1 Introduction and Historical Background.- 1.1 Historical Uses of Extractives and Exudates.- 1.1.1 Introduction.- 1.1.2 Major Uses of Extractives and Exudates.- 1.1.2.1 The Use of Durable Woods.- 1.1.2.2 Exudates.- 1.1.2.2.1 Varnishes.- 1.1.2.2.2 Lacquers.- 1.1.2.2.3 Gums.- 1.1.2.3 Tannins.- 1.1.2.4 Dyes.- 1.1.2.5 Perfumes.- 1.1.2.6 Rubber.- 1.1.2.7 Medicines.- 1.1.3 Lessons from History.- References.- 1.2 Natural Products Chemistry — Past and Future.- 1.2.1 Introduction.- 1.2.2 Isolation and Purification.- 1.2.3 Structure Determination.- 1.2.4 The Future of Natural Products Science.- References.- 2 Fractionation and Proof of Structure of Natural Products.- 2.1 Introduction.- 2.2 Novel Techniques and Recent Developments in Fractionation and Isolation.- 2.2.1 Countercurrent Chromatography.- 2.2.1.1 Coil Countercurrent Chromatography.- 2.2.1.2 Droplet Countercurrent Chromatography.- 2.2.1.3 Rotation Locular Countercurrent Chromatography.- 2.2.1.4 Centrifugal Partition Chromatography.- 2.2.1.5 Comparison of Partition Chromatographic Methods.- 2.2.2 Adsorption Chromatography.- 2.2.2.1 Ion-Pair Chromatography.- 2.2.2.2 Other New Methods of Column Chromatography.- 2.2.2.3 Supercritical Fluid Chromatography.- 2.3 Nuclear Magnetic Resonance Spectroscopy.- 2.3.1 Proton Nuclear Magnetic Resonance.- 2.3.1.1 Difference Decoupling.- 2.3.1.2 Difference NOE.- 2.3.1.3 Contact Shifts.- 2.3.1.4 Partial Relaxation.- 2.3.2 Carbon Nuclear Magnetic Resonance.- 2.3.2.1 J-Modulated Spin Echo.- 2.3.2.2 Insensitive Nuclei Enhanced by Polarization Transfer.- 2.3.2.3 Distortionless Enhancement by Polarization Transfer.- 2.3.2.4 Carbon-Proton Heteronuclear Coupling.- 2.3.2.5 Carbon-Proton Heteronuclear NOE.- 2.3.2.6 Deuterium Isotopic Shifts.- 2.3.3 Two-Dimensional NMR Spectroscopy.- 2.3.3.1 Two Dimensional J-Resolved Proton NMR Spectroscopy.- 2.3.3.2 Two Dimensional Correlation Spectroscopy.- 2.3.3.3 Two Dimensional-INADEQUATE (Incredible Natural Abundance Double Quantum Transfer Experiment).- 2.4 Other Spectroscopic Techniques.- 2.4.1 Mass Spectrometry.- 2.4.1.1 Techniques That Enhance Sample Volatilization.- 2.4.1.2 Modern Techniques of Ionization/Desorption.- 2.4.1.3 Tandem Mass Spectrometry.- 2.4.2 Ultraviolet-Visible Spectroscopy.- 2.4.3 Infra-Red Spectroscopy.- 2.4.4 Circular Dichroism.- 2.4.4.1 The Nature of Circular Dichroism.- 2.4.4.2 The Additivity Relation in A Values.- 2.5 General Conclusions.- References.- 3 Evolution of Natural Products.- 3.1 Convergent Synthesis and the Origin of RNA-Based Life.- 3.2 Expansion of the Acetate, Mevalonate, and ?-Aminolevulinate Pathways in Bacteria and Algae.- 3.3 Expansion of the Shikimate Pathway in Terrestrial Plants.- 3.4 Phytochemistry and Plant Defense.- 3.5 Oxidation Levels of Angiospermous Micromolecules.- 3.6 Skeletal Specialization of Angiospermous Micromolecules.- 3.7 Quantification of Micromolecular Parameters.- 3.8 Phytochemical Gradients in Angiosperms.- 3.9 Future Perspectives.