ChemicalBook Product Catalog Chemical Reagents Organic reagents Aromatic ketones Acetovanillone

Acetovanillone

Acetovanillone Basic information
Product Name:Acetovanillone
Synonyms:1-(4-hydroxy-3-methoxyphenyl)-ethanon;1-(4-Hydroxy-3-methoxyphenyl)-ethanone (acetovanillone);1-(4-HYDROXY-3-METHOXYPHENYL) ETHANONE;Acetovanillone~Apocynin;4'-Hydroxy-3'-Methoxyacetophenone 3-Methoxy-4-Hydroxyacetophenone 3'-Methoxy-4'-Hydroxyacetophenone;ACETOVANILLONE 98+%;acetovanillone,1-(4-hydroxy-3-methoxyphenyl)-ethanone,apocynin;ACETAVANILLONE
CAS:498-02-2
MF:C9H10O3
MW:166.17
EINECS:207-854-5
Product Categories:Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Protein Kinase Inhibitors and Activators;Adehydes, Acetals & Ketones;Anisoles, Alkyloxy Compounds & Phenylacetates;Phenols;Aromatic Acetophenones & Derivatives (substituted);pharmacetical;FINE Chemical & INTERMEDIATES;Inhibitors;bc0001
Mol File:498-02-2.mol
Acetovanillone Structure
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)
Fp >230 °F
storage temp. Sealed in dry,Room Temperature
solubility Acetonitrile (Slightly), Chloroform (Slightly), Ethyl Acetate (Slightly), Methan
pka8.18±0.18(Predicted)
form Solid
color Yellow to brown
Odorat 100.00 %. faint sweet vanillin
Odor Typevanilla
Water Solubility soluble in hot water
Merck 14,741
BRN 637373
LogP1.389 (est)
CAS DataBase Reference498-02-2(CAS DataBase Reference)
NIST Chemistry ReferenceEthanone, 1-(4-hydroxy-3-methoxyphenyl)-(498-02-2)
EPA Substance Registry SystemAcetovanillone (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 Information
ProviderLanguage
4'-Hydroxy-3'-methoxyacetophenone English
SigmaAldrich English
ACROS English
ALFA English
Acetovanillone Usage And Synthesis
Chemical Propertiesyellowish to brown powder
UsesAcetovanillone is an inhibitor of NADPH oxidase (an enzyme responsible for reactive oxygen species production) and is useful in the treatment of various inflammatory diseases.
Uses4'-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.
PreparationAlso obtained by Fries rearrangement of guaiacol acetate in the presence of zinc chloride.
DefinitionChEBI: An aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3.
Synthesis Reference(s)The Journal of Organic Chemistry, 60, p. 739, 1995 DOI: 10.1021/jo00108a046
General DescriptionAcetovanillone 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.
storageStore at RT
Purification MethodsCrystallise apocynin from water, or EtOH/pet ether. [Beilstein 8 IV 1814.]
Acetovanillone Preparation Products And Raw materials
Preparation ProductsAcetylacetone-->4-Hydroxy-3-methoxystyrene-->METHOXYBENZOQUINONE-->4-chloro-6,7-dimethoxyquinoline-->1-(2-hydroxy-3-methoxy-phenyl)ethanone-->1-(4,5-DIMETHOXY-2-NITRO-PHENYL)-ETHANONE-->4-Ethylresorcinol-->4-METHOXY-3-HYDROXYACETOPHENONE-->2,4-Dimethoxyacetophenone-->Quinoline, 4-chloro-6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]--->4-(4-Acetyl-2-Methoxyphenoxy)-butanoic Acid Ethyl Ester-->2-bromo-1-(4-hydroxy-3-methoxyphenyl)ethanone
4'-Methoxyacetophenone diethyl (3,4,5-trimethoxybenzoyl)malonate 3'-Methylacetophenone 3-Aminoacetophenone 3-Nitroacetophenone 2,3,3',4'-TETRAMETHOXYBENZOPHENONE 4-Nitroacetophenone 5,6-Dimethoxy-1-indanone 2-HYDROXYACETOPHENONE 3,4-Dimethoxyacetophenone Glycitein Paeonol 2'-AMINO-4',5'-DIMETHOXYACETOPHENONE 6,7-DIMETHOXY-2,2-DIMETHYL-4-CHLOROMANONE CHLOROPHOSPHONAZO III 3,4-(METHYLENEDIOXY)PROPIOPHENONE 3-Methoxyacetophenone 3',5'-Dimethoxyacetophenone
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