Terpene: Aromen, Düfte, Pharmaka, Pheromone
Saved in:
| Main Author: | |
|---|---|
| Format: | Book |
| Language: | German |
| Published: |
Weinheim
Wiley-VCH
2005
|
| Edition: | 2., vollst. überarb. und erw. Aufl. |
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | IX, 210 S. graph. Darst. |
| ISBN: | 9783527314980 3527314989 |
Staff View
MARC
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| 020 | |a 3527314989 |9 3-527-31498-9 | ||
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| 100 | 1 | |a Breitmaier, Eberhard |d 1939- |e Verfasser |0 (DE-588)115576320 |4 aut | |
| 245 | 1 | 0 | |a Terpene |b Aromen, Düfte, Pharmaka, Pheromone |c Eberhard Breitmaier |
| 250 | |a 2., vollst. überarb. und erw. Aufl. | ||
| 264 | 1 | |a Weinheim |b Wiley-VCH |c 2005 | |
| 300 | |a IX, 210 S. |b graph. Darst. | ||
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| 999 | |a oai:aleph.bib-bvb.de:BVB01-013357445 | ||
Record in the Search Index
| _version_ | 1804133606129401856 |
|---|---|
| adam_text | Inhaltsverzeichnis
1
Terpene,
Bedeutung, Bauprinzip, Biosynthese...................................................1
1.1 Begriff und Bedeutung..............................................................................................1
1.2 Bauprinzip: Isopren-Regel.........................................................................................2
1.3 Biosynthese...............................................................................................................3
2 Hemi- und
Monoterpene
.......................................................................................10
2.1 Hemiterpene............................................................................................................10
2.2 Acyclische
Monoterpene
.........................................................................................10
2.3 Monocyclische
Monoterpene
..................................................................................13
2.3.1 Cyclopropan- und Cyclobutan-Monoterpene..........................................................................14
2.3.2 Cyclopentan-Monoterpene......................................................................................................14
2.3.3 Cyclohexan-Monoterpene.......................................................................................................15
2.4 Bicyclische
Monoterpene
........................................................................................18
2.4.1 Übersicht.................................................................................................................................18
2.4.2 Carane und Thujane...............................................................................................................19
2.4.3 Pinane.....................................................................................................................................20
2.4.4 Camphane und Fenchane......................................................................................................20
2.5 Cannabinoide..........................................................................................................22
3 Sesquiterpene.......................................................................................................23
3.1 Farnesane...............................................................................................................23
3.2 Monocyclische Famesan-Sesquiterpene................................................................24
3.2.1 Cyclofamesane und Bisabolane.............................................................................................24
3.2.2 Germacrane und
Eternane
......................................................................................................25
3.2.3 Humulane................................................................................................................................26
3.3
Polycyclische
Farnesan-Sesquiterpene..................................................................27
3.3.1 Caryophyllane.........................................................................................................................27
3.3.2 Eudesmane und Furanoeudesmane.......................................................................................28
3.3.3 Eremophilane, Furanoeremonphilane und Vaterane..............................................................30
3.3.4 Cadinane.................................................................................................................................33
3.3.5 Drimane..................................................................................................................................35
3.3.6 Guajane und Cycloguajane.....................................................................................................36
3.3.7 Himachalane, Longipinane und Longifolane...........................................................................40
3.3.8 Picrotoxane.............................................................................................................................41
3.3.9 Isodaucane und Daucane.......................................................................................................41
3.3.10 Protoilludane,
Illudane
und Illudalane.....................................................................................42
3.3.11 Marasmane, Isolactarane, Lactarane, Sterpurane.................................................................43
3.3.12 Acorane...................................................................................................................................44
VI
Inhaltsverzeichnis
3.3.13
Chamigrane
............................................................................................................................44
3.3.14
Cedrane
und Isocedrane........................................................................................................45
3.3.15
Zizaane
und
Prezizaane
.........................................................................................................46
3.3.16
Campherenane
und
Santalane
...............................................................................................46
3.3.17
Thujopsane
.............................................................................................................................47
3.3.18
Hirsutane
