Homovanillyl alcohol supplier

Name
Homovanillyl alcohol
EINECS 219-175-1
CAS No. 2380-78-1
Article Data23
CAS DataBase
Density 1.182 g/cm³
Solubility Soluble in water
Melting Point 40-42 °C(lit.)
Formula C₉H₁₂O₃
Boiling Point 316.8 °C at 760 mmHg
Molecular Weight 168.192
Flash Point 145.4 °C
Transport Information
Appearance yellow to light brown crystalline chunks
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Phenethylalcohol, 4-hydroxy-3-methoxy- (6CI,7CI,8CI);2-(3-Methoxy-4-hydroxyphenyl)ethanol;2-(4-Hydroxy-3-methoxyphenyl)ethanol;3-Methoxy-4-hydroxyphenethanol;3-Methoxy-4-hydroxyphenethyl alcohol;4-(2-Hydroxyethyl)-2-methoxyphenol;4-(2-Hydroxyethyl)guaiacol;4-Hydroxy-3-methoxyphenethyl alcohol;Ba 2772;Homovanillic alcohol;Homovanillyl alcohol;Vanillylmethanol;
PSA 49.69000
LogP 0.93560

Synthetic route

: tert-butyl 4-(2-tert-butoxyethyl)-2-methoxyphenyl carbonate

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
With erbium(III) triflate In ethanol for 50h; Microwave irradiation;	98%

: 97-53-0
4-allylguaiacol

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
Stage #1: 4-allylguaiacol With ozone In ethanol at -55℃; Stage #2: With sodium tetrahydroborate In ethyl acetate at 20℃;	98%
Multi-step reaction with 2 steps 1: ozone / sodium hydrogencarbonate / dichloromethane; methanol / 2 h / -78 °C 2: sodium tetrahydroborate; methanol / dichloromethane / 2 h / -78 - 20 °C / Inert atmosphere View Scheme

: 124-41-4
sodium methylate

: 196081-78-4
3-bromo-4-hydroxyphenylethyl alcohol

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
With copper(I) bromide In N,N-dimethyl-formamide at 120℃; for 1h;	97.3%
Stage #1: sodium methylate With copper(I) bromide In methanol; N,N-dimethyl-formamide Stage #2: 3-bromo-4-hydroxyphenylethyl alcohol In methanol; N,N-dimethyl-formamide at 100℃; Temperature;	92%
With methanol; copper(I) bromide In N,N-dimethyl-formamide at 90℃; for 3h;	87.6%
With copper(I) bromide In water; N,N-dimethyl-formamide
copper(I) bromide In methanol; N,N-dimethyl-formamide at 120℃;

: tert-butyl 4-(2-hydroxyethyl)-2-methoxyphenyl carbonate

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
With erbium(III) triflate In ethanol for 50h; Microwave irradiation;	94%

: 1044264-42-7
C21H40O3Si2

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
With methanol; trimethylsilyl bromide at 20℃; for 5h; chemoselective reaction;	92%

: 1135-24-6
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
With β-D-glucose; oxygen In aq. phosphate buffer at 37℃; for 18h; pH=7.0; Enzymatic reaction;	91.9%
Multi-step reaction with 4 steps 1: Bacillus licheniformis strain CGMCC 7172 phenolic acid decarboxylase / 6 h / Enzymatic reaction 2: oxygen; β-D-glucose; styrene monooxygenase (AF031161.1) from Pseudomonas sp. VLB120 / Enzymatic reaction 3: styrene oxide isomerase (KF540254.1) from Rhodococcus opacus 1CP / Enzymatic reaction 4: alcohol dehydrogenase (NC_001145.3) from Saccharomyces cerevisiae S288C View Scheme

Yield

With β-D-glucose; oxygen In aq. phosphate buffer at 37℃; for 18h; pH=7.0; Enzymatic reaction;

91.9%

Multi-step reaction with 4 steps
1: Bacillus licheniformis strain CGMCC 7172 phenolic acid decarboxylase / 6 h / Enzymatic reaction
2: oxygen; β-D-glucose; styrene monooxygenase (AF031161.1) from Pseudomonas sp. VLB120 / Enzymatic reaction
3: styrene oxide isomerase (KF540254.1) from Rhodococcus opacus 1CP / Enzymatic reaction
4: alcohol dehydrogenase (NC_001145.3) from Saccharomyces cerevisiae S288C
View Scheme

