| Identification | More | [Name]
Acetovanillone | [CAS]
498-02-2 | [Synonyms]
1-(4-HYDROXY-3-METHOXYPHENYL)ETHAN-1-ONE
1-(4-HYDROXY-3-METHOXYPHENYL) ETHANONE
3'-METHOXY-4'-HYDROXYACETOPHENONE
3-METHOXY-4-HYDROXYACETOPHENONE
4'-HYDROXY-3'-METHOXYACETOPHENONE
4-HYDROXY-3-METHOXYACETOPHENONE
ACETOVANILLON
ACETOVANILLONE
AKOS BBS-00003229
APOCYNIN
AURORA KA-3667
TIMTEC-BB SBB008060
1-(4-hydroxy-3-methoxyphenyl)-ethanon
1-(4-Hydroxy-3-methoxyphenyl)-ethanone (acetovanillone)
3-Metoksy-4-hydroksyacetofenon
4’-hydroxy-3’-methoxy-acetophenon
4-Acetyl-2-methoxyphenol
4-Hydroxy-3-methoxyphenyl methyl ketone
Acetoguaiacon
Acetoguaiacone | [EINECS(EC#)]
207-854-5 | [Molecular Formula]
C9H10O3 | [MDL Number]
MFCD00008747 | [Molecular Weight]
166.17 | [MOL File]
498-02-2.mol |
| Chemical Properties | Back Directory | [Appearance]
yellowish to brown powder | [Melting point ]
112-115 °C (lit.) | [Boiling point ]
263-265 °C/17 mmHg (lit.) | [density ]
1.1708 (rough estimate) | [refractive index ]
1.5101 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Acetonitrile (Slightly), Chloroform (Slightly), Ethyl Acetate (Slightly), Methan | [form ]
Solid | [pka]
8.18±0.18(Predicted) | [color ]
Yellow to brown | [Odor]
at 100.00 %. faint sweet vanillin | [Odor Type]
vanilla | [Water Solubility ]
soluble in hot water | [Detection Methods]
GC,NMR | [Merck ]
14,741 | [BRN ]
637373 | [LogP]
1.389 (est) | [CAS DataBase Reference]
498-02-2(CAS DataBase Reference) | [NIST Chemistry Reference]
Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-(498-02-2) | [EPA Substance Registry System]
498-02-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
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
| [RTECS ]
AM8800000
| [TSCA ]
Yes | [HS Code ]
29145000 |
| Hazard Information | Back Directory | [Chemical Properties]
yellowish to brown powder | [Uses]
Acetovanillone is an inhibitor of NADPH oxidase (an enzyme responsible for reactive oxygen species production) and is useful in the treatment of various inflammatory diseases.
| [Definition]
ChEBI: An aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3. | [Preparation]
Also obtained by Fries rearrangement of guaiacol acetate in the presence of zinc chloride. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 60, p. 739, 1995 DOI: 10.1021/jo00108a046 | [General Description]
Acetovanillone is an aromatic plant ketone, which is a selective inhibitor of NADPH oxidase. It is mainly secreted in the urine of mammals as the corresponding glucuronide conjugate. | [storage]
Store at RT | [Purification Methods]
Crystallise apocynin from water, or EtOH/pet ether. [Beilstein 8 IV 1814.] |
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