Ethyl-4'-hydroxy-3'-methoxycinnamat
ETHYL FERULATE · methoxycinnamate · FERULIC ACID ETHYL ESTER · NSC 14879 · Natural Ethyl Ferulate · ETHYL 4-HYDROXY-3-METHOXYCINNAMATE · Ethyl 3-(4-hydroxy-3-methoxyphenyl)acrylate · 4-HYDROXY-3-METHOXYCINNAMIC ACID ETHYL ESTER
Identifikatoren & physikalische Daten
| CAS No. | 4046-02-0 |
|---|---|
| Summenformel | C12H14O4 |
| Durchschnittliche Molmasse | 222,24 g/mol |
| SMILES | CCOC(=O)/C=C/c1ccc(O)c(OC)c1 |
| InChIKey | ATJVZXXHKSYELS-FNORWQNLSA-N |
| PubChem CID | 736681 |
| ChEMBL | CHEMBL286796 |
| EC No. | 223-745-5 |
| Lokaler Name | Ethyl-4'-hydroxy-3'-methoxycinnamat |
Chemische & physikalische Eigenschaften
| XLogP | 2,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 55,8 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 16 |
| Formalladung | 0 |
| Komplexität | 249 |
| Schmelzpunkt | 63-65 °C(lit.) |
| Siedepunkt | 164-166 °C0.5 mm Hg(lit.) |
| Dichte | 1.0643 (rough estimate) |
| Brechungsindex | 1.4560 (estimate) |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Löslichkeit | Chloroform (Slightly), Ethyl Acetate (Slightly) |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 8.88±0.18(Predicted) |
| Farbe | White to Off-White |
| BRN | 2696807 |
| Stabilität | Hygroscopic, Light Sensitive |
| Kosmetik-Inhaltsstoffe Funktionen | ANTIOXIDANT |
| InChI | 1S/C12H14O4/c1-3-16-12(14)7-5-9-4-6-10(13)11(8-9)15-2/h4-8,13H,3H2,1-2H3/b7-5+ |
| InChIKey | ATJVZXXHKSYELS-FNORWQNLSA-N |
| SMILES | CCOC(=O)\C=C\c1ccc(O)c(OC)c1 |
| LogP (Verteilungskoeffizient) | 1.940 (est) |
| CAS Datenbank | 4046-02-0(CAS DataBase Reference) |
| NIST chemische Informationen | ethyl ferulate(4046-02-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 69 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29189900 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 26-37/39-36 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Beschreibung
Ferulic acid is a hydroxycinnamic acid that is abundant in plants and originally derived from giant fennel (F. communis). This naturally-occurring phenolic has antioxidant activities that provide protection against inflammation and cancer. Ferulic acid ethyl ester is a lipophilic derivative of ferulic acid, demonstrating increased ability to cross cell membranes. Ferulic acid ethyl ester has less antioxidant capacity than ferulic acid in neuronal PC12 cells (IC50 = 66.7 μM for ferulic acid ethyl ester vs. 44.6 μM for ferulic acid, 2,2-diphenyl-1-picrylhydrazyl radical scavenging). However, ferulic acid ethyl ester increases the expression of heme oxygenase-1, Hsp70, and Hsp72, providing neuroprotection against amyloid β-peptide. Moreover, ferulic acid ethyl ester (25 μM) completely prevents cytotoxicity induced by ultraviolet B irradiation of normal human epidermal melanocytes, again associated with an induced expression of heme oxygenase-1 and Hsp70.
Verwenden
Ferulic acid ethyl ester is an ethyl ester derivative of Ferulic acid (F308900), which is used as an antioxidant and food preservative.