: 64881-05-6
1-<4-(benzyloxy)-3-methoxyphenyl>ethan-2-ol

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol under 750.06 Torr; for 1h;	91%

: 60563-13-5
ethyl homovanillate

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 3h; Inert atmosphere; Reflux;	89%

: 67-56-1
methanol

: 94492-22-5
cistanoside C

A: 2380-78-1
homovanillyl alcohol

B: 3843-74-1, 67667-67-8
Methyl caffeate

Conditions

Conditions	Yield
With acetyl chloride for 0.5h; Heating;

...Expand

: 67-56-1
methanol

: 94492-21-4
cistanoside D

A: 2380-78-1
homovanillyl alcohol

B: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
With acetyl chloride for 0.5h; Heating;

...Expand

: 93236-41-0
cistanoside

: 75-36-5
acetyl chloride

A: 97966-29-5
methyl (E)-3-(3-hydroxy-4-methoxyphenyl)-2-propenoate

B: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
In methanol for 0.5h; Heating; Title compound not separated from byproducts;

...Expand

: cistanoside

: 75-36-5
acetyl chloride

A: 2380-78-1
homovanillyl alcohol

B: 3843-74-1, 67667-67-8
Methyl caffeate

Conditions

Conditions	Yield
In methanol for 0.5h; Heating; Title compound not separated from byproducts;

...Expand

: 75-21-8
oxirane

: 7368-78-7
4-bromoguaiacol

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
(i) nBuLi, Et2O, (ii) /BRN= 102378/, Et2O, benzene; Multistep reaction;

: 63057-72-7
2-benzyloxy-5-bromoanisole

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) Mg, 1,2-dibromoethane, 2.) 1,5-cyclooctadiene copper(I) chloride / 1.) THF, reflux, 5 h, 2.) THF, 0 deg C - 14 deg C, 16 h 2: 91 percent / H2 / 5percent Pd/C / methanol / 1 h / 750.06 Torr View Scheme

: tert-butyl 4-(2-tert-butoxyethyl)-2-methoxyphenyl carbonate

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
With erbium(III) triflate In ethanol for 50h; Microwave irradiation;	98%

: 97-53-0
4-allylguaiacol

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
Stage #1: 4-allylguaiacol With ozone In ethanol at -55℃; Stage #2: With sodium tetrahydroborate In ethyl acetate at 20℃;	98%
Multi-step reaction with 2 steps 1: ozone / sodium hydrogencarbonate / dichloromethane; methanol / 2 h / -78 °C 2: sodium tetrahydroborate; methanol / dichloromethane / 2 h / -78 - 20 °C / Inert atmosphere View Scheme

: 124-41-4
sodium methylate

: 196081-78-4
3-bromo-4-hydroxyphenylethyl alcohol

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
With copper(I) bromide In N,N-dimethyl-formamide at 120℃; for 1h;	97.3%
Stage #1: sodium methylate With copper(I) bromide In methanol; N,N-dimethyl-formamide Stage #2: 3-bromo-4-hydroxyphenylethyl alcohol In methanol; N,N-dimethyl-formamide at 100℃; Temperature;	92%
With methanol; copper(I) bromide In N,N-dimethyl-formamide at 90℃; for 3h;	87.6%
With copper(I) bromide In water; N,N-dimethyl-formamide
copper(I) bromide In methanol; N,N-dimethyl-formamide at 120℃;

: tert-butyl 4-(2-hydroxyethyl)-2-methoxyphenyl carbonate

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
With erbium(III) triflate In ethanol for 50h; Microwave irradiation;	94%

: 1044264-42-7
C21H40O3Si2

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
With methanol; trimethylsilyl bromide at 20℃; for 5h; chemoselective reaction;	92%

