Ethyl 4-methoxycinnamate
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
- LogP
- 2.650 (est)
- NIST Chemistry Reference
- Ethyl p-methoxycinnamate(24393-56-4)
Safety Information
- Risk Statements
- 36/37/38
- Safety Statements
- 26-36/37/39-24/25
- WGK Germany
- 3
- HS Code
- 29189900
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.
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Ethyl 4-methoxycinnamate(24393-56-4)Related Product Information
- Ethylparaben
- Ethanol
- Ethyl formate
- Ethyl acetate
- 3,4-Dimethoxycinnamonitrile
- Ethyl cinnamate
- ISOXADIFEN-ETHYL
- Ethyl 4-methylcinnamate
- 4-(Trifluoromethyl)cinnamic acid
- Ethyl 4-methoxybenzoate
- Ethyl acrylate
- Ethyl oleate
- Acrylic acid
- 4-Bromocinnamic acid
- 4-Methoxycinnamic acid
- Octyl 4-methoxycinnamate
- Ethyl pyruvate
- Ethyl cyanoacetate