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Food Carbohydrate Chemistry

ISBN: 978-0-8138-2665-3
240 pages
February 2012, Wiley-Blackwell
Food Carbohydrate Chemistry (0813826659) cover image
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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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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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.
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