Deakin J. Organic Chemistry: Miracles from Plants

Cover
Half Title
Organic Chemistry. Miracles from Plants
Copyright
Contents
Preface
About Biography
Part I. Introduction
	Organic Chemistry
	Context: Miraculous Chemicals from Plants
	References
		Nomenclature
		Botanical names
		Scope of chemistry
Part II. Medical Marvels
	Introduction
	Central America’s Humble Potato!
		Steroids
		The Search for the Modern Birth Control Pill
		Isolation of Natural Diosgenin from the Mexican Potato
		Chemical Magic in the Laboratory—Synthesis of Norethindrone
		Biological Studies of Progesterone to Prevent Ovulation
		Medical Approval and Social Acceptance
		The Profound Social, Cultural and Economic Impacts of Reliable Oral Contraception
		Transformation of Production
		Hydrocarbons
		Saturated Hydrocarbons—Alkanes and Cycloalkanes
		Crude Oil and Industrial Fractional Distillation
		Benzene and Aromatic Compounds—Physical and Chemical Properties
		Theory of the Molecular Structure of Benzene
	Suggested Further Reading
	Reference
	Europe Solves a Headache! Emergence of Aspirin
		Salicin and Salicyclic Acid
		Carboxylic Acids
		Phenol and Phenolic Compounds
		Acetylation of the Hydroxyl Group of Salicylic Acid to Form Aspirin
	Suggested Further Reading
	Reference
	Attacking Malaria: a South American Treasure and a Chinese Miracle
		Malaria
		Cinchona
		Isolation of Quinine
		Synthesis of Quinine in the Laboratory
		Uses of Quinine
		Artemisinin
		Carbon–Oxygen Single Bonds and Oxygen–Oxygen Single Bonds in Organic Compounds
		The Peroxide Link and the Peroxide Bridge in Artemisinin
	Suggested Further Reading
	References
	A Steroid in Your Garden
		The Foxglove and Digoxigenin
		Esters are Formed from Alcohols and Acids
		Properties and Uses of Esters
		Introducing Cyclic Esters Known as Lactones
		Lactones as Building Blocks in Nature
		Vitamins
		Vitamin C, Ascorbic Acid
		Commercial Uses of Lactones
	Suggested Further Reading
	Reference
	Africa’s Gift to the World
		Discovery of the Periwinkle Plant and Its Properties
		Serendipity
		Modern Research and Therapeutic Value
		The Alkaloids, Vincristine and Vinblastine
		Isolation of Vincristine and Vinblastine from Plants
	Suggested Further Reading
	Saving the Pacific Yew Tree
		The Nature of Paclitaxel
		Medical Value of Paclitaxel
		Modern-Day Preparation of Paclitaxel
		Terpenes and Isoprene as Building Blocks in Nature
		Isomers
		Isomers and Stereo-Chemistry
		Isomers and Chirality
		Nuclear Magnetic Resonance (NMR) Spectroscopy and Molecular Structure
	References
	Vaccines, Adjuvants and Organic Chemistry
		How the Chemistry of Natural Products Enhances Vaccines
		Vaccines
		Adjuvants
		The Development of Adjuvants
		A Vaccine Against Covid-19
		Saponins
		Natural Sources of Saponin
		New Biochemical Approaches
		Molecular Biochemistry
		Summary
	References
Part III. Nutrition—Ancient and Modern Miracles
	Introduction
	Rediscovering Traditional Grains of the Americas—Chia and Quinoa
		Chia
		Quinoa
		Gluten Sensitivity
		Lipids
		Fats, Oils and Human Health
		Waxes
		Vegetable Oil and Biodiesel
	Suggested Further Reading
	Wheat—Ancient and Modern
		Possible Origins of Ancient Wheat
		Modern Wheat Varieties
		Nutritional Importance and the Grinding of Wheat
		Importance of Proteins
		Peptide Bond
		The Condensation Reaction
		Proteins and Amino Acids
		Amino Acids, Proteins and DNA
		Fascinating Influence of Chirality on Life Systems on Earth
		The Shikimic Acid Pathway in Phyto-Chemistry—a Route to Aromatic Amino Acids
		Sustainability and Society’s Challenges in Enhancing Agricultural Production
	Suggested Further Reading
	References
	Asian Staple—Rice
		Carbohydrates and Saccharides; Oxygen in the Organic Ring
		Monosaccharides
		Disaccharides
		The Glycoside Link
		Oligosaccharides
		Polysaccharides
		Chemical Properties of Carbohydrates—Monosaccharides
		The Value of Monosaccharides, Disaccharides and Polysaccharides to Living Organisms
		Human Nutrition
		Optical Isomerism
		Optical Isomerism and the Pharmaceutical Industry
	Suggested Further Reading
	Chinese Cordyceps—Winter Worm, Summer Grass
		The Life Cycle of Cordyceps Sinensis
		The Perceived Health Benefits of Cordyceps Sinensis
		What Is Fermentation?
