Handbook of essential oils: science, technology, and applications

Cover
Half Title
Title Page
Copyright Page
Contents
Editors
Contributors
Chapter 1: Introduction
Chapter 2: History and Sources of Essential Oil Research
	2.1 Ancient Historical Background
	2.2 First Systematic Investigations
	2.3 Research during the Last Half Century
		2.3.1 Essential Oil Preparation Techniques
			2.3.1.1 Industrial Processes
			2.3.1.2 Laboratory-Scale Techniques
			2.3.1.3 Microsampling Techniques
		2.3.2 Chromatographic Separation Techniques
			2.3.2.1 Thin-Layer Chromatography
			2.3.2.2 GC
			2.3.2.3 Liquid Column Chromatography
			2.3.2.4 Supercritical Fluid Chromatography
			2.3.2.5 Countercurrent Chromatography
		2.3.3 Hyphenated Techniques
			2.3.3.1 Gas Chromatography-Mass Spectrometry
			2.3.3.2 High-Resolution GC-FTIR Spectroscopy
			2.3.3.3 GC-UV Spectroscopy
			2.3.3.4 Gas Chromatography-Atomic Emission Spectroscopy
			2.3.3.5 Gas Chromatography-Isotope Ratio Mass Spectrometry
			2.3.3.6 High-Performance Liquid Chromatography-Gas Chromatography
			2.3.3.7 HPLC-MS, HPLC-NMR Spectroscopy
			2.3.3.8 Supercritical Fluid Extraction–Gas Chromatography
			2.3.3.9 Supercritical Fluid Chromatography-Gas Chromatography
			2.3.3.10 Couplings of SFC-MS and SFC-FTIR Spectroscopy
		2.3.4 Identification of Multicomponent Samples without Previous Separation
			2.3.4.1 UV Spectroscopy
			2.3.4.2 IR Spectroscopy
			2.3.4.3 Mass Spectrometry
			2.3.4.4 13C-NMR Spectroscopy
	References
Chapter 3: Sources of Essential Oils
	3.1 “Essential Oil–Bearing Plants”: Attempt of a Definition
	3.2 Phytochemical Variation
		3.2.1 Chemotaxonomy
		3.2.2 Inter- and Intraspecific Variation
			3.2.2.1 Lamiaceae (Labiatae) and Verbenaceae
			3.2.2.2 Asteraceae (Compositae)
	3.3 Identification of Source Materials
	3.4 Genetic and Protein Engineering
	3.5 Resources of Essential Oils: Wild Collection or Cultivation of Plants
		3.5.1 Wild Collection and Sustainability
		3.5.2 Domestication and Systematic Cultivation
		3.5.3 Factors Influencing the Production and Quality of Essential Oil-Bearing Plants
			3.5.3.1 Genetic Variation and Plant Breeding
			3.5.3.2 Plant Breeding and Intellectual Property Rights
			3.5.3.3 Intraindividual Variation between Plant Parts and Depending on the Developmental Stage (Morpho- and Ontogenetic Variation)
			3.5.3.4 Environmental Influences
			3.5.3.5 Cultivation Measures, Contaminations, and Harvesting
	3.6 International Standards for Wild Collection and Cultivation
		3.6.1 GA(C)P: Guidelines for Good Agricultural (and Collection) Practice of Medicinal and Aromatic Plants
		3.6.2 ISSC-MAP: The International Standard on Sustainable Wild Collection of Medicinal and Aromatic Plants
		3.6.3 FairWild
	3.7 Conclusion
	References
Chapter 4: Natural Variability of Essential Oil Components
	4.1 Manifestation of Variability
	4.2 Variability at Different Taxonomic Levels
		4.2.1 Species
		4.2.2 Populations
	4.3 Connections of Chemical Diversity with Other Plant Characteristics
		4.3.1 Propagation and Genetics
		4.3.2 Morphological Characteristics
	4.4 Morphogenetic and Ontogenetic Manifestation of the Chemical Variability
	4.5 Origin of Essential Oil Variability
	4.6 Chemotaxonomic Aspects
	4.7 Considerations for Proper Assessment of Natural Variability
	References
Chapter 5: Production of Essential Oils
	5.1 Introduction
		5.1.1 General Remarks
		5.1.2 Definition and History
		5.1.3 Production
		5.1.4 Climate
		5.1.5 Soil Quality and Soil Preparation
		5.1.6 Water Stress and Drought
		5.1.7 Insect Stress and Microorganisms
		5.1.8 Location of Oil Cells
		5.1.9 Types of Biomass Used
		5.1.10 Timing of the Harvest
		5.1.11 Agricultural Crop Establishment
		5.1.12 Propagation from Seed and Clones
		5.1.13 Commercial Essential Oil Extraction Methods
		5.1.14 Expression
		5.1.15 Steam Distillation
		5.1.16 Concluding Remarks
	Acknowledgments
	References
Chapter 6: Chemistry of Essential Oils
	6.1 Introduction
	6.2 Basic Biosynthetic Pathways
	6.3 Polyketides and Lipids
	6.4 Shikimic Acid Derivatives
	6.5 Terpenoids
		6.5.1 Hemiterpenoids
		6.5.2 Monoterpenoids
		6.5.3 Sesquiterpenoids
	6.6 Synthesis of Essential Oil Components
	References
Chapter 7: Analysis of Essential Oils
	7.1 Introduction
	7.2 Classical Analytical Techniques
	7.3 Modern Analytical Techniques
		7.3.1 The Use of Gas Chromatography and Gas Chromatography-Mass Spectrometry (GC-MS), and Linear Retention Indices in Essential Oil Analysis
		7.3.2 Fast Gas Chromatography for Essential Oil Analysis
		7.3.3 Gas Chromatography-Olfactometry for the Assessment of Odor-Active Components of Essential Oils
		7.3.4 Gas Chromatographic Enantiomeric Characterization of Essential Oils
		7.3.5 Multidimensional Gas Chromatography (MDGC)
			7.3.5.1 Multidimensional Gas Chromatographic Techniques (MDGC)
			7.3.5.2 Multidimensional Preparative Gas Chromatography
			7.3.5.3 Multidimensional Gas Chromatography Coupled to Isotope Ratio Mass Spectrometry (MDGC-IRMS)
		7.3.6 Comprehensive Two-Dimensional Gas Chromatography and Multidimensional Liquid-Gas Chromatography
			7.3.6.1 Analysis of Essential Oils through Comprehensive  Two-Dimensional Gas Chromatography (GC × GC)
			7.3.6.2 On-Line and Off-Line Coupled Liquid Chromatography-Gas Chromatography
		7.3.7 Liquid Chromatography, Liquid Chromatography Hyphenated to Mass Spectrometry, and Multidimensional Liquid Chromatographic Technique in the Analysis of Essential Oils
	7.4 General Considerations on Essential Oil Analysis
	References
Chapter 8: Use of Linear Retention Indices in GC-MS Libraries for Essential Oil Analysis
	8.1 Introduction
	8.2 Retention Index Theories
	8.3 Linear Retention Indices Present in the Databases
	8.4 Accuracy of Retention Indices
	8.5 Retention Index Compilations
	8.6 Research Software
	8.7 Application of Retention Indices in GC-FID and GC-MS Essential Oil Analyses
	8.8 Gas Chromatographic Enantiomer Characterization Supported by Retention Indices
	8.9 Retention Indices Applied to Multidimensional Gas Chromatographic Analysis
	8.10 Concluding Remarks
	References
Chapter 9: Safety Evaluation of Essential Oils: Constituent-Based Approach Utilized for Flavor Ingredients—An Update
