Ethylcinnamat
CINNAMIC ACID ETHYL ESTER · 2-Propenoic acid, 3-phenyl-, ethyl ester · FEMA 2430 · Ethylphenylacryate · ETHYL TRANS-CINNAMATE · Ethyl 3-phenylacrylate · Ethyl 3-phenyl-2-propenoate · Ethyl (E)-3-phenylprop-2-enoate
Identifikatoren & physikalische Daten
| CAS No. | 103-36-6 |
|---|---|
| Summenformel | C11H12O2 |
| Durchschnittliche Molmasse | 176,21 g/mol |
| Monoisotopische Masse | 176,08372962 g/mol |
| SMILES | CCOC(=O)C=Cc1ccccc1 |
| InChIKey | KBEBGUQPQBELIU-UHFFFAOYSA-N |
| PubChem CID | 7649 |
| ChEMBL | CHEMBL3182745 |
| DTXSID | DTXSID9022520 |
| Lokaler Name | Ethylcinnamat |
Chemische & physikalische Eigenschaften
| XLogP | 3 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 179 |
| Schmelzpunkt | 6-8 °C (lit.) |
| Siedepunkt | 271 °C (lit.) |
| Dichte | 1.049 g/mL at 20 °C (lit.) |
| Dampfdruck | 6Pa at 20℃ |
| Brechungsindex | n20/D 1.558(lit.) |
| FEMA | 2430 | ETHYL CINNAMATE |
| Flammpunkt | >230 °F |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.insoluble |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless to pale yellow |
| Geruch | at 100.00 %. sweet balsam fruity spicy powdery berry plum |
| Geruchsart | balsamic |
| Biologische Quelle | synthetic |
| Merck | 14,2299 |
| JECFA Number | 659 |
| BRN | 1238804 |
| Henry-Konstante | 2.3×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Dielektrizitätskonstante | 5.3(19℃) |
| Stabilität | Stable. Incompatible with strong oxidizing agents, acids, bases, reducing agents. Combustible. |
| Hauptanwendungen | flavors and fragrances |
| Kosmetik-Inhaltsstoffe Funktionen | UV ABSORBERPERFUMING |
| InChI | 1S/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8+ |
| InChIKey | KBEBGUQPQBELIU-CMDGGOBGSA-N |
| SMILES | CCOC(=O)\C=C\c1ccccc1 |
| LogP (Verteilungskoeffizient) | 3.01 at 23.6℃ |
| CAS Datenbank | 103-36-6(CAS DataBase Reference) |
| NIST chemische Informationen | trans-Ethyl cinnamate(103-36-6) |
| EPA chemische Informationen | Ethyl cinnamate (103-36-6) |
Sicherheit & Vorschriften
| Wassergefährdungsklasse (WGK) | 1 |
|---|---|
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29163990 |
| RTECS-Nr. | GD9010000 |
| R-Sätze (R) | 20-22 |
| Toxizität | The acute oral LD50 value in rats was reported as 7.8 g/kg (7.41-8.19 g/kg) (Russell, 1973). The acute dermal LD50 value in rabbits was reported as > 5 g/kg (Russell, 1973). |
| Sicherheitshinweise (S) | 23-24/25 |
| Lagerklasse | 10 - Combustible liquids |
Anwendungen & Verwendung
Beschreibung
Ethyl cinnamate is the ester of cinnamic acid and ethanol, and is typically found in the essential oil of cinnamon. It is noteworthy that pure ethyl cinnamate has an aroma of cinnamon, complicated by balsamic and red fruit nuances,all of which can be characteristic of a fine Nebbiolo wine's aromatics.
Occurrence
Normally occurring in the trans-form; a cis-form also exists. Reported found in Oriental styrax, in the oil of Campheria galanga and in the rhizomes of Hedychium spicatum. Also reported found in cherry, American cranberry, pineapple, guava, strawberry, fresh blackberry, strawberry jam, soybean, yellow passion fruit juice, hybrid passion fruit juice, apple brandy, quince, prickly pear, strawberry wine, Bourbon vanilla, sea buckthorn, cinnamon leaf and root bark, clove, brandy, rum, sherry, grape wines, cocoa, soybean and other natural sources.
Verwenden
Ethyl cinnamate is used in medical intermediate, as a pharmaceutical intermediate and in organic synthesis.
Herstellung & Synthese
synthetische
By heating to 100°C cinnamic acid, alcohol and sulfuric acid in the presence of aluminum sulfate; also by Claisen condensation of benzaldehyde and ethyl acetate