The chemistry and biology of volatiles
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020 | |a 9780470777787 |9 978-0-470-77778-7 | ||
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245 | 1 | 0 | |a The chemistry and biology of volatiles |c ed. by Andreas Herrmann |
250 | |a 1. publ. | ||
264 | 1 | |a Hoboken, N.J. |b Wiley |c 2010 | |
300 | |a XXV, 402 S. |b Ill., graph. Darst. | ||
336 | |b txt |2 rdacontent | ||
337 | |b n |2 rdamedia | ||
338 | |b nc |2 rdacarrier | ||
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650 | 0 | 7 | |a Organische Verbindungen |0 (DE-588)4043816-8 |2 gnd |9 rswk-swf |
653 | |a Volatile organic compounds | ||
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700 | 1 | |a Herrmann, Andreas |d 1970- |0 (DE-588)129532533 |4 edt | |
856 | 4 | 2 | |m Digitalisierung UB Regensburg |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=020662036&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
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DE-BY-TUM_call_number | 1302 CHE 815f 2010 A 10091 |
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DE-BY-TUM_katkey | 1749221 |
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DE-BY-TUM_media_number | 040007267832 |
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DE-BY-UBR_media_number | 069038840197 |
_version_ | 1822756721211211776 |
adam_text | Contents
Foreword
xiii
List of Contributors
xv
Acknowledgements
xvii
Abbreviations
xix
1
Volatiles
-
An Interdisciplinary Approach
1
Andreas Herrmann
1.1
Introduction
1
1.2
Geraniol
-
A Typical Example
2
1.3
Conclusion
8
References
8
2
Biosynthesis and Emission of
Isoprene, Methylbutanol
and Other
Volatile Plant Isoprenoids
11
Hartmut
К.
Lichtenthaler
2.1
Introduction
11
2.2
Plant Isoprenoids
12
2.3
Two IPP-Yielding Pathways in Plants
15
2.4
Prenyl Chain Formation and Elongation
16
2.5
Compartmentation of Plant Isoprenoid Biosynthesis
16
2.6
The Enzyme Steps of the Plastidic DOXP/MEP Pathway
of IPP Formation
17
2.7
Cross-Talk Between the Two IPP Biosynthesis Pathways
19
2.8
Biosynthesis and Emission of Volatile
Isoprene
at High Irradiance
22
2.8.1
Regulation of
Isoprene
Emission
25
2.9
Inhibition of
Isoprene
Biosynthesis
26
2.9.1
Fosmidomycin and
5-Ketoclomazone
26
2.9.2
Diuron
27
2.10
Inhibition of Carotenoid and Chlorophyll Biosynthesis
by Fosmidomycin and S-Ketoclomazone
27
2.11
Biosynthesis and Emission of Methylbutenol at High Irradiance
28
2.12
Source of Pyruvate for
Isoprene
and Methylbutenol Biosynthesis
29
2.13
Branching Point of DOXP/MEP Pathway with Other
Metabolic
Chloroplast
Pathways
30
2.14
Is There a Physiological Function of
Isoprene
and
MBO
Emission?
