Acetovanillone
- CAS No.
- 498-02-2
- Chemical Name:
- Acetovanillone
- Synonyms
- APOCYNIN;4-HYDROXY-3-METHOXYACETOPHENONE;1-(4-HYDROXY-3-METHOXYPHENYL)ETHAN-1-ONE;Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-;Acetovanilone;ACETOVANILLON;Apocynin (Acetovanillone);4'-HYDROXY-3'-METHOXYACETOPHENONE;Apocynin - CAS 498-02-2 - Calbiochem;NSC 2146
- CBNumber:
- CB7484931
- Molecular Formula:
- C9H10O3
- Molecular Weight:
- 166.17
- MOL File:
- 498-02-2.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/6/3 16:56:37
| 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
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H315-H319-H335 | |||||||||
| Precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 | |||||||||
| Hazard Codes | Xi | |||||||||
| Risk Statements | 36/37/38 | |||||||||
| Safety Statements | 26-36 | |||||||||
| WGK Germany | 2 | |||||||||
| RTECS | AM8800000 | |||||||||
| TSCA | Yes | |||||||||
| HS Code | 29145000 | |||||||||
| NFPA 704 |
|
Acetovanillone price More Price(16)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | W508454 | Acetovanillone ≥98%, FG | 498-02-2 | 1SAMPLE | ₹5141.88 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | W508454 | Acetovanillone ≥98%, FG | 498-02-2 | 100G | ₹7101.2 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | W508454 | Acetovanillone ≥98%, FG | 498-02-2 | 1KG | ₹37454.5 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | W508454 | Acetovanillone ≥98%, FG | 498-02-2 | 10KG | ₹273298.78 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A10809 | 4′-Hydroxy-3′-methoxyacetophenone 98% | 498-02-2 | 25G | ₹2814.5 | 2022-06-14 | Buy |
Acetovanillone Chemical Properties,Uses,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
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.
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.
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
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| GLR Innovations | 58 |
| GRK RESEARCH LABORATORIES PVT LTD | 58 |
| SANIKA CHEMICALS PVT.LTD. | 58 |
| chakrachem Lifesciences | 58 |
| SYNOVA CHEMICALS | 58 |
| Bhausa Life Sciences | 58 |
| Pratap Organics Pvt Ltd | 58 |
| Ralington Pharma | 58 |
| SLN Pharmachem | 58 |
| Alliance Pharma | 58 |
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