- References.- 4 Carbohydrates.- 4.1 Introduction.- 4.2 Sucrose.- 4.3 Higher Oligosaccharides Related to Sucrose.- 4.4 Other Oligosaccharides.- 4.5 Monosaccharides.- 4.6 Alditols.- 4.7 Cyclitols.- 4.7.1 myo-Inositol.- 4.7.2 D-chiro-Inositol.- 4.7.3 Quebrachitol.- 4.7.4 D-Quercitol.- 4.7.5 Conduritol.- 4.7.6 Quinic Acid.- 4.8 Plant Glycosides.- 4.9 Starch.- 4.10 Extractable Polysaccharides.- 4.10.1 Arabinogalactans.- 4.10.1.1 Larch Arabinogalactans.- 4.10.1.2 Other Extractable, Nonexudate Arabinogalactans.- 4.10.2 Other Extractable Polysaccharides; The Pectic Polysaccharides….- 4.10.3 Exudate Gums.- 4.10.3.1 Acacia Gums.- 4.10.3.2 Exudate Gums of Other Rosales Genera.- 4.10.3.3 Gums of Combretaceae (Myrtiflorae) Genera.- 4.10.3.4 Exudate Gums of Anacardiaceae (Sapindales).- 4.10.3.5 Exudate Gums of Families in the Orders Rutales, Parietales, and Malvales.- 4.10.3.6 Exudate Gums from Other Orders.- 4.10.3.7 Exudate Gums with Xylan Cores.- References.- 5 Nitrogenous Extractives.- 5.1 Amino Acids, Proteins, Enzymes, and Nuccleic Acids.- 5.1.1 Introduction.- 5.1.2 Composition.- 5.1.2.1 Free and Bound Amino Acids.- 5.1.2.2 Proteins and Enzymes.- 5.1.2.3 Nucleic Acids and Related Products.- 5.1.3 Factors Determining Composition.- 5.1.3.1 Genetics.- 5.1.3.2 Genetics x Environment.- 5.1.3.3 Growth and Development.- 5.1.3.4 Pathology.- 5.1.3.5 Impact of Humans.- 5.1.4 Conclusion.- References.- 5.2 The Alkaloids.- 5.2.1 Introduction.- 5.2.2 True Alkaloids.- 5.2.2.1 Alkaloids from Ornithine.- 5.2.2.1.1 Coca Alkaloids.- 5.2.2.1.2 Elaeocarpus Alkaloids.- 5.2.2.2 Alkaloids from Lysine.- 5.2.2.2.1 Punica Alkaloids.- 5.2.2.2.2 Lythraceae Alkaloids.- 5.2.2.2.3 Securinega Alkaloids.- 5.2.2.2.4 Cytisus Alkaloids.- 5.2.2.3 Alkaloids from Anthranilic Acid.- 5.2.2.3.1 Quinoline and Furoquinoline Alkaloids.- 5.2.2.3.2 Acridone Alkaloids.- 5.2.2.3.3 Evodia Alkaloids.- 5.2.2.3.4 Carbazole Alkaloids.- 5.2.2.4 Alkaloids from Nicotinic Acid (Celastraceae Alkaloids).- 5.2.2.5 Alkaloids from Phenylalanine and Tyrosine.- 5.2.2.5.1 Benzylisoquinoline Alkaloids.- 5.2.2.5.2 Curare Alkaloids.- 5.2.2.5.3 Sinomenine.- 5.2.2.5.4 Aporphine-type Alkaloids.- 5.2.2.5.5 Berberine.- 5.2.2.5.6 Nitidine.- 5.2.2.5.7 Erythrina Alkaloids.- 5.2.2.5.8 Cephalotaxus Alkaloids.- 5.2.2.5.9 Ipecacuanha and Alangium Alkaloids.- 5.2.2.6 Alkaloids from Tryptophan.- 5.2.2.6.1 Calycanthus Alkaloids.- 5.2.2.6.2 Picrasma (Pentaceras) and Carboline Alkaloids.- 5.2.2.6.3 Rauwolfia Alkaloids.- 5.2.2.6.4 Tabernanthe Alkaloids.- 5.2.2.6.5 Ochrosia Alkaloids.- 5.2.2.6.6 Ervatamia Alkaloids.- 5.2.2.6.7 Uncaria-Mitragyna Alkaloids.- 5.2.2.6.8 Yohimbe Alkaloids.- 5.2.2.6.9 Cinchona Alkaloids.- 5.2.2.6.10 Guettarda Alkaloids.- 5.2.2.6.11 Strychnos Alkaloids.- 5.2.2.6.12 Gelsemium Alkaloids.- 5.2.2.6.13 Gardneria Alkaloids.- 5.2.2.6.14 Camptothecins.- 5.2.3 Pseudoalkaloids.- 5.2.3.1 Alkaloids from Polyketides.- 5.2.3.1.1 Pinidine.- 5.2.3.1.2 Galbulimima Alkaloids.