.................................................................................................................................48
3.4 Andere polycyclische
Sesquiterpene
......................................................................49
3.4.1
Pinguisane
..............................................................................................................................49
3.4.2
Presilphiperfoliane, Silphiperfoliane, Silphinane, Isocomane
.................................................49
4
Diterpene
................................................................................................................51
4.1
Phytane
...................................................................................................................51
4.2
Cyclophytane
...........................................................................................................51
4.3
Bicyclophytane
........................................................................................................53
4.3.1 Labdane..................................................................................................................................53
4.3.2 Umgelagerte Labdane............................................................................................................54
4.4
Tricyclophytane
.......................................................................................................56
4.4.1
Pimarane
und Isopimarane.....................................................................................................56
4.4.2
Cassane, Cleistanthane
und Isocopalane..............................................................................58
4.4.3
Abietane
und
Totarane
...........................................................................................................60
4.5
Tetracyclophytane
...................................................................................................62
4.5.1 Übersicht.................................................................................................................................62
4.5.2
Beyerane
.................................................................................................................................63
4.5.3 Kaurane und
Villanovane
........................................................................................................64
4.5.4
Atisane
....................................................................................................................................65
4.5.5
Gibberellane
............................................................................................................................65
4.5.6
Graynatoxane
.........................................................................................................................66
4.6
Cembrane
und Cyclocembrane...............................................................................67
4.6.1 Übersicht.................................................................................................................................67
4.6.2
Cembrane
...............................................................................................................................69
4.6.3
Casbane
..................................................................................................................................70
4.6.4
Lathyrane
..........................................................
ZZZZZZZZZZ Z. .
......................70
4.6.5
Jatrophane
...................................................................................
ZZI
..............................71
4.6.6
Tigliane
..........................................................................................
ZZI
..............................71
4.6.7
Rhamnofolane
und Daphnane................................................................................................72
4.6.8
Eunicellane
und
Asbestinane
.................................................................................................72
4.6.9
Biarane
...................................................... 73
4.6.10
Dolabellane
.................................................
ZZZZZZZZZZZZZZZZZZ...73
4.6.11
Dolastane
..............................................................
ZZZZZZZZZZZZZ. .
74
4.6.12
Fusicoccane
........................................................................................ , ...............................75
4.6.13
Verticillane
und
Taxane
..........................................................................................................75
4.6.14
Trinervitane
und
Kempane
......................................................................................................75
4.7
Prenylsequiterpene
.................................................................................................76
4.7.1
Xenicane
und
Xeniaphyllane
..........................................................., . . ...............................77
4.7.2
Prenylgermacrane
und Lobane......................................................................................77
Inhaltsverzeichnis
VII
4.7.3 Prenyleudesmane und Biflorane.............................................................................................78
4.7.4
Sacculatane (Prenyldrimane)
..................................................................................................79
4.7.5 Prenylguajane und Prenylaromadendrane.............................................................................79
4.7.6 Sphenolobane (Prenyldaucane).............................................................................................80
4.8 Ginkgolide...............................................................................................................80
5 Sesterterpene........................................................................................................81
5.1 Acyclische Sesterterpene........................................................................................81
5.2 Monocyclische Sesterterpene.................................................................................81
5.3 Polycyclische Sesterterpene...................................................................................82
5.3.1 Bicyclische Sesterterpene......................................................................................................82
