Product Name

  • Name

    Homovanillic acid

  • EINECS 206-176-7
  • CAS No. 306-08-1
  • Article Data40
  • CAS DataBase
  • Density 1.307 g/cm3
  • Solubility Soluble in water
  • Melting Point 142-145 °C(lit.)
  • Formula C9H10O4
  • Boiling Point 368.7 °C at 760 mmHg
  • Molecular Weight 182.176
  • Flash Point 151.9 °C
  • Transport Information
  • Appearance white to beige crystalline powder
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 306-08-1 (Homovanillic acid)
  • Hazard Symbols IrritantXi
  • Synonyms Aceticacid, (4-hydroxy-3-methoxyphenyl)- (6CI,8CI);(4-Hydroxy-3-methoxyphenyl)aceticacid;3-Methoxy-4-hydroxyphenylacetic acid;4-Hydroxy-3-methoxybenzeneaceticacid;HVA;NSC 16682;Vanilacetic acid;
  • PSA 66.76000
  • LogP 1.02790

Synthetic route

4-hydroxy-3-methoxyphenylacetonitrile
4468-59-1

4-hydroxy-3-methoxyphenylacetonitrile

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 80℃; for 48h; Inert atmosphere;89%
With potassium hydroxide In ethanol Heating;74%
With sodium hydroxide In 2-methoxy-ethanol
4-hydroxy-3-methoxy-mandelic acid
55-10-7

4-hydroxy-3-methoxy-mandelic acid

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
With hydrogenchloride; tin(ll) chloride In water at 80℃; for 4h;88%
75%
With 5%-palladium/activated carbon; hydrogen; acetic acid In water
3-methoxy-4-hydroxy mandelic acid
13244-77-4

3-methoxy-4-hydroxy mandelic acid

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
With formic acid; phosphoric acid; sodium hydrogensulfite In water at 100℃; under 3750.3 Torr; for 9h;71%
4-Acetoxy-3-methoxyphenylacetaldehyde
6391-59-9

4-Acetoxy-3-methoxyphenylacetaldehyde

A

Homovanillic acid
306-08-1

Homovanillic acid

B

2-(4-acetoxy-3-methoxyphenyl)acetic acid
5447-38-1

2-(4-acetoxy-3-methoxyphenyl)acetic acid

Conditions
ConditionsYield
With potassium permanganate; magnesium sulfate; acetone
4-(4-acetoxy-3-methoxy-benzylidene)-2-methyl-4H-oxazol-5-one
60470-82-8, 39600-31-2

4-(4-acetoxy-3-methoxy-benzylidene)-2-methyl-4H-oxazol-5-one

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
With sodium hydroxide anschliessend Behandeln mit wss. H2O2;
2-(4-acetoxy-3-methoxyphenyl)acetic acid
5447-38-1

2-(4-acetoxy-3-methoxyphenyl)acetic acid

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
With sodium hydroxide
m-methoxy-p-acetoxy-α-benzoylaminocinnamic acid azlactone
18692-68-7, 71413-82-6, 74857-79-7

m-methoxy-p-acetoxy-α-benzoylaminocinnamic acid azlactone

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
folgend Behandeln mit Wasserstoffperoxyd in Eisessig;
(4-acetoxy-3-methoxy-phenyl)-acetonitrile
5438-51-7

(4-acetoxy-3-methoxy-phenyl)-acetonitrile

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
With potassium hydroxide
1-benzoyloxy-4-chloromethyl-2-methoxy-benzene
873376-14-8

1-benzoyloxy-4-chloromethyl-2-methoxy-benzene

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
With potassium cyanide anschliessend Erhitzen mit wss. Natronlauge;

A

Homovanillic acid
306-08-1

Homovanillic acid

B

5-[2-(4-Hydroxy-3-methoxy-phenyl)-ethyl]-dihydro-furan-2-one

5-[2-(4-Hydroxy-3-methoxy-phenyl)-ethyl]-dihydro-furan-2-one

Conditions
ConditionsYield
for 168h; biotransformation by aspergillus niger;A 60 mg
B 36 mg
4-benzyloxy-3-methoxyphenylacetic acid
29973-91-9