- 5.2.3.2 Alkaloids from Mevalonate.- 5.2.3.2.1 Spiraea Alkaloids.- 5.2.3.2.2 Erythrophleum Alkaloids.- 5.2.3.2.3 Daphniphyllum Alkaloids.- 5.2.3.2.4 Apocynaceae Steroidal Alkaloids.- 5.2.3.2.5 Buxaceae Steroidal Alkaloids.- References.- 6 Aliphatic and Alicyclic Extractives.- 6.1 Simple Organic Acids.- 6.1.1 Introduction.- 6.1.2 Organic Acids in the TCA and Glyoxylate Cycles.- 6.1.2.1 Citric Acid.- 6.1.2.2 AconiticAcid.- 6.1.2.3 Isocitric Acid.- 6.1.2.4 ?-Ketoglutaric Acid.- 6.1.2.5 Succinic Acid.- 6.1.2.6 Fumaric Acid.- 6.1.2.7 Malic Acid.- 6.1.2.8 Oxaloacetic Acid.- 6.1.2.9 Glyoxylic Acid.- 6.1.3 Other Metabolically Important Organic Acids.- 6.1.3.1 Glycolic Acid.- 6.1.3.2 Glyceric Acid.- 6.1.3.3 Pyruvic Acid.- 6.1.3.4 Malonic Acid.- 6.1.3.5 Shikimic Acid and Quinic Acid.- 6.1.4 Organic Acids of an End-Product Nature.- 6.1.4.1 Lactic Acid.- 6.1.4.2 Oxalic Acid.- 6.1.4.3 Tartaric Acid.- 6.1.4.4 Chelidonic Acid.- 6.1.4.5 Fluoroacetic Acid.- References.- 6.2 Complex Aliphatic and Alicyclic Extractives.- 6.2.1 Introduction.- 6.2.2 ?-Lactones.- 6.2.3 ?-Lactones (2-Pyrones).- 6.2.4 Cyanogenic Glycosides and Related Compounds.- 6.2.5 Highly Oxygenated Cyclohexanes.- 6.2.6 Cyclohexane Diols.- 6.2.7 Polycyclic Compounds.- 6.2.8 Miscellaneous.- References.- 6.3 Fats and Fatty Acids.- 6.3.1 Introduction.- 6.3.2 Fats as Food Reserves.- 6.3.3 Aliphatic Monocarboxylic Acids.- 6.3.3.1 Volatile Fatty Acids.- 6.3.3.2 Constituent Fatty Acids of Fats.- References.- 6.4 Chemistry, Biochemistry, and Function of Suberin and Associated Waxes.- 6.4.1 Introduction.- 6.4.2 Waxes.- 6.4.2.1 Analysis of Plant Waxes.- 6.4.2.2 Composition of Suberin-Associated Waxes.- 6.4.2.2.1 Hydrocarbons in Suberin-Associated Waxes.- 6.4.2.2.2 Wax Esters.- 6.4.2.2.3 Free Fatty Alcohols.- 6.4.2.2.4 Free Fatty Acids.- 6.4.2.2.5 Polar Wax Components.- 6.4.2.2.6 Ferulic Acid Esters.- 6.4.2.2.7 Tabular Survey of Bark Wax Components.- 6.4.2.3 Biosynthesis of Wax Components.- 6.4.2.3.1 Very Long Fatty Acids.- 6.4.2.3.2 Fatty Alcohols.- 6.4.2.3.3 Wax Esters.- 6.4.2.3.4 Hydrocarbons and Derivatives.- 6.4.3 Suberin.- 6.4.3.1 Ultrastructure.- 6.4.3.1.1 Ultrastructural Characterization.- 6.4.3.1.2 Ultrastructural Identification of Suberin in Bark.- 6.4.3.2 Chemical Composition and Structure of the Polymer.- 6.4.3.2.1 Composition of the Aliphatic Portion.- 6.4.3.2.2 Phenolic Composition.- 6.4.3.2.3 Structure.- 6.4.3.3 Suberin Biosynthesis.- 6.4.3.3.1 Biosynthesis of the Aliphatic Monomers.- 6.4.3.3.1.1 ?-Hydroxylation of Fatty Acids.- 6.4.3.3.1.2 Oxidation of ?-Hydroxy Acids.- 6.4.3.3.1.3 Biosynthesis of Mid-Chain Oxygenated Suberin Monomers.- 6.4.3.3.2 Biosynthesis of the Aromatic Components of Suberin.- 6.4.3.3.3 Biosynthesis of Suberin from Aliphatic and Aromatic Monomers.- 6.4.3.4 Function of Suberin and Associated Waxes.- 6.4.3.4.1 Prevention of Water Loss.- 6.4.3.4.2 Suberization in Wound Healing.- 6.4.3.4.3 Suberization in Response to Stress.