: 1135-24-6
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
With β-D-glucose; oxygen In aq. phosphate buffer at 37℃; for 18h; pH=7.0; Enzymatic reaction;	91.9%
Multi-step reaction with 4 steps 1: Bacillus licheniformis strain CGMCC 7172 phenolic acid decarboxylase / 6 h / Enzymatic reaction 2: oxygen; β-D-glucose; styrene monooxygenase (AF031161.1) from Pseudomonas sp. VLB120 / Enzymatic reaction 3: styrene oxide isomerase (KF540254.1) from Rhodococcus opacus 1CP / Enzymatic reaction 4: alcohol dehydrogenase (NC_001145.3) from Saccharomyces cerevisiae S288C View Scheme

Yield

With β-D-glucose; oxygen In aq. phosphate buffer at 37℃; for 18h; pH=7.0; Enzymatic reaction;

91.9%

: 64881-05-6
1-<4-(benzyloxy)-3-methoxyphenyl>ethan-2-ol

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol under 750.06 Torr; for 1h;	91%

: 60563-13-5
ethyl homovanillate

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 3h; Inert atmosphere; Reflux;	89%

: 67-56-1
methanol

: 94492-22-5
cistanoside C

A: 2380-78-1
homovanillyl alcohol

B: 3843-74-1, 67667-67-8
Methyl caffeate

Conditions

Conditions	Yield
With acetyl chloride for 0.5h; Heating;

...Expand

: 67-56-1
methanol

: 94492-21-4
cistanoside D

A: 2380-78-1
homovanillyl alcohol

B: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
With acetyl chloride for 0.5h; Heating;

...Expand

: 93236-41-0
cistanoside

: 75-36-5
acetyl chloride

A: 97966-29-5
methyl (E)-3-(3-hydroxy-4-methoxyphenyl)-2-propenoate

B: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
In methanol for 0.5h; Heating; Title compound not separated from byproducts;

...Expand

: cistanoside

: 75-36-5
acetyl chloride

A: 2380-78-1
homovanillyl alcohol

B: 3843-74-1, 67667-67-8
Methyl caffeate

Conditions

Conditions	Yield
In methanol for 0.5h; Heating; Title compound not separated from byproducts;

...Expand

: 75-21-8
oxirane

: 7368-78-7
4-bromoguaiacol

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
(i) nBuLi, Et2O, (ii) /BRN= 102378/, Et2O, benzene; Multistep reaction;

: 63057-72-7
2-benzyloxy-5-bromoanisole

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) Mg, 1,2-dibromoethane, 2.) 1,5-cyclooctadiene copper(I) chloride / 1.) THF, reflux, 5 h, 2.) THF, 0 deg C - 14 deg C, 16 h 2: 91 percent / H2 / 5percent Pd/C / methanol / 1 h / 750.06 Torr View Scheme

: 1286729-19-8
1-tert-butoxy-4-(2-tert-butoxyethyl)-2-methoxybenzene

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
With erbium(III) triflate In methanol at 100℃; for 0.75h; Microwave irradiation;

: 5703-24-2
2-(4-hydroxy-3-methoxyphenyl)acetaldehyde

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
With methanol; sodium tetrahydroborate In dichloromethane at -78 - 20℃; for 2h; Inert atmosphere;
With alcohol dehydrogenase (NC_001145.3) from Saccharomyces cerevisiae S288C

lignin acetosolv type: lignin acetosolv type

A: 645-56-7
4-n-Propylphenol

B: 93-51-6
2-Methoxy-4-methylphenol

C: 2785-87-7
2-methoxy-4-n-propylphenol

D: 97-54-1
2-methoxy-4-propenylphenol

E: 2785-89-9
4-Ethylguaiacol

F: 2380-78-1
homovanillyl alcohol

G: 2525-02-2
4-propylbenzene-1,2-diol

H: 120-80-9
benzene-1,2-diol

I: 90-05-1
2-methoxy-phenol

J: 452-86-8
4-methyl-1,2-dihydroxybenzene

Conditions

Conditions	Yield
With 5% palladium on Al2O3; hydrogen In water at 25 - 310℃; under 37503.8 Torr; for 1h; Autoclave;