4-benzyloxy-3-methoxyphenylacetic acid

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol
trans-coniferyl aldehyde
458-36-6

trans-coniferyl aldehyde

A

methoxyhydroquinone
824-46-4

methoxyhydroquinone

B

3-methoxy-4-hydroxybenzoic acid
121-34-6

3-methoxy-4-hydroxybenzoic acid

C

Homovanillic acid
306-08-1

Homovanillic acid

D

vanillin
121-33-5

vanillin

Conditions
ConditionsYield
With peracetic acid In ethanol for 1h; pH=7; Product distribution; Further Variations:; Reagents; Oxidation;A 10.1 % Chromat.
B 13.6 % Chromat.
C 10.9 % Chromat.
D 7.1 % Chromat.
4-Acetoxy-3-methoxyphenylacetaldehyde
6391-59-9

4-Acetoxy-3-methoxyphenylacetaldehyde

magnesium sulfate
7487-88-9

magnesium sulfate

acetone
67-64-1

acetone

KMnO4

KMnO4

A

Homovanillic acid
306-08-1

Homovanillic acid

B

2-(4-acetoxy-3-methoxyphenyl)acetic acid
5447-38-1

2-(4-acetoxy-3-methoxyphenyl)acetic acid

azlactone of/the/ 3-methoxy-4-acetoxy-α-benzamino-cinnamic acid

azlactone of/the/ 3-methoxy-4-acetoxy-α-benzamino-cinnamic acid

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
With sodium hydroxide man gibt zu der Loesung erst Eisessig und dann H2O2;
(3-methoxy-4-oxo-cyclohexa-2,5-dienyliden)-acetonitrile
91054-36-3

(3-methoxy-4-oxo-cyclohexa-2,5-dienyliden)-acetonitrile

hydrogen iodide
10034-85-2

hydrogen iodide

A

Homovanillic acid
306-08-1

Homovanillic acid

B

2,3-bis-(4-hydroxy-3-methoxy-phenyl)-succinonitrile

2,3-bis-(4-hydroxy-3-methoxy-phenyl)-succinonitrile

Conditions
ConditionsYield
5-min. Erhitzen;
4-amino-butyric acid 2-(4-hydroxy-3-methoxy-phenyl)-2-oxo-ethyl ester
284043-11-4

4-amino-butyric acid 2-(4-hydroxy-3-methoxy-phenyl)-2-oxo-ethyl ester

A

Homovanillic acid
306-08-1

Homovanillic acid

B

2,4'-dihydroxy-3'-methoxyacetophenone
18256-48-9

2,4'-dihydroxy-3'-methoxyacetophenone

C

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

D

4-amino-n-butyric acid
56-12-2

4-amino-n-butyric acid

Conditions
ConditionsYield
With water Hydrolysis; reduction; rearrangement; UV-irradiation;
γ-O-(4-hydroxy-3-methoxyphenacetyl) L-glutamate, trifuoroacetate salt

γ-O-(4-hydroxy-3-methoxyphenacetyl) L-glutamate, trifuoroacetate salt

A

L-glutamic acid
56-86-0

L-glutamic acid

B

Homovanillic acid
306-08-1

Homovanillic acid

C

2,4'-dihydroxy-3'-methoxyacetophenone
18256-48-9

2,4'-dihydroxy-3'-methoxyacetophenone

D

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With water Hydrolysis; rearrangement; reduction; UV-irradiation;
4-hydroxymethyl-2-methoxyphenol
498-00-0

4-hydroxymethyl-2-methoxyphenol

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 percent / dimethylformamide / 20 h / 130 °C
2: 74 percent / KOH / ethanol / Heating
View Scheme
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 24 h / 120 °C / Inert atmosphere
2: sodium hydroxide / ethanol; water / 48 h / 80 °C / Inert atmosphere
View Scheme
α-bromo-3-methoxy-4-hydroxyacetophenone
69638-06-8

α-bromo-3-methoxy-4-hydroxyacetophenone

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: DBU / dioxane / 12 h / 0 - 20 °C
2: TFA / 4 h / 0 °C
3: H2O / UV-irradiation
View Scheme
Multi-step reaction with 3 steps
1: 57 percent / DBU / benzene / 12 h / 20 °C
2: 95.3 percent / TFA / 4 h / 0 °C
3: H2O / UV-irradiation
View Scheme
1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 47 percent / cupric bromide / CHCl3; ethyl acetate / 4 h / 20 °C
2: DBU / dioxane / 12 h / 0 - 20 °C
3: TFA / 4 h / 0 °C
4: H2O / UV-irradiation
View Scheme
Multi-step reaction with 4 steps
1: 47 percent / cupric bromide / CHCl3; ethyl acetate / 4 h / 20 °C
2: 57 percent / DBU / benzene / 12 h / 20 °C
3: 95.3 percent / TFA / 4 h / 0 °C
4: H2O / UV-irradiation
View Scheme
2-(4-hydroxy-3-methoxyphenyl)-2-oxoethyl-4-[(tert-butoxycarbonyl)amino]butanoate
284043-13-6