31
2.15
Biosynthesis and Emission of Monoterpenes, Sesquiterpenes
and Diterpenes
33
vi
Contents
2.15.1
Monoterpenes
35
2.15.2
Diterpenes
36
2.15.3
Sesquiterpenes
36
2.16
Some General
Remarks on the Regulation of
Terpene
Biosynthesis in Plants
36
2.17
Volatile Terpenoids as Aroma Compounds of Wine
37
2.18
Function of
Terpenes
in Plant Defence
38
2.19
Conclusion
38
Acknowledgements
39
References
40
3
Analysis of the Plant Volatile Fraction
49
Patrizia
Rubiolo, Barbara
Sgorbiili,
Erica
Liberto, Chiara
Cordero
and Carlo
Biechi
49
50
51
51
52
54
55
56
56
56
59
59
61
65
66
70
75
3.4
Further Developments
76
3.5
Conclusion
85
Acknowledgements
87
References
87
4
Plant Volatile Signalling: Multitrophic Interactions in the Headspace
95
André
Kessler
and
Kimbe
rly Morrell
4.1
Introduction
95
4.2
The Specificity and Complexity of Herbivore-Induced VOC Production
97
4.2.1
Plant Endogenous Wound Signalling
99
4.2.2
Herbivore-Derived EHcitors of VOC Emission
102
4.3
Ecological Consequences of VOC Emission
104
4.3.1
Within-Plant Defence Signalling
104
3.1
Introduction
3.2
Sample Preparation
3.2.1
Liquid Phase Sampling
3.2.2
Headspace Sampling
3.2.3
Headspace-Solid Phase
Microextraction
3.2.4
In-Tube Sorptive
Extraction
3.2.5
Headspace Sorptive Extraction
3.2.6
Static and Trapped Headspace
3.2.7
Solid-Phase Aroma Concentrate Extraction
3.2.8
Headspace Liquid-Phase
Microextraction
3.2.9
Large Surface Area High Concentration Capacity
Headspace Sampling
3.3
Analysis
3.3.1
Fast-GC and Fast-GC-qMS EO Analysis
3.3.2
Qualitative Analysis
3.3.3
Quantitative Analysis
3.3.4
Enantioselective GC
3.3.5
Multidimensional GC Techniques
Contents
vii
4.3.2
Herbivore-Induced VOC Emission as Part of a Metabolic
Reconfiguration of the Plant
105
4.3.3
Herbivores Use VOCs to Select Host Plants
107
4.3.4
VOCs as Indirect Defences Against Herbivores
108
4.3.5
VOCs in Plant-Plant Interactions
111
4.4
Conclusion
112
Acknowledgements
114
References
114
5
Pheromones in Chemical Communication
123
Kenji Mori
5.1
Introduction
123
5.1.1
Definition of Pheromones
123
5.1.2
Classification of Pheromones
123
5.2
History of Pheromone Research
125
5.3
Research Techniques in Pheromone Science
127
5.3.1
The Collecting of Pheromones
127
5.3.2
Bioassay-Guided Purification
128
5.3.3
Structure Determination and Synthesis
128
5.3.4
Field Bioassay
129
5.3.5
Structure Elucidation of the Male-Produced Aggregation
Pheromone of the Stink Bug Eysarcoris
lewisi
-
A Case Study
129
5.4
Structural Diversity Among Pheromones
132
5.5
Complexity of Multicomponent Pheromones
137
5.6
Stereochemistry and Pheromone Activity
139
5.6.1
Only a Single Enantiomer is Bioactive and its Opposite
Enantiomer Does Not Inhibit the Response to
the Active
Isomer 139
5.6.2
Only One Enantiomer is Bioactive, and its Opposite
Enantiomer Inhibits the Response to the Pheromone
139
5.6.3
Only One Enantiomer is Bioactive, and its
Diastereomer Inhibits the Response to the Pheromone
139
5.6.4
The Natural Pheromone is a Single Enantiomer, and
its Opposite Enantiomer or Diastereomer is Also Active
140
5.6.5
The Natural Pheromone is a Mixture of Enantiomers or
Diastereomers, and Both of the Enantiomers, or All of
the Diastereomers are Separately Active
141
5.6.6
Different Enantiomers or Diastereomers are Employed
