Grundinformationen
- Standard-SMILES
COc1cc(C(C)=O)ccc1O- InChIKey
DFYRUELUNQRZTB-UHFFFAOYSA-N- Summenformel
- C9H10O3
- Durchschnittliche Molmasse
- 166,17 g/mol
- Monoisotopische Masse
- 166,06299418
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
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
498-02-2- PubChem CID
- 2214
- DTXSID
DTXSID7060097- ChEMBL
CHEMBL346919- ChEBI
CHEBI:2781- UNII
- B6J7B9UDTR
- EC Number
- 207-854-5
- Nikkaji
- J13.670K
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
Kovats Retention Index
1447;1503;1461;1448.3
1496;1491;1498.7;1480;1497;1539;1485;1498;1487;1539;1490;1491;1483;1484.1;1486.5;1482;1478.6;1484;1494
2676;2667;2606;2620;2620;2667;2664;2664;2623;2664;2640;2651.5;2637;2626;2638;2640;2640;2640.1
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
- pka
- 8.18 · 8.18±0.18(Predicted)
- Aggregatzustand
- Solid
- Farbe
- Yellow to brown
- Geruch (Odor)
- 100 % · at 100.00 %. faint sweet vanillin
- Geruchsart
- vanilla
- Biologische Quelle
- synthetic
- Wasserlöslichkeit
- soluble in hot water
- Merck
- 14 · 14,741
- BRN
- 637373 · 637373
- Henry's Law Constant
- 6.3 · 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
- 1.389 · 1.389 (est)
- CAS Datenbank
- 498 · 498-02-2(CAS DataBase Reference)
- NIST chemische Informationen
- 1 · Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-(498-02-2)
- EPA chemische Informationen
- Acetovanillone (498-02-2)
Sicherheit und Regulatorisches
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];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 exposure; Respiratory 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.
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
Regulatorische Informationen
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
Sicherheitsdaten
- wgk
- 2
- tsca
- TSCA listed
- hs_code
- 29145000
- 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
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.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: 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.
Zugehörige Reaktionen
Verknüpfte Notizen
Wird geladen…