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| CAS No.: | 498-02-2 |
|---|---|
| Name: | Acetovanillone |
| Article Data: | 87 |
| Molecular Structure: | |
|
|
|
| Formula: | C9H10O3 |
| Molecular Weight: | 166.177 |
| 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; |
| EINECS: | 207-854-5 |
| Density: | 1.158 g/cm3 |
| Melting Point: | 112-115 °C(lit.) |
| Boiling Point: | 297.5 °C at 760 mmHg |
| Flash Point: | 125.5 °C |
| Solubility: | soluble in hot water |
| Appearance: | yellowish to brown powder |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 26-36 |
| PSA: | 46.53000 |
| LogP: | 1.60340 |
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| 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% |
- 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 | 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% |
- 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 | 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; |
- 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 | 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% |
- 1445875-26-2
C18H30O3Si
- 498-02-2
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% |
- 84272-48-0
4-hydroxy-3-methoxybenzoylacetic acid
- 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone
| Conditions | Yield |
|---|---|
| With sulfuric acid Heating; | 66% |
- 132255-78-8
4'-tert-butyldimethylsilyloxy-3'-methoxyacetophenone
- 498-02-2
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% |
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Chemistry
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
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.
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. |
Consensus Reports
Reported in EPA TSCA Inventory.
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: 
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
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.