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Cas Database |
| Name |
(E,E)-Germacra-3,7(11),9-trien-6-one |
EINECS | N/A |
| CAS No. | 6902-91-6 | Density | 0.916 g/cm3 |
| PSA | 17.07000 | LogP | 4.35850 |
| Solubility | N/A | Melting Point |
55-58 °C |
| Formula | C15H22O | Boiling Point | 330.274 °C at 760 mmHg |
| Molecular Weight | 218.339 | Flash Point | 148.419 °C |
| Transport Information | N/A | Appearance | N/A |
| Safety | 23-24/25 | Risk Codes | N/A |
| Molecular Structure |
|
Hazard Symbols | N/A |
| Synonyms |
3,7-Cyclodecadien-1-one,3,7-dimethyl-10-(1-methylethylidene)-, (E,E)-;Germacra-3,7(11),9-trien-6-one,(E,E)- (8CI);Germacrone (6CI,7CI);(E,E)-Germacrone;Germacron; |
Article Data | 2 |
(E,E)-Germacra-3,7(11),9-trien-6-one Synthetic route
- 87920-50-1
(3E,7E)-1-Hydroxy-10-isopropylidene-3,7-dimethyl-cyclodeca-3,7-dienecarbonitrile
- 6902-91-6
germacrone
| Conditions | Yield |
|---|---|
| With sodium hydroxide In diethyl ether for 0.333333h; Yield given; |
- 37905-03-6
8-hydroxygeranyl acetate
- 6902-91-6
germacrone
| Conditions | Yield |
|---|---|
| Multi-step reaction with 13 steps 2: 65 percent / triphenylphosphine / palladium acetate / tetrahydrofuran / 5 h / Heating 3: 95 percent / sodium hydride / diethyl ether / 0 °C 4: 70 percent / diethyl ether / -10 °C 5: 90 percent / triphenylphosphine, carbon tetrachloride / 12 h / Heating 6: diisobutylaluminium hydride / tetrahydrofuran / -40 °C 7: manganese dioxide / hexane / Ambient temperature 8: KCN, 18-crown-6 / 1 h / 0 °C 9: trimethylbenzylammonium fluoride / tetrahydrofuran; H2O / 0 °C 11: 79 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 56 °C 12: p-toluenesulfonic acid / methanol / 1 h / 0 °C 13: 2percent aqueous sodium hydroxide / diethyl ether / 0.33 h View Scheme |
- 87920-44-3
(4E,8E)-10-Chloro-2-isopropylidene-5,9-dimethyl-deca-4,8-dien-1-ol
- 6902-91-6
germacrone
| Conditions | Yield |
|---|---|
| Multi-step reaction with 7 steps 1: manganese dioxide / hexane / Ambient temperature 2: KCN, 18-crown-6 / 1 h / 0 °C 3: trimethylbenzylammonium fluoride / tetrahydrofuran; H2O / 0 °C 5: 79 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 56 °C 6: p-toluenesulfonic acid / methanol / 1 h / 0 °C 7: 2percent aqueous sodium hydroxide / diethyl ether / 0.33 h View Scheme |
- 87920-45-4
(4E,8E)-10-Chloro-2-isopropylidene-5,9-dimethyl-deca-4,8-dienal
- 6902-91-6
germacrone
| Conditions | Yield |
|---|---|
| Multi-step reaction with 6 steps 1: KCN, 18-crown-6 / 1 h / 0 °C 2: trimethylbenzylammonium fluoride / tetrahydrofuran; H2O / 0 °C 4: 79 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 56 °C 5: p-toluenesulfonic acid / methanol / 1 h / 0 °C 6: 2percent aqueous sodium hydroxide / diethyl ether / 0.33 h View Scheme |
- 87920-42-1
(4E,8E)-10-Hydroxy-2-isopropylidene-5,9-dimethyl-deca-4,8-dienoic acid methyl ester
- 6902-91-6
germacrone
| Conditions | Yield |
|---|---|
| Multi-step reaction with 9 steps 1: 90 percent / triphenylphosphine, carbon tetrachloride / 12 h / Heating 2: diisobutylaluminium hydride / tetrahydrofuran / -40 °C 3: manganese dioxide / hexane / Ambient temperature 4: KCN, 18-crown-6 / 1 h / 0 °C 5: trimethylbenzylammonium fluoride / tetrahydrofuran; H2O / 0 °C 7: 79 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 56 °C 8: p-toluenesulfonic acid / methanol / 1 h / 0 °C 9: 2percent aqueous sodium hydroxide / diethyl ether / 0.33 h View Scheme |
- 87920-43-2
(4E,8E)-10-Chloro-2-isopropylidene-5,9-dimethyl-deca-4,8-dienoic acid methyl ester
- 6902-91-6
germacrone
| Conditions | Yield |
|---|---|
| Multi-step reaction with 8 steps 1: diisobutylaluminium hydride / tetrahydrofuran / -40 °C 2: manganese dioxide / hexane / Ambient temperature 3: KCN, 18-crown-6 / 1 h / 0 °C 4: trimethylbenzylammonium fluoride / tetrahydrofuran; H2O / 0 °C 6: 79 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 56 °C 7: p-toluenesulfonic acid / methanol / 1 h / 0 °C 8: 2percent aqueous sodium hydroxide / diethyl ether / 0.33 h View Scheme |