	9.1 Introduction
	9.2 Constituent-Based Evaluation of Essential Oils
	9.3 Scope of Essential Oils: Used as Flavor Ingredients
		9.3.1 Plant Sources
		9.3.2 Processing of Essential Oils for Flavor Functions
		9.3.3 Chemical Composition and Congeneric Groups
		9.3.4 Chemical Assay Requirements and Chemical Description of Essential Oil
			9.3.4.1 Intake of the Essential Oil
			9.3.4.2 Analytical Limits on Constituent Identification
			9.3.4.3 Intake of Congeneric Groups
	9.4 Safety Considerations for Essential Oils, Constituents, and Congeneric Groups
		9.4.1 Essential Oils
			9.4.1.1 Safety of Essential Oils: Relationship to Food
		9.4.2 Safety of Constituents and Congeneric Groups in Essential Oils
	9.5 Guide and Example for the Safety Evaluation of Essential Oils
		9.5.1 Introduction
		9.5.2 Elements of the Guide for the Safety Evaluation of the Essential Oil
			9.5.2.1 Introduction
			9.5.2.2 Prioritization of Essential Oil According to Presence in Food
			9.5.2.3 Organization of Chemical Data: Congeneric Groups and Classes of Toxicity
		9.5.3 Summary
	References
Chapter 10: Metabolism of Terpenoids in Animal Models and Humans
	10.1 Introduction
	10.2 Metabolism of Monoterpenes
		10.2.1 Borneol
		10.2.2 Camphene
		10.2.3 Camphor
		10.2.4 3-Carene
		10.2.5 Carvacrol
		10.2.6 Carvone
		10.2.7 1,4-Cineole
		10.2.8 1,8-Cineole
		10.2.9 Citral
		10.2.10 Citronellal
		10.2.11 p-Cymene
		10.2.12 Fenchone
		10.2.13 Geraniol
		10.2.14 Limonene
		10.2.15 Linalool
		10.2.16 Linalyl Acetate
		10.2.17 Menthofuran
		10.2.18 Menthol
		10.2.19 Menthone
		10.2.20 Myrcene
		10.2.21 a- and ß-Pinene
		10.2.22 Pulegone
		10.2.23 a-Terpineol
		10.2.24 Terpinen-4-ol
		10.2.25 a- and ß-Thujone
		10.2.26 Thymol
	10.3 Metabolism of Sesquiterpenes
		10.3.1 Caryophyllene
		10.3.2 Farnesol
		10.3.3 Longifolene
		10.3.4 Patchoulol
	References
Chapter 11: Central Nervous System Effects of Essential Oil Compounds
	11.1 Overview
	11.2 Introduction
		11.2.1 Translatability and Reproducibility
	11.3 Review Methodology
		11.3.1 Literature Review
		11.3.2 Identification of EOs and/or their Compounds with Psychopharmacologic Action
	11.4 Compounds from EOs with Psychopharmacology Potential
		11.4.1 Alcohols
		11.4.2 Phenols and Aromatic Methyl Ethers
		11.4.3 Hydrocarbons
		11.4.4 Carbonyl Compounds
		11.4.5 Monoterpene Epoxides and Furanes
		11.4.6 Nitrogenated Compounds
	11.5 Compounds from EOs with Anxiolytic Properties
		11.5.1 Assessing Anxiolytic Properties
			11.5.1.1 Methods
			11.5.1.2 Mechanisms of Action
		11.5.2 Anxiolytic Properties of EO Compounds
	11.6 Hypnotic Properties of Compounds from EOs
		11.6.1 Assessing Hypnotic Properties
			11.6.1.1 Methods
			11.6.1.2 Mechanisms of Action
		11.6.2 Hypnotic Properties of EO Compounds
	11.7 Compounds Reported to Possess Anticonvulsant Effects
		11.7.1 Assessing Antiepileptic Properties
			11.7.1.1 Methods
			11.7.1.2 Mechanisms of Action
		11.7.2 Anticonvulsant Properties of EO Compounds
	11.8 Antidepressant Properties
		11.8.1 Assessing Antidepressant Properties
			11.8.1.1 Methods
			11.8.1.2 Mechanisms of Action
		11.8.2 Antidepressant Properties of OE Compounds
	11.9 Neuroprotector Properties of Compounds from EOs
		11.9.1 Assessing Neuroprotective Properties
			11.9.1.1 Methods
			11.9.1.2 Mechanisms of Action
		11.9.2 Neuroprotective Properties of EO Compounds
	11.10 Concluding Remarks and Perspectives
	References
Chapter 12: Effects of Essential Oils on Human Cognition
	12.1 Introduction
	12.2 Activation and Arousal: Definition and Neuroanatomical Considerations
	12.3 Influence of Essential Oils and Fragrances on Brain Potentials Indicative of Arousal
		12.3.1 Spontaneous EEG Activity
		12.3.2 Contingent Negative Variation
	12.4 Effects of Essential Oils and Fragrances on Selected Basic and Higher Cognitive Functions
		12.4.1 Alertness and Attention
		12.4.2 Learning and Memory
		12.4.3 Other Cognitive Tasks
	12.5 Conclusions
	References
Chapter 13: Aromatherapy: An Overview and Global Perspectives
	13.1 Introduction
	13.2 The Image of Aromatherapy: Treat or Treatment?
	13.3 Defining Aromatherapy: Is There Consensus?
	13.4 Aroma Therapy or Aroma Care?
	13.5 Aromatherapy: Scientific or Energetic?
	13.6 An Aromatic Evolution: Different Aromatherapy Styles
		13.6.1 Subtle Aromatherapy
		13.6.2 Self-Care Aromatherapy
		13.6.3 Holistic Aromatherapy
		13.6.4 Cosmetic Aromatherapy
		13.6.5 Clinical Aromatherapy
		13.6.6 Medical Aromatherapy
	13.7 Different Cultures, Different Aromatherapy Styles
	13.8 Evaluating Efficacy: Does it Work?
	13.9 Aromatherapy: An Evolving Therapy
		13.9.1 Personalized Aroma Inhaler Devices
	13.10 Aromatherapy: A Safe Healing Modality?
		13.10.1 Safety to the Therapist
		13.10.2 Safety to the Patient/Consumer
	13.11 Conclusion: Moving Toward Greater Integration
	References
Chapter 14: Essential Oils in Cancer Therapy
	14.1 Introduction
	14.2 Cancer Cell Lines
	14.3 Tests to Assess Cytotoxic Activity
		14.3.1 MTT Assay
		14.3.2 TUNEL Assay
		14.3.3 Flow Cytometry
	14.4 EOs against Diverse Human Cancer Cell Lines
	14.5 EOs against Breast Cancer
	14.6 EOs against Prostate Cancer
	14.7 EOs against Liver Cancer
	14.8 EOs against Lung Cancer
	14.9 EOs against Melanoma
	14.10 EOs against Colorectal Cancer
	14.11 EOs against Ehrlich Carcinoma
	14.12 EOs against Glioblastoma
	14.13 Conclusion
	References
Chapter 15: Antimicrobial Activity of Selected Essential Oils and Aroma Compounds against Airborne Microbes
