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| | Ethyl 4-methoxycinnamate Basic information |
| Product Name: | Ethyl 4-methoxycinnamate | | Synonyms: | 4-METHOXYCINNAMIC ACID ETHYL ESTER;3-(4-METHOXYPHENYL)ACRYLIC ACID ETHYL ESTER;ETHYL P-METHOXYCINNAMATE;ETHYL 3-(4-METHOXYPHENYL)ACRYLATE;ETHYL 4-METHOXYCINNAMATE;RARECHEM AL BI 0241;Methoxycinnamicacidethylester;4-METHOXYCINNAMIC ACID ETHYL ESTER 98+% | | CAS: | 24393-56-4 | | MF: | C12H14O3 | | MW: | 206.24 | | EINECS: | 202-494-5 | | Product Categories: | Cinnamic acid | | Mol File: | 24393-56-4.mol |  |
| | Ethyl 4-methoxycinnamate Chemical Properties |
| Melting point | 49°C | | Boiling point | 187 °C / 15mmHg | | density | 1.080±0.06 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | solubility | Chloroform (Slightly), Methanol (Slightly) | | form | Solid | | color | Off-White | | Water Solubility | insoluble in water | | BRN | 2210033 | | Major Application | 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 | 2.650 (est) | | NIST Chemistry Reference | Ethyl p-methoxycinnamate(24393-56-4) |
| Risk Statements | 36/37/38 | | Safety Statements | 26-36/37/39-24/25 | | WGK Germany | 3 | | HS Code | 29189900 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral |
| | Ethyl 4-methoxycinnamate Usage And Synthesis |
| Chemical Properties | White crystalline, soluble in methanol, ethanol, DMSO and other organic solvents, derived from cinnamon. | | Uses | 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. | | Preparation | 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 | | General Description | Ethyl p-methoxycinnamate (EPMC) is a natural product found in K. galanga and C. zedoaria extracts with anti-inflammatory, antiangiogenic, antifungal, larvicidal, and analgesic activities. It inhibits COX-1 and COX-2 in vitro (IC50s = 1.12 and 0.83 μM, respectively) and reduces IL-1 and TNF-α production in vivo. EPMC inhibits granuloma tissue formation and acts as an analgesic, delaying tail flick time, in a dose-dependent manner in rats. It inhibits blood vessel growth in rat aortic explants (IC50 = 91.9 μg/ml). EPMC (<10 μg/ml) also reduces growth of T. rubrum, A. niger, S. cerevisiae, and E. floccosum and is larvicidal (LC50 = 53.64 ppm) against Ae. aegypti. | | in vivo | (E)-Ethyl p-methoxycinnamate (40-200 μM, sc, single dose) inhibits bFGF and heparin-induced angiogenesis, exhibits antiangiogenic activity in mouse matrigel plug models[3].
| Animal Model: | Mouse matrigel plug models[3] | | Dosage: | 40-200 μM | | Administration: | sc, single dose | | Result: | Inhibited angiogenesis. |
| | IC 50 | COX-1: 1.12 μM (IC50); COX-2: 0.83 μM (IC50) |
| | Ethyl 4-methoxycinnamate Preparation Products And Raw materials |
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