by Different Species
141
5.6.7
Both Enantiomers are Necessary for Bioactivity
141
5.6.8
One Enantiomer is More Active Than the Other,
but an Enantiomeric or Diastereomeric Mixture is More
Active Than the Enantiomer Alone
141
viii Contents
5.6.9
One Enantiomer is Active on Males, While the Other is
Active on Females
142
5.6.10
Only the meso-lsomer is Active
142
5.7
Pheromones With
Kairomonal
Activities
142
5.8
Mammalian Pheromones
143
5.9
Invention of Pheromone Mimics
145
5.10
Conclusion
147
Acknowledgements
147
References
147
6
Use of
Volatiles
in Pest Control
151
J. Richard M. Thacker and Margaret R. Train
6.1
Introduction
151
6.2
Repellents (DEET,
Neem,
Essential Oils)
151
6.3
Volatile Synthetic Chemicals and Fumigants
154
6.4
Pheromones
158
6.5
Volatile Allelochemicals
165
6.6
Plant
Volatiles
and Behavioural Modification of Beneficial Insects
166
6.7
Concluding Comments
167
References
168
7
Challenges in the Synthesis of Natural and Non-Natural
Volatiles
173
Anthony A. Birkbeck
7.1
Introduction
-
The Art of Organic Synthesis
173
7.2
Overcoming Challenges in the Small-Scale Synthesis of Natural
Volatile Compounds
174
7.2.1
D^-Caryophyllene
(1964) 174
7.2.2
/3-Vetivone(1973)
175
7.3
Overcoming Challenges in the Large-Scale Synthesis of Nature
Identical and Non-Natural Molecules
176
7.3.1
(Z)-3-Hexenol
176
7.3.2
Citral
177
7.3.3
H-Menthol
179
7.3.4
Habanolide
180
7.4
Remaining Challenges in the Large-Scale Synthesis of Natural
and Non-Natural
Volatiles
180
7.5
Design and Synthesis of Novel
Odorants
and Potential Industrial
Routes to a Natural Product
182
7.5.1
Cassis (Blackcurrant)
182
7.5.2
Patchouli
184
7.5.3
Musk
187
7.5.4 Sandalwood 189
7.6
Other Challenges
193
7.7
Conclusion
193
Acknowledgements
194
Contents ix
Dedication
195
References
195
The Biosynthesis of Volatile Sulfur Flavour Compounds
203
Meriel G. Jones
8.1
Introduction: Flavours as Secondary Metabolites
203
8.2
Sulfur in Plant Biology
204
8.3
Sulfur Compounds as Flavour
Volatiles
205
8.4
The Alk(en)yl
Cysteine Sulfoxide
Flavour Precursors
206
8.5
Biosynthesis of the Flavour Precursors of Allium
207
8.5.1
The Biosynthesis of Allium Flavour Precursors via
γ
-Glutamyl
Peptides
208
8.5.2
The Biosynthesis
oí
Allium Flavour Precursors via
Cysteine Synthases
209
8.6
Formation of
Volatiles
from CSOs
210
8.6.1
S-Methyl-L-cysteine sulfoxide
210
8.6.2
Release of the Allium CSOs
211
8.7
The Allium Flavour
Volatiles
212
8.8
The Enzyme Alliinase
213
8.9
The Enzyme Lachrymatory Factor Synthase
214
8.10
The Biological Roles of the Flavour Precursors
215
8.11
The Glucosinolate Flavour Precursors
216
8.12
GS and Their Biosynthetic Pathways
216
8.13
Release of Volatile GS Hydrolysis Products
218
8.14
The Biological Role of Glucosinolates
220
8.15
Application of Transgenic Technology to Applied Aspects of
GS Biosynthesis
222
8.16
Volatile Sulfur Compounds from Other Plants
222
8.16.1
Complex Organic Sulfur
Volatiles
222
8.16.2
Simple Sulfur
Volatiles
223
8.16.3
Hydrogen
Sulfide
223
8.16.4
Methanethiol
224
8.17
Conclusion
224
References
224
Thermal Generation of Aroma-Active
Volatiles
in Food
231
Christoph
Сету
9.1
Introduction
231
9.2
The
Maillard
Reaction
233
9.2.1
The Amadori Rearrangement
234
9.2.2
Deoxyosones
235
9.2.3