2-(4-hydroxy-3-methoxyphenyl)-2-oxoethyl-4-[(tert-butoxycarbonyl)amino]butanoate

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TFA / 4 h / 0 °C
2: H2O / UV-irradiation
View Scheme
γ-O-(4-hydroxy-3-methoxyphenacetyl) t-butyl N-t-boc L-glutamate
284043-05-6

γ-O-(4-hydroxy-3-methoxyphenacetyl) t-butyl N-t-boc L-glutamate

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95.3 percent / TFA / 4 h / 0 °C
2: H2O / UV-irradiation
View Scheme
methyl 4-benzyloxy-3-methoxyphenylethanoate
16209-54-4

methyl 4-benzyloxy-3-methoxyphenylethanoate

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 10percent KOH / methanol; H2O
2: H2 / 10percent Pd-C / aq. ethanol
View Scheme
4-(hydroxymethyl)-2-methoxyphenyl benzoate
174840-51-8

4-(hydroxymethyl)-2-methoxyphenyl benzoate

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: calcium chloride; thionyl chloride
2: aqueous potassium cyanide / anschliessend Erhitzen mit wss. Natronlauge
View Scheme
eugenol acetate
93-28-7

eugenol acetate

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethyl acetate; ozone / und anschliesende Hydrierung an Palladium/Kohle
2: potassium permanganate; magnesium sulfate; aqueous acetone
View Scheme
Multi-step reaction with 2 steps
1: KMnO4; water
2: NaOH-solution
View Scheme
4-allylguaiacol
97-53-0

4-allylguaiacol

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
2: KMnO4; water
3: NaOH-solution
View Scheme
2-methoxy-4-((methylamino)methyl)phenol
42973-53-5

2-methoxy-4-((methylamino)methyl)phenol

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethylformamide
2: aq. NaOH / 2-methoxy-ethanol
View Scheme
vanillin
121-33-5

vanillin

Homovanillic acid
306-08-1

Homovanillic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (i) EtOH, (ii) H2, PtO2
2: dimethylformamide
3: aq. NaOH / 2-methoxy-ethanol
View Scheme
Multi-step reaction with 3 steps
1: sodium tetrahydroborate / methanol / 24.5 h / 0 - 20 °C / Inert atmosphere
2: N,N-dimethyl-formamide / 24 h / 120 °C / Inert atmosphere
3: sodium hydroxide / ethanol; water / 48 h / 80 °C / Inert atmosphere
View Scheme
8-O-4′-diferulic acid
215872-63-2

8-O-4′-diferulic acid

A

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

3-(4-hydroxy-3-methoxyphenyl)acrylic acid

B

3-(3-hydroxyphenyl)-propanoic acid
621-54-5

3-(3-hydroxyphenyl)-propanoic acid

C

3-(4-hydroxy-3-methoxyphenyl)propionic acid
1135-23-5

3-(4-hydroxy-3-methoxyphenyl)propionic acid

D

caffeic acid
331-39-5

caffeic acid

E

3,4-dihydroxyphenylacetate
102-32-9

3,4-dihydroxyphenylacetate

F

Homovanillic acid
306-08-1

Homovanillic acid

G

dihydrocaffeic acid
1078-61-1

dihydrocaffeic acid

H

danshensu
23028-17-3

danshensu

I

3-(4-hydroxy-3-methoxyphenyl)lactic acid
2475-56-1

3-(4-hydroxy-3-methoxyphenyl)lactic acid

J

3-(4-hydroxy-3-methoxyphenyl)-2-oxopropanoic acid
1081-71-6

3-(4-hydroxy-3-methoxyphenyl)-2-oxopropanoic acid

Conditions
ConditionsYield
With D-glucose In dimethyl sulfoxide at 37℃; aq. buffer; anaerobic atmosphere; Enzymatic reaction;
methanol
67-56-1

methanol

Homovanillic acid
306-08-1

Homovanillic acid

2-(4-hydroxy-3-methoxyphenyl)acetic acid methyl ester
15964-80-4

2-(4-hydroxy-3-methoxyphenyl)acetic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid for 3h; Reflux;100%
With toluene-4-sulfonic acid
With sulfuric acid at 20℃; for 4h; Reflux;
Homovanillic acid
306-08-1