- 6.4.3.4.4 Suberization as a Means of Compartmentalization.- 6.4.3.5 Regulation of Suberization.- 6.4.3.6 Enzymatic Degradation of Suberin.- References.- 7 Benzenoid Extractives.- 7.1 Monoaryl Natural Products.- 7.1.1 Introduction.- 7.1.2 Simple Phenols (C6).- 7.1.3 Phenolic Acids, Salicins and Other C6–C1 Compounds.- 7.1.3.1 Benzoic Acids and Related Compounds.- 7.1.3.2 Salicins and Related Compounds.- 7.1.4 Acetophenones and Other C6–C2 Compounds.- 7.1.5 Cinnamic Acids, Coumarins and Other Phenylpropanoids (C6–C3).- 7.1.5.1 Cinnamic Acids.- 7.1.5.2 Coumarins.- 7.1.5.3 Other Phenylpropanoids.- 7.1.6 Miscellaneous Monoaryl Compounds.- References.- 7.2 Gallic Acid Derivatives and Hydrolyzable Tannins.- 7.2.1 Introduction.- 7.2.2 Metabolism of Gallic Acid — General Observations.- 7.2.3 Biosynthesis of Gallic Acid.- 7.2.4 Metabolites of Gallic Acid.- 7.2.4.1 Simple Esters Occurrence and Detection.- 7.2.4.2 Depside Metabolites Group 2A.- 7.2.4.3 Metabolites Formed by Oxidative Coupling of Galloyl Esters Groups 2B and 2C, Ellagitannins.- 7.2.4.3.1 Hexahydroxydiphenoyl Esters.- 7.2.4.3.2 Dehydrohexahydroxydiphenoyl Esters.- 7.2.4.3.3 Group 2B Metabolites.- 7.2.4.3.4 Group 2C Metabolites.- 7.2.4.3.5 Postscript.- 7.2.5 The Interaction of Proteins with Metabolites of Gallic Acid.- References.- 7.3 Lignans.- 7.3.1 Introduction.- 7.3.2 Nomenclature and Numbering.- 7.3.3 Chemistry.- 7.3.4 Oligomeric Lignoids.- References.- 7.4 Stilbenes, Conioids, and Other Polyaryl Natural Products.- 7.4.1 Introduction.- 7.4.2 Stilbenes and Structurally Related Compounds.- 7.4.3 Conioids (Norlignans), Including Condensed and Structurally Related Compounds.- 7.4.4 Aucuparins and Structurally Related Biphenyls.- 7.4.5 Diarylheptanoids, Structurally Related Diarylheptanoids, and Bridged Biphenyls (Cyclophanes).- 7.4.6 Miscellaneous Diaryl and Polyaromatic Compounds.- 7.4.7 Concluding Remarks.- References.- 7.5 Flavonoids.- 7.5.1 Introduction.- 7.5.2 Structural Types.- 7.5.2.1 Flavones and Flavonols.- 7.5.2.2 Flavonones and Flavononols.- 7.5.2.3 Chalcones and Aurones.- 7.5.2.4 Isoflavonoids and Neoflavonoids.- 7.5.3 Distribution.- 7.5.3.1 Distribution within the Plant.- 7.5.3.2 Patterns in Gymnosperm Woods.- 7.5.3.3 Patterns in Angiosperm Woods.- 7.5.3.3.1 Heartwood Flavonoids of the Anacardiaceae.- 7.5.3.3.2 Heartwood Flavonoids of the Leguminosae.- 7.5.4 Properties and Function.- References.- 7.6 Biflavonoids and Proanthocyanidins.- 7.6.1 Introduction.- 7.6.2 Biflavonoids.- 7.6.2.1 Structural Variations of Biflavonoids.- 7.6.2.2 Distribution of Biflavonoids.- 7.6.2.3 Significant Properties of Biflavonoids.- 7.6.3 Proanthocyanidins.- 7.6.3.1 Flavan-3-ols.- 7.6.3.1.1 Structure of Flavan-3-ols.- 7.6.3.1.2 Distribution of Flavan-3-ols.- 7.6.3.1.3 Reactions of Flavan-3-ols.- 7.6.3.2 Flavan-3,4-diols.- 7.6.3.2.1 Structure of Flavan-3,4-diols.- 7.6.3.2.2 Distribution of Flavan-3,4-diols.- 7.6.3.2.3 Reactions of Flavan-3,4-diols.