...Expand

: 501-94-0
p-hydroxyphenethyl alcohol

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium bromide; oxone / acetone; water / 20 °C 2.1: copper(I) bromide / N,N-dimethyl-formamide; methanol 2.2: 100 °C View Scheme
Multi-step reaction with 2 steps 1: sodium bromide; oxone\|\|potassium monopersulfate triple salt / acetone; water / 15 h / 0 °C 2: copper(I) bromide; methanol / N,N-dimethyl-formamide / 3 h / 90 °C View Scheme
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / methanol / 3 h / 20 °C 2.1: copper(I) bromide; sodium methylate / methanol / 15 h / 100 °C 2.2: 12 h / 20 °C View Scheme

: 25379-88-8
2-(3,4-dihydroxyphenyl)acetic acid methyl ester

A: 50602-41-0
2-(3-hydroxy-4-methoxyphenyl)ethanol

B: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid / dichloromethane / 8 h / Inert atmosphere; Darkness; Reflux 2: lithium aluminium tetrahydride / diethyl ether / 3 h / 0 °C / Inert atmosphere 3: Amberlyst 15 / methanol / 8 h / Reflux 4: methyltransferase I from Desulfitobacterium hafniense / methanol / 24 h / 30 °C / pH 6.5 / Inert atmosphere; Glovebox; Enzymatic reaction View Scheme

: 10597-60-1
hydroxytyrosol

: 90-05-1
2-methoxy-phenol

A: 50602-41-0
2-(3-hydroxy-4-methoxyphenyl)ethanol

B: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
With methyltransferase I from Desulfitobacterium hafniense In methanol at 30℃; for 24h; pH=6.5; Solvent; Inert atmosphere; Glovebox; Enzymatic reaction; regioselective reaction;

...Expand

: 38515-62-7
2-(2,2-dimethylbenzo[1,3]dioxol-5-yl)acetic acid methyl ester

A: 50602-41-0
2-(3-hydroxy-4-methoxyphenyl)ethanol

B: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / diethyl ether / 3 h / 0 °C / Inert atmosphere 2: Amberlyst 15 / methanol / 8 h / Reflux 3: methyltransferase I from Desulfitobacterium hafniense / methanol / 24 h / 30 °C / pH 6.5 / Inert atmosphere; Glovebox; Enzymatic reaction View Scheme

: 119054-91-0
2-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)ethan-1-ol

A: 50602-41-0
2-(3-hydroxy-4-methoxyphenyl)ethanol

B: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Amberlyst 15 / methanol / 8 h / Reflux 2: methyltransferase I from Desulfitobacterium hafniense / methanol / 24 h / 30 °C / pH 6.5 / Inert atmosphere; Glovebox; Enzymatic reaction View Scheme

: 102-32-9
3,4-dihydroxyphenylacetate

A: 50602-41-0
2-(3-hydroxy-4-methoxyphenyl)ethanol

B: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: sulfuric acid / 2 h / Inert atmosphere; Darkness; Reflux 2: toluene-4-sulfonic acid / dichloromethane / 8 h / Inert atmosphere; Darkness; Reflux 3: lithium aluminium tetrahydride / diethyl ether / 3 h / 0 °C / Inert atmosphere 4: Amberlyst 15 / methanol / 8 h / Reflux 5: methyltransferase I from Desulfitobacterium hafniense / methanol / 24 h / 30 °C / pH 6.5 / Inert atmosphere; Glovebox; Enzymatic reaction View Scheme

Yield

Multi-step reaction with 5 steps
1: sulfuric acid / 2 h / Inert atmosphere; Darkness; Reflux
2: toluene-4-sulfonic acid / dichloromethane / 8 h / Inert atmosphere; Darkness; Reflux
3: lithium aluminium tetrahydride / diethyl ether / 3 h / 0 °C / Inert atmosphere
4: Amberlyst 15 / methanol / 8 h / Reflux
5: methyltransferase I from Desulfitobacterium hafniense / methanol / 24 h / 30 °C / pH 6.5 / Inert atmosphere; Glovebox; Enzymatic reaction
View Scheme

dewaxed lignin from Chinese quince fruits (Chaenomeles sinensis), extracted at 200 °C over 90 min by 60percent ethanol-water mixture: dewaxed lignin from Chinese quince fruits (Chaenomeles sinensis), extracted at 200 °C over 90 min by 60percent ethanol-water mixture

