498-02-2

yellowish to brown powder

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.

ChEBI: An aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3.

Also obtained by Fries rearrangement of guaiacol acetate in the presence of zinc chloride.

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.

The Journal of Organic Chemistry, 60, p. 739, 1995 DOI: 10.1021/jo00108a046

Store at RT

Crystallise apocynin from water, or EtOH/pet ether. [Beilstein 8 IV 1814.]

[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.