- 7.6.3.3 Oligomeric Proanthocyanidins.- 7.6.3.3.1 Structure and Distribution of Oligomeric Proanthocyanidins.- 7.6.3.3.1.1 Proquibourtinidins.- 7.6.3.3.1.2 Profisetinidins.- 7.6.3.3.1.3 Prorobinetinidins.- 7.6.3.3.1.4 Proteracacidins and Promelacacidins.- 7.6.3.3.1.5 Propelargonidins.- 7.6.3.3.1.6 Procyanidins.- 7.6.3.3.1.7 Prodelphinidins.- 7.6.3.3.2 Reactions of Oligomeric Proanthocyanidins.- References.- 7.7 Condensed Tannins.- 7.7.1 Introduction.- 7.7.2 Structure and Properties.- 7.7.2.1 Isolation and Purification.- 7.7.2.2 Elucidation of the Structure of Type 1 Proanthocyanidin Polymers.- 7.7.2.3 Structure of Type 2 Proanthocyanidin Polymers.- 7.7.2.4 Molecular Weight Distribution.- 7.7.2.5 Conformation and Solution Properties.- 7.7.2.6 Complexation.- 7.7.3 Distribution in Plants.- 7.7.3.1 Chemotaxonomic and Phylogenetic Significance.- 7.7.3.2 Distribution and Structural Variations within Plants.- 7.7.4 Metabolism.- 7.7.4.1 Biosynthesis.- 7.7.4.2 Seasonal Variation and Fate in Senescent Tissues.- 7.7.5 Role in Plants.- 7.7.5.1 Resistance to Insects.- 7.7.5.2 Resistance to Decay Fungi.- 7.7.5.3 Allelopathic Relationships.- References.- 8 Isoprenoids.- 8.1 Terpenoids.- 8.1.1 Introduction.- 8.1.1.1 Nomenclature.- 8.1.1.2 Biosynthesis.- 8.1.2 Occurrence in Woody Plants.- 8.1.3 Classes: Distribution and Structural Types.- 8.1.3.1 Hemiterpenoids.- 8.1.3.2 Monoterpenoids.- 8.1.3.2.1 Distribution.- 8.1.3.2.2 Structural Types.- 8.1.3.2.3 Tropolones.- 8.1.3.3 Sesquiterpenoids.- 8.1.3.3.1 Distribution.- 8.1.3.3.2 Structural Types.- 8.1.3.4 Diterpenoids.- 8.1.3.4.1 Distribution.- 8.1.3.4.2 Structural Types.- 8.1.3.5 Sesterterpenoids.- 8.1.3.6 Non-Steroidal Triterpenoids.- 8.1.3.6.1 Distribution.- 8.1.3.6.2 Structural Types.- 8.1.3.7 Tetraterpenoids: Carotenoids.- 8.1.3.8 Polyterpenoids: Polyprenols.- 8.1.3.9 Meroterpenoids.- 8.1.4 Biological Role.- References.- 8.2 Steroids.- 8.2.1 Introduction.- 8.2.1.1 Meaning of the Terms “Steroid” and “Sterol”.- 8.2.1.2 Nomenclature.- 8.2.1.3 Biosynthesis of Basic Steroidal Structure.- 8.2.2 Sterols.- 8.2.2.1 Names, Structures, and Organismic Relationships.- 8.2.2.2 Identification of Sterols.- 8.2.2.3 Occurrence in Wood and Bark.- 8.2.2.4 Biosynthetic Origin of Individual Sterols.- 8.2.2.5 Function of Sterols.- 8.2.2.6 Phyletic and Phylogenetic Relationships.- 8.2.2.7 Industrial Utilization of Tree Sterols.- 8.2.3 Esters.- 8.2.4 Glycosides.- 8.2.5 Spiroketals (Saponins).- 8.2.6 Ecdysteroids.- 8.2.6.1 Names, Structures, and Occurrence.- 8.2.6.2 Function of Plant Ecdysteroids.- 8.2.7 Cardiac Glycosides.- References.- 9 The Influence of Extractives on Wood Properties and Utilization.- 9.1 Contribution of Extractives to Wood Characteristics.- 9.1.1 Introduction.- 9.1.2 Color in Wood.- 9.1.2.1 Chemical Structure and Color.- 9.1.2.2 Color of Wood.- 9.1.2.3 Pigments Occurring in Wood.- 9.1.3 Odor in Wood.- 9.1.3.1 Volatile Components.- 9.1.3.2 Fragrant Components.- 9.1.3.3 Foul-Smelling Components.