ETHYL CAFFEATE Chemical Properties

Melting point:

149.5 °C

Boiling point:

377.0±32.0 °C(Predicted)

Density 

1.271±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO: 250 mg/mL (1200.71 mM)

form 

Solid

pka

8.71±0.18(Predicted)

color 

Light yellow to yellow

LogP

2.560

ETHYL CAFFEATE Usage And Synthesis

Description

Ethyl Caffeate is a natural phenolic compound isolated from Bidens pilosa. It suppresses NF-κB activation and its downstream inflammatory mediators, inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), and prostaglandin E2 (PGE2) in vitro or in mouse skin.

Chemical Properties

Yellow to tan crystals; characteristic aromatic odor. Insoluble in water; very soluble in alcohol.

Uses

Food antioxidant.

Definition

ChEBI: Ethyl trans-caffeate is an ethyl ester resulting from the formal condensation of the carboxy group of trans-caffeic acid with ethanol. It has a role as an anti-inflammatory agent and an antineoplastic agent. It is an alkyl caffeate ester and an ethyl ester. It is functionally related to a trans-caffeic acid.

Synthesis

Caffeic acid (0.5 g, 2.77 mmol) was dissolved in dry ethanol (20 mL) followed by the addition of concentrated sulfuric acid (0.5 mL, 96%, v/v). The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (100 mL) and washed with 5% aqueous sodium bicarbonate to neutral pH. the organic layer was subsequently washed with distilled water and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure and the residue was purified by silica gel column chromatography (40% ethyl acetate-hexane as eluent) to afford the target product ethyl 3,4-dihydroxycinnamate (382 mg, 81%) as a white solid. The product characterization data were as follows: melting point 128-140 °C; 1H NMR (400 MHz, DMSO-d6, 25 °C) δ (ppm): 9.58 (br s, 1H, OH), 9.14 (br s, 1H, OH), 7.47 (d, J = 15.93 Hz, 1H, CH=CH), 7.05 (s, 1H, ArH), 7.00 (dd, J = 8.24, 1.16 Hz, 1H, ArH), 6.76 (d, J = 8.12 Hz, 1H, ArH), 6.26 (d, J = 15.89 Hz, 1H, CH=CO), 4.16 (q, J = 7.04 Hz, 2H, CH2CH3), 1.24 (t, J = 7.08 Hz, 3H, CH2CH3) ; 13C NMR (101 MHz, DMSO-d6, 25 °C) δ (ppm): 167.01, 148.83, 146.02, 145.45, 125.97, 121.80, 116.19, 115.26, 114.51, 60.15, 14.73; HRMS m/z calculated for C10H12O4 (H+): 209.0808; found: 209.0811.

IC 50

iNOS; NF-κB; COX-2

References

[1] Journal of Pharmacy and Pharmacology, 2018, vol. 70, # 10, p. 1349 - 1356
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 22, p. 7182 - 7193
[3] Molecules, 2010, vol. 15, # 9, p. 6152 - 6167
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 19, p. 6085 - 6088
[5] Journal of Agricultural and Food Chemistry, 2008, vol. 56, # 4, p. 1376 - 1386

ETHYL CAFFEATE(102-37-4)Related Product Information

• METHYL CAFFEATE
• Phenethyl caffeate
• Chlorogenic acid
• ETHYL CAFFEATE
• CYNARIN
• ECHINACOSIDE
• RESCINNAMINE
• 3,4,5-TRIMETHOXYCINNAMIC ACID ETHYL ESTER
• Ethyl 4-hydroxy-3-methoxycinnamate
• ChicoricAcid
• Caffeic acid
• Rosmarinic acid
• ETHYL 3-(2-CHLORO-3,4-DIMETHOXYPHENYL)ACRYLATE
• 2-PHENYL-4-PIPERONYLIDENE-2-OXAZOLIN-5-ONE
• Cyclohexanecarboxylic acid, 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, monopotassium salt, [1S-(1alpha,3beta,4alpha,5alpha)]-, compd. with 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione (1:1)
• 2-(1-THIENYL)ETHYL 3,4-DIHYDROXYBENZYLIDENECYANOACETATE
• ETHYL 3-(1,3-BENZODIOXOL-5-YL)-2-CYANOACRYLATE
• ISOBUTYL ALPHA-CYANO-3,4-METHYLENEDIOXYCINNAMATE