	15.1 Introduction
	15.2 Methods
		15.2.1 General
		15.2.2 Studies in Small Examination Rooms
			15.2.2.1 Examined Essential Oils
			15.2.2.2 Examined Aroma Compounds
		15.2.3 Studies in Large Examination Rooms
			15.2.3.1 Examined Essential Oils
			15.2.3.2 Examined Aroma Compounds
	15.3 Results
		15.3.1 Studies in Small Examination Rooms
			15.3.1.1 Results for Essential Oils
			15.3.1.2 Results for Aroma Compounds
		15.3.2 Studies in Large Examination Rooms
			15.3.2.1 Results for Essential Oils
			15.3.2.2 Results for Aroma Compounds
		15.3.3 Identified Airborne Microbes
	15.4 Discussion
	15.5 Conclusion
	Acknowledgement and Dedication
	References
Chapter 16: Quorum Sensing and Essential Oils
	16.1 Introduction
		16.1.1 Cell-to-Cell Communication
		16.1.2 Quorum Sensing: Definition
	16.2 QS In Bacteria
		16.2.1 Gram-Negative Bacteria
			16.2.1.1 The LUXRI -System
			16.2.1.2 Vibrio harveyi
			16.2.1.3 Vibrio parahaemolyticus
			16.2.1.4 Pseudomonas aeruginosa
			16.2.1.5 Chromobacterium violaceum
		16.2.2 Gram-Positive Bacteria
			16.2.2.1 Staphylococcus aureus
	16.3 QS In Fungi
		16.3.1 EOs as Biofilm Inhibitors in C. albicans.?
	16.4 QS In Saccharomyces cerevisiae
	16.5 QS In Viruses
	16.6 QS and Biofilm Formation
	16.7 QS Inhibitors (QSIs)
		16.7.1 Practical Applicability of QS Inhibitors
	16.8 EOs as QS Inhibitors
		16.8.1 Principle of QSI Activity Testing of EOs
		16.8.2 Materials and Methods
			16.8.2.1 Sensor Strains
			16.8.2.2 QS-Inhibition Detection Assays
			16.8.2.3 Biofilm Inhibition
			16.8.2.4 Other Assays
		16.8.3 Research on EOs as QSI
			16.8.3.1 Clove, Cinnamon, Peppermint, and Lavender Oil
			16.8.3.2 Rose, Lavender, Geranium and Rosemary Oil
			16.8.3.3 Oils of Piper Species
			16.8.3.4 EOs from Columbian Plants
			16.8.3.5 Tea Tree and Rosemary Oils
			16.8.3.6 Clary Sage, Juniper, Lemon, and Marjoram Oils
			16.8.3.7 Clove, Rose, Chamomile, and Pine Turpentine Oils
			16.8.3.8 Clove Oil
			16.8.3.9 Oregano and Carvacrol
			16.8.3.10 Lemongrass and Cinnamon Oils
			16.8.3.11 EOs from South American Species
			16.8.3.12 Lavender Oil
			16.8.3.13 Lippia alba Oils
			16.8.3.14 Ferula and Dorema Oils
			16.8.3.15 Hyptis dilatata Oil
			16.8.3.16 Peppermint Oil and Menthol
			16.8.3.17 Cinnamon Oil
			16.8.3.18 Coriander and (S)-(+)-Linalool
			16.8.3.19 Cinnamon Oil
			16.8.3.20 Spice Oil Nano-Emulsions
			16.8.3.21 Eucalyptus Oils
			16.8.3.22 Mandarin Oil
			16.8.3.23 Thyme Oil, Thymol and Carvacrol
			16.8.3.24 Murraya koenigii CO2-Extract—A Preclinical Infectious Model
			16.8.3.25 Lavender, Rosemary, and Eucalyptus Oils
			16.8.3.26 Green Cardamom EO
			16.8.3.27 Corsican Mentha suaveolens ssp. insularis Oil and Others
			16.8.3.28 South African Oils Plus a Gas Chromatography-Based Metabolomics Approach
			16.8.3.29 Thymus daenensis and Satureja hortensis Oils
			16.8.3.30 Carum copticum EO
			16.8.3.31 Cinnamomum tamala oil Combined with DNase
	16.9 Overview of the Results
		16.9.1 Positively Tested Oils
			16.9.1.1 Disc Diffusion Assay
			16.9.1.2 Flask Incubation Assay
			16.9.1.3 QS Inhibiting EOs Evaluated by Other Assays
		16.9.2 Negatively Tested Oils
		16.9.3 EOs Tested on the Inhibition of QS-Related Processes
	16.10 Discussion
		16.10.1 The QS Activity of EOs Can Only Be Valued Individually for the Respective Assay
		16.10.2 An EO Being an Active Inhibitor of AHL-Based QS in One Strain is Not Necessarily Active in Another Strain Also Producing AHLs
		16.10.3 EOs Often Not Only Inhibit QS but Also Inhibit Growth
		16.10.4 Extraction Method and Collecting Site of the EOs Influences Test Results
	16.11 Conclusion
	16.12 Abbreviations
	References
Chapter 17: Functions of Essential Oils and Natural Volatiles in Plant-Insect Interactions