A: 2033-89-8
3,4-dimethoxyphenol

B: 97-53-0
4-allylguaiacol

C: 91-10-1
1,3-dimethoxy-2-hydroxy-benzene

D: 93-51-6
2-Methoxy-4-methylphenol

E: 2785-87-7
2-methoxy-4-n-propylphenol

F: 934-00-9
3-methocycatechol

G: 634-36-6
1,2,3-trimethoxybenzene

H: 480-66-0
2,4,6-trihydroxyacetophenone

I: 6627-88-9
4-allyl-2,6-dimethoxyphenol

J: 2478-38-8
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

K: 7786-61-0
3-methoxy-4-hydroxystyrene

L: 2785-89-9
4-Ethylguaiacol

M: 2503-46-0
1-(4-hydroxy-3-methoxyphenyl)2-propanone

N: 1509-06-4
1-(2,4,6-trihydroxy-3-methylphenyl)butan-1-one

O: 20481-17-8
3-hydroxy-5-tert-butyl-catechol

P: 2380-78-1
homovanillyl alcohol

Q: 120-80-9
benzene-1,2-diol

R: 90-05-1
2-methoxy-phenol

S: 452-86-8
4-methyl-1,2-dihydroxybenzene

T: 134-96-3
syringic aldehyde

U: 108-95-2
phenol

Conditions

Conditions	Yield
at 500℃; for 0.00555556h; Pyrolysis;

...Expand

dewaxed lignin from Chinese quince fruits (Chaenomeles sinensis), extracted at 240 °C over 90 min by 60percent ethanol-water mixture: dewaxed lignin from Chinese quince fruits (Chaenomeles sinensis), extracted at 240 °C over 90 min by 60percent ethanol-water mixture

A: 97-53-0
4-allylguaiacol

B: 91-10-1
1,3-dimethoxy-2-hydroxy-benzene

C: 93-51-6
2-Methoxy-4-methylphenol

D: 2785-87-7
2-methoxy-4-n-propylphenol

E: 526-75-0
2,3-Dimethylphenol

F: 934-00-9
3-methocycatechol

G: 634-36-6
1,2,3-trimethoxybenzene

H: 7507-89-3
2,6-dihydroxy-4-methoxy-acetophenone

I: 6627-88-9
4-allyl-2,6-dimethoxyphenol

J: 2478-38-8
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

K: 7786-61-0
3-methoxy-4-hydroxystyrene

L: 2785-89-9
4-Ethylguaiacol

M: 2503-46-0
1-(4-hydroxy-3-methoxyphenyl)2-propanone

N: 2380-78-1
homovanillyl alcohol

O: 120-80-9
benzene-1,2-diol

P: 90-05-1
2-methoxy-phenol

Q: 134-96-3
syringic aldehyde

R: 108-95-2
phenol

Conditions

Conditions	Yield
at 500℃; for 0.00555556h; Pyrolysis;

...Expand

: 501-94-0
p-hydroxyphenethyl alcohol

A: 953422-35-0
2-(4'-hydroxy-3'-methoxyphenyl)ethyl methyl carbonate

B: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / methanol / 3 h / 20 °C 2: copper(I) bromide; sodium methylate / methanol / 15 h / 100 °C View Scheme

: 616-38-6
carbonic acid dimethyl ester

: 196081-78-4
3-bromo-4-hydroxyphenylethyl alcohol

: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
Stage #1: carbonic acid dimethyl ester; 3-bromo-4-hydroxyphenylethyl alcohol With sodium methylate; copper(I) bromide In methanol at 100℃; for 15h; Stage #2: With potassium carbonate In methanol at 20℃; for 12h;

: 616-38-6
carbonic acid dimethyl ester

: 196081-78-4
3-bromo-4-hydroxyphenylethyl alcohol

A: 953422-35-0
2-(4'-hydroxy-3'-methoxyphenyl)ethyl methyl carbonate

B: 2380-78-1
homovanillyl alcohol

Conditions

Conditions	Yield
With sodium methylate; copper(I) bromide In methanol at 100℃; for 15h;