- 9.1.3.4 Removal of Foul Odors.- 9.1.3.5 Insect Attractants.- 9.1.4 Physical Properties.- 9.1.4.1 Wood Density and Strength.- 9.1.4.2 Other Physical Properties.- References.- 9.2 Role of Wood Exudates and Extractives in Protecting Wood from Decay.- 9.2.1 Introduction.- 9.2.1.1 Decay.- 9.2.1.2 Decay-Causing Organisms and Their Effect on Wood Structure.- 9.2.2 How Trees Defend Themselves Against Decay.- 9.2.2.1 Role of Wounds.- 9.2.2.2 Toxic Heartwood Components.- 9.2.2.2.1 Formation of Antimicrobial Compounds.- 9.2.2.2.2 Chemical Nature of Antimicrobial Compounds.- 9.2.3 Evaluation of Decay Resistance.- 9.2.3.1 Isolation and Evaluation of Compounds.- 9.2.3.2 Physiology of Decay Inhibition.- 9.2.3.3 Variation in Decay Resistance.- 9.2.3.3.1 Variation Between Tree Species.- 9.2.3.3.2 Variation Between Individuals of the Same Species.- 9.2.3.3.3 Variation Within an Individual Tree.- References.- 9.3 Effect of Extractives on Pulping.- 9.3.1 Introduction.- 9.3.2 Pulping Processes.- 9.3.2.1 Mechanical.- 9.3.2.2 Semichemical.- 9.3.2.3 Chemical.- 9.3.3 Pulpwood Quality.- 9.3.3.1 Effect of Extractives on Pulp Yield.- 9.3.3.2 Effect of Storage.- 9.3.4 Increased Consumption of Pulping Liquors.- 9.3.5 Effect on Pulping Processes.- 9.3.5.1 Reduced Penetrability of Liquors.- 9.3.5.2 Reduced Lignin Solubility.- 9.3.6 Effect on Equipment during Pulping.- 9.3.6.1 Wear and Corrosion.- 9.3.6.2 Blockage and Deposits.- 9.3.7 Pulp Properties.- 9.3.7.1 Color Changes Arising during Pulping and Bleaching.- 9.3.7.1.1 Mechanical Pulps.- 9.3.7.1.2 Chemical Pulps.- 9.3.7.2 Speck Formation and Pitch Problems during Pulping and Bleaching.- 9.3.7.3 Wettability.- 9.3.7.4 Sticking to Press Rolls.- 9.3.8 Spent Liquor Recovery.- 9.3.8.1 Concentration and Burning Difficulties.- 9.3.8.2 Foaming during Concentration and Oxidation.- 9.3.8.3 By-Product Recovery.- 9.3.9 Observations.- References.- 9.4 Effect of Extractives on the Utilization of Wood.- 9.4.1 Introduction.- 9.4.2 Inhibition of Resin and Glue Curing by Extractives.- 9.4.2.1 Phenolic Resin Adhesives.- 9.4.2.2 Amino Resin Adhesives.- 9.4.3 Inhibition of Cement Hardening by Extractives.- 9.4.3.1 Effect of Extractives on Cement Hardening.- 9.4.3.2 Effect of Light Exposure on Wood Panels Used with Cement.- 9.4.4 Color Change by Light.- 9.4.4.1 Color Changes Upon Exposure to Light.- 9.4.4.2 Color Changes by Other Agents.- References.- 9.5 Health Hazards Associated with Extractives.- 9.5.1 Introduction.- 9.5.2 Toxic Extractives.- 9.5.2.1 Alkaloids and Amino Acids.- 9.5.2.2 Saponins and Glycosides.- 9.5.2.3 Quinones.- 9.5.2.4 Phenolics.- 9.5.2.5 Terpenes.- 9.5.3 Allergenic Extractives.- 9.5.3.1 Quinones.- 9.5.3.2 Alkyl Phenols.- 9.5.3.3 Terpenes.- 9.5.3.4 Phenolics.- 9.5.3.5 Other Allergenic Extractives.- 9.5.4 Carcinogenic Extractives.- 9.5.4.1 Early Work.- 9.5.4.2 Hausen’s Contributions.- 9.5.4.3 Tannin.- 9.5.4.4 Other Carcinogenic Extractives.- 9.5.5 Hygiene and Safety.