	17.1 Introduction
		17.1.1 Brief Historical Overview of Essential Oil (EO) Functional Ecology
		17.1.2 Challenges in Identifying EO Functional Roles and Selective Pressures
	17.2 Aromatic Medicinal Herbs with Multiple EO Functions
		17.2.1 Glandular Plants of Mediterranean Biomes
		17.2.2 Focal Studies on Thymus vulgaris EO Chemotypes in the Garrigue
			17.2.2.1 Biotic Interactions in a Geographic Mosaic
			17.2.2.2 Geographic Variation and Abiotic Stress
			17.2.2.3 Thymol in Nectar, Impacts on Bee Health
	17.3 Functional Ecological Links between EOs and Resins
		17.3.1 Oleoresin in Conifers and Multi-product TPS Enzymes
		17.3.2 EOs, Resins, and TPS Enzymes in Angiosperms
		17.3.3 Resins as Resources for Nest-Making Bees
			17.3.3.1 Resin Collection from Aromatic Tropical Trees
			17.3.3.2 Resin Collection from Dalechampia and Clusia Flowers
		17.3.4 Cistus and Lavandula: Pollinator Hubs in the Phrygana
	17.4 EO-Mediated Pollinator Specialization: Lessons from Aroids
		17.4.1 Perfume-Collecting Male Orchid Bees as a Pollination Niche
		17.4.2 Scent-Driven Pollinator Modes in the Araceae
	References
Chapter 18: Essential Oils as Lures for Invasive Ambrosia Beetles
	18.1 Introduction
	18.2 Redbay Ambrosia Beetle
		18.2.1 Background
		18.2.2 Host Attractants
		18.2.3 Field Lures
			18.2.3.1 Manuka and Phoebe Oils
			18.2.3.2 Cubeb Oil
			18.2.3.3 Copaiba Oil and Enriched a-Copaene Oil
	18.3 Chemical Analysis of the a-Copaene Lure
		18.3.1 Method
		18.3.2 Results
	18.4 Euwallacea Shot-Hole Borers
		18.4.1 Background
		18.4.2 Host Attractants
		18.4.3 Field Lures
			18.4.3.1 Quercivorol
			18.4.3.2 Enriched a-Copaene Lure
	18.5 Other Applications
	References
Chapter 19: Adverse Effects and Intoxication with Essential Oils
	19.1 Introduction
		19.1.1 General Side Effects
	19.2 Camphor and Camphor-Containing Essential Oils
		19.2.1 Case Reports
			19.2.1.1 Dose Range for Oral Intoxication
			19.2.1.2 Neurotoxic Effects
			19.2.1.3 Effects Following Inhalative Application
	19.3 Eucalyptus Oil
		19.3.1 Case Reports
			19.3.1.1 Dose Range for Oral Intoxication
			19.3.1.2 Intoxication after Ingestion
			19.3.1.3 Intoxication after Topical Application and Inhalation
		19.3.2 Eucalyptol (1,8-Cineole)
	19.4 Thujone-Containing Essential Oils
		19.4.1 Case Reports
	19.5 Peppermint Oil
		19.5.1 Adulterations
		19.5.2 Case Reports
		19.5.3 Menthol
			19.5.3.1 Cooling vs. Irritating Effect
			19.5.3.2 Menthol-Induced Analgesia
			19.5.3.3 Menthol and Tobacco-Related Chemicals
			19.5.3.4 Menthol and Dermal Penetration
	19.6 Pennyroyal Oil
		19.6.1 Case Reports
		19.6.2 Pulegone and Menthofuran
		19.6.3 Precautions
	19.7 Wintergreen Oil
		19.7.1 Methyl Salicylate
	19.8 Tea Tree Oil (Melaleuca Oil)
		19.8.1 Toxicity Following Oral Exposure
		19.8.2 Toxicity Following Dermal Exposure
		19.8.3 Systemic Reactions
		19.8.4 Ototoxicity
		19.8.5 Developmental Toxicity
		19.8.6 In Vitro. Toxicity
	19.9 Sassafras Oil
		19.9.1 Safrole
	19.10 Clove Oil (Oleum Caryophylli., Caryophylli floris aetheroleum)
		19.10.1 Case Reports
		19.10.2 Eugenol, Isoeugenol
			19.10.2.1 Repeated Dose Toxicity
			19.10.2.2 Developmental and Reproductive Toxicity
			19.10.2.3 Skin Sensitization
		19.10.3 Methyleugenol
	19.11 Bergamot Oil
	19.12 Essential Oils of Nutmeg and Other Spices
	19.13 Conclusion
	References
Chapter 20: Adulteration of Essential Oils
	20.1 Introduction
		20.1.1 General Remarks
	20.2 Definition and History
	20.3 Adulteration