Homovanillic acid

isopropyl bromide
75-26-3

isopropyl bromide

isopropyl 2-(4-isopropoxy-3-methoxyphenyl)acetate
1256581-67-5

isopropyl 2-(4-isopropoxy-3-methoxyphenyl)acetate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 24h; Reflux; Inert atmosphere;100%
Homovanillic acid
306-08-1

Homovanillic acid

recorcinol
108-46-3

recorcinol

1-(2,4-dihydroxyphenyl)-2-(4'-hydroxy-3'-methoxyphenyl)ethanone
40456-49-3

1-(2,4-dihydroxyphenyl)-2-(4'-hydroxy-3'-methoxyphenyl)ethanone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate at 60 - 70℃; for 1h;99%
With bis(trifluoromethanesulfonyl)amide In various solvent(s) at 90℃; for 0.0666667h; Friedel-Crafts reaction; microwave irradiation;70%
With boron trifluoride diethyl etherate In N,N-dimethyl-formamide at 120℃; for 0.166667h; Friedel-Crafts reaction;57%
ethanol
64-17-5

ethanol

Homovanillic acid
306-08-1

Homovanillic acid

ethyl homovanillate
60563-13-5

ethyl homovanillate

Conditions
ConditionsYield
With sulfuric acid for 2h; Reflux;99%
With sulfuric acid99%
With sulfuric acid for 2h; Reflux;80%
With sulfuric acid Reflux;
With sulfuric acid at 90℃; for 7h;
Homovanillic acid
306-08-1

Homovanillic acid

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

tert-butyldimethyl 2-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)acetate
78324-15-9

tert-butyldimethyl 2-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)acetate

Conditions
ConditionsYield
With 1H-imidazole In tetrahydrofuran at 20℃; for 14h; Inert atmosphere;98%
With 1H-imidazole In tetrahydrofuran at 20℃; for 14h; Inert atmosphere;64%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 3h;
Homovanillic acid
306-08-1

Homovanillic acid

2-(3,4-dihydroxy-5-methoxyphenyl)acetic acid
2989-10-8

2-(3,4-dihydroxy-5-methoxyphenyl)acetic acid

Conditions
ConditionsYield
With Agaricus bisporus; oxygen In aq. phosphate buffer; dichloromethane at 25℃; for 24h; pH=7;98%
Homovanillic acid
306-08-1

Homovanillic acid

acetic anhydride
108-24-7

acetic anhydride

2-(4-acetoxy-3-methoxyphenyl)acetic acid
5447-38-1

2-(4-acetoxy-3-methoxyphenyl)acetic acid

Conditions
ConditionsYield
With sulfuric acid97%
With sulfuric acid Ambient temperature;79%
2-(methylamino)-1-phenylethanol
68579-60-2

2-(methylamino)-1-phenylethanol

Homovanillic acid
306-08-1

Homovanillic acid

2-(4-hydroxy-3-methoxy-phenyl)-N-(2-hydroxy-2-phenyl-ethyl)-N-methyl-acetamide
749247-36-7

2-(4-hydroxy-3-methoxy-phenyl)-N-(2-hydroxy-2-phenyl-ethyl)-N-methyl-acetamide

Conditions
ConditionsYield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane97%
4-Methylbenzyl alcohol
589-18-4

4-Methylbenzyl alcohol

Homovanillic acid
306-08-1

Homovanillic acid

1-(4-hydroxy-3-methoxyphenyl)-3-(4-methylphenyl)propan-2-one

1-(4-hydroxy-3-methoxyphenyl)-3-(4-methylphenyl)propan-2-one

Conditions
ConditionsYield
Stage #1: 4-Methylbenzyl alcohol; Homovanillic acid With dmap; dicyclohexyl-carbodiimide In 1,2-dichloro-ethane at 55℃; for 4h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran for 2h; Temperature; Inert atmosphere; Cooling with ice;
96.8%
Homovanillic acid
306-08-1

Homovanillic acid

benzyl bromide
100-39-0

benzyl bromide

benzyl 2-(4-(benzyloxy)-3-methoxyphenyl)acetate
65340-85-4

benzyl 2-(4-(benzyloxy)-3-methoxyphenyl)acetate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 4h; Reflux;95%
With potassium carbonate In acetonitrile at 80℃; for 8h;88%
With sodium In methanol
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

