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Acetovanillone
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Name

Acetovanillone

 EINECS 207-854-5
CAS No. 498-02-2 Density 1.158 g/cm3
PSA 46.53000 LogP 1.60340
Solubility soluble in hot water Melting Point 112-115 °C(lit.)
Formula C9H10O3 Boiling Point 297.5 °C at 760 mmHg
Molecular Weight 166.177 Flash Point 125.5 °C
Transport Information N/A Appearance yellowish to brown powder
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 498-02-2 (Acetovanillone) Hazard Symbols IrritantXi
Synonyms

Acetophenone,4'-hydroxy-3'-methoxy- (8CI);1-(4-Hydroxy-3-methoxyphenyl)ethanone;2-Methoxy-4-acetylphenol;3'-Methoxy-4'-hydroxyacetophenone;4-Acetyl-2-methoxyphenol;4-Acetylguaiacol;4-Hydroxy-3-methoxyphenyl methylketone;4'-Hydroxy-3'-methoxyacetophenone;Acetoguaiacon;Acetoguaiacone;Acetoguaicone;Apocynin;Apocynine;

Article Data 87

Acetovanillone Synthetic route

121-34-6

3-methoxy-4-hydroxybenzoic acid

4CH3(1-)*Zn(2+)*Li(1+)

498-02-2

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

Conditions
ConditionsYield
Stage #1: 3-methoxy-4-hydroxybenzoic acid; 4CH3(1-)*Zn(2+)*Li(1+) In tetrahydrofuran; diethyl ether; hexane at 20℃; Schlenk technique; Inert atmosphere;
Stage #2: With iodine In tetrahydrofuran; diethyl ether; hexane at 20℃; Solvent; Schlenk technique; Inert atmosphere; chemoselective reaction;		96%
7382-68-5

1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethanol

A

90-05-1

2-methoxy-phenol

B

498-02-2

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

Conditions
ConditionsYield
With sodium tetrahydroborate; palladium on activated charcoal In water; ethyl acetate at 80℃; for 14h;A n/a
B 96%
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere;A 86%
B 82%
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere; Green chemistry;A 86%
B 82%
With C22H17Cl3N3ORh; sodium hydroxide In water for 60h; Inert atmosphere;
613-70-7

2-methoxyphenyl acetate

498-02-2

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

Conditions
ConditionsYield
With aluminum (III) chloride In nitrobenzene at 40℃; for 3h; Reagent/catalyst; Temperature; Large scale;90.23%
With methanesulfonic acid In dichloromethane under 15751.6 Torr; Reagent/catalyst; Fries Phenol Ester Rearrangement; Flow reactor;75%
With methanesulfonic acid; phosphorus pentoxide at 90℃; for 5h; Fries rearrangement;67%
22317-35-7

1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethan-1-one

A

90-05-1

2-methoxy-phenol

B

498-02-2

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

Conditions
ConditionsYield
With formic acid; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation;A 84%
B 78%
With RuH2(CO)(PPh3)3; hydrogen; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In (2)H8-toluene at 135℃; under 760.051 Torr; for 20h;
1197-09-7

1-(3,4-dihydroxyphenyl)ethan-1-one

74-88-4

methyl iodide

A

6100-74-9

3-hydroxy-4-methoxyacetophenone

B

498-02-2

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

C

1131-62-0

1-(3,4-dimethoxyphenyl)ethanone

Conditions
ConditionsYield
With lithium carbonate In N,N-dimethyl-formamide at 55℃; for 18h; Inert atmosphere; chemoselective reaction;A 84%
B 6%
C 4%

C29H37NO8

A

2150-38-1

methyl 3,4-dimethoxybenzoate

B

C19H18O7

C

498-02-2

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

Conditions
ConditionsYield
With sulfuric acid In methanol at 80℃; for 1h;A 80%
B 5%
C 83%
91-16-7

1,2-dimethoxybenzene

75-36-5

acetyl chloride

498-02-2

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

Conditions
ConditionsYield
With ytterbium(III) triflate In carbon disulfide for 6h; Friedel-Crafts reaction; Heating;79%
1445875-26-2

C18H30O3Si

498-02-2

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

Conditions
ConditionsYield
With water; acetic acid; N,N,N',N'-tetramethylguanidine In tetrahydrofuran; acetonitrile at 20℃;75%
With acetic acid In tetrahydrofuran; water; acetonitrile at 20℃; for 12h; pH=7.5;63%
84272-48-0

4-hydroxy-3-methoxybenzoylacetic acid

498-02-2

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

Conditions
ConditionsYield
With sulfuric acid Heating;66%
132255-78-8

4'-tert-butyldimethylsilyloxy-3'-methoxyacetophenone

498-02-2

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

Conditions
ConditionsYield
With acetic acid In tetrahydrofuran; water; acetonitrile at 20℃; for 12h; pH=7.5;63%
With water; acetic acid; N,N,N',N'-tetramethylguanidine In tetrahydrofuran; acetonitrile at 20℃;63%

Acetovanillone Chemical Properties

Molecular Structure of Acetovanillone (CAS NO.498-02-2):

IUPAC Name: 1-(4-hydroxy-3-methoxyphenyl)ethanone
CAS: 498-02-2
Molecular Formula: C9H10O3
Molecular Weight: 166.17
EINECS: 207-854-5
Melting point: 112-115 °C(lit.)
Boiling point: 263-265 °C17 mm Hg(lit.)
Flash point: >230 °F
Water Solubility: soluble in hot water
Merck:  14,741
BRN:  637373
Index of Refraction: 1.537
Molar Refractivity: 44.84 cm3
Molar Volume: 143.3 cm3
Polarizability: 17.77*10-24cm3
Surface Tension: 41.5 dyne/cm
Density: 1.158 g/cm3
Enthalpy of Vaporization: 55.89 kJ/mol
Vapour Pressure: 0.000759 mmHg at 25°C
InChI
InChI=1/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3
Smiles
c1(cc(ccc1O)C(C)=O)OC
Product Categories: Fine chemical & intermediates; Aromatic Acetophenones & Derivatives (substituted); pharmacetical; Adehydes, Acetals & Ketones; Anisoles, Alkyloxy Compounds & Phenylacetates; Phenols

Acetovanillone Uses

 Acetovanillone (CAS NO.498-02-2) is a plant-derived, cartilage-saving drug which might be mainly used in the treatment of rheumatoid arthritis.

Acetovanillone Toxicity Data With Reference

1.    

mmo-smc 400 mg/L

     MUREAV    Mutation Research. 119 (1983),272.
2.    

orl-mus LD50:9 g/kg

     BCTKAG    Bromatologia i Chemia Toksykologiczna. 14 (1984),301.
3.    

ipr-mus LD50:650 mg/kg

     JMCMAR    Journal of Medicinal Chemistry. 7 (1964),178.

Acetovanillone Consensus Reports

Reported in EPA TSCA Inventory.

Acetovanillone Safety Profile

Moderately toxic by intraperitoneal route. Mildly toxic by ingestion. Mutation data reported. When heated to decomposition it emits acrid smoke and fumes.
Hazard Codes: 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: 2
HS Code: 29145000

Acetovanillone Specification

 Acetovanillone (CAS NO.498-02-2) is also named as 4-Hydroxy-3-methoxyacetophenone ; Apocynin ; Acetovanillone~Apocynin ; 4-Hydroxy-3-methoxybenzoic acid ; 3-Methoxy-4-Hydroxy Acetophenone and so on. It is usually light yellow to yellow solid with faint vanilla odor.

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