		20.3.1 Unintended Adulteration
		20.3.2 Intentional Adulteration
		20.3.3 Prices
		20.3.4 Availability
		20.3.5 Demand of Clients
		20.3.6 Regulations
		20.3.7 Aging
		20.3.8 Cupidity
		20.3.9 Simple Sports?
	20.4 Possible Adulterations for Essential Oils
		20.4.1 Water
		20.4.2 Ethanol
		20.4.3 Fatty Oils or Mineral Oils
		20.4.4 High Boiling Glycols
		20.4.5 Oils from Other Parts of the Same Species or Other Species with Similar Essential Oil Composition
		20.4.6 Related Botanical Species
		20.4.7 Fractions of Essential Oils
		20.4.8 Natural Isolates
		20.4.9 Chemically Derived Synthetic Compounds, Which Are Proved to Appear in Nature
		20.4.10 Steam Distilled Residues from Expression
		20.4.11 Enzymatically Produced Chemicals (Natural by Law)
	20.5 Methods to Detect Adulterations
		20.5.1 Organoleptic Methods
			20.5.1.1 Appearance and Color
			20.5.1.2 Odor
			20.5.1.3 Physical–Chemical Methods
			20.5.1.4 Calculation of Relationship Coefficient
		20.5.2 Analytical Methods
			20.5.2.1 General Tests
			20.5.2.2 Thin-Layer Chromatography
			20.5.2.3 Gas Chromatography (GC, GLC, HRGC, GC-FID, GC-MS)
			20.5.2.4 Chiral Analysis
			20.5.2.5 GC-GC and GC.×.GC (Two-Dimensional Gas Chromatography, 2D GC)
			20.5.2.6 13C NMR (Nuclear Magnetic Resonance)
	20.6 Important Essential Oils and Their Possible Adulteration
		20.6.1 Ambrette Seed Oil
		20.6.2 Amyris Oil
		20.6.3 Angelica Oils
		20.6.4 Anise Fruit Oil
		20.6.5 Armoise Oil
		20.6.6 Basil Oils
		20.6.7 Bergamot Oil
		20.6.8 Bitter Orange Oil
		20.6.9 Bitter Orange Petitgrain Oil
		20.6.10 Cajeput Oil
		20.6.11 Camphor Oil
		20.6.12 Cananga Oil
		20.6.13 Caraway Oil
		20.6.14 Cardamom Oil
		20.6.15 Cassia Oil
		20.6.16 Cedar Leaf Oil
		20.6.17 Cedarwood Oils
		20.6.18 Celery Seed Oil
		20.6.19 Chamomile Oil Blue
		20.6.20 Chamomile Oil Roman
		20.6.21 Cinnamon Bark Oil
		20.6.22 Cinnamon Leaf Oil
		20.6.23 Citronella Oil
		20.6.24 Clary Sage Oil
		20.6.25 Clove Oils
		20.6.26 Coriander Fruit Oil
		20.6.27 Corymbia Citriodora Oil
		20.6.28 Corn Mint Oil
		20.6.29 Cumin Fruit Oil
		20.6.30 Cypress Oil
		20.6.31 Dill Oils
		20.6.32 Dwarf Pine Oil
		20.6.33 Elemi Oil
		20.6.34 Eucalyptus Oil
		20.6.35 Fennel Oil Sweet
		20.6.36 Fennel Oil Bitter
		20.6.37 Geranium Oils
		20.6.38 Grapefruit Oil
		20.6.39 Juniper Berry Oil
		20.6.40 Lavandin Oils
		20.6.41 Lavender Oil
		20.6.42 Lemon Oil
		20.6.43 Lemongrass Oil
		20.6.44 Lime Oil Distilled
		20.6.45 Lime Oil Expressed
		20.6.46 Litsea cubeba Oil
		20.6.47 Mandarin Oil
		20.6.48 Melissa Oil (Lemon Balm)
		20.6.49 Mentha citrata Oil
		20.6.50 Mountain Pine Oil
		20.6.51 Neroli Oil
		20.6.52 Nutmeg Oil
		20.6.53 Orange Oil Sweet
		20.6.54 Origanum Oil
		20.6.55 Palmarosa Oil
		20.6.56 Parsley Oil
		20.6.57 Pine Oil Siberian
		20.6.58 Patchouli Oil
		20.6.59 Pepper Oil
		20.6.60 Peppermint Oil
		20.6.61 Petitgrain Oil Paraguay Type
		20.6.62 Pimento Oils
		20.6.63 Rose Oil
		20.6.64 Rosemary Oil
		20.6.65 Rosewood Oil
		20.6.66 Sage Oil (Salvia officinalis)
		20.6.67 Sage Oil Spanish Type
		20.6.68 Sandalwood Oil
		20.6.69 Spearmint Oils
		20.6.70 Spike Lavender Oil
		20.6.71 Star Anise Oil
		20.6.72 Tarragon Oil
		20.6.73 Tea Tree Oil
		20.6.74 Thyme Oil
		20.6.75 Turpentine Oil
		20.6.76 Vetiver Oil
		20.6.77 Ylang-Ylang Oils
	References
Chapter 21: Essential Oils and Volatiles in Bryophytes
	21.1 Introduction
	21.2 Terpenoids and Other Volatiles from Bryophytes
		21.2.1 Chemical Diversity of Natural Volatiles in Bryophytes
