Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
Homovanillic acid
Conditions | Yield |
---|---|
With formic acid; phosphoric acid; sodium hydrogensulfite In water at 100℃; under 3750.3 Torr; for 9h; | 71% |
4-Acetoxy-3-methoxyphenylacetaldehyde
A
Homovanillic acid
B
2-(4-acetoxy-3-methoxyphenyl)acetic acid
Conditions | Yield |
---|---|
With potassium permanganate; magnesium sulfate; acetone |
4-(4-acetoxy-3-methoxy-benzylidene)-2-methyl-4H-oxazol-5-one
Homovanillic acid
Conditions | Yield |
---|---|
With sodium hydroxide anschliessend Behandeln mit wss. H2O2; |
Conditions | Yield |
---|---|
With sodium hydroxide |
m-methoxy-p-acetoxy-α-benzoylaminocinnamic acid azlactone
Homovanillic acid
Conditions | Yield |
---|---|
folgend Behandeln mit Wasserstoffperoxyd in Eisessig; |
Conditions | Yield |
---|---|
With potassium hydroxide |
1-benzoyloxy-4-chloromethyl-2-methoxy-benzene
Homovanillic acid
Conditions | Yield |
---|---|
With potassium cyanide anschliessend Erhitzen mit wss. Natronlauge; |
[6]-shogaol
A
Homovanillic acid
Conditions | Yield |
---|---|
for 168h; biotransformation by aspergillus niger; | A 60 mg B 36 mg |
4-benzyloxy-3-methoxyphenylacetic acid
Homovanillic acid
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol |
trans-coniferyl aldehyde
A
methoxyhydroquinone
B
3-methoxy-4-hydroxybenzoic acid
C
Homovanillic acid
D
vanillin
Conditions | Yield |
---|---|
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
magnesium sulfate
acetone
A
Homovanillic acid
B
2-(4-acetoxy-3-methoxyphenyl)acetic acid
Homovanillic acid
Conditions | Yield |
---|---|
With sodium hydroxide man gibt zu der Loesung erst Eisessig und dann H2O2; |
(3-methoxy-4-oxo-cyclohexa-2,5-dienyliden)-acetonitrile
hydrogen iodide
A
Homovanillic acid
Conditions | Yield |
---|---|
5-min. Erhitzen; |
4-amino-butyric acid 2-(4-hydroxy-3-methoxy-phenyl)-2-oxo-ethyl ester
A
Homovanillic acid
B
2,4'-dihydroxy-3'-methoxyacetophenone
C
1-(3-methoxy-4-hydroxyphenyl)ethanone
D
4-amino-n-butyric acid
Conditions | Yield |
---|---|
With water Hydrolysis; reduction; rearrangement; UV-irradiation; |
A
L-glutamic acid
B
Homovanillic acid
C
2,4'-dihydroxy-3'-methoxyacetophenone
D
1-(3-methoxy-4-hydroxyphenyl)ethanone
Conditions | Yield |
---|---|
With water Hydrolysis; rearrangement; reduction; UV-irradiation; |
Conditions | Yield |
---|---|
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
Homovanillic acid
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
Homovanillic acid
Conditions | Yield |
---|---|
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
Homovanillic acid
Conditions | Yield |
---|---|
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
Homovanillic acid
Conditions | Yield |
---|---|
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
Homovanillic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: calcium chloride; thionyl chloride 2: aqueous potassium cyanide / anschliessend Erhitzen mit wss. Natronlauge View Scheme |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 2: KMnO4; water 3: NaOH-solution View Scheme |
2-methoxy-4-((methylamino)methyl)phenol
Homovanillic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dimethylformamide 2: aq. NaOH / 2-methoxy-ethanol View Scheme |
Conditions | Yield |
---|---|
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
A
3-(4-hydroxy-3-methoxyphenyl)acrylic acid
B
3-(3-hydroxyphenyl)-propanoic acid
C
3-(4-hydroxy-3-methoxyphenyl)propionic acid
D
caffeic acid
E
3,4-dihydroxyphenylacetate
F
Homovanillic acid
G
dihydrocaffeic acid
H
danshensu
I
3-(4-hydroxy-3-methoxyphenyl)lactic acid
J
3-(4-hydroxy-3-methoxyphenyl)-2-oxopropanoic acid
Conditions | Yield |
---|---|
With D-glucose In dimethyl sulfoxide at 37℃; aq. buffer; anaerobic atmosphere; Enzymatic reaction; |
methanol
Homovanillic acid
2-(4-hydroxy-3-methoxyphenyl)acetic acid methyl ester
Conditions | Yield |
---|---|
With sulfuric acid for 3h; Reflux; | 100% |
With toluene-4-sulfonic acid | |
With sulfuric acid at 20℃; for 4h; Reflux; |
Homovanillic acid
isopropyl bromide
isopropyl 2-(4-isopropoxy-3-methoxyphenyl)acetate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 24h; Reflux; Inert atmosphere; | 100% |
Homovanillic acid
recorcinol
1-(2,4-dihydroxyphenyl)-2-(4'-hydroxy-3'-methoxyphenyl)ethanone
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With sulfuric acid for 2h; Reflux; | 99% |
With sulfuric acid | 99% |
With sulfuric acid for 2h; Reflux; | 80% |
With sulfuric acid Reflux; | |
With sulfuric acid at 90℃; for 7h; |
Homovanillic acid