53.2 Tricyclische Sesterterpene.....................................................................................................83
5.3.3 Tetra- und pentacyclische Sesterterpene...............................................................................84
6 Triterpene...............................................................................................................85
6.1 Lineare Triterpene...................................................................................................85
6.2 Tetracyclische Triterpene, Gonan-Typ....................................................................87
6.2.1 Übersicht.................................................................................................................................87
6.2.2
Protostane
und Fusidane........................................................................................................88
6.2.3 Dammarane............................................................................................................................88
6.2.4 Apotirucallane.........................................................................................................................90
6.2.5 Tirucallane und Euphane........................................................................................................90
6.2.6 Lanostane...............................................................................................................................91
6.2.7 Cycloartane.............................................................................................................................92
6.2.8 Cucurbitane.............................................................................................................................93
6.3 Pentacyclische Triterpene, Baccaran-Typ..............................................................94
6.3.1 Übersicht.................................................................................................................................94
6.3.2 Baccarane und
Lupane
...........................................................................................................96
6.3.3 Oleanane................................................................................................................................96
6.3.4 Taraxerane, Multiflorane und Bauerane.................................................................................97
6.3.5 Glutinane, Friedelane und Pachysanane................................................................................98
6.3.6 Taraxastane und Ursane........................................................................................................99
6.4 Pentacyclische Triterpene,
Hopan
-Тур
.................................................................100
6.4.1 Übersicht...............................................................................................................................100
6.4.2 Hopane und Neohopane.......................................................................................................101
6.4.3
Ferrane
.................................................................................................................................102
6.4.4 Adianane und Filicane..........................................................................................................103
6.4.5 Gammacerane......................................................................................................................103
6.5 Weitere pentacyclische Triterpene........................................................................104
6.5.1 Übersicht...............................................................................................................................104
6.5.2 Stictane und Arborane..........................................................................................................105
6.5.3 Onocerane und
Serratane
....................................................................................................105
6.6
Iridale....................................................................................................................
106
7 Tetraterpene........................................................................................................108
7.1 Carotenoide...........................................................................................................108
VIII Inhaltsverzeichnis
7.2
Apocarotenoide
.....................................................................................................110
7.3
Diapocarotenoide
..................................................................................................111
7.4
Megastigmane
.......................................................................................................112
8 Polyterpene und
Predichinone........................................................................
114
8.1
Polyterpene
...........................................................................................................114
8.2
Prenylchinone
........................................................................................................115
9 Ausgewählte
Terpen-Synthesen........................................................................
118
9.1
Monoterpene
.........................................................................................................118
9.1.1 Konzept industrieller Monoterpen-Riechstoffsynthesen.......................................................118
9.1.2 (RH+J-Citronellal.................................................................................................................120
9.1.3 Rosenoxid.............................................................................................................................120
9.1.4 Chrysanthemumsäuremethylester........................................................................................121
9.1.5 (1/?,3R,4S)-H-Menthol........................................................................................................122
9.1.6 a-Terpineol...........................................................................................................................123
9.1.7 Campher aus a-Pinen..........................................................................................................124
9.1.8 a-Pinen und Derivate als Edukte zur stereospezifischen Synthese chiraler
Monoterpene..
