Ethyl 4-hydroxy-3-methoxycinnamate Chemical Properties

Melting point:

63-65 °C(lit.)

Boiling point:

164-166 °C0.5 mm Hg(lit.)

Density 

1.0643 (rough estimate)

refractive index 

1.4560 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Solid

pka

8.88±0.18(Predicted)

color 

White to Off-White

Sensitive 

Light Sensitive

BRN 

2696807

Stability:

Hygroscopic, Light Sensitive

InChIKey

ATJVZXXHKSYELS-FNORWQNLSA-N

LogP

1.940 (est)

CAS DataBase Reference

4046-02-0(CAS DataBase Reference)

NIST Chemistry Reference

ethyl ferulate(4046-02-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29189900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Ethyl 4-hydroxy-3-methoxycinnamate Usage And Synthesis

Description

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.

Uses

Ferulic acid ethyl ester is an ethyl ester derivative of Ferulic acid (F308900), which is used as an antioxidant and food preservative.

Synthesis

To an ice-chilled suspension of trans-ferulic acid (1.942 g, 10 mmol, 1 eq) in absolute ethanol (20 mL) was added thionyl chloride (0.87 mL, 12 mmol, 1.2 eq). The resulting mixture was refluxed with stirring for 20 h. The solution was concentrated in vacuo, dissolved in ethyl acetate (30 mL) and washed with a 1 M HCI solution (15 mL), saturated NaHCOs solution (15 mL) and brine (15 mL). The organic layer was dried over anhydrous NajSC and concentrated in vacuo to afford Ethyl 4-hydroxy-3-methoxycinnamate as an orange oil (2.185 g, yield: 98%).

Ethyl 4-hydroxy-3-methoxycinnamate(4046-02-0)Related Product Information

• Ethyl acetate
• Ferulic Acid
• Cinnamic acid
• ISOXADIFEN-ETHYL
• Ethyl pyruvate
• Ethyl formate
• Sodium ferulic
• 2-Ethylhexyl ferulate
• Ethyl acrylate
• Octyl 4-methoxycinnamate
• Ethyl oleate
• Ethanol
• Ethyl glycolate
• Ethyl cinnamate
• Ethyl 4-methylcinnamate
• Ethyl cyanoacetate
• Ethylparaben
• 4-Hydroxycinnamic acid