		Industrial Production of Bio-Ethanol
	Suggested Further Reading
Part IV. Beverages
	Introduction
	Tea: from Legend to Healthy Obsession!
		The Tea Plant
		Historical Notes on Tea as a Beverage
		The Growing and Processing of Tea
		Tea and Possible Health Benefits
		The Properties of Phenol and Phenols
		Catechins—Key Phenolic Compounds in Green Tea
	Selected further reading
	Cocoa (Cacao)—Food of the Gods
		Origins
		Processing Cacao Beans
		Cocoa and Cardiac Health
		Cocoa and Diabetes
		Chemical Constituents of Cocoa
	Suggested Further Reading
	Coffee—Wake Up and Smell the Aroma!
		Early Use
		Coffee and Caffeine
		Zwitterions
		Cyclic Aromatic Amines
		The Process of Decaffeination of Coffee
	Suggested Further Reading
	Maca from the High Andes in South America
		The Maca Plant
		Maca as a Beverage and a Food
		The Medicinal Value of Maca
		Chemical Composition of Maca
		Indole
		Key Chemical Properties of Indole
		Acid-Base Extraction
		Purification of Indole Alkaloids by Acid-Base Extraction
		Indole Alkaloids
	Suggested Further Reading
	Reference
Part V. Euphorics
	Introduction
	Suggested Further Reading
	Morphine: A Double-Edged Sword
		The Double-Edged Sword
		The Production of Morphine in the Natural World
		Purification, Chemical Composition and Properties of Morphine
		Chemical Composition and Properties of Codeine
		Chemical Composition and Properties of Heroin
		Medicinal Uses of Morphine
		Summary
	Suggested Further Reading
	Cannabis and Marijuana
		Cannabis
		Introducing Cannabinoids
		Terpenes
		Classification of Terpenes
		Terpenes and Elimination Reactions
		The Condensation Reaction
	Suggested Further Reading
	Coca and Cocaine
		Coca and the Coca Plant
		Cocaine
		Chemical Properties of Cocaine
		Isolation of Cocaine
		Legitimate Applications of Cocaine
	Suggested Further Reading
	Tobacco: A Profound Impact on the World
		Tobacco
		Nicotine
		Amines
		Heterocyclic Aromatic Compounds
		Properties of Nicotine
		Uses of Nicotine
	Suggested Further Reading
	Reference
Part VI. Exotic Potions, Lotions and Oils
	Introduction
	Suggested Further Reading
	A Plant from the East Indies, Camphor
		The Classification and Structure of Camphor
		Diverse Uses of Camphor
		Extraction of Camphor by Steam Distillation
		The Carbonyl Group and Nucleophilic Addition Reactions
		Infra-Red Spectroscopy and the Determination of the Structure of Organic Molecules
		Atmospheric Absorption of Infra-Red Radiation; Greenhouse Effect and Global Warming
		Carbon Dioxide and Global Warming
	Suggested Further Reading
	Biblical Resins: Frankincense and Myrrh
		Sources and Uses of Frankincense and Myrrh
		Frankincense
		Myrrh
		Classification of Cyclic Terpenes
		Steric Hindrance
	Suggested Further Reading
	References
	European Lavender
		European Lavender
		Distribution
		Value of Lavender
		Essential Oils—Hydrosol from Lavender
		Hydrosols and Colloids
		Vegetable Oils and Fats
		Hydrolysis of Esters
		Soap
		How Soap Works
	Suggested Further Reading
	Global Aloe
		Aloe Vera
		Aloe Vera and Skin Treatment
		Aloe Vera and Polysaccharides
		Galactomannans
		Hydraulic 'Fracking'
		Anthraquinones Found in Aloe Vera
		Chromatography
		Thin Layer and Column Chromatography
		Gas Chromatography and Gas-Liquid Chromatography
