ChemicalBook > CAS DataBase List > Acetovanillone

Acetovanillone

Product Name
Acetovanillone
CAS No.
498-02-2
Chemical Name
Acetovanillone
Synonyms
APOCYNIN;4-HYDROXY-3-METHOXYACETOPHENONE;Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-;1-(4-HYDROXY-3-METHOXYPHENYL)ETHAN-1-ONE;Acetovanilone;ACETOVANILLON;Apocynin (Acetovanillone);4'-HYDROXY-3'-METHOXYACETOPHENONE;Apocynin - CAS 498-02-2 - Calbiochem;NSC 2146
CBNumber
CB7484931
Molecular Formula
C9H10O3
Formula Weight
166.17
MOL File
498-02-2.mol
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Acetovanillone Property

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)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
2
RTECS 
AM8800000
TSCA 
Yes
HS Code 
29145000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
A10809
Product name
4′-Hydroxy-3′-methoxyacetophenone
Purity
98%
Packaging
25g
Price
$41.6
Updated
2024/03/01
Sigma-Aldrich
Product number
178385
Product name
Apocynin - CAS 498-02-2 - Calbiochem
Purity
A cell-permeable, anti-inflammatory phenolic compound that acts as a potent and selective inhibitor of NADPH oxidase.
Packaging
1g
Price
$96.7
Updated
2024/03/01
Sigma-Aldrich
Product number
73536
Product name
Acetovanillone
Purity
analytical standard
Packaging
100mg
Price
$62.8
Updated
2022/05/15
TCI Chemical
Product number
H0261
Product name
4'-Hydroxy-3'-methoxyacetophenone
Purity
>98.0%(GC)
Packaging
25g
Price
$69
Updated
2024/03/01
TCI Chemical
Product number
H0261
Product name
4'-Hydroxy-3'-methoxyacetophenone
Purity
>98.0%(GC)
Packaging
100g
Price
$207
Updated
2024/03/01
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Acetovanillone Chemical Properties,Usage,Production

Chemical Properties

Acetovanillone is a yellowish to brown powder, soluble in alcohol, essential oils, and perfume chemicals. It is slightly soluble in water at room temperature but readily dissolves in hot water. It has a very faint, sweet odor, faintly reminiscent of vanillin, but with less spiciness and somewhat fresher notes. It occurs widely in nature, including in Orris root distillate.

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: Apocynin is an aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3. It has a role as a non-narcotic analgesic, a non-steroidal anti-inflammatory drug, an antirheumatic drug, a peripheral nervous system drug, an EC 1.6.3.1. [NAD(P)H oxidase (H2O2-forming)] inhibitor and a plant metabolite. It is a member of acetophenones, a methyl ketone and an aromatic ketone.

Preparation

Synthetically by methylation of 3,4-Dihydroxyacetophenone. It can also be obtained by Fries rearrangement of guaiacol acetate in the presence of zinc chloride. It can be isolated from the extract of the roots of Indian hemp, Apocynum cannabinum L.

Production Methods

Synthetically by methylation of 3,4- Dihydroxy acetophenone. Also from Guaiacol acetate with Zinc chloride and Acetic anhydride. Can be isolated from the extract of the roots of Indian hemp, Apocynum cannabinum L.

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.]

References

[1] GARA N DEXTER. Bacterial catabolism of acetovanillone, a lignin-derived compound.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2022: e2213450119. DOI:10.1073/pnas.2213450119.
[2] YUDAI HIGUCHI. The Catabolic System of Acetovanillone and Acetosyringone in Sphingobium sp. Strain SYK-6 Useful for Upgrading Aromatic Compounds Obtained through Chemical Lignin Depolymerization.[J]. Applied and Environmental Microbiology, 2022, 88 16: e0072422. DOI:10.1128/aem.00724-22.
[3] CHIARA RIGANTI. The NADPH oxidase inhibitor apocynin (acetovanillone) induces oxidative stress[J]. Toxicology and applied pharmacology, 2006, 212 3: Pages 179-187. DOI:10.1016/j.taap.2005.07.011.
[4] GJERTSEN FB Scheline R Solheim E. Metabolism of aromatic plant ketones in rats: Acetovanillone and paeonol[J]. Journal of ethnopharmacology, 1988, 23 2: Page 342. DOI:10.1016/0378-8741(88)90035-9.