...Expand

: 61914-52-1
1-(3,4-dimethoxyphenyl)-5-hydroxydecan-3-one

A: 2380-78-1
homovanillyl alcohol

B: C18H28O5

C: C18H30O5

D: C18H30O5

E: 7417-21-2
2-(3,4-dimethoxyphenyl)ethyl alcohol

Conditions

Conditions	Yield
With Colletotrichum gloeosporioides In water; dimethyl sulfoxide at 30℃; for 120h; Microbiological reaction;

...Expand

: 2380-78-1
homovanillyl alcohol

: 108-24-7
acetic anhydride

: 32022-28-9
4-(2-acetoxyethyl)-2-methoxy-1-acetoxy-benzene

Conditions

Conditions	Yield
In neat (no solvent) Molecular sieve; Microwave irradiation; Green chemistry;	100%
With acetic acid at 50℃;	95%
With acetic acid at 50℃;	95.3%
With pyridine	95%
With acetic acid at 50℃; for 12h;	67%

: 2380-78-1
homovanillyl alcohol

: 616-38-6
carbonic acid dimethyl ester

: 953422-35-0
2-(4'-hydroxy-3'-methoxyphenyl)ethyl methyl carbonate

Conditions

Conditions	Yield
With sulfuric acid for 7h; Reflux;	100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; for 7.5h;	98%

: 2380-78-1
homovanillyl alcohol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1044264-42-7
C21H40O3Si2

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;	100%
With 1H-imidazole

: 2380-78-1
homovanillyl alcohol

: 75-36-5
acetyl chloride

: 2-(4'-hydroxy-3'-methoxyphenyl)ethyl acetate

Conditions

Conditions	Yield
In carbonic acid dimethyl ester at 20℃; for 24h;	100%

: 105-38-4
vinyl propionate

: 2380-78-1
homovanillyl alcohol

: C12H16O4

Conditions

Conditions	Yield
With Candida antarctica lipase In various solvent(s) at 40℃; for 1.5h;	98.1%

: 111-63-7
vinyl stearate

: 2380-78-1
homovanillyl alcohol

: 4-hydroxy-3-methoxyphenethyl stearate

Conditions

Conditions	Yield
With Candida antarctica lipase In various solvent(s) at 40℃; for 4h;	98%

: 2380-78-1
homovanillyl alcohol

: 100-52-7
benzaldehyde

: 6-methoxy-1-phenylisochroman-7-ol

Conditions

Conditions	Yield
With sulfuric acid at 20℃;	98%

: 4704-31-8
vinyl caprate

: 2380-78-1
homovanillyl alcohol

: C19H30O4

Conditions

Conditions	Yield
With Candida antarctica lipase In various solvent(s) at 40℃; for 1.5h;	97.5%

: 2380-78-1
homovanillyl alcohol

: 10597-60-1
hydroxytyrosol

Conditions

Conditions	Yield
With 3-mercaptopropionic acid ethyl ester In aq. buffer at 30℃; for 24h; pH=6.5; Inert atmosphere; Glovebox; Enzymatic reaction;	97%
Stage #1: homovanillyl alcohol With aluminum (III) chloride In ethanethiol at 0 - 20℃; for 42h; Stage #2: With hydrogenchloride; water Cooling with ice;	94.7%
With sodium periodate In water; ethyl acetate Concentration; Reagent/catalyst; Temperature; Solvent; Time;	78%

: 108-05-4
vinyl acetate

: 2380-78-1
homovanillyl alcohol

: 2-(4'-hydroxy-3'-methoxyphenyl)ethyl acetate

Conditions

Conditions	Yield
With Candida antarctica lipase In various solvent(s) at 40℃; for 1h;	96.8%
With Candida antarctica lipase In tert-butyl methyl ether at 40℃; Enzymatic reaction;	96.5%

: 637-59-2
1-Bromo-3-phenylpropane

: 2380-78-1
homovanillyl alcohol

: 2-[3-methoxy-4-(3-phenylpropoxy)phenyl]ethanol

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 7h; Reflux;	95%

: 5963-14-4
8-methylnonanoic acid

: 2380-78-1
homovanillyl alcohol

: 951221-74-2
8-methylnonanoic acid 2-(4-hydroxy-3-methoxyphenyl)ethyl ester

Conditions

Conditions	Yield
novozyme 435 at 50℃; for 16h; Enzymatic reaction; Neat (no solvent);	93.2%

