Acetovanillone

Apocynin

Names
Preferred IUPAC name 1-(4-Hydroxy-3-methoxyphenyl)ethan-1-one
Other names 1-(4-Hydroxy-3-methoxyphenyl)ethanone 4-Hydroxy-3-methoxyacetophenone Acetovanillone
Identifiers
CAS Number	498-02-2 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:2781 Y
ChEMBL	ChEMBL346919 Y
ChemSpider	21106900 Y
ECHA InfoCard	100.007.141
KEGG	C11380 Y
PubChem	2214
UNII	B6J7B9UDTR Y
InChI InChI=1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3 Y Key: DFYRUELUNQRZTB-UHFFFAOYSA-N Y InChI=1/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3 Key: DFYRUELUNQRZTB-UHFFFAOYAW
SMILES Oc1ccc(cc1OC)C(C)=O
Properties
Chemical formula	C9H10O3
Molar mass	166.17 g/mol
Melting point	115 °C (239 °F; 388 K)
Boiling point	295–300 °C (563–572 °F; 568–573 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox 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.

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.

Apocynin is a solid with a melting point of 115 °C and the faint odor of vanilla. It is soluble in hot water, alcohol, benzene, chloroform, and ether.

NADPH oxidase is an enzyme that effectively reduces O₂ to superoxide (O₂^–•), which can be used by the immune system to kill bacteria and fungi. Apocynin is an inhibitor of NADPH oxidase activity and thus is effective in preventing the production of the superoxide in human white blood cells or neutrophilic granulocytes. It does not however obstruct the phagocytic or other defense roles of granulocytes. Due to the selectivity of its inhibition, apocynin can be widely used as an inhibitor of NADPH oxidase without interfering in other aspects of the immune system.