122 Modified Starches 122 Physical Modifications 123 Chemical Modifications 125 Resistant Starch 127 Concluding Remarks 129 Vocabulary 129 References 131 8 Plant CellWall Polysaccharides 135 Introduction: Why Plant Cell Walls are Important 135 Cellulose 137 Hemicelluloses 139 Xyloglucans 139 Heteroxylans 140 (1-->3),(1-->4)--D-Glucans 140 Mannans 141 Pectic Polysaccharides 141 Interactions Between Polysaccharides and Cellulose 143 The Plant Cell Wall Structure 144 Vocabulary 145 References 145 9 Nutritional Roles of Carbohydrates 147 Introduction 147 The Digestive Process: From the Bucchal Cavity through the Small Intestine 148 Absorption of Sugars 149 Sugar Metabolism 152 The Large Intestine and the Digestive Process 153 The Colon 153 Intestinal Microflora 153 Fate of Nonabsorbed Monosaccharides, Sugar Derivatives, and Oligosaccharides 155 Dietary Fiber 158 Carbohydrate Nutrition and Human Health 159 Vocabulary 162 References 163 Appendices 165 Unit 1. Laboratory/Homework Exercise--Building Molecular Models of Sugar Molecules 167 Unit 2. Homework Exercise--Recognizing Hemiacetal, Hemiketal, Acetal, and Ketal Functional Groups 171 Unit 3. Laboratory/Homework Exercise--Specification of Conformation (C-1 or 1-C), Chiral Family (D or L), and Anomeric Form (or ) of Sugar Pyranoid Ring Structures 175 Unit 4. Demonstration of the Existence of Plane-Polarized Light and the Ability of Sugar Solutions to Rotate Plane-Polarized Light 181 Unit 5. Laboratory Exercise--Sugar Polarimetry 183 Unit 6. Laboratory Exercise or Lecture Demonstration--The Fehling's Test for Reducing Sugars 187 Unit 7. Laboratory Exercise--Student-Designed Maillard Browning Experiments 189 Unit 8. Laboratory Exercise or Lecture Demonstration--Microscopic Examination of Starch 193 Unit 9. Names and Structures of Oligosaccharides 197 Index 211
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