Acetovanillone Preparation Products And Raw materials

Raw materials

Preparation Products

Acetylacetone
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Acetovanillone Suppliers

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View Lastest Price from Acetovanillone manufacturers

Hebei Chuanghai Biotechnology Co,.LTD
Product
Acetovanillone 498-02-2
Price
US $5.00-2.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10000kg
Release date
2024-08-20
Hebei Weibang Biotechnology Co., Ltd
Product
Acetovanillone 498-02-2
Price
US $10.00/PCS
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2021-04-02
R&D Scientific Inc.
Product
3-Methoxy-4-hydroxyacetophenone 498-02-2
Price
US $600.00/Kg
Min. Order
1Kg
Purity
98
Supply Ability
500 Kg
Release date
2024-04-19

498-02-2, AcetovanilloneRelated Search:

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

  • Apocynin - CAS 498-02-2 - Calbiochem
  • 1-(4-hydroxy-3-methoxyphenyl)-ethanon
  • 1-(4-Hydroxy-3-methoxyphenyl)-ethanone (acetovanillone)
  • 1-(4-HYDROXY-3-METHOXYPHENYL)ETHAN-1-ONE
  • 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
  • Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-
  • ACETAVANILLONE
  • Ethanone,1-(4-hydroxy-3-me
  • ETHANONE,1-(4-HYDROXY-3-METHO
  • Acetovanillone, 98% 100GR
  • ACETOVANILLONE (4-HYDROXY-3-METHOXYACETOPHENONE)
  • 4'-hydroxy-3'-methoxyacetophenone,1-(4-hydroxy-3-methoxy)ethanone
  • 4-Acetylguaiacol
  • Acetovanillone ,99%
  • 4μ-Hydroxy-3μ-methoxyacetophenone, Acetovanillone, Apocynin
  • 1-(4-Hydroxy-3-methoxyphenyl)ethan-1-one, Acetovanillone
  • AcetovaniL
  • 4’-hydroxy-3’-methoxy-acetophenon
  • 4-Acetyl-2-methoxyphenol
  • 4-Hydroxy-3-methoxyphenyl methyl ketone
  • Acetoguaiacon
  • Acetoguaiacone
  • Acetophenone, 4'-hydroxy-3'-methoxy-
  • Acetovanilone
  • Acetovanyllon
  • -Acetylguaiacol
  • Apocynine
  • -Hydroxy-3-methoxyphenyl methyl keton
  • -Methoxy-4-acetylphenol
  • '-Methoxy-4'-hydroxyacetophenone
  • Phenol, 4-acetyl-2-methoxy
  • 3-Metoksy-4-hydroksyacetofenon
  • TIMTEC-BB SBB008060
  • APOCYNIN
  • AURORA KA-3667
  • ACETOVANILLON
  • ACETOVANILLONE
  • AKOS BBS-00003229
  • 3'-METHOXY-4'-HYDROXYACETOPHENONE
  • 3-METHOXY-4-HYDROXYACETOPHENONE
  • 4'-HYDROXY-3'-METHOXYACETOPHENONE
  • 4-HYDROXY-3-METHOXYACETOPHENONE
  • NSC 209524
  • NSC 2146
  • Acetovanillon/ Apocynin
  • 2-Methoxy-4-acetylphenol
  • Acetoguaicone
  • Apocynin (Acetovanillone)
  • Apocynin, >=98%
  • Vanilloyl methyl keton
  • Acetovanillone, 98.5%
  • 4-Hydroxy 3-Methoxy Acetophenone (Acetovanillone)
  • Acetovanillone, 98.5%, for synthesis
  • 4'-Hydroxy-3'-methoxyacetophenone&gt