| Contents | 6 |
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| List of Contributors | 19 |
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| Preface | 25 |
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| Editors’ Acknowledgements | 26 |
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| Authors’ Acknowledgements | 26 |
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| Editors’ Notes on the Use of this Book | 27 |
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| Abbreviations | 29 |
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| Special Molecules, Special Properties | 31 |
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| A. Introduction | 31 |
| B. Structure, Properties and Function | 32 |
| 1. Three-dimensional shape | 32 |
| 2. The conjugated double-bond system | 33 |
| 3. Molecular interactions | 34 |
| C. Functions of Carotenoids | 35 |
| D. Metabolites and Breakdown Products | 36 |
| E. Conclusions | 36 |
| Structure and Chirality | 37 |
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| A. Introduction | 37 |
| B. Three-dimensional Carotenoid Structures | 37 |
| C. Methods for Structure Determination | 39 |
| References | 44 |
| E/Z Isomers and Isomerization | 45 |
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| A. Introduction | 45 |
| B. E/Z Isomers | 45 |
| 1. Geometrical isomerism: Definition and nomenclature | 45 |
| 2. Structural examples of common Z isomers | 49 |
| 3. Physical properties | 49 |
| 4. Spectroscopy | 50 |
| 5. Total synthesis | 52 |
| C. E/Z Isomerization | 52 |
| 1. Thermodynamic and kinetic aspects | 53 |
| 2. Photochemical isomerization catalysed by iodine | 56 |
| 3. Photochemical isomerization catalysed by diphenyl diselenide | 59 |
| 4. Avoiding unwanted E/Z isomerization | 61 |
| 5. Isolation artefacts | 61 |
| D. Biological Implications of Carotenoid Z Isomers | 61 |
| 1. Biosynthesis | 61 |
| 2. Photosynthesis | 62 |
| 3. Transport, accumulation, and E/Z isomerization in biological tissues | 62 |
| 4. Metabolic conversions | 63 |
| 5. Antioxidant properties | 64 |
| 6. Formation during food and feed processing | 64 |
| 7. Conclusion | 64 |
| References | 64 |
| Three-dimensional Structures of Carotenoids by X-ray Crystallography | 67 |
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| A. Survey of Previously Reported Carotenoid Crystal Structures | 67 |
| B. New Experimental Methods | 71 |
| 1. Methods for crystallization of free carotenoids | 71 |
| 2. Data collection | 71 |
| C. New Determinations of Crystal Structures | 73 |
| 1. Astaxanthin and related xanthophylls | 73 |
| 2. Carotenes | 79 |
| D. Conclusions | 81 |
| References | 81 |
| Aggregation and Interface Behaviour of Carotenoids | 83 |
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| A. Introduction | 83 |
| 1. Molecular aggregates | 83 |
| 2. Aggregates of carotenoids | 84 |
| B. Aggregation in Solution | 86 |
| 1. Optical and related properties | 86 |
| 2. Light scattering | 100 |
| 3. Raman spectroscopy | 101 |
| C. Aggregation in Different Environments | 103 |
| 1. Surfaces and interfaces | 103 |
| 2. Vesicles, lipid bilayers and miscellaneous environments | 107 |
| 3. Influence of additives | 116 |
| 4. Natural and artificial nanosized particles containing carotenoids: non-crystalline, crystalline and crystalloidal materials | 117 |
| References | 125 |
| Carotenoid-Protein Interactions | 129 |
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| A. Introduction: Interactions of Carotenoids with Other Molecules | 129 |
| B. Carotenoid-protein Complexes in Plants and Microorganisms | 130 |
| 1. Photosynthetic pigment-protein complexes | 130 |
| 2. Soluble proteins | 130 |
| C. Carotenoid-Protein Interactions in Animals | 131 |
| 1. Blood lipoproteins | 131 |
| 2. Fish muscle | 132 |
| 3. Feathers | 133 |
| D. Carotenoproteins | 133 |
| 1. General features | 133 |
| 2. Crustacyanin | 134 |
| 3. The X-ray structure of ß-crustacyanin | 136 |
| 4. The carotenoid-binding site | 137 |
| 5. Carotenoid-protein interactions | 138 |
| 6. Mechanism of the spectral shift | 142 |
| 7. Other carotenoproteins | 144 |
| 8. Conclusions - future prospects | 147 |
| References | 147 |
| Carotenoid Radicals and Radical Ions | 149 |
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| A. Introduction | 149 |
| 1. Definitions | 149 |
| 2. The roles of carotenoid radicals | 150 |
| B. Radical Ions | 152 |
| 1. Formation and detection of carotenoid radical ions | 152 |
| 2. Structural and spectroscopic properties of carotenoid radical ions | 154 |
| 3. Reduction (redox) potentials for carotenoid radical ions | 162 |
| C. Carotenoid Neutral Radicals | 166 |
| 1. Formation and detection of carotenoid neutral radicals | 166 |
| D. Unidentified Carotenoid Radicals | 167 |
| E. Reaction of Carotenoids with Oxidizing Free Radicals | 167 |
| 1. Factors that influence the mechanism of reactions of free radicals with carotenoids | 167 |
| 2. Free-radical scavenging mechanisms in environments of low polarity | 168 |
| 3. Free-radical scavenging mechanisms in polar and heterogeneous environments | 168 |
| F. Reactions of Carotenoid Radicals | 170 |
| 1. Carotenoid radical cations (CAR +) | 170 |
| 2. Carotenoid radical anions (CAR) | 174 |
| 3. Carotenoid neutral radicals | 176 |
| G. Antioxidant and Pro-oxidant Properties | 177 |
| H. Conclusion | 180 |
| References | 180 |
| Structure and Properties of Carotenoid Cations<
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