Ethyl methoxycinnamate
ETHYL P-METHOXYCINNAMATE · Ethyl trans-4-methoxycinnamate · 4-METHOXYCINNAMIC ACID ETHYL ESTER · ETHYL 3-(4-METHOXYPHENYL)ACRYLATE · (E)-Ethyl p-methoxycinnamate · ethyl (E)-4-methoxycinnamate · EPMC · RARECHEM AL BI 0241
Identifikatoren & physikalische Daten
| CAS No. | 1929-30-2 |
|---|---|
| Summenformel | C12H14O3 |
| Durchschnittliche Molmasse | 206,24 g/mol |
| Monoisotopische Masse | 206,09429431 g/mol |
| SMILES | CCOC(=O)/C=C/c1ccc(OC)cc1 |
| InChIKey | DHNGCHLFKUPGPX-RMKNXTFCSA-N |
| PubChem CID | 5281783 |
| ChEMBL | CHEMBL95956 |
| ChEBI | CHEBI:228868 |
| EC No. | 106-617-2 |
| DTXSID | DTXSID401308962 |
Chemische & physikalische Eigenschaften
| XLogP | 3 |
|---|---|
| Polarare Oberfläche (TPSA) | 35,5 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 15 |
| Formalladung | 0 |
| Komplexität | 215 |
| Kosmetika | Uv absorber |
| SpringerMaterials Properties | Chemical structure |
| Schmelzpunkt | 49 - 50 °C49°C |
| Physical Description | Solid |
| Siedepunkt | 187 °C / 15mmHg |
| Dichte | 1.080±0.06 g/cm3(Predicted) |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Löslichkeit | Chloroform (Slightly), Methanol (Slightly)insoluble in water |
| Aggregatzustand | Solid |
| Farbe | Off-White |
| BRN | 2210033 |
| Hauptanwendungen | food and beverages |
| InChI | InChI=1S/C12H14O3/c1-3-15-12(13)9-6-10-4-7-11(14-2)8-5-10/h4-9H,3H2,1-2H3/b9-6+ |
| InChIKey | DHNGCHLFKUPGPX-RMKNXTFCSA-N |
| SMILES | C(OCC)(=O)/C=C/C1=CC=C(OC)C=C1 |
| LogP (Verteilungskoeffizient) | 2.650 (est) |
| NIST chemische Informationen | Ethyl p-methoxycinnamate(24393-56-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: 2-Propenoic acid, 3-(4-methoxyphenyl)-, ethyl ester |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29189900 |
| R-Sätze (R) | 36/37/38 |
| Sicherheitshinweise (S) | 26-36/37/39-24/25 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Acute Tox. 4 Oral |
Anwendungen & Verwendung
Verwenden
Ethyl 4-methoxycinnamate is an derivative of 4-methoxycinnamic acid, an antihyperglycemic/hypoglycemic agent that works by stimulating insulin secretion from pancreas and could be developed into a new potential for therapeutic agent used in type 2 diabetic patients.
Herstellung & Synthese
synthetische
Ethyl 4-methoxycinnamate synthesis: 4-Methoxycinnamic Acid (0.60 g, 3.36 mmol) was dissolved in 10 mL of dry N,N-dimethylformamide (DMF) in a 25-mL, roundbottomed flask. Cesium carbonate (1.65 g, 5.06 mmol) was added followed by iodoethane (1.0 mL, 12.5 mmol). The flask was capped (rubber septum) and the heterogeneous mixture stirred vigorously at 50 °C for one hour. After this time, HCl (1.0 M, 4.0 mL) was added to quench the reaction. The liquid was decanted from any remaining solid and extracted with 3 : 1 hexanes/ethyl acetate (2 x 10 mL). The organic layer was washed with brine (20 mL), dried with MgSO4, filtered, and solvent removed. The remaining oil solidified on standing to form colorless prisms.Synthesis of ethyl 4-methoxycinnamate