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
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)
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.
N-Bromosuccinimide Price
- Product number
- A10809
- Product name
- 4′-Hydroxy-3′-methoxyacetophenone
- Purity
- 98%
- Packaging
- 25g
- Price
- $41.6
- Updated
- 2024/03/01
- 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
- Product number
- 73536
- Product name
- Acetovanillone
- Purity
- analytical standard
- Packaging
- 100mg
- Price
- $62.8
- Updated
- 2022/05/15
- Product number
- H0261
- Product name
- 4'-Hydroxy-3'-methoxyacetophenone
- Purity
- >98.0%(GC)
- Packaging
- 25g
- Price
- $69
- Updated
- 2024/03/01
- Product number
- H0261
- Product name
- 4'-Hydroxy-3'-methoxyacetophenone
- Purity
- >98.0%(GC)
- Packaging
- 100g
- Price
- $207
- Updated
- 2024/03/01
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
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View Lastest Price from Acetovanillone manufacturers
- 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
- Product
- Acetovanillone 498-02-2
- Price
- US $10.00/PCS
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 10 mt
- Release date
- 2021-04-02
- 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