- 9.5.6 Discussion and Further Research.- 9.5.6.1 Discussion.- 9.5.6.2 Future Research.- References.- 10 The Utilization of Wood Extractives.- 10.1 Naval Stores.- 10.1.1 Introduction.- 10.1.2 Naval Stores Sources.- 10.1.2.1 Gum Naval Stores.- 10.1.2.2 Wood Naval Stores.- 10.1.2.3 Sulfate (Kraft) Naval Stores 9$.- 10.1.2.4 Potential New Sources.- 10.1.3 Turpentine.- 10.1.3.1 Pine Oil.- 10.1.3.2 Polyterpene Resins.- 10.1.3.3 Flavors and Fragrances.- 10.1.3.4 Insecticides.- 10.1.3.5 Miscellaneous Uses.- 10.1.4 Rosin.- 10.1.4.1 Paper Size.- 10.1.4.2 Polymerization Emulsifiers.- 10.1.4.3 Adhesives.- 10.1.4.4 Inks.- 10.1.4.5 Other Market Areas.- 10.1.5 Fatty Acids.- 10.1.5.1 Intermediate Chemicals.- 10.1.5.2 Protective Coatings.- 10.1.5.3 Other Uses.- 10.1.6 Miscellaneous Products.- 10.1.7 The Future for Naval Stores.- References.- 10.2 Gums.- 10.2.1 Introduction.- 10.2.2 Larch Arabinogalactan.- 10.2.2.1 Source.- 10.2.2.2 Production.- 10.2.2.3 Purification.- 10.2.2.4 Properties.- 10.2.2.5 Uses.- 10.2.3 Gum Arabic (Gum Acacia, Acacia Gum).- 10.2.3.1 Source, Production, and Purification.- 10.2.3.2 Properties.- 10.2.3.3 Uses.- 10.2.4 Gum Karaya.- 10.2.5 Gum Tragacanth.- 10.2.6 Gum Ghatti.- 10.2.7 Predictions.- References.- 10.3 Significance of the Condensed Tannins.- 10.3.1 Introduction.- 10.3.2 Tannins as Human and Animal Nutrition Factors.- 10.3.3 Pharmacological and Physiological Properties.- 10.3.4 Tannins as Insect, Mollusc, Bacterial, and Fungal Control Factors.- 10.3.5 Leather Tannage.- 10.3.5.1 Mechanisms of Vegetable Tanning.- 10.3.5.2 Vegetable Tanning Processes.- 10.3.5.3 Treatment of Vegetable Tanning Spent Liquors.- 10.3.6 Condensed Tannins in Wood Adhesives.- 10.3.6.1 Wattle Tannin-Based Particleboard Adhesives.- 10.3.6.2 Wattle Tannin-Based Plywood Adhesives.- 10.3.6.3 Wattle Tannin-Based Laminating Adhesives.- 10.3.6.4 Other Wattle Tannin-Based Adhesives.- 10.3.6.5 Conifer Bark and Related Tannins as Particleboard Adhesives….- 10.3.6.6 Conifer Bark and Related Tannins as Plywood Adhesives.- 10.3.6.7 Conifer Bark and Related Tannins in Cold-Setting Phenolic Resins.- 10.3.7 Specialty Polymer Applications.- References.- 10.4 Rubber, Gutta, and Chicle.- 10.4.1 Introduction.- 10.4.2 Historical Development of Natural Rubber Production.- 10.4.2.1 Hevea brasiliensis.- 10.4.2.2 Guayule.- 10.4.3 Natural Rubber Production Processes.- 10.4.3.1 Rubber Tree Growing.- 10.4.3.2 Latex Collection.- 10.4.3.3 Production of Latex Concentrate.- 10.4.3.4 Production of Dry Rubber.- 10.4.4 Packing and Market Grades.- 10.4.4.1 Packing.- 10.4.4.2 Grading.- 10.4.5 Properties.- 10.4.5.1 Natural Rubber.- 10.4.5.2 Modified Natural Rubber.- 10.4.5.2.1 Deproteinized Rubber.- 10.4.5.2.2 Depolymerized Rubber.- 10.4.5.2.3 Peptized Rubber.- 10.4.5.2.4 Oil Extended Natural Rubber (OENR).- 10.4.5.2.5 MG Rubbers.- 10.4.5.2.6 SP Rubbers.- 10.4.6 Natural Rubber Utilization.- 10.4.6.1 Vulcanization.- 10.4.6.2 Transportation Items.