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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 | Hazard Symbols | Xi | |
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 |
Conditions | Yield |
---|---|
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% |
1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethanol
A
2-methoxy-phenol
B
1-(3-methoxy-4-hydroxyphenyl)ethanone
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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% |
1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethan-1-one
A
2-methoxy-phenol
B
1-(3-methoxy-4-hydroxyphenyl)ethanone
Conditions | Yield |
---|---|
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; |
1-(3,4-dihydroxyphenyl)ethan-1-one
methyl iodide
A
3-hydroxy-4-methoxyacetophenone
B
1-(3-methoxy-4-hydroxyphenyl)ethanone
C
1-(3,4-dimethoxyphenyl)ethanone
Conditions | Yield |
---|---|
With lithium carbonate In N,N-dimethyl-formamide at 55℃; for 18h; Inert atmosphere; chemoselective reaction; | A 84% B 6% C 4% |
Conditions | Yield |
---|---|
With sulfuric acid In methanol at 80℃; for 1h; | A 80% B 5% C 83% |
Conditions | Yield |
---|---|
With ytterbium(III) triflate In carbon disulfide for 6h; Friedel-Crafts reaction; Heating; | 79% |
C18H30O3Si
1-(3-methoxy-4-hydroxyphenyl)ethanone
Conditions | Yield |
---|---|
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% |
4-hydroxy-3-methoxybenzoylacetic acid
1-(3-methoxy-4-hydroxyphenyl)ethanone
Conditions | Yield |
---|---|
With sulfuric acid Heating; | 66% |
4'-tert-butyldimethylsilyloxy-3'-methoxyacetophenone
1-(3-methoxy-4-hydroxyphenyl)ethanone
Conditions | Yield |
---|---|
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% |
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 (CAS NO.498-02-2) is a plant-derived, cartilage-saving drug which might be mainly used in the treatment of rheumatoid arthritis.
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. |
Reported in EPA TSCA Inventory.
Moderately toxic by intraperitoneal route. Mildly toxic by ingestion. Mutation data reported. When heated to decomposition it emits acrid smoke and fumes.
Hazard Codes: 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: 2
HS Code: 29145000
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.