2-Methoxy-4-vinylphenol
2-METHOXY-4-VINYLPHENOL · 4-VINYLGUAIACOL · p-Vinylguaiacol · 4-VINYL-2-METHOXYPHENOL · 4-Ethenyl-2-methoxyphenol · FEMA 2675 · 2-Methoxy-4-vinylphenol (4-vinylguaiacol) · 3-Methoxy-4-hydroxystyrene
Identifikatoren & physikalische Daten
| CAS No. | 7786-61-0 |
|---|---|
| Summenformel | C9H10O2 |
| Durchschnittliche Molmasse | 150,17 g/mol |
| Monoisotopische Masse | 150,06807956 g/mol |
| SMILES | C=Cc1ccc(O)c(OC)c1 |
| InChIKey | YOMSJEATGXXYPX-UHFFFAOYSA-N |
| PubChem CID | 332 |
| ChEMBL | CHEMBL1232595 |
| ChEBI | CHEBI:42438 |
| EC No. | 232-101-2 |
| DTXSID | DTXSID7052529 |
| Lokaler Name | 2-Methoxy-4-vinylphenol |
Chemische & physikalische Eigenschaften
| XLogP | 2,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 29,5 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 134 |
| Schmelzpunkt | 25-29°C |
| Siedepunkt | 224 °C(lit.) |
| Dichte | 1.11 g/mL at 25 °C(lit.) |
| Brechungsindex | n20/D 1.582(lit.) |
| FEMA | 2675 | 2-METHOXY-4-VINYLPHENOL |
| Flammpunkt | >230 °F |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)Miscible with water. |
| pKa (Säurekonstante) | 10.00±0.31(Predicted) |
| Aggregatzustand | Liquid |
| Farbe | Colourless to Off-White Oil |
| Geruch | at 0.10 % in dipropylene glycol. sweet spicy clove carnation phenolic peppery smoky woody powdery |
| Geruchsart | spicy |
| Biologische Quelle | synthetic |
| JECFA Number | 725 |
| BRN | 2044521 |
| Stabilität | Light Sensitive |
| Hauptanwendungen | cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMING |
| InChI | 1S/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3 |
| InChIKey | YOMSJEATGXXYPX-UHFFFAOYSA-N |
| SMILES | COc1cc(C=C)ccc1O |
| LogP (Verteilungskoeffizient) | 1.93 |
| CAS Datenbank | 7786-61-0(CAS DataBase Reference) |
| NIST chemische Informationen | 2-Methoxy-4-vinylphenol(7786-61-0) |
| EPA chemische Informationen | Phenol, 4-ethenyl-2-methoxy- (7786-61-0) |
Sicherheit & Vorschriften
| Wassergefährdungsklasse (WGK) | 3 |
|---|---|
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN1760 |
| Zollcode | 29095000 |
| RTECS-Nr. | SL8205000 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36 |
| Gefahrenklasse | 8Eye Dam. 1Skin Corr. 1B |
| Lagerklasse | 8B - Non-combustible corrosive hazardous materials |
Anwendungen & Verwendung
Occurrence
Reported found among the steam-distillable phenols from the alcoholic fermentation of cereal grains, especially corn; probably formed from ferulic acid. Reported found in tobacco, beans, coffee, malt, apple, grapefruit juice, grapes, raspberry, strawberry, asparagus, kohlrabi, carrot, celery, tomato, rye bread, smoked fish, cured pork, beer, cognac, rum, cider, sherry, grape wines, coffee, tea, peanut, popcorn,soybean, passion fruit, beans,starfruit,sesame seed, mango, cauliflower, tamarind, fig, corianderseed, rice, quince, rhubarb, dill, lovage root, corn oil, sweet corn, malt, wort, Texas sage, okra, cuttlefish and Chinese quince.
Verwenden
p-Vinylguaiacol is an aromatic substance and one of the compounds responsible for the natural aroma of buckwheat. It is also one of the major pyrolytic products of (E)-N-[(4-hydroxy-3-methoxy)-phenethyl]-3-[(3-methoxy-4-O-β-D-glucopyranosyloxy) phenyl] acrylamide; a new gycloside in tobacco.
Herstellung & Synthese
synthetische
From vanillin by reacting with acetic anhydride and sodium acetate yielding 3-methoxy-4-hydroxycinnamic acid on sub sequent hydrolysis; the latter, heated with quinoline in the presence of hydroquinone, is decarboxylated to 4-vinylguaiacol.