2-Methyltetrahydrofuran-3-on
DIHYDRO-2-METHYL-3(2H)-FURANONE · 3(2H)-Furanone, dihydro-2-methyl- · COFFEE FURANONE · 2-Methyloxolan-3-one · FEMA 3373 · Dihyro-2-methyl-3(2H)-furanone · 2-Methyl-3-ketotetrahydrofuran · Bread Ketone
Identifikatoren & physikalische Daten
| CAS No. | 3188-00-9 |
|---|---|
| Summenformel | C5H8O2 |
| Durchschnittliche Molmasse | 100,12 g/mol |
| Monoisotopische Masse | 100,0524295 g/mol |
| SMILES | CC1OCCC1=O |
| InChIKey | FCWYQRVIQDNGBI-UHFFFAOYSA-N |
| PubChem CID | 18522 |
| ChEMBL | CHEMBL3188615 |
| ChEBI | CHEBI:173339 |
| EC No. | 221-685-4 |
| DTXSID | DTXSID9047677 |
| Lokaler Name | 2-Methyltetrahydrofuran-3-on |
Chemische & physikalische Eigenschaften
| XLogP | 0 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 7 |
| Formalladung | 0 |
| Komplexität | 88,1 |
| Duftstoffe | Fragrance Ingredient (2-Methyltetrahydrofuran-3-one) -> IFRA transparency List |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 1.180-1.1851.034 g/mL at 25 °C (lit.) |
| Aromastoffe | EU Flavoring substances |
| Löslichkeit | slightlySlightly soluble in oilsSoluble (in ethanol) |
| Siedepunkt | 138.00 to 139.00 °C. @ 760.00 mm Hg139 °C139 °C (lit.) |
| Brechungsindex | 1.534-1.537n20/D 1.429(lit.) |
| Physical Description | LiquidColourless liquidWintergreen-like aroma |
| FEMA | 3373 | 2-METHYLTETRAHYDROFURAN-3-ONE |
| Flammpunkt | 103 °F |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Aggregatzustand | clear liquid |
| Farbe | Colorless to Yellow to Green |
| Wichte | 1.034 |
| Geruch | at 10.00 % in dipropylene glycol. sweet solvent bread buttery nutty |
| Geruchsart | bready |
| Biologische Quelle | synthetic |
| JECFA Number | 1448 |
| BRN | 1341334 |
| Hauptanwendungen | flavors and fragrances |
| InChI | 1S/C5H8O2/c1-4-5(6)2-3-7-4/h4H,2-3H2,1H3 |
| InChIKey | FCWYQRVIQDNGBI-UHFFFAOYSA-N |
| SMILES | CC1OCCC1=O |
| LogP (Verteilungskoeffizient) | -0.65 |
| CAS Datenbank | 3188-00-9(CAS DataBase Reference) |
| NIST chemische Informationen | 3(2H)-Furanone, dihydro-2-methyl-(3188-00-9) |
| EPA chemische Informationen | 3(2H)-Furanone, dihydro-2-methyl- (3188-00-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH226 (100%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1664 reports by companies from 6 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: 3(2H)-Furanone, dihydro-2-methyl-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 12-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/263003(2H)-Furanone, dihydro-2-methyl-: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Flam. Liq. 3 (100%) |
| F | 3-9 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1224 3/PG 3 |
| Zollcode | 29329990 |
| RTECS-Nr. | LU3579000 |
| R-Sätze (R) | 10-22-36/37/38-2017/10/2 |
| Gefahrensymbole | Xn,T,Xi |
| hazard_note | Toxic |
| Sicherheitshinweise (S) | 16-26-36/37/39-24/25-36 |
| Gefahrenklasse | 3Acute Tox. 4 OralFlam. Liq. 3 |
| Verpackungsgruppe | III |
| Lagerklasse | 3 - Flammable liquids |
Anwendungen & Verwendung
Beschreibung
2-Methyltetrahydrofuran-3-one has a bread, buttery topnote. May be prepared by hydrolytic decarboxylation of 2-methyl-4-carbomethoxytetrahydrofuran- 3-one; by acid-catalyzed ring closure of p-alkoxy- diazoketones.
Occurrence
Reported found as a constituent in coffee aroma; also as a volatile flavor component in roasted filbert nuts. Also reported found in guava, raisin, pineapple, onion, baked and fried potato, tomato, wheat bread, crispbread, smoked fish, cooked beef and pork, pork liver, rum, cocoa, coffee, peanuts, potato chips, passion fruit, beans, mushroom, tamarind, sweet potato, licorice, malt, dried bonito, cherimoya, okra and maté
Verwenden
2-Methyltetrahydro-3-furanone has been employed as an quorum sensing inhibitor-molecule to investigate its effect on growth and biofilm formation in Hafnia alvei.
Herstellung & Synthese
synthetische
By hydrolytic decarboxylation of 2-methyl-4-carbomethoxytetrahydrofuran-3-one; by acid-catalyzed ring closure of β-alkoxy-diazoketones