Homovanillic acid
306-08-1

Homovanillic acid

2-(3-methoxy-4-(trifluoromethylsulfonyloxy)phenyl)acetic acid
1243245-99-9

2-(3-methoxy-4-(trifluoromethylsulfonyloxy)phenyl)acetic acid

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃;95%
Homovanillic acid
306-08-1

Homovanillic acid

4-Methoxyphenethylamine
55-81-2

4-Methoxyphenethylamine

2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-methoxyphenyl)ethyl]acetamide
1395084-66-8

2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-methoxyphenyl)ethyl]acetamide

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene for 16h; Reflux; Inert atmosphere;95%
Homovanillic acid
306-08-1

Homovanillic acid

N-(benzyloxy)octan-1-amine
122149-21-7

N-(benzyloxy)octan-1-amine

N-benzyloxy-N-octyl-2-(4-hydroxy-3-methoxyphenyl)acetamide
1400943-51-2

N-benzyloxy-N-octyl-2-(4-hydroxy-3-methoxyphenyl)acetamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 4.5h; Inert atmosphere;94%
Homovanillic acid
306-08-1

Homovanillic acid

O-benzyl-N-heptylhydroxylamine
112151-61-8

O-benzyl-N-heptylhydroxylamine

N-benzyloxy-N-heptyl-2-(4-hydroxy-3-methoxyphenyl)acetamide
1400943-49-8

N-benzyloxy-N-heptyl-2-(4-hydroxy-3-methoxyphenyl)acetamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane93%
Homovanillic acid
306-08-1

Homovanillic acid

Phenyl-acetic acid (1aR,1bS,4aS,7aS,7bS,8R,9R,9aS)-9a-acetoxy-4a,7b-dihydroxy-3-hydroxymethyl-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl ester
850163-67-6

Phenyl-acetic acid (1aR,1bS,4aS,7aS,7bS,8R,9R,9aS)-9a-acetoxy-4a,7b-dihydroxy-3-hydroxymethyl-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl ester

13-acetyl-20-homovanillyl-12-phenylacetyl-4α-phorbol
777859-96-8

13-acetyl-20-homovanillyl-12-phenylacetyl-4α-phorbol

Conditions
ConditionsYield
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 1h;91%
Å molecular sieve

Å molecular sieve

Homovanillic acid
306-08-1

Homovanillic acid

3-(3,4-dimethylphenyl)propylamine
142332-70-5

3-(3,4-dimethylphenyl)propylamine

KR-25003
142333-36-6

KR-25003

Conditions
ConditionsYield
In dichloromethane90%
Homovanillic acid
306-08-1

Homovanillic acid

3-(3,4-dimethylphenyl)propylamine
142332-70-5

3-(3,4-dimethylphenyl)propylamine

KR-25003
142333-36-6

KR-25003

Conditions
ConditionsYield
molecular sieve In dichloromethane90%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 15h;
Homovanillic acid
306-08-1

Homovanillic acid

benzylamine
100-46-9

benzylamine

N-benzyl-4-hydroxy-3-methoxyphenylacetamide
391609-30-6

N-benzyl-4-hydroxy-3-methoxyphenylacetamide

Conditions
ConditionsYield
With 4 A molecular sieve at 140 - 150℃; for 3h;89%
Homovanillic acid
306-08-1

Homovanillic acid

3-iodobenzylamine hydrochloride
3718-88-5

3-iodobenzylamine hydrochloride

2-(4-hydroxy-3-methoxyphenyl)-N-(3-iodobenzyl)acetamide
873099-30-0

2-(4-hydroxy-3-methoxyphenyl)-N-(3-iodobenzyl)acetamide

Conditions
ConditionsYield
With 1-hydroxy-7-aza-benzotriazole; triethylamine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;88%
Homovanillic acid
306-08-1

Homovanillic acid

2-(3-methoxyphenyl)-1-ethanamine
2039-67-0

2-(3-methoxyphenyl)-1-ethanamine

2-(4-hydroxy-3-methoxyphenyl)-N-[2-(3-methoxyphenyl)ethyl]acetamide

2-(4-hydroxy-3-methoxyphenyl)-N-[2-(3-methoxyphenyl)ethyl]acetamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 70℃; for 4h;88%
methanol
67-56-1

methanol

Homovanillic acid
306-08-1

Homovanillic acid

trimethyl orthoformate
149-73-5

trimethyl orthoformate

2-(4-hydroxy-3-methoxyphenyl)acetic acid methyl ester
15964-80-4

2-(4-hydroxy-3-methoxyphenyl)acetic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid for 18h; Heating / reflux;85%
3,3-dimethyl-5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-1H-indole
844901-56-0

