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Basic Information
CAS No.: 6902-91-6
Name: (3Z,7Z)-3,7-Dimethyl-10-propan-2-ylidene-cyclodeca-3,7-dien-1-one
Molecular Structure:
Molecular Structure of 6902-91-6 ((3Z,7Z)-3,7-Dimethyl-10-propan-2-ylidene-cyclodeca-3,7-dien-1-one)
Formula: C15H22O
Molecular Weight: 218.339
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;
Density: 0.916 g/cm3
Melting Point: 55-58 °C
Boiling Point: 330.274 °C at 760 mmHg
Flash Point: 148.419 °C
Safety: 23-24/25
PSA: 17.07000
LogP: 4.35850
Related products
Synthetic route
87920-50-1

(3E,7E)-1-Hydroxy-10-isopropylidene-3,7-dimethyl-cyclodeca-3,7-dienecarbonitrile

6902-91-6

germacrone

Conditions
ConditionsYield
With sodium hydroxide In diethyl ether for 0.333333h; Yield given;
37905-03-6

8-hydroxygeranyl acetate

6902-91-6

germacrone

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
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Chemistry

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

Toxicity Data With Reference

1.    

orl-mus TDLo:25 mg/kg

     BIPBU*    Biological & pharmaceutical bulletin. 25 (2002),627.

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.

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 .