- 87920-47-6
(5E,9E)-11-Chloro-2-hydroxy-3-isopropylidene-6,10-dimethyl-undeca-5,9-dienenitrile
- 6902-91-6
germacrone
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 2: 79 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 56 °C 3: p-toluenesulfonic acid / methanol / 1 h / 0 °C 4: 2percent aqueous sodium hydroxide / diethyl ether / 0.33 h View Scheme |
- 87920-46-5
(5E,9E)-11-Chloro-3-isopropylidene-6,10-dimethyl-2-trimethylsilanyloxy-undeca-5,9-dienenitrile
- 6902-91-6
germacrone
| Conditions | Yield |
|---|---|
| Multi-step reaction with 5 steps 1: trimethylbenzylammonium fluoride / tetrahydrofuran; H2O / 0 °C 3: 79 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 56 °C 4: p-toluenesulfonic acid / methanol / 1 h / 0 °C 5: 2percent aqueous sodium hydroxide / diethyl ether / 0.33 h View Scheme |
- 87920-40-9
(4E,8E)-2-Acetyl-10-(1-ethoxy-ethoxy)-5,9-dimethyl-deca-4,8-dienoic acid methyl ester
- 6902-91-6
germacrone
| Conditions | Yield |
|---|---|
| Multi-step reaction with 11 steps 1: 95 percent / sodium hydride / diethyl ether / 0 °C 2: 70 percent / diethyl ether / -10 °C 3: 90 percent / triphenylphosphine, carbon tetrachloride / 12 h / Heating 4: diisobutylaluminium hydride / tetrahydrofuran / -40 °C 5: manganese dioxide / hexane / Ambient temperature 6: KCN, 18-crown-6 / 1 h / 0 °C 7: trimethylbenzylammonium fluoride / tetrahydrofuran; H2O / 0 °C 9: 79 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 56 °C 10: p-toluenesulfonic acid / methanol / 1 h / 0 °C 11: 2percent aqueous sodium hydroxide / diethyl ether / 0.33 h View Scheme |
- 87920-48-7
(5E,9E)-11-Chloro-2-(1-ethoxy-ethoxy)-3-isopropylidene-6,10-dimethyl-undeca-5,9-dienenitrile
- 6902-91-6
germacrone
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: 79 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 56 °C 2: p-toluenesulfonic acid / methanol / 1 h / 0 °C 3: 2percent aqueous sodium hydroxide / diethyl ether / 0.33 h View Scheme |
(E,E)-Germacra-3,7(11),9-trien-6-one Chemical Properties
IUPAC Name: (3E,7E)-3,7-Dimethyl-10-propan-2-ylidenecyclodeca-3,7-dien-1-one
CAS: 6902-91-6
Formula : C15H22O
Molecular Weight: 218.33458
Molecular Structure of (3E,7E)-3,7-Dimethyl-10-propan-2-ylidenecyclodeca-3,7-dien-1-one (6902-91-6):
Density: 0.916 g/cm3
Flash Point: 148.4 °C
Melting Point: 55-58 °C
Boiling Point: 330.3 °C at 760 mmHg
Index of Refraction: 1.485
Molar Refractivity: 68.34 cm3
Molar Volume: 238.3 cm3
Polarizability: 27.09×10-24cm3
Surface Tension: 29.2 dyne/cm
Appearance: fanit yellow crystal
Enthalpy of Vaporization: 57.28 kJ/mol
Vapour Pressure: 0.000168 mmHg at 25°C
Water Solubility: 0.8354(mg/L)at 25°C
(E,E)-Germacra-3,7(11),9-trien-6-one Toxicity Data With Reference
| 1. | orl-mus TDLo:25 mg/kg | BIPBU* Biological & pharmaceutical bulletin. 25 (2002),627. |
(E,E)-Germacra-3,7(11),9-trien-6-one Safety Profile
A poison by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.
Safety Information about (3E,7E)-3,7-Dimethyl-10-propan-2-ylidenecyclodeca-3,7-dien-1-one (6902-91-6):
S23: Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer).
S24/25: Avoid contact with skin and eyes.
(E,E)-Germacra-3,7(11),9-trien-6-one Specification
The chemical synonyms of (3E,7E)-3,7-Dimethyl-10-propan-2-ylidenecyclodeca-3,7-dien-1-one (6902-91-6) are (3Z,7Z)-3,7-Dimethyl-10-propan-2-ylidene-cyclodeca-3,7-dien-1-one ; (E,E)-Germacra-3,7(11),9-trien-6-one ; (E,E)-3,7-Dimethyl-10-(1-methylethylidene)-3,7-cyclodecadien-1-one ; 3,7-Cyclodecadien-1-one, 3,7-dimethyl-10-(1-methylethylidene)-, (E,E)- ; 3,7-Dimethyl-10-(1-methylethylidene)-3,7-cyclodecadien-1-one ; Germacra-3,7(11),9-trien-6-one, (E,E)- ; Germacron ; Trans,trans-3,7-Dimethyl-10-isopropylidene-3,7-cyclodecadien-1-one .
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