Retro-Aldolization
235
9.3
Formation of Aroma Compounds in the Later Stages of the
Maillard
Reaction
237
9.3.1
2-Furfurylthiol
237
χ
Contents
9.3.2
4-Hydroxy-2,5-dimethyl-3(2tf)-furanone
239
9.3.3
Alkyl
and Alkenylpyrazines
239
9.3.4
2-Acetyl-l-pyrroline
241
9.4
The
Strecker
Degradation
241
9.5
Caramelization
244
9.6
Thiamin Degradation
246
9.7
Feralic Acid Degradation
246
9.8
Fat Oxidation
247
9.9
Conclusion
250
References
250
10
Human Olfactory Perception
253
Alan Gelperin
10.1
Introduction
253
10.2
Historical Perspective on Olfactory Perception
254
10.3
Human Olfactory Pathway
255
10.4
Functional Studies in Human Subjects
256
10.5
Functional Studies in Brain-Damaged Subjects
259
10.6
Single
Odorants,
Binary Mixtures and Complex Odour Objects
259
10.7
Olfactory Versus Trigeminal
Odorant
Identification
262
10.8
Orthonasal
Versus Retronasal Odour Perception
263
10.9
Specific Anosmias
264
10.10
MHC-Correlated Odour Preferences in Human Subjects
265
10.11
Odour Deprivation and Odour Perception
266
10.12
Age-Related Decline in Olfactory Perception
267
10.13
New Neurons in Adult Brains
268
10.14
Epidemiological Studies of Human
Olfaction
268
10.15
Active Sampling and Olfactory Perception
269
10.16
Human Olfactory Imagery
270
10.17
Top-Down Influences on Olfactory Perception
271
10.18
Reproductive State and Olfactory Sensitivity
272
10.19
Olfaction,
Hunger and Satiety
273
10.20
Odour Perception Bias by Odour Names
274
10.21
Olfaction
and Disease States
275
10.22
Prenatal and Postnatal Influences on Infant Odour/Flavour
Preferences
276
10.23
Future Directions
277
Acknowledgements
277
References
278
11
Perfumery
-
The Wizardry of Volatile Molecules
291
Christophe
Laudamiel
11.1
The Big Picture
291
11.2
Wizardry No.
1:
Full Holograms Create Real Emotions
292
11.3
Volatiles
Need a Language Wizard
296
Contents xi
11.4
Wizardry No.
2:
The Perfumer in the Jungle of
Volatiles
to
Create Emotions
298
11.5
Wizardry No.
3:
End Results Are Music to the Nose
303
References
304
12
Microencapsulation Techniques for Food Flavour
307
Youngjae Byun, Young
Teek Kim, Kashappa Goud
H. Desai
and Hyun Jin Park
12.1
Demands
307
12.2
Microencapsulation in the Food Industry
307
12.3
Techniques and Materials for Flavour Microencapsulation
308
12.3.1
Spray Drying
308
12.3.2
Extrusion
312
12.3.3
Cyclodextrin Inclusion Complexes
314
12.3.4
Helical Inclusion Complexes
316
12.3.5
Fluidized
Bed Coating
318
12.3.6
Top Spray
Fluidized
Bed Coating
318
12.3.7
Bottom Spray System
318
12.3.8
Wurster
System
320
12.3.9
Tangential Spray or Rotary
Fluidized
Bed Coating
320
12.3.10
Coacervation
320
12.3.11
Double or Multiple Emulsion with Freeze Drying
321
12.3.12
Co-Crystallization
322
12.3.13
Spray Chilling and Spray Cooling
322
12.3.14
Supercritical Fluids
323
12.3.15
Other Techniques
323
12.4
Conclusion and Future Trends
325
References
326
13
Profragrances
and
Properfumes
333
Andreas Herrmann
13.1
Introduction
333
13.2
Release of Alcohols
335
13.2.1
Enzymatic Hydrolysis
335
13.2.2
Neighbouring-Group-Assisted, Non-Enzymatic Hydrolysis
340
13.3
Release of Carbonyl Derivatives
346
13.3.1
Oxidations
346
13.3.2
Reversible Systems
350
13.3.3
Retro
1,4-
Additions
354
13.4
Profragrance
and
Properfume
Strategies
356
13.4.1
Performance and Cost Efficiency
