| Identification | Back Directory | [Name]
ETHYL CAFFEATE | [CAS]
102-37-4 | [Synonyms]
Ethyl caffeate
Ethyl caffeoate
Caffeoyl acetate
ETHYL CAFFEATE b
CaffeoylEthylEster
Caffeic acid ethyl ester
Caffeic acidETHYL CAFFEATE
4-dihydroxyphenyl)acrylate
Ethyl Caffeate CAS 102-37-4
CAFFEIC ACID ETHYLESTER(RG)
Ethyl 3-(3,4-dihydroxyphenyl)
Ethyl 3-(3,4-dihydroxyphenyl)acrylate
3,4-Dihydroxycinnamic acid ethyl ester
3,4-Dihydroxybenzeneacrylic acid ethyl ester
Ethyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
3-(3,4-Dihydroxyphenyl)acrylic acid ethyl ester
3-(3,4-Dihydroxyphenyl)propenoic acid ethyl ester
2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, ethyl ester | [EINECS(EC#)]
-0 | [Molecular Formula]
C11H12O4 | [MDL Number]
MFCD00045754 | [MOL File]
102-37-4.mol | [Molecular Weight]
208.211 |
| Chemical Properties | Back Directory | [Appearance]
Yellow to tan crystals; characteristic aromatic odor. Insoluble in water; very soluble in alcohol. | [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 | [Uses]
Food antioxidant. |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow to tan crystals; characteristic aromatic odor. Insoluble in water; very soluble in alcohol. | [Definition]
ChEBI: An ethyl ester resulting from the formal condensation of the carboxy group of trans-caffeic acid with ethanol. | [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. | [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 | [storage]
4°C, protect from light | [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 |
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