4'-Hydroxy-3'-methoxyacetophenon
Acetovanillone
Grundinformationen
- CAS
498-02-2- Standard-SMILES
COc1cc(C(C)=O)ccc1O- InChIKey
DFYRUELUNQRZTB-UHFFFAOYSA-N- Summenformel
- C9H10O3
- Durchschnittliche Molmasse
- 166,17 g/mol
- Monoisotopische Masse
- 166,06299418
Überblick
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-steroidal anti-inflammatory drug, a non-narcotic analgesic, 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.
Namen und Bezeichner
- Bevorzugter Name
- Acetovanillone
- IUPAC
- 1-(4-hydroxy-3-methoxyphenyl)ethanone
- Lokaler Name
- 4'-Hydroxy-3'-methoxyacetophenon
- Englischer Name
- Acetovanillone
- Summenformel
- C9H10O3
- Molmasse
- 166.17
Namen und Synonyme
Acetovanilloneapocynin498-02-24'-Hydroxy-3'-methoxyacetophenone1-(4-Hydroxy-3-methoxyphenyl)ethanoneAcetoguaiaconeApocynine4-Acetyl-2-methoxyphenolAcetoguaiacon1-(4-hydroxy-3-methoxyphenyl)ethan-1-oneEthanone, 1-(4-hydroxy-3-methoxyphenyl)-4-Hydroxy-3-methoxyphenyl methyl ketone
Weitere Namen anzeigen
4-HYDROXY-3-METHOXYACETOPHENONEACETOVANILLONApocynin (Acetovanillone)3'-METHOXY-4'-HYDROXYACETOPHENONE
B6J7B9UDTRNSC-209524DTXSID7060097CHEBI:2781RefChem:552432DTXCID1040740207-854-5Acetovanilone
Datenbank-Bezeichner
- CAS
498-02-2- PubChem CID
- 2214
- DTXSID
DTXSID7060097- ChEMBL
CHEMBL346919
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,5
- Polarare Oberfläche (TPSA)
- 46,5 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 12
- Formalladung
- 0
- Komplexität
- 167
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
FragrancesFragrance Ingredient (4'-Hydroxy-3'-methoxyacetophenone) -> IFRA transparency List
Flavoring AgentsEU Flavoring substances
Endocrine DisruptorsPotential endocrine disrupting compound
Physikochemische Eigenschaften
- Schmelzpunkt
- 112 · 112-115 °C (lit.)
- Siedepunkt
- 263 · 263-265 °C/17 mmHg (lit.)
- Dichte
- 1.1708 · 1.1708 (rough estimate)
- Brechungsindex
- 1.5101 · 1.5101 (estimate)
- Flammpunkt
- 230 °F · >230 °F
- storage temp.
- Sealed in dry,Room Temperature
- Löslichkeit
- Acetonitrile (Slightly), Chloroform (Slightly), Ethyl Acetate (Slightly), Methan
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 65.7% (94 of 143) of all reports.
Warning
H315 (34.3%): Causes skin irritation [Warning Skin corrosion/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.
Gefahrenhinweise
Regulatory Information
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 CategoriesSkin Irrit. 2 (34.3%)
Sicherheitsdaten
- wgk
- 2
- tsca
- TSCA listed
- hs_code
- 2914509090
- RTECS-Nr.
- AM8800000
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Verwendung und Herstellung
Use ClassificationFragrance Ingredients
General Manufacturing InformationEthanone, 1-(4-hydroxy-3-methoxyphenyl)-: ACTIVE
Anwendungen
VerwendenAcetovanillone is an inhibitor of NADPH oxidase (an enzyme responsible for reactive oxygen species production) and is useful in the treatment of various inflammatory diseases.
Darstellung
synthetischeSynthetically 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.
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