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)

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.

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