• Name

  3-methyl-1-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-1,4-dien-3-ol

• EINECS 226-006-5
• CAS No. 5208-93-5
• Article Data3
• CAS DataBase
• Density 0.948 g/cm³
• Solubility 151mg/L at 25℃
• Melting Point
• Formula C₁₅H₂₄O
• Boiling Point 315.3 °C at 760 mmHg
• Molecular Weight 220.355
• Flash Point 115.5 °C
• Transport Information
• Appearance
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 3-Methyl-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)penta-1,4-dien-3-ol;3-Methyl-3-hydroxy-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,4-pentadiene;3-Methyl-5-(2,6,6-trimethyl-1-cyclohexenyl)-1,4-pentadien-3-ol;
• PSA 20.23000
• LogP 4.00620

Synthetic route

79-77-6

4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

3536-96-7

vinylmagnesium chloride

5208-93-5

2-vinyl-β-ionol

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 10℃; for 2h;	90%

79-77-6

(E)-β-ionone

1826-67-1

vinyl magnesium bromide

5208-93-5

2-vinyl-β-ionol

Conditions

Conditions	Yield
at 0 - 20℃; for 10h; Grignard Reaction;	58%

5208-93-5

2-vinyl-β-ionol

618-41-7

Benzenesulfinic acid

50464-14-7

1-Benzolsulfonyl-3-methyl-5-(2',6',6'-trimethyl-cyclohex-1-enyl)-penta-2,4-dien

Conditions

Conditions	Yield
In water at 40℃; Temperature; Microwave irradiation;	99%

14918-80-0

3-methyl-4-oxobut-2-enyl acetate

5208-93-5

2-vinyl-β-ionol

127-47-9

Retinol acetate

Conditions

Conditions	Yield
Stage #1: 2-vinyl-β-ionol With toluene-4-sulfonic acid; triphenylphosphine In toluene at 12℃; Inert atmosphere; Sealed tube; Stage #2: 3-methyl-4-oxobut-2-enyl acetate In toluene at 12℃; Temperature; Inert atmosphere; Sealed tube;	92.8%

5208-93-5

2-vinyl-β-ionol

6399-81-1

triphenylphosphine hydrobromide

[3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)penta-2,4-dien-1-yl]triphenylphosphanium bromide

Conditions

Conditions	Yield
In methanol at 20℃; Inert atmosphere;	77%

5208-93-5

2-vinyl-β-ionol

A

67777-14-4

oxovinylionol

B

1432964-99-2

tert-butylperoxyvinylionol

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; copper(II) acetylacetonate hydrate In pyridine; water at 40℃; for 10h; Reagent/catalyst; Concentration; Time; Temperature; Solvent;	A 46.6% B 5.9%

5208-93-5

2-vinyl-β-ionol

67777-14-4

oxovinylionol

Conditions

Conditions	Yield
Stage #1: 2-vinyl-β-ionol With tert.-butylhydroperoxide; 1,10-Phenanthroline; cobalt(II) 2-ethylhexanoate In water at 68 - 72℃; Stage #2: With piperidine In water at 70℃; for 12h; Reagent/catalyst; Time; Solvent; Concentration; Temperature;	43.2%

75-91-2

tert.-butylhydroperoxide

5208-93-5

2-vinyl-β-ionol

A

67777-14-4

oxovinylionol

B

1432964-99-2

tert-butylperoxyvinylionol

Conditions

Conditions	Yield
With cobalt(II) bromide In pyridine; water at 40℃; for 10h; Reagent/catalyst; Time; Temperature; Concentration;	A 16.9% B 42.8%

...Expand

116-11-0

2-Methoxypropene

5208-93-5

2-vinyl-β-ionol

1196448-69-7

2-[(E)-3-(1-methoxy-1-methyl-ethoxy)-3-methyl-penta-1,4-dienyl]-1,3,3-trimethyl-cyclohexene

Conditions

Conditions	Yield
phosphoric acid In acetone at -20 - 0℃; Inert atmosphere;

5208-93-5

2-vinyl-β-ionol

A

1432965-26-8

1-(4-hydroxy-3-oxo-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-3-trimethylsiloxy-1,4-pentadiene

B

1432965-13-3

C21H38O3Si2

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tert.-butylhydroperoxide; cobalt(II) 2-ethylhexanoate; 1,10-Phenanthroline / water / 68 - 72 °C 1.2: 12 h / 70 °C 2.1: tetrabutylammomium bromide; triethylamine / acetonitrile / 24 h / 20 - 25 °C / Reflux View Scheme
Multi-step reaction with 2 steps 1: cobalt(II) bromide / water; pyridine / 10 h / 40 °C 2: tetrabutylammomium bromide; triethylamine / acetonitrile / 24 h / 20 - 25 °C / Reflux View Scheme
Multi-step reaction with 2 steps 1: copper(II) acetylacetonate hydrate; tert.-butylhydroperoxide / water; pyridine / 10 h / 40 °C 2: tetrabutylammomium bromide; triethylamine / acetonitrile / 24 h / 20 - 25 °C / Reflux View Scheme

5208-93-5

2-vinyl-β-ionol

84592-32-5

3-methyl-5-(2,6,6-trimethyl-4-hydroxy-1-cyclohexene-3-carbonyl)-2,4-pentadiene-1-bromotriphenylphosphine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: cobalt(II) bromide / water; pyridine / 10 h / 40 °C 2.1: tetrabutylammomium bromide; triethylamine / acetonitrile / 24 h / 20 - 25 °C / Reflux 3.1: hydrogen bromide / dichloromethane / 0.67 h / -5 - 0 °C 3.2: 20 h / 1 °C / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: copper(II) acetylacetonate hydrate; tert.-butylhydroperoxide / water; pyridine / 10 h / 40 °C 2.1: tetrabutylammomium bromide; triethylamine / acetonitrile / 24 h / 20 - 25 °C / Reflux 3.1: hydrogen bromide / dichloromethane / 0.67 h / -5 - 0 °C 3.2: 20 h / 1 °C / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: tert.-butylhydroperoxide; cobalt(II) 2-ethylhexanoate; 1,10-Phenanthroline / water / 68 - 72 °C 1.2: 12 h / 70 °C 2.1: tetrabutylammomium bromide; triethylamine / acetonitrile / 24 h / 20 - 25 °C / Reflux 3.1: hydrogen bromide / dichloromethane / 0.67 h / -5 - 0 °C 3.2: 20 h / 1 °C / Reflux View Scheme

5208-93-5

2-vinyl-β-ionol

A

C23H32O2

B

C23H32O2

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: methanol / 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.53 h / -20 °C / Inert atmosphere 2.2: 4 h / -20 - 20 °C / Inert atmosphere View Scheme

5208-93-5

2-vinyl-β-ionol

603-35-0

triphenylphosphine

1062-12-0

β-Jonylidenaethyl-triphenyl-phosphonium-chlorid

Conditions

Conditions	Yield
With hydrogenchloride In water at 53℃; under 150015 Torr; for 1.5h; Temperature; Pressure; Autoclave; Inert atmosphere;
Stage #1: 2-vinyl-β-ionol With triethylamine In methanol for 0.166667h; Large scale; Stage #2: triphenylphosphine With hydrogenchloride; 2,6-di-tert-butyl-4-methyl-phenol In methanol; water Time; Inert atmosphere; Reflux; Large scale;

Vinylionol Specification