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Basic Information
CAS No.: 80054-40-6
Name: (E,E)-2,6-DiMethyl-2,6-octadienedial
Molecular Structure:
Molecular Structure of 80054-40-6 ((E,E)-2,6-DiMethyl-2,6-octadienedial)
Formula: C10H14O2
Molecular Weight: 166.22
Synonyms: 2E-10-oxocitral;(2E,6E)-2,6-dimethylocta-2,6-dien-1,8-dial;2,6-Octadienedial,2,6-dimethyl-,(Z,E);10-oxogeranial;2,6-Octadienedial,2,6-dimethyl-,(Z,Z);8-Oxocitral;(2E,6E)-8-oxogeranial;(2E,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial;
Density: 0.949±0.06 g/cm3(Predicted)
Boiling Point: 307.7±30.0 °C(Predicted)
PSA: 34.14000
LogP: 2.05700
Synthetic route
38290-51-6

(2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienal

80054-40-6

(2E,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial

Conditions
ConditionsYield
With manganese(IV) oxide In chloroform for 48h;88%
26488-97-1

8-hydroxygeraniol

80054-40-6

(2E,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane for 3h; Ambient temperature;70%
141-27-5

3,7-dimethyl-2,6-octadienal

80054-40-6

(2E,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial

Conditions
ConditionsYield
With selenium(IV) oxide In dichloromethane at 20℃; for 72h; Inert atmosphere;19%
5392-40-5

(E/Z)-3,7-dimethyl-2,6-octadienal

A

80054-37-1

(2E,8E)-8-hydroxy-3,7-dimethyl-2,6-octadienal

B

80054-40-6

(2E,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial

C

80054-36-0

(2Z,6E)-8-hydroxyneral

D

80054-41-7

(2Z,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial

Conditions
ConditionsYield
With selenium(IV) oxide In ethanol for 0.75h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
108526-78-9

<1-(3)H>-10-hydroxygeraniol

A

38290-51-6

(2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienal

B

80054-37-1

(2E,8E)-8-hydroxy-3,7-dimethyl-2,6-octadienal

C

80054-40-6

(2E,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial

Conditions
ConditionsYield
With NAD Rauwolfia serpentina cell suspension cultures, pH 6.5, incubation;
156155-53-2

2,6-dimethylocta-2E/Z,6E-dienediol

A

80054-40-6

(2E,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial

B

80054-41-7

(2Z,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial

Conditions
ConditionsYield
With manganese(IV) oxide In chloroform for 60h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

[(2)H2]-8-Hydroxygeraniol

80054-40-6

(2E,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial

Conditions
ConditionsYield
With Plagiodera versicolora defensive secretion In phosphate buffer pH=7.5; Oxidation;
5392-40-5

(E/Z)-3,7-dimethyl-2,6-octadienal

A

80054-40-6

(2E,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial

B

80054-41-7

(2Z,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial

Conditions
ConditionsYield
With selenium(IV) oxide In dichloromethane at 25℃; Title compound not separated from byproducts.;
105-87-3

3,7-dimethyl-2E,6-octadien-1-yl acetate

80054-40-6

(2E,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 40 percent / SeO2, t-BuOOH / toluene / 120 h / Ambient temperature
2: 87 percent / aq. K2CO3 / methanol / 1 h
3: 88 percent / MnO2 / CHCl3 / 48 h
View Scheme
37905-02-5

(2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate

80054-40-6

(2E,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 87 percent / aq. K2CO3 / methanol / 1 h
2: 88 percent / MnO2 / CHCl3 / 48 h
View Scheme
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