| 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 | [biological source]
synthetic | [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. | [Production Methods]
Synthetically by methylation of 3,4-
Dihydroxy acetophenone. Also from Guaiacol
acetate with Zinc chloride and Acetic anhydride. Can be isolated from the extract of
the roots of Indian hemp, Apocynum cannabinum L. | [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. | [Biological Activity]
Cell permeable: yes''Primary Target
NADPH oxidase''Product does not compete with ATP.''Reversible: no | [storage]
Store at RT | [Purification Methods]
Crystallise apocynin from water, or EtOH/pet ether. [Beilstein 8 IV 1814.] | [References]
[1] GARA N DEXTER. Bacterial catabolism of acetovanillone, a lignin-derived compound.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2022: e2213450119. DOI:10.1073/pnas.2213450119.
[2] YUDAI HIGUCHI. The Catabolic System of Acetovanillone and Acetosyringone in Sphingobium sp. Strain SYK-6 Useful for Upgrading Aromatic Compounds Obtained through Chemical Lignin Depolymerization.[J]. Applied and Environmental Microbiology, 2022, 88 16: e0072422. DOI:10.1128/aem.00724-22.
[3] CHIARA RIGANTI. The NADPH oxidase inhibitor apocynin (acetovanillone) induces oxidative stress[J]. Toxicology and applied pharmacology, 2006, 212 3: Pages 179-187. DOI:10.1016/j.taap.2005.07.011.
[4] GJERTSEN FB Scheline R Solheim E. Metabolism of aromatic plant ketones in rats: Acetovanillone and paeonol[J]. Journal of ethnopharmacology, 1988, 23 2: Page 342. DOI:10.1016/0378-8741(88)90035-9. |
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