- 10.4.6.3 Mechanical Rubber Goods.- 10.4.6.4 Footwear.- 10.4.6.5 Miscellaneous Uses.- 10.4.6.6 Health and Safety Factors.- 10.4.7 Natural Rubber Economy.- 10.4.8 Gutta Percha and Balata.- 10.4.8.1 Production.- 10.4.8.2 Properties and Uses.- 10.4.9 Chicle.- References.- 10.5 Other Extractives and Chemical Intermediates.- 10.5.1 Introduction.- 10.5.2 Conifer Extractives Utilization.- 10.5.2.1 Balsams, Copals, Amber, and Other Products.- 10.5.2.2 Cedar Wood Oils.- 10.5.2.3 Non-Commercial Extractives.- 10.5.2.3.1 Conidendrin.- 10.5.2.3.2 Dihydroquercetin.- 10.5.2.3.3 Juvabione and Related Insect Hormones.- 10.5.2.3.4 Occidentals.- 10.5.2.3.5 PlicaticAcid.- 10.5.2.3.6 Thujaplicins, Thujic Acid, and Methyl Esters.- 10.5.2.3.7 Waxes.- 10.5.3 Hardwood Extractives Utilization.- 10.5.4 Prospects.- References.- 10.6 Pharmacologically Active Metabolites.- 10.6.1 Introduction.- 10.6.2 Sources of Information.- 10.6.3 Currently Used Drugs Produced in Wood.- 10.6.3.1 Alkaloids.- 10.6.3.1.1 Tropane.- 10.6.3.1.2 Quinolizidine.- 10.6.3.1.3 Phenylalanine Derivatives.- 10.6.3.1.3.1 Simple Tyramine Derivatives.- 10.6.3.1.3.2 Protoberberine.- 10.6.3.1.3.3 Phthalideisoquinoline.- 10.6.3.1.3.4 Benzo(c)phenanthridine.- 10.6.3.1.3.5 Ipecac.- 10.6.3.1.4 Tryptophane Derivatives.- 10.6.3.1.4.1 Indole.- 10.6.3.1.4.2 Quinoline.- 10.6.3.2 Quinoids.- 10.6.3.3 Lignans.- 10.6.3.4 Triterpenes.- 10.6.3.5 Pyrones.- 10.6.3.6 Coumarins.- 10.6.4 Potential Drugs Derived from Secondary Metabolites of Wood.- 10.6.4.1 Alkaloids.- 10.6.4.1.1 Tropane.- 10.6.4.1.2 Isoquinoline.- 10.6.4.1.3 Indole Alkaloids.- 10.6.4.1.4 Ansamacrolides.- 10.6.4.1.5 Quinazoline.- 10.6.4.1.6 Pyrazine Derivatives.- 10.6.4.2 Quinoids.- 10.6.4.3 Lignans.- 10.6.4.4 Diterpenes.- 10.6.4.5 Triterpenes.- 10.6.4.6 Flavonoids.- 10.6.5 Summary and Conclusions.- References.- 11 The Future of Wood Extractives.- 11.1 Introduction.- 11.2 Requirements for Future Wood Extractives Ventures.- 11.2.1 Low Investment Risk.- 11.2.2 Good Sales Potential.- 11.2.3 Inexpensive Raw Material.- 11.2.4 Shared Capital Expense.- 11.2.5 National Priority.- 11.2.6 Realistic Research, Development, and Engineering.- 11.3 Prospects for Existing Extractives-Based Industries.- 11.3.1 Natural Rubber.- 11.3.2 Rosin and Terpenes from Pine.- 11.3.3 Carbohydrate Gums.- 11.3.4 Tannins.- 11.4 Failed Wood Extractives Ventures.- 11.5 Future Directions for Industrially Oriented Extractives Research.- 11.5.1 Control of Extractives Deposition.- 11.5.2 Manipulation of Wood Growth by Chemicals.- 11.5.3 New Techniques for Extractives Isolation.- 11.6 Areas of Needed Basic Research.- 11.6.1 Cambial Constituents: Growth Regulators.- 11.6.2 Root Constituents: Role of Mycorrhizae.- 11.6.3 Environmental Relationships.- 11.6.4 Pharmacologically Active Compounds.- 11.6.5 Phenolic Polymers.- 11.6.6 Sites and Control Mechanisms of Biosynthesis.- 11.7 Conclusions.- References.- Index of Plant Genera and Species.- Organic Compounds Index.