		High Pressure Liquid Chromatography
		Ion Exchange Chromatography
	Suggested Further Reading
	Reference
Part VII. Colorful Chemistry, a Natural Palette of Plant Dyes and Pigments
	Introduction
	Selected Reading
	Our World of Green Plants—Human Survival
		Green Plants
		The Vital Process of Photosynthesis
		Chlorophyll
		Chlorophyll and Color
		Chromophores
		Molecular Interaction with Electromagnetic Radiation
		Ultraviolet Absorption Spectroscopy and Organic Chemistry
		Ultraviolet Absorption Spectroscopy and Molecular Structure
		Green Plants, Sustainability and Limiting Climate Change
	Suggested Further Reading
	References
	Saffron and Carotenoids—Yellow and Orange Dyes
		Saffron—the Plant
		Crocin
		Carotenoids and Autumnal Color
		Carotene Carotenoids
		Xanthophyll Carotenoids
		The Allyl Functional Group
		Human Health; Vitamin A, Retinol and Retinal
	Suggested Further Reading
	Reference
	Woad (Isatis Tinctoria) and Indigo
		Indigo through the Ages
		Indigo from Plants
		Extraction of Indigo
		Indigo and Dyeing Textiles
		Azo Dyes
	Suggested Further Reading
	Reference
	Red Dyes from Henna, Dyer’s Bugloss and Madder
		Quinones as Building Blocks in Nature
		Naphthoquinones
		Anthraquinones
		Textile Dyes—Color Fastness and Mordants
	Suggested Further Reading
	References
	Reversible Colors in Flowers, Berries and Fruit
		The Inestimable Value of Color in Flowers, Berries and Fruit
		The Beautiful Color of Autumn Leaves
		Flavonoids
		Flavonoids and Anthocyanins
		Anthocyanins—Reversible Dyes
		Reversible Dyes and Acid/Base Indicators
		Phytochrome—a Reversible Pigment and a Biological Light Switch
		Phytochrome in Photoperiodism and in Phototropism
	Suggested Further Reading
	References
Part VIII. Plant Materials
	Introduction
	The Wonderful World of Wood
		What Is Wood?
		Carbohydrates That Are Non-Sugars
		The Value of Cellulose
		The Value of Starch
		Lignin—the Structural Partner of Cellulose
		Distribution of Trees across the World
		Conservation and Environmental Significance
	References
	Secrets of a Sticky Secretion
		Latex
		Natural Rubber
		Historical Intrigue
		Summary
	References
	Suggested Further Reading
	The Green Credentials of Bioplastic
		Polymerization and Plastics
		Bioplastics
		Recycling Terminology—Let’s Be Clear
		Bioplastics and the Environment
		Summary
	References
	Suggested Further Reading
Part IX. Plants and the Natural Environment
	Introduction
	Seaweed and ‘Blue’ Carbon
		Seaweed and Algae
		Important Natural Products Derived from Algae
		Value to Man
		Farming
		Mitigation of Climate Change
		‘Blue’ Carbon Storage
		Soil Chemistry and Seaweed Fertilizer
		Summary
	References
	Suggestions for Further Reading
	Garlic and Pungent Smells
		Garlic
		Organo-Sulfur Compounds
		Amino Acids That Contain Sulfur
		Fossil Fuels and Acid Rain
		Scrubbing Gaseous Effluent Gases at Industrial Plants
		An Alternative Method of Reducing Sulfur Dioxide Emissions
	Suggested Further Reading
	Learning to Love Legumes
		Legumes
		Nitrogen Fixing
		Nitrogen Cycle
		Industrial Production of Nitrogen Fertilizer
		Alternative, Sustainable Routes for Synthesizing Nitrogen Fertilizer
		Summary
	References
Glossary
Organic Chemistry: Miracles from Plants
Acknowledgments
Index