			21.2.1.1 Liverwort Components
			21.2.1.2 Volatile Components in Mosses and Hornworts
		21.2.2 Microbial Terpene Synthase-Like Genes in Bryophytes
	21.3 Significance for Chemotaxonomic Studies
		21.3.1 Chemotaxonomic Value of Essential Oils
		21.3.2 Chemotaxonomic Value of Volatile Extracts
	21.4 Biological Functions
		21.4.1 Chemical Defense
		21.4.2 Allelopathic Activity
		21.4.3 Medical Uses
	21.5 Conclusions
	References
Chapter 22: Biotransformation of Monoterpenoids by Microorganisms, Insects, and Mammals
	22.1 Introduction
	22.2 Metabolic Pathways of Acyclic Monoterpenoids
		22.2.1 Acyclic Monoterpene Hydrocarbons
			22.2.1.1 Myrcene
			22.2.1.2 Citronellene
		22.2.2 Acyclic Monoterpene Alcohols and Aldehydes
			22.2.2.1 Geraniol, Nerol, (+)- and (-)-Citronellol, Citral, and (+)- and (-)-Citronellal
			22.2.2.2 Linalool and Linalyl Acetate
			22.2.2.3 Dihydromyrcenol
	22.3 Metabolic Pathways of Cyclic Monoterpenoids
		22.3.1 Monocyclic Monoterpene Hydrocarbon
			22.3.1.1 Limonene
			22.3.1.2 Isolimonene
			22.3.1.3 p-Menthane
			22.3.1.4 1-p-Menthene
			22.3.1.5 3-p-Menthene
			22.3.1.6 a-Terpinene
			22.3.1.7 -Terpinene
			22.3.1.8 Terpinolene
			22.3.1.9 a-Phellandrene
			22.3.1.10 p-Cymene
		22.3.2 Monocyclic Monoterpene Aldehyde
			22.3.2.1 Perillaldehyde
			22.3.2.2 Phellandral and 1,2-Dihydrophellandral
			22.3.2.3 Cuminaldehyde
		22.3.3 Monocyclic Monoterpene Alcohol
			22.3.3.1 Menthol
			22.3.3.2 Neomenthol
			22.3.3.3 (+)-Isomenthol
			22.3.3.4 Isopulegol
			22.3.3.5 a-Terpineol
			22.3.3.6 (-)-Terpinen-4-ol
			22.3.3.7 Thymol and Thymol Methyl Ether
			22.3.3.8 Carvacrol and Carvacrol Methyl Ether
			22.3.3.9 Carveol
			22.3.3.10 Dihydrocarveol
			22.3.3.11 Piperitenol
			22.3.3.12 Isopiperitenol
			22.3.3.13 Perillyl Alcohol
			22.3.3.14 Carvomenthol
		22.3.4 Monocyclic Monoterpene Ketone
			22.3.4.1 a, ß-Unsaturated Ketone
			22.3.4.2 Saturated Ketone
			22.3.4.3 Cyclic Monoterpene Epoxide
	22.4 Metabolic Pathways of Bicyclic Monoterpenoids
		22.4.1 Bicyclic Monoterpene
			22.4.1.1 a-Pinene
			22.4.1.2 ß-Pinene
			22.4.1.3 (±)-Camphene
			22.4.1.4 3-Carene and Carane
		22.4.2 Bicyclic Monoterpene Aldehyde
			22.4.2.1 Myrtenal and Myrtanal
		22.4.3 Bicyclic Monoterpene Alcohol
			22.4.3.1 Myrtenol
			22.4.3.2 Myrtanol
			22.4.3.3 Pinocarveol
			22.4.3.4 Pinane-2,3-Diol
			22.4.3.5 Isopinocampheol (3-Pinanol)
			22.4.3.6 Borneol and Isoborneol
			22.4.3.7 Fenchol and Fenchyl Acetate
			22.4.3.8 Verbenol
			22.4.3.9 Nopol and Nopol Benzyl Ether
		22.4.4 Bicyclic Monoterpene Ketones
			22.4.4.1 a-, ß-Unsaturated Ketone
			22.4.4.2 Saturated Ketone
	22.5 Summary
		22.5.1 Metabolic Pathways of Monoterpenoids by Microorganisms
		22.5.2 Microbial Transformation of Terpenoids as Unit Reaction
	References
Chapter 23: Biotransformation of Sesquiterpenoids, Ionones, Damascones, Adamantanes, and Aromatic Compounds by Green Algae, Fungi, and Mammals
	23.1 Introduction
	23.2 Biotransformation of Sesquiterpenoids by Microorganisms
		23.2.1 Highly Efficient Production of Nootkatone (2) from Valencene (1)
		23.2.2  Biotransformation of Valencene (1) by .Aspergillus niger and Aspergillus wentii
		23.2.3 Biotransformation of Nootkatone (2) by .Aspergillus niger
		23.2.4 Biotransformation of Nootkatone (2) by Fusarium culmorum and Botryosphaeria dothidea
		23.2.5 Biotransformation of (+)-1(10)-Aristolene (36) from the Crude Drug Nardostachys chinensis by Chlorella fusca., Mucor species, and .Aspergillus niger
