Acetovanillone Chemical Properties

Melting point:

112-115 °C (lit.)

Boiling point:

263-265 °C/17 mmHg (lit.)

Density 

1.1708 (rough estimate)

refractive index 

1.5101 (estimate)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Acetonitrile (Slightly), Chloroform (Slightly), Ethyl Acetate (Slightly), Methan

pka

8.18±0.18(Predicted)

form 

Solid

color 

Yellow to brown

Odor

at 100.00 %. faint sweet vanillin

Odor Type

vanilla

Water Solubility 

soluble in hot water

Merck 

14,741

BRN 

637373

LogP

1.389 (est)

CAS DataBase Reference

498-02-2(CAS DataBase Reference)

NIST Chemistry Reference

Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-(498-02-2)

EPA Substance Registry System

Acetovanillone (498-02-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

2

RTECS 

AM8800000

TSCA 

Yes

HS Code 

29145000

MSDS

• Language:English Provider:4'-Hydroxy-3'-methoxyacetophenone
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Acetovanillone Usage And Synthesis

Chemical Properties

yellowish to brown powder

Uses

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.

Uses

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.

Definition

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

Preparation

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

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.]

Acetovanillone(498-02-2)Related Product Information

• 2'-Methoxyacetophenone
• 2'-Hydroxyacetophenone
• 4'-Bromoacetophenone
• 2',4'-Dichloroacetophenone
• 3'-Methylacetophenone
• 3-Nitroacetophenone
• 4-Nitroacetophenone
• 3',5'-Dimethoxyacetophenone
• 3-Methoxyacetophenone
• CHLOROPHOSPHONAZO III
• Acetophenone
• 2-HYDROXYACETOPHENONE
• 4'-Methoxyacetophenone
• 3-Aminoacetophenone
• 3,4-Dimethoxyacetophenone
• 4'-Hydroxyacetophenone
• Calcium lactate
• 3,4-Methylenedioxyacetophenone