Acetovanillone

Chemical properties

Acetovanillone is a yellowish to brown powder, soluble in alcohol, essential oils, and perfume chemicals. It is slightly soluble in water at room temperature but readily dissolves in hot water. It has a very faint, sweet odor, faintly reminiscent of vanillin, but with less spiciness and somewhat fresher notes. It occurs widely in nature, including in Orris root distillate.

The Uses of Acetovanillone

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.

The Uses of Acetovanillone

4'-Hydroxy-3'-methoxyacetophenone is used as an inhibitor of nicotinamide adenine dinucleotide phosphate (NADPH) oxidase, which is an enzyme responsible for reactive oxygen species production. It is also useful in the treatment of various inflammatory diseases and atherosclerosis. Further, it shows an anti-inflammatory activity and improves endothelial function by reducing oxidative stress. In addition to this, it is used for studying nitric oxide regulated processes in plants.

What are the applications of Application

Apocynin is a methoxy-substituted catechol commonly used as an inhibitor of NADPH oxidase

Definition

ChEBI: Apocynin is an aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3. It has a role as a non-narcotic analgesic, a non-steroidal anti-inflammatory drug, an antirheumatic drug, a peripheral nervous system drug, an EC 1.6.3.1. [NAD(P)H oxidase (H2O2-forming)] inhibitor and a plant metabolite. It is a member of acetophenones, a methyl ketone and an aromatic ketone.

Preparation

Synthetically by methylation of 3,4-Dihydroxyacetophenone. It can also be obtained by Fries rearrangement of guaiacol acetate in the presence of zinc chloride. It can be isolated from the extract of the roots of Indian hemp, Apocynum cannabinum L.

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.

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.