		23.2.6 Biotransformation of Various Sesquiterpenoids by Microorganisms
	23.3 Biotransformation of Sesquiterpenoids by Mammals, Insects, and Cytochrome P-450
		23.3.1 Animals (Rabbits) and Dosing
		23.3.2 Sesquiterpenoids
	23.4 Biotransformation of Ionones, Damascones, and Adamantanes
	23.5 Biotransformation of Aromatic Compounds
	References
Chapter 24: Use of Essential Oils in Agriculture
	24.1 Introduction
		24.1.1 Essential Oils: Very Complex Natural Mixes
	24.2 Essential Oils as Antipests
		24.2.1 Health and Environmental Impact of Botanical Antipests
		24.2.2 Pesticidal and Repellent Action of Essential Oils
			24.2.2.1 Insecticidal Activities of Essential Oils
		24.2.3 Development and Commercialization of Botanical
			24.2.3.1 Examples of Essential Oils Used as Antipests
	24.3 Essential Oils as Herbicides
		24.3.1 Phytotoxicity
		24.3.2 Prospects of Organic Weed Control
		24.3.3 Examples of Essential Oils in Weed Control
			24.3.3.1 Thymus vulgaris
			24.3.3.2 Mentha sp.
			24.3.3.3 Cymbopogon sp.
			24.3.3.4 Eucalyptus sp.
			24.3.3.5 Lavandula sp.
			24.3.3.6 Origanum sp.
			24.3.3.7 Artemisia scoparia
			24.3.3.8 Zataria multiflora
			24.3.3.9 Tanacetum sp.
	24.4 Essential Oils as Inhibitors of Various Pests
		24.4.1 Effect on Bacteria
		24.4.2 Effect on Fungi
		24.4.3 Effect on Viruses
		24.4.4 Effect on Nematodes
	24.5 Effect of Essential Oils on the Condition of the Soil
		24.5.1 Effects of Essential Oils on Microorganisms and Soil
		24.5.2 Examples of Essential Oils with an Effect on Soil Conditions
			24.5.2.1 Mentha spicata
			24.5.2.2 Lavandula sp.
			24.5.2.3 Salvia sp.
			24.5.2.4 Myrtus communis
			24.5.2.5 Laurus nobilis
			24.5.2.6 Cymbopogon sp.
	24.6 EOs Used in Post-Harvest Disease Control
		24.6.1 Effects of Essential Oils on Stored-Product Pests
		24.6.2 Examples of Essential Oils Used on Stored Products
			24.6.2.1 Thymus zygis
			24.6.2.2 Cinnamomum. sp
			24.6.2.3 Cymbopogon citratus
			24.6.2.4 Laurus nobilis
	24.7 Conclusion
	References
Chapter 25: Essential Oils Used in Veterinary Medicine
	25.1 Introduction
	25.2 Oils Attracting Animals
	25.3 Oils Repelling Animals
	25.4 Oils against Pests
		25.4.1 Insecticidal, Pest Repellent, and Antiparasitic Oils
		25.4.2 Fleas and Ticks
		25.4.3 Mosquitoes
		25.4.4 Moths
		25.4.5 Aphids, Caterpillars, and Whiteflies
			25.4.5.1 Garlic Oil
		25.4.6 Ear Mites
		25.4.7 Antiparasitic
	25.5 Essential Oils Used in Animal Feed
		25.5.1 Ruminants
		25.5.2 Poultry
			25.5.2.1 Studies with CRINA® Poultry
			25.5.2.2 Studies with Herbromix®
		25.5.3 Pigs
	25.6 Essential Oils Used in Treating Diseases in Animals
	References
Chapter 26: Encapsulation and Other Programmed/Sustained-Release Techniques for Essential Oils and Volatile Terpenes
	26.1 Introduction
	26.2 Controlled Release of Volatiles
	26.3 Use of Hydrophilic Polymers
	26.4 Alginate
	26.5 Stabilization of Essential Oil Constituents
	26.6 Controlled Release of Volatiles from Nonvolatile Precursors
	26.7 Cyclodextrin Complexation of Volatiles
	26.8 Enhanced Biological Effect by Prolonged Delivery of Volatiles and Essential Oils
	26.9 Methods for Producing Prolonged Delivery Units of Volatiles
	26.10 Presenting Volatiles in Nano-Emulsions
	26.11 Concluding Remarks
	References
Chapter 27: Essential Oils as Carrier Oils
	27.1 Introduction
	27.2 Essential Oils in General
	27.3 Essential Oils as Penetration Enhancers
	27.4 Terpenes
		27.4.1 Classes and Complexes
		27.4.2 Hydrophilic, Lipophilic, Amphiphilic Terpenes
		27.4.3 Structure of Terpenes
		27.4.4 Boiling Point of Terpenes
		27.4.5 Concentration of Terpenes
		27.4.6 Increase of Terpenes
		27.4.7 Vehicles of Terpenes
	27.5 Skin
		27.5.1 Layers
		27.5.2 Stratum Corneum (SC)
		27.5.3 Skin Models
		27.5.4 Franz Cell
	27.6 Advantages
		27.6.1 Advantages of Natural Penetration Enhancers
		27.6.2 Advantages of Transdermal Drug Delivery
	27.7 Side Effects of Natural Penetration Enhancers
		27.7.1 Skin Irritancy and Toxicity
		27.7.2 Transepidermal Water Loss (TEWL)
	27.8 Mechanism of Action
		27.8.1 Effect on Stratum Corneum Lipids
		27.8.2 Effect on Hydrogen Bond Networks
		27.8.3 Effect on SC Partition of Drugs
		27.8.4 Affecting Factors
		27.8.5 Screening-Techniques
	27.9 Combination of Penetration Enhancers and Drugs
		27.9.1 Essential Oils and Anti-Inflammatory Drugs
			27.9.1.1 Chuanxiong Oil and Ibuprofen
			27.9.1.2 Rosemary Essential Oil and Na-Diclofenac