3,3-dimethyl-5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-1H-indole

Homovanillic acid
306-08-1

Homovanillic acid

4-(2-{3,3-dimethyl-5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-1H-indol-1-yl}-2-oxoethyl)-2-methoxyphenol
847064-35-1

4-(2-{3,3-dimethyl-5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-1H-indol-1-yl}-2-oxoethyl)-2-methoxyphenol

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 0 - 20℃;82%
8-methyl-1-nonanol
55505-26-5

8-methyl-1-nonanol

Homovanillic acid
306-08-1

Homovanillic acid

8-methylnonyl homovanillate
951221-76-4

8-methylnonyl homovanillate

Conditions
ConditionsYield
With magnesium sulfate; novozyme 435 In toluene at 50℃; for 16h; Enzymatic reaction;81.5%
Homovanillic acid
306-08-1

Homovanillic acid

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(3-hydroxy-4-methoxyphenyl)acetamide
361389-65-3

N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(3-hydroxy-4-methoxyphenyl)acetamide

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;79%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;79%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;
propan-1-ol
71-23-8

propan-1-ol

Homovanillic acid
306-08-1

Homovanillic acid

Propyl-2-(4-hydroxy-3-methoxy-phenyl)acetate
52744-26-0

Propyl-2-(4-hydroxy-3-methoxy-phenyl)acetate

Conditions
ConditionsYield
With acetyl chloride at 60℃; for 3h;78.2%
With sulfuric acid at 90℃; for 7h;
2-phenylethanol
60-12-8

2-phenylethanol

Homovanillic acid
306-08-1

Homovanillic acid

2-phenylethyl 2-(4-hydroxy-3-methoxyphenyl)acetate

2-phenylethyl 2-(4-hydroxy-3-methoxyphenyl)acetate

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; thiamine diphosphate In tetrahydrofuran at 20℃; Mitsunobu esterification;78%
2-Phenoxyethanol
122-99-6

2-Phenoxyethanol

Homovanillic acid
306-08-1

Homovanillic acid

2-phenoxyethyl 2-(4-hydroxy-3-methoxyphenyl)acetate

2-phenoxyethyl 2-(4-hydroxy-3-methoxyphenyl)acetate

Conditions
ConditionsYield
With sulfuric acid In toluene for 2h; Dean-Stark; Reflux;77.3%
piperidine
110-89-4

piperidine

Homovanillic acid
306-08-1

Homovanillic acid

2-(4-Hydroxy-3-methoxy-phenyl)-1-piperidin-1-yl-ethanone
53283-49-1

2-(4-Hydroxy-3-methoxy-phenyl)-1-piperidin-1-yl-ethanone

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3h;75%

Homovanillic acid Chemical Properties

IUPAC Name: 2-(4-Hydroxy-3-methoxyphenyl)acetic acid 
Molecular Structure:
 
Molecular Formula: C9H10O4
Molecular Weight: 182.1733 
Synonyms of Homovanillic acid (CAS NO.306-08-1): Acetic acid, (4-hydroxy-3-methoxyphenyl)-; Vanilacetic acid; 4-hydroxy-3-methoxy-benzeneaceticaci; 4-hydroxy-3-methoxy-Benzeneaceticacid; Vanillacetic Acid
Melting Point: 142-145 °C(lit.)
Flash Point: 151.9 °
Boiling Point: 368.7 °C at 760 mmHg
Density: 1.307 g/cm3 
Vapour Pressure: 4.36E-06 mmHg at 25°
Index of Refraction: 1.573 
Storage temp.: Store at RT.
Water Solubility: soluble
Solvent Solubility: soluble in benzene, slightly soluble in alcohol, ether, insoluble in cyclohexane
Appearance: almost a white to brown-gray powder.

Homovanillic acid Uses

 Homovanillic acid (CAS NO.306-08-1) is a major metabolite of catecholamine metabolism. It is used as a reagent for the determination of oxidative enzymes.

Homovanillic acid Safety Profile

Hazard Codes of Homovanillic acid (CAS NO.306-08-1): IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing.
WGK Germany: 3
F: 10-23
TSCA: T
HazardClas:s IRRITANT

Homovanillic acid Standards and Recommendations

ASSAY: 98.0% min

Homovanillic acid Specification

Storage: Keep container in a cool, well-ventilated area. Keep container tightly closed.

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