Skip to content
apocynin

Structure via PubChem · Public domain (PubChem)

EntityQ414754· pop 14· linked from 8 articles

Also 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

Wikidata facts

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
Sources (4)

via Wikidata · CC0

~6 min read

Encyclopedic overview

6 sections
Contents
  • 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.