126
9.2 Sesquiterpene.......................................................................................................128
9.2.1 ß-Selinen...............................................................................................................................128
9.2.2 isocomen..............................................................................................................................129
9.2.3 Cedren..................................................................................................................................132
9.2.4 PeriplanonB.........................................................................................................................134
9.3
Diterpene
...............................................................................................................137
9.3.1 Vitamin
A (Retinolacetat)
......................................................................................................137
9.3.2 Cafestol.................................................................................................................................140
9.3.3 Baccatin
III
als Vorstufe des Taxols......................................................................................144
9.4 Triterpene..............................................................................................................151
Lupeol...................................................................................................................................151
10 Isolierung und Strukturaufklärung....................................................................159
10.1 Isolierung aus Pflanzen.........................................................................................159
10.2 Geeignete Methoden der Strukturaufklärung........................................................159
10.3 Strukturaufklärung eines Sesquiterpens...............................................................160
10.3.1 Doppelbindungsäquivalente..................................................................................................160
10.3.2 Funktionelle Gruppen und Teilstrukturen aus dem C-NMR-Spektrum..............................161
10.3.3 Konstitution (Atomverknüpfung)...........................................................................................162
10.3.4 Relative Konfiguration...........................................................................................................168
10.3.5 Absolute Konfiguration..........................................................................................................170
10.4 Kristallstrukturbestimmung....................................................................................172
10.5 Über Struktur und Geruch von
Terpenen
..............................................................175
Bibliographie.......................................................................................................179
Übersicht bedeutender Terpen-Grundskelette.................................................184
Sachverzeichnis..................................................................................................196
|
| any_adam_object | 1 |
| author | Breitmaier, Eberhard 1939- |
| author_GND | (DE-588)115576320 |
| author_facet | Breitmaier, Eberhard 1939- |
| author_role | aut |
| author_sort | Breitmaier, Eberhard 1939- |
| author_variant | e b eb |
| building | Verbundindex |
| bvnumber | BV020036313 |
| classification_rvk | VK 8550 WD 5600 |
| classification_tum | CHE 697f |
| ctrlnum | (OCoLC)76778913 (DE-599)BVBBV020036313 |
| dewey-full | 540 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 540 - Chemistry and allied sciences |
| dewey-raw | 540 |
| dewey-search | 540 |
| dewey-sort | 3540 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Biologie Chemie |
| edition | 2., vollst. überarb. und erw. Aufl. |
| format | Book |
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| id | DE-604.BV020036313 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T20:11:23Z |
| institution | BVB |
| isbn | 9783527314980 3527314989 |
| language | German |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-013357445 |
| oclc_num | 76778913 |
| open_access_boolean | |
| owner | DE-91G DE-BY-TUM DE-12 DE-210 DE-29T DE-M49 DE-BY-TUM DE-20 DE-1046 DE-19 DE-BY-UBM DE-634 DE-83 DE-91S DE-BY-TUM DE-11 DE-188 DE-355 DE-BY-UBR |
| owner_facet | DE-91G DE-BY-TUM DE-12 DE-210 DE-29T DE-M49 DE-BY-TUM DE-20 DE-1046 DE-19 DE-BY-UBM DE-634 DE-83 DE-91S DE-BY-TUM DE-11 DE-188 DE-355 DE-BY-UBR |
| physical | IX, 210 S. graph. Darst. |
| publishDate | 2005 |
| publishDateSearch | 2005 |
| publishDateSort | 2005 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Breitmaier, Eberhard 1939- Verfasser (DE-588)115576320 aut Terpene Aromen, Düfte, Pharmaka, Pheromone Eberhard Breitmaier 2., vollst. überarb. und erw. Aufl. Weinheim Wiley-VCH 2005 IX, 210 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Terpene (DE-588)4184779-9 gnd rswk-swf Terpene (DE-588)4184779-9 s DE-604 Digitalisierung UB Regensburg application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=013357445&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Breitmaier, Eberhard 1939- Terpene Aromen, Düfte, Pharmaka, Pheromone Terpene (DE-588)4184779-9 gnd |
| subject_GND | (DE-588)4184779-9 |
| title | Terpene Aromen, Düfte, Pharmaka, Pheromone |
| title_auth | Terpene Aromen, Düfte, Pharmaka, Pheromone |
| title_exact_search | Terpene Aromen, Düfte, Pharmaka, Pheromone |
| title_full | Terpene Aromen, Düfte, Pharmaka, Pheromone Eberhard Breitmaier |
| title_fullStr | Terpene Aromen, Düfte, Pharmaka, Pheromone Eberhard Breitmaier |
| title_full_unstemmed | Terpene Aromen, Düfte, Pharmaka, Pheromone Eberhard Breitmaier |
| title_short | Terpene |
| title_sort | terpene aromen dufte pharmaka pheromone |
| title_sub | Aromen, Düfte, Pharmaka, Pheromone |
| topic | Terpene (DE-588)4184779-9 gnd |
| topic_facet | Terpene |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=013357445&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT breitmaiereberhard terpenearomenduftepharmakapheromone |