tert-butyldimethylsilyl chloride
tert-butyldimethyl 2-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)acetate
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With Agaricus bisporus; oxygen In aq. phosphate buffer; dichloromethane at 25℃; for 24h; pH=7; | 98% |
Homovanillic acid
acetic anhydride
2-(4-acetoxy-3-methoxyphenyl)acetic acid
Conditions | Yield |
---|---|
With sulfuric acid | 97% |
With sulfuric acid Ambient temperature; | 79% |
2-(methylamino)-1-phenylethanol
Homovanillic acid
2-(4-hydroxy-3-methoxy-phenyl)-N-(2-hydroxy-2-phenyl-ethyl)-N-methyl-acetamide
Conditions | Yield |
---|---|
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane | 97% |
Conditions | Yield |
---|---|
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
benzyl bromide
benzyl 2-(4-(benzyloxy)-3-methoxyphenyl)acetate
Conditions | Yield |
---|---|
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
Homovanillic acid
2-(3-methoxy-4-(trifluoromethylsulfonyloxy)phenyl)acetic acid
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; | 95% |
Homovanillic acid
4-Methoxyphenethylamine
2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-methoxyphenyl)ethyl]acetamide
Conditions | Yield |
---|---|
In 5,5-dimethyl-1,3-cyclohexadiene for 16h; Reflux; Inert atmosphere; | 95% |
Homovanillic acid
N-(benzyloxy)octan-1-amine
N-benzyloxy-N-octyl-2-(4-hydroxy-3-methoxyphenyl)acetamide
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 4.5h; Inert atmosphere; | 94% |
Homovanillic acid
O-benzyl-N-heptylhydroxylamine
N-benzyloxy-N-heptyl-2-(4-hydroxy-3-methoxyphenyl)acetamide
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane | 93% |
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
13-acetyl-20-homovanillyl-12-phenylacetyl-4α-phorbol
Conditions | Yield |
---|---|
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 1h; | 91% |
Conditions | Yield |
---|---|
In dichloromethane | 90% |
Conditions | Yield |
---|---|
molecular sieve In dichloromethane | 90% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 15h; |
Homovanillic acid
benzylamine
N-benzyl-4-hydroxy-3-methoxyphenylacetamide
Conditions | Yield |
---|---|
With 4 A molecular sieve at 140 - 150℃; for 3h; | 89% |
Homovanillic acid
3-iodobenzylamine hydrochloride
2-(4-hydroxy-3-methoxyphenyl)-N-(3-iodobenzyl)acetamide
Conditions | Yield |
---|---|
With 1-hydroxy-7-aza-benzotriazole; triethylamine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; | 88% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 70℃; for 4h; | 88% |
methanol
Homovanillic acid
trimethyl orthoformate
2-(4-hydroxy-3-methoxyphenyl)acetic acid methyl ester
Conditions | Yield |
---|---|
With sulfuric acid for 18h; Heating / reflux; | 85% |
3,3-dimethyl-5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-1H-indole
Homovanillic acid
4-(2-{3,3-dimethyl-5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-1H-indol-1-yl}-2-oxoethyl)-2-methoxyphenol
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 0 - 20℃; | 82% |
Conditions | Yield |
---|---|
With magnesium sulfate; novozyme 435 In toluene at 50℃; for 16h; Enzymatic reaction; | 81.5% |
Homovanillic acid
2-(3,4-dimethoxyphenyl)-ethylamine
N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(3-hydroxy-4-methoxyphenyl)acetamide
Conditions | Yield |
---|---|
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
Homovanillic acid
Propyl-2-(4-hydroxy-3-methoxy-phenyl)acetate
Conditions | Yield |
---|---|
With acetyl chloride at 60℃; for 3h; | 78.2% |
With sulfuric acid at 90℃; for 7h; |
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; thiamine diphosphate In tetrahydrofuran at 20℃; Mitsunobu esterification; | 78% |
Conditions | Yield |
---|---|
With sulfuric acid In toluene for 2h; Dean-Stark; Reflux; | 77.3% |
piperidine
Homovanillic acid
2-(4-Hydroxy-3-methoxy-phenyl)-1-piperidin-1-yl-ethanone
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3h; | 75% |
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 °C
Boiling Point: 368.7 °C at 760 mmHg
Density: 1.307 g/cm3
Vapour Pressure: 4.36E-06 mmHg at 25°C
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 (CAS NO.306-08-1) is a major metabolite of catecholamine metabolism. It is used as a reagent for the determination of oxidative enzymes.
Hazard Codes of Homovanillic acid (CAS NO.306-08-1): Xi
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
ASSAY: 98.0% min
Storage: Keep container in a cool, well-ventilated area. Keep container tightly closed.
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