: 2380-78-1
homovanillyl alcohol

: 106-95-6
allyl bromide

: C12H16O3

Conditions

Conditions	Yield
With potassium carbonate In acetone Reflux;	93%

: 2380-78-1
homovanillyl alcohol

: 74-88-4
methyl iodide

: 7417-21-2
2-(3,4-dimethoxyphenyl)ethyl alcohol

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide for 0.5h;	93%

: 24424-99-5
di-tert-butyl dicarbonate

: 2380-78-1
homovanillyl alcohol

: tert-butyl 4-(2-tert-butoxyethyl)-2-methoxyphenyl carbonate

Conditions

Conditions	Yield
With mesoporous silica MCM-41 supported erbium(III) at 40℃; for 9h; Neat (no solvent); ultrasound irradiation; Inert atmosphere;	92%

: 123-20-6
vinyl n-butyrate

: 2380-78-1
homovanillyl alcohol

: C13H18O4

Conditions

Conditions	Yield
With Candida antarctica lipase In various solvent(s) at 40℃; for 1.5h;	90.9%

: 2380-78-1
homovanillyl alcohol

: 2616-64-0
UDP-glucuronic acid

A: 2-[3′-hydroxy-4′-(β-D-glucopyranosyluronic acid)phenyl]ethanol

B: homovanillic alcohol 1-O-β-D-glucuronide

Conditions

Conditions	Yield
With Tris-HCl buffer; calcium chloride; diothiothreitol; benzenesulfonamide; uridine 5'-diphosphoglucuronyl transferases (porcine liver) In water; dimethyl sulfoxide at 35℃; for 6h; pH=8.0; Enzymatic reaction;	A 88% B 6.1%

...Expand

Homovanillyl alcohol Specification

The CAS register number of Homovanillyl alcohol is 2380-78-1. It also can be called as 4-Hydroxy-3-methoxyphenethyl alcohol and the IUPAC name about this chemical is 4-(2-hydroxyethyl)-2-methoxyphenol. It belongs to the following product categories, such as Benzhydrols, Benzyl & Special Alcohols, Alcohols, Anisoles, Alkyloxy Compounds & Phenylacetates, Fluorine Compounds, Bromine Compounds, Iodine Compounds and so on. This chemical is a metabolite of serotonin and norepinephrine.

Physical properties about Homovanillyl alcohol are: (1)ACD/LogP: 0.33; (2)ACD/LogD (pH 5.5): 0.33; (3)ACD/LogD (pH 7.4): 0.33; (4)ACD/BCF (pH 5.5): 1.04; (5)ACD/BCF (pH 7.4): 1.04; (6)ACD/KOC (pH 5.5): 35.9; (7)ACD/KOC (pH 7.4): 35.85; (8)#H bond acceptors: 3; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 5; (11)Polar Surface Area: 27.69Å²; (12)Index of Refraction: 1.558; (13)Molar Refractivity: 45.89 cm³; (14)Molar Volume: 142.1 cm³; (15)Polarizability: 18.19x10^-24cm³; (16)Surface Tension: 46.9 dyne/cm; (17)Enthalpy of Vaporization: 58.93 kJ/mol; (18)Boiling Point: 316.8 °C at 760 mmHg; (19)Vapour Pressure: 0.000169 mmHg at 25°C.

Preparation: this chemical can be prepared by 4-benzyloxy-3-methoxyphenethyl alcohol. This reaction will need reagent H₂, catalyst 5percent Pd/C and solvent methanol. The reaction time is 1 hour(s) with reaction pressure of 750.06. The yield is about 91 %.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: Oc1ccc(cc1OC)CCO
(2)InChI: InChI=1/C9H12O3/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,10-11H,4-5H2,1H3
(3)InChIKey: XHUBSJRBOQIZNI-UHFFFAOYAP
(4)Std. InChI: InChI=1S/C9H12O3/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,10-11H,4-5H2,1H3
(5)Std. InChIKey: XHUBSJRBOQIZNI-UHFFFAOYSA-N

Product Name

Homovanillyl alcohol

Synthetic route

Homovanillyl alcohol Specification

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