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2,6-Dimethoxyphenol
MCP · Phenol, 2,6-dimethoxy- · aldrich · Dimethoxyphenol · 2,6-Dimethoxyphenol (syringol) · 2,6-Dimethoxyphenyl · Natural 2,6-Dimethoxyphenol · 1,3-Dimethoxy-2-hydroxybenzene
Identifikatoren & physikalische Daten
| CAS No. | 91-10-1 |
|---|---|
| Summenformel | C8H10O3 |
| Durchschnittliche Molmasse | 154,16 g/mol |
| Monoisotopische Masse | 154,06299418 g/mol |
| SMILES | COc1cccc(OC)c1O |
| InChIKey | KLIDCXVFHGNTTM-UHFFFAOYSA-N |
| PubChem CID | 7041 |
| ChEMBL | CHEMBL109652 |
| ChEBI | CHEBI:955 |
| EC No. | 202-041-1 |
| DTXSID | DTXSID2052607 |
| Lokaler Name | 2,6-Dimethoxyphenol |
Chemische & physikalische Eigenschaften
| XLogP | 1,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 38,7 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 104 |
| Stoffklassen | Other Classes -> Other Aromatic Compounds |
| Duftstoffe | Fragrance Ingredient (2,6-Dimethoxyphenol) -> IFRA transparency List |
| LogP (Verteilungskoeffizient) | 1.15 |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Aromastoffe | EU Flavoring substances |
| Löslichkeit | 17.2 mg/mL at 13 °Cslightly soluble in watersoluble in oilsmoderately soluble (in ethanol)Chloroform (Slightly), Ethyl Acetate (Slightly)2 g/100 mL (13 ºC) |
| Siedepunkt | 260.00 to 261.00 °C. @ 760.00 mm Hg261-262 °C261 °C(lit.) |
| Schmelzpunkt | 55 - 56 °C50-57 °C(lit.) |
| Physical Description | Light brown solidified mass or fragments[Aldrich MSDS]White or colourless crystals, woody medicinal rather dry odour |
| Dichte | 1.1690 (rough estimate) |
| Brechungsindex | 1.4745 (estimate) |
| FEMA | 3137 | 2,6-DIMETHOXYPHENOL |
| Flammpunkt | >230 °F |
| Lagerbedingungen | Keep in dark place,Inert atmosphere,Room temperature |
| Aggregatzustand | Crystalline Powder, Crystals, or Crystalline Solid |
| pKa (Säurekonstante) | 9.97±0.10(Predicted) |
| Farbe | Off-white or gray to brown |
| Geruch | at 1.00 % in dipropylene glycol. smoky phenolic balsamic bacon powdery woody |
| Geruchsart | smoky |
| Biologische Quelle | synthetic |
| JECFA Number | 721 |
| BRN | 1526871 |
| Henry-Konstante | 3.7×101 mol/(m3Pa) at 25℃, Sagebiel et al. (1992) |
| InChI | 1S/C8H10O3/c1-10-6-4-3-5-7(11-2)8(6)9/h3-5,9H,1-2H3 |
| InChIKey | KLIDCXVFHGNTTM-UHFFFAOYSA-N |
| SMILES | COc1cccc(OC)c1O |
| LogP (Verteilungskoeffizient) | 0.77 |
| CAS Datenbank | 91-10-1(CAS DataBase Reference) |
| NIST chemische Informationen | Phenol, 2,6-dimethoxy-(91-10-1) |
| EPA chemische Informationen | Phenol, 2,6-dimethoxy- (91-10-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1711) of reports.WarningH302 (> 99.9%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1711 reports by companies from 12 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: Phenol, 2,6-dimethoxy-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 27-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24958Phenol, 2,6-dimethoxy-: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Causes somnolence and dyspnea in intravenous lethal-dose study of catsCauses general anesthesia in oral lethal-dose study of ratsCauses weight loss in 36-day oral studies of rats[RTECS] Safe when used as a flavoring agent in food[JECFA] A skin and strong eye irritantHarmful by ingestion and skin absorption[Aldrich MSDS] |
| Hazard Classes and Categories | Acute Tox. 4 (> 99.9%) |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2811 6.1/PG 1 |
| Zollcode | 29095090 |
| RTECS-Nr. | SL0900000 |
| R-Sätze (R) | 22-36/37/38 |
| Gefahrensymbole | Xn,Xi |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 26-36-37/39 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Occurrence
Reported found in beechwood tar creosote, onion, garlic, leek, chive, nira (Allium tuberosum Rotti), nobira (Allium grayi Regal) and caucus (Allium victoralis L.)
Verwenden
2,6-Dimethoxyphenol has been used as a metabolite of lignin depolymerisation.It is also used as flavoring agent or adjuvant.It is reported to be the single most important flavor chemical in smoke flavors. It is used in smoke flavors, whisky, rum, tea, spice, savory, seafood, meat, liquorices, coffee, and nut flavors.
Herstellung & Synthese
synthetische
2,6-Dimethoxyphenol is prepared by reacting pyrogallol with methyl iodide in alkaline aqueous medium; by demethylation of pyrogallol trimethyl ether in aqueous alkali or in alcohol.