Structure via PubChem · Public domain (PubChem)
apocynin
Sign in to saveAlso known as Acetovanillone, 4'-hydroxy-3'-methoxyacetophenone, Acetoguaiacone, 4-Hydroxy-3-methoxyphenyl methyl ketone, 4-Acetyl-2-methoxyphenol, Acetoguaiacon, 1-(4-Hydroxy-3-methoxyphenyl)ethanone, 1-(4-hydroxy-3-methoxy-phenyl)ethanone
Apocynin, also known as acetovanillone, is a natural organic compound structurally related to vanillin. It has been isolated from a variety of plant sources and is being studied for its variety of pharmacological properties.
Chemical data
- Formula
- C9H10O3
- Molecular weight
- 166.17 g/mol
- IUPAC name
- 1-(4-hydroxy-3-methoxyphenyl)ethanone
- SMILES
- CC(=O)C1=CC(=C(C=C1)O)OC
- InChIKey
- DFYRUELUNQRZTB-UHFFFAOYSA-N
- XLogP
- 0.5
- Polar surface area
- 46.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 1
- Molecule type
- Small molecule
- Indications
- cardiovascular disease, chronic obstructive pulmonary disease, asthma
via ChEMBL · EBI
Research
2,701 papers- Pharmacology of apocynin: a natural acetophenone.Drug metabolism reviews · 2021
- Apocynin: molecular aptitudes.Mediators of inflammation · 2008
- Targeting benign prostate hyperplasia treatments: AR/TGF-β/NOX4 inhibition by apocynin suppresses inflammation and proliferation.Journal of advanced research · 2024
- Apocynin, a low molecular oral treatment for neurodegenerative disease.BioMed research international · 2014
- Apocynin Mitigates Diabetic Muscle Atrophy by Lowering Muscle Triglycerides and Oxidative Stress.International journal of molecular sciences · 2025
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 166.063
Show 6 more facts
- found in taxon
- Dendrobium nobile
- canonical SMILES
- CC(=O)C1=CC(=C(C=C1)O)OC
- chemical formula
- C₉H₁₀O₃
- subject has role
- antioxidant
- melting point
- 114.5
- Commons category
- Apocynin
via Wikidata · CC0
~6 min read
Encyclopedic overview
6 sectionsContents
- History
- In food flavoring
- Physical properties
- Mode of action
- Research
- References
Apocynin, also known as acetovanillone, is a natural organic compound structurally related to vanillin. It has been isolated from a variety of plant sources and is being studied for its variety of pharmacological properties.
== History == Apocynin was first described by Oswald Schmiedeberg, a German pharmacologist, in 1883 and was first isolated by Horace Finnemore, in 1908, from the root of Canadian hemp (Apocynum cannabinum). At the time, this plant was already used for its known effectiveness against edema and heart problems. In 1971, apocynin was also isolated from Picrorhiza kurroa, a small plant that grows at high altitudes in the western Himalayas. P. kurroa was used for ages as a treatment for liver and heart problems, jaundice, and asthma. In 1990, Simons et al. isolated apocynin to a pharmacologically useful level using an actively guided isolation procedure. Apocynin's observed anti-inflammatory capabilities proved to be a result of its ability to selectively prevent the formation of free radicals, oxygen ions, and peroxides in the body. Apocynin has since been extensively studied to help determine its disease-fighting capabilities and applications.
Excerpted from Wikipedia’s “apocynin” article, available under the CC BY-SA 4.0 licence.