102-37-4

基本信息
咖啡酸乙酯標(biāo)準(zhǔn)品
咖啡酸乙酯(分析標(biāo)準(zhǔn)品)
3,4-二羥基肉桂酸乙酯
3-(3,4-二羥基苯基)丙烯酸乙酯
乙基3-(3,4-二羥基苯基)丙烯酸酯
ETHYL CAFFEATE 咖啡酸乙酯
Ethyl caffeoate
Caffeoyl acetate
ETHYL CAFFEATE b
CaffeoylEthylEster
Caffeic acid ethyl ester
4-dihydroxyphenyl)acrylate
Caffeic acidETHYL CAFFEATE
CAFFEIC ACID ETHYLESTER(RG)
Ethyl Caffeate CAS 102-37-4
物理化學(xué)性質(zhì)
常見問題列表


64-17-5

331-39-5

66648-50-8
將咖啡酸(0.5 g,2.77 mmol)溶解于干燥的乙醇(20 mL)中,隨后加入濃硫酸(0.5 mL,96%,v/v)。反應(yīng)混合物在室溫下攪拌2小時。反應(yīng)完成后,將混合物冷卻至室溫,用乙酸乙酯(100 mL)稀釋,并用5%碳酸氫鈉水溶液洗滌至中性pH。有機層隨后用蒸餾水洗滌,并用無水硫酸鎂干燥。減壓蒸餾除去溶劑,殘余物通過硅膠柱色譜法(40%乙酸乙酯-己烷為洗脫劑)純化,得到目標(biāo)產(chǎn)物3,4-二羥基肉桂酸乙酯(382 mg,81%),為白色固體。產(chǎn)物表征數(shù)據(jù)如下:熔點128-140℃;1H NMR (400 MHz, DMSO-d6, 25℃) 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℃) 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.
參考文獻:
[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
【2】萬春平, 祁燕, 鄭喜,等. 基于MAPK信號通路研究地膽草成分咖啡酸乙酯抑制T細(xì)胞活化的分子機制[C]// 全國中西醫(yī)結(jié)合風(fēng)濕病學(xué)術(shù)會議. 2014.
NF-κB
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COX-2
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Ethyl Caffeate markedly suppresses the lipopolysaccharide (LPS)-induced nitric oxide (NO) production with IC 50 of 5.5?μg/ml.