			27.9.1.3 Alpinia oxyphylla Essential Oil and Indomethacin
			27.9.1.4 Lippia sidoides Essential Oil and Salicylic Acid
			27.9.1.5 Sweet Basil Oil and Indomethacin
			27.9.1.6 Zanthoxylum bungeanum Essential Oil and Indomethacin/5-Fluorouracil
		27.9.2 Essential Oils and Antiseptic Drugs
			27.9.2.1 1,8-Cineole and Chlorhexidine
		27.9.3 Essential Oils and Vesicular Carriers
			27.9.3.1 Terpenes and Ultra-Deformable Liposomes of Sodium Fluorescein
			27.9.3.2 Terpenes and Liposomes of Antisense Oligonucleotide
			27.9.3.3 Eucalyptus Oil and Transferosomes of Ketoconazole
			27.9.3.4 Speranskia tuberculata Essential Oil and Glycerosomes of Paeoniflorin
		27.9.4 Essential Oils and Cytostatic Drugs
			27.9.4.1 Myrica rubra Essential Oil and Doxorubicin
			27.9.4.2 Mentha x villosa Essential Oil and 5-Fluorouracil
			27.9.4.3 Zanthoxylum bungeanum Essential Oil and 5-Fluorouracil (5-FU)/Indomethacin
		27.9.5 Essential Oils and Cardiovascular Drugs
			27.9.5.1 Zanthoxylum bungeanum Essential Oil and Osthole/Tetramethylpyrazine/Ferulic Acid/Puerarin/Geniposide
			27.9.5.2 Eucalyptus Oil and Tetramethylpyrazine
			27.9.5.3 Basil Oil and Labetolol Hydrochloride
			27.9.5.4 Anethol, Menthone, Eugenol, and Valsartan
			27.9.5.5 Basil Oil, Petit Grain Oil, Thyme Oil, and Nitrendipine
	27.10 Essential Oils and the Influence of Temperature
		27.10.1 Borneol, Osthole, and Increasing Temperature
	27.11 Essential Oils and the Effect on Cytochrome P450
		27.11.1 Zataria multiflora. Essential Oils with Cancer Chemopreventive Effect
	27.12 Essential Oils and their Synergistic Effects
		27.12.1 1,8-Cineole and Camphor
	27.13 Conclusion
	References
Chapter 28: Influence of Light on Essential Oil Constituents
	28.1 Introduction
	28.2 Mechanisms of Photodegradation
		28.2.1 Double-Bond Isomerization
		28.2.2 Photooxidation and Epoxidation Reactions
		28.2.3 Polymerization Reactions
		28.2.4 Other Reaction Mechanisms
		28.2.5 Influence of Reaction Conditions
			28.2.5.1 Effect of Solvent
			28.2.5.2 Effect of Duration and Intensity
	28.3 Phototoxicity
		28.3.1 Methods for the in vitro Assessment of Phototoxicity
			28.3.1.1 3T3 NRU Assay
			28.3.1.2 Photohemolysis Test and RBC PT
			28.3.1.3 Reconstituted 3D Human Skin Models
			28.3.1.4 Photoirritation Factor (PIF) and Mean Photo Effect (MPE)
		28.3.2 Phototoxic Essential Oils and Essential Oil Constituents
	28.4 Conclusion
	References
Chapter 29: Influence of Air on Essential Oil Constituents
	29.1 Introduction
	29.2 Essential Oils and Terpenoids
	29.3 Reaction Mechanisms of Terpenoid Oxidation Patterns
		29.3.1 Linalool
			29.3.1.1 The Ene-Type Mechanism
			29.3.1.2 The Free-Radical Chain Reaction
			29.3.1.3 The Direct Reaction Pathway
		29.3.2 Geraniol
			29.3.2.1 Initiation Phase
			29.3.2.2 Propagation Step 1
			29.3.2.3 Propagation Step 2
	29.4 Chemistry of Fragrance Terpenoid Autoxidation
		29.4.1 Linalool
		29.4.2 Linalyl Acetate
		29.4.3 ß-Caryophyllene
		29.4.4 Lavender Oil
		29.4.5 Limonene
		29.4.6 Geraniol
		29.4.7 Geranial
		29.4.8 Tea Tree Oil and a-Terpinene
	29.5 Conclusion
	References
Chapter 30: The Essential Oil Trade
Chapter 31: Industrial Uses of Essential Oils
	Acknowledgments
	References
	Further Reading
	Web Sites
Chapter 32: Storage, Labeling, and Transport of Essential Oils
	32.1 Marketing of Essential Oils: The Fragrant Gold of Nature Postulates Passion, Experience, and Knowledge
	32.2 Impact and Consequences on the Classification of Essential Oils as Natural but Chemical Substances IN REACH
	32.3 Dangerous Substances and Dangerous Goods
		32.3.1 Material Safety Data Sheet
	32.4 Packaging of Dangerous Goods
	32.5 Labeling
	32.6 List of Regulations for the Consideration of Doing Business in the EU
	Acronyms
	References
Chapter 33: Recent EU Legislation on Flavours and Fragrances and Its Impact on Essential Oils
	33.1 Introduction
	33.2 Former Flavouring Directive and Current Flavouring Regulation: Impact on Essential Oils
		33.2.1 Maximum Levels of “Restricted Substances”
			33.2.1.1 (Restricted Substances under Former) Flavouring Directive 88/388/EC
			33.2.1.2 (Restricted Substances under) Current Flavouring Regulation 1334/2008/EC
		33.2.2 Definition of “Natural”
			33.2.2.1 (Definition of “Natural” under) Former Flavouring Directive 88/388/EC
			33.2.2.2 (Definition of “Natural” under) Current Flavouring Regulation 1334/2008/EC
	33.3 Conclusion
	33.A Appendix
	References
Index