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4'-Hydroxy-3'-methoxyacetophenon
APOCYNIN · 4-HYDROXY-3-METHOXYACETOPHENONE · ACETOVANILLON · Ethanone, 1-(4-hydroxy-3-methoxyphenyl)- · 1-(4-HYDROXY-3-METHOXYPHENYL)ETHAN-1-ONE · Acetovanilone · 4-Acetyl-2-methoxyphenol · Apocynin (Acetovanillone)
Identifikatoren & physikalische Daten
| CAS No. | 498-02-2 |
|---|---|
| Summenformel | C9H10O3 |
| Durchschnittliche Molmasse | 166,17 g/mol |
| Monoisotopische Masse | 166,06299418 g/mol |
| SMILES | COc1cc(C(C)=O)ccc1O |
| InChIKey | DFYRUELUNQRZTB-UHFFFAOYSA-N |
| PubChem CID | 2214 |
| ChEMBL | CHEMBL346919 |
| ChEBI | CHEBI:2781 |
| EC No. | 207-854-5 |
| DTXSID | DTXSID7060097 |
| Lokaler Name | 4'-Hydroxy-3'-methoxyacetophenon |
Chemische & physikalische Eigenschaften
| XLogP | 0,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 46,5 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 167 |
| Kovats Retention Index | 1447150314611448.3149614911498.714801497153914851487149014831484.11486.514821478.6149426762667260626202664262326402651.52637262626382640.1 |
| Schmelzpunkt | 112-115 °C (lit.) |
| Siedepunkt | 263-265 °C/17 mmHg (lit.) |
| Dichte | 1.1708 (rough estimate) |
| Brechungsindex | 1.5101 (estimate) |
| Flammpunkt | >230 °F |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Löslichkeit | Acetonitrile (Slightly), Chloroform (Slightly), Ethyl Acetate (Slightly), Methansoluble in hot water |
| pKa (Säurekonstante) | 8.18±0.18(Predicted) |
| Aggregatzustand | Solid |
| Farbe | Yellow to brown |
| Geruch | at 100.00 %. faint sweet vanillin |
| Geruchsart | vanilla |
| Biologische Quelle | synthetic |
| Merck | 14,741 |
| BRN | 637373 |
| Henry-Konstante | 6.3×103 mol/(m3Pa) at 25℃, McFall et al. (2020) |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONING - MISCELLANEOUS |
| InChI | 1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3 |
| InChIKey | DFYRUELUNQRZTB-UHFFFAOYSA-N |
| SMILES | COc1cc(ccc1O)C(C)=O |
| LogP (Verteilungskoeffizient) | 1.389 (est) |
| CAS Datenbank | 498-02-2(CAS DataBase Reference) |
| NIST chemische Informationen | Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-(498-02-2) |
| EPA chemische Informationen | Acetovanillone (498-02-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 65.7% (94 of 143) of all reports.WarningH315 (34.3%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (34.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (33.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 143 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 94 of 143 reports by companies.There are 7 notifications provided by 49 of 143 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Irrit. 2 (34.3%)Eye Irrit. 2 (34.3%)STOT SE 3 (33.6%) |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29145000 |
| RTECS-Nr. | AM8800000 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Verwenden
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.
Herstellung & Synthese
synthetische
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.