Ethyl caffeate
 Chemical structure of ethyl caffeate | |
| Names | |
|---|---|
| IUPAC name
Ethyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate | |
| Other names | |
| Identifiers | |
| 102-37-4 | |
| 3D model (Jmol) | Interactive image |
| ChEBI | CHEBI:132714 |
| ChemSpider | 4476132 |
| PubChem | 5317238 |
| UNII | 76GBB1JU5Y  |
| |
| |
| Properties | |
| C11H12O4 | |
| Molar mass | 208.21 g/mol |
| UV-vis (λmax) | 324 nm and a shoulder at c. 295 nm in acidified methanol |
| Related compounds | |
| Related compounds |
Caffeic acid |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Ethyl caffeate is an ester of an hydroxycinnamic acid, a naturally occurring organic compound.
Natural occurrences
It can be found in Bidens pilosa,[1] in Polygonum amplexicaule var. sinense (Chinese name: Xuesanqi), a widely distributed medicinal plant in China[2] and in Physalis alkekengi.[3]
It is also found in Huáng bǎi, one of the fifty fundamental herbs of traditional Chinese medicine, also known also as Cortex Phellodendri, the bark of one of two species of Phellodendron tree: Phellodendron amurense or Phellodendron chinense.[4]
It is also found in wines such as Verdicchio, a white wine from Marche, Italy.[5]
Health effects
Ethyl caffeate suppresses NF-kappaB activation and its downstream inflammatory mediators, iNOS, COX-2 and PGE2 in vitro or in mouse skin.[1]
Ethyl caffeate administered intraperitoneally in rats previously is able to prevent the dimethylnitrosamine-induced loss in body and liver weight, as well as to reduce the degree of liver injury. It can be considered as a promising natural compound for future application in chronic liver disease.[5]
Chemistry
Ethyl caffeate reacts with methylamine to produce green pigments.[6]
See also
References
- 1 2 Chiang, Yi-Ming; Lo, Chiu-Ping; Chen, Yi-Ping; Wang, Sheng-Yang; Yang, Ning-Sun; Kuo, Yueh-Hsiung; Shyur, Lie-Fen (2005). "Ethyl caffeate suppresses NF-κB activation and its downstream inflammatory mediators, iNOS, COX-2, and PGE2in vitroor in mouse skin". British Journal of Pharmacology. 146 (3): 352–63. doi:10.1038/sj.bjp.0706343. PMC 1576288
. PMID 16041399. - ↑ Isolation, identification and determination of methyl caffeate, ethyl caffeate and other phenolic compounds from Polygonum amplexicaule var. sinense. Meixian Xiang, Hanwen Su, Jinyue Hu and Yunjun Yan, Journal of Medicinal Plants Research Vol., 4 May 2011, 5(9), pages 1685–1691 (abstract)
- ↑ Chemical constituents of Physalis alkekengivar. franchetii(Ⅱ). Yuan Ye, Xu Nan, Bu Xian-kun, Zhan Hong-li and Zhang Meng-meng, Chinese Traditional and Herbal Drugs (abstract)
- ↑ Wang, M; Ji, TF; Yang, JB; Su, YL (2009). "Studies on the chemical constituents of Phellodendron chinense". Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 32 (2): 208–10. PMID 19504962.
- 1 2 Boselli, Emanuele; Bendia, Emanuele; Di Lecce, Giuseppe; Benedetti, Antonio; Frega, Natale G. (2009). "Ethyl caffeate from Verdicchio wine: Chromatographic purification andin vivoevaluation of its antifibrotic activity". Journal of Separation Science. 32 (21): 3585–90. doi:10.1002/jssc.200900304. PMID 19813225.
- ↑ Matsui, T (1981). "Greening pigments produced reaction of ethyl caffeate with methylamine". Journal of nutritional science and vitaminology. 27 (6): 573–82. PMID 7334427.