Acetovanillone

Base Information

• Chemical Name: Acetovanillone
• CAS No.: 498-02-2
• Molecular Formula: C9H10O3
• Molecular Weight: 166.177
• Hs Code.: 29145000
• European Community (EC) Number: 207-854-5
• NSC Number: 209524,2146
• UNII: B6J7B9UDTR
• DSSTox Substance ID: DTXSID7060097
• Nikkaji Number: J13.670K
• Wikipedia: Apocynin
• Wikidata: Q414754
• Metabolomics Workbench ID: 52971
• ChEMBL ID: CHEMBL346919
• Mol file: 498-02-2.mol

Synonyms:4'-hydroxy-3'-methoxyacetophenone;4-hydroxy-3-methoxyacetophenone;acetovanillone;apocynin;apocynine

Chemical Property of Acetovanillone

Chemical Property:

• Appearance/Colour: yellowish to brown powder
• Vapor Pressure: 0.000759mmHg at 25°C
• Melting Point: 112-115 °C(lit.)
• Refractive Index: 1.537
• Boiling Point: 297.5 °C at 760 mmHg
• PKA: 8.18±0.18(Predicted)
• Flash Point: 125.5 °C
• PSA: 46.53000
• Density: 1.158 g/cm³
• LogP: 1.60340
• Storage Temp.: Refrigerator
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), Ethyl Acetate (Slightly), Methan
• Water Solubility.: soluble in hot water
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 166.062994177
• Heavy Atom Count: 12
• Complexity: 167

Purity/Quality:

99% ^*data from raw suppliers

Apocynin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C1=CC(=C(C=C1)O)OC
• Recent ClinicalTrials: The Effect of Local Antioxidant Therapy on Racial Differences in Vasoconstriction
• 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. 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.

Technology Process of Acetovanillone

There total 88 articles about Acetovanillone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethanol (7382-68-5) → 2-methoxy-phenol (90-05-1) + 1-(3-methoxy-4-hydroxyphenyl)ethanone (498-02-2)

Guidance literature:

With sodium tetrahydroborate; palladium on activated charcoal; In water; ethyl acetate; at 80 ℃; for 14h;

DOI:10.1002/cssc.201500117

Reference yield: 96.0%

3-methoxy-4-hydroxybenzoic acid (121-34-6) + 4CH3(1-)*Zn(2+)*Li(1+) → 1-(3-methoxy-4-hydroxyphenyl)ethanone (498-02-2)

Guidance literature:

3-methoxy-4-hydroxybenzoic acid; 4CH₃^(1-)*Zn⁽²⁺⁾*Li⁽¹⁺⁾; In tetrahydrofuran; diethyl ether; hexane; at 20 ℃; Schlenk technique; Inert atmosphere;

With iodine; In tetrahydrofuran; diethyl ether; hexane; at 20 ℃; Solvent; chemoselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1002/asia.201500308

Reference yield: 84.0%

1-(3,4-dihydroxyphenyl)ethan-1-one (1197-09-7) + methyl iodide (74-88-4) → 3-hydroxy-4-methoxyacetophenone (6100-74-9) + 1-(3-methoxy-4-hydroxyphenyl)ethanone (498-02-2) + 1-(3,4-dimethoxyphenyl)ethanone (1131-62-0)

Guidance literature:

With lithium carbonate; In N,N-dimethyl-formamide; at 55 ℃; for 18h; chemoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2019.03.016

upstream raw materials:

methyl magnesium iodide

4-benzoyloxy-3-methoxybenzaldehyde

2-methoxyphenyl acetate

2-chloro-1-(4-hydroxy-3-methoxyphenyl)ethan-1-one

Downstream raw materials:

4-benzyloxy-3-methoxyacetophenone

2,4'-dihydroxy-3'-methoxy-trans-chalcone

1,3-bis(4-hydroxy-3-methoxyphenyl)-1-phenyl-2-propen-1-one

(4-acetyl-2-methoxy-phenoxy)-acetonitrile

Refernces

• 1、 Mehta, Mohit J.,Kulshrestha, Akshay,Sharma, Shweta,Kumar, Arvind. "Room temperature depolymerization of lignin using a protic and metal based ionic liquid system: an efficient method of catalytic conversion and value addition". . p. 1240 - 1247. Retrieved 2021/02/26.
• 2、 Alvigini, Laura,Fraaije, Marco W.,Gran-Scheuch, Alejandro,Guo, Yiming,Mattevi, Andrea,Saifuddin, Mohammad,Trajkovic, Milos. "Discovery, Biocatalytic Exploration and Structural Analysis of a 4-Ethylphenol Oxidase from Gulosibacter chungangensis". . p. 3225 - 3233. Retrieved 2021/10/04.