356
13.4.2
Stability
357
13.5
Conclusion
357
Acknowledgements
358
References
358
xii Contents
14
Reactions of Biogenic Volatile Organic Compounds in the Atmosphere
363
Russell K. Monson
14.1
Introduction
363
14.2
The Relative Importance of Anthropogenic Versus Biogenic
VOC Emissions to Atmospheric Chemistry
364
14.3
Overview of BVOC Oxidation
365
14.4
The Types of Emitted BVOCs and General Roles in Atmospheric
Chemistry
370
14.5
Gas Phase Oxidation of BVOCs
372
14.6
Gas Phase Chemistry of BVOCs in Urban and Suburban Airsheds
374
14.7
Gas Phase Chemistry Within and Above Forests
375
14.8
BVOC Emissions and
SOA
Formation
377
14.9
Conclusion
381
References
381
Index
389
|
any_adam_object | 1 |
author2 | Herrmann, Andreas 1970- |
author2_role | edt |
author2_variant | a h ah |
author_GND | (DE-588)129532533 |
author_facet | Herrmann, Andreas 1970- |
building | Verbundindex |
bvnumber | BV036744642 |
classification_rvk | VK 8500 |
classification_tum | CHE 815f |
ctrlnum | (OCoLC)695933002 (DE-599)BSZ332659933 |
dewey-full | 612.0157 |
dewey-hundreds | 600 - Technology (Applied sciences) |
dewey-ones | 612 - Human physiology |
dewey-raw | 612.0157 |
dewey-search | 612.0157 |
dewey-sort | 3612.0157 |
dewey-tens | 610 - Medicine and health |
discipline | Chemie / Pharmazie Biologie Medizin |
edition | 1. publ. |
format | Book |
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id | DE-604.BV036744642 |
illustrated | Illustrated |
indexdate | 2024-12-24T00:12:27Z |
institution | BVB |
isbn | 9780470777787 0470777788 |
language | English |
oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-020662036 |
oclc_num | 695933002 |
open_access_boolean | |
owner | DE-11 DE-29T DE-91S DE-BY-TUM DE-355 DE-BY-UBR |
owner_facet | DE-11 DE-29T DE-91S DE-BY-TUM DE-355 DE-BY-UBR |
physical | XXV, 402 S. Ill., graph. Darst. |
publishDate | 2010 |
publishDateSearch | 2010 |
publishDateSort | 2010 |
publisher | Wiley |
record_format | marc |
spellingShingle | The chemistry and biology of volatiles VOC Ökologische Chemie (DE-588)4351499-6 gnd Naturstoff (DE-588)4041418-8 gnd Flüchtiger Stoff (DE-588)4281393-1 gnd Organische Verbindungen (DE-588)4043816-8 gnd |
subject_GND | (DE-588)4351499-6 (DE-588)4041418-8 (DE-588)4281393-1 (DE-588)4043816-8 |
title | The chemistry and biology of volatiles |
title_auth | The chemistry and biology of volatiles |
title_exact_search | The chemistry and biology of volatiles |
title_full | The chemistry and biology of volatiles ed. by Andreas Herrmann |
title_fullStr | The chemistry and biology of volatiles ed. by Andreas Herrmann |
title_full_unstemmed | The chemistry and biology of volatiles ed. by Andreas Herrmann |
title_short | The chemistry and biology of volatiles |
title_sort | the chemistry and biology of volatiles |
topic | VOC Ökologische Chemie (DE-588)4351499-6 gnd Naturstoff (DE-588)4041418-8 gnd Flüchtiger Stoff (DE-588)4281393-1 gnd Organische Verbindungen (DE-588)4043816-8 gnd |
topic_facet | VOC Ökologische Chemie Naturstoff Flüchtiger Stoff Organische Verbindungen |
url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=020662036&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
work_keys_str_mv | AT herrmannandreas thechemistryandbiologyofvolatiles |