Ethyl caffeate
 Chemical structure of ethyl caffeate
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| Names | |
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| Preferred IUPAC name
Ethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate | |
| Other names
Caffeic acid ethyl ester
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C11H12O4 | |
| Molar mass | 208.213 g·mol−1 |
| UV-vis (λmax) | 324 nm and a shoulder at c. 295 nm in acidified methanol |
| Related compounds | |
Related compounds
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Caffeic acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ethyl caffeate is an ester of a hydroxycinnamic acid, a naturally occurring organic compound.
Natural occurrences
[edit | edit source]It can be found in Bidens pilosa,[1] in Polygonum amplexicaule var. sinense.
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.[2]
It is also found in wines such as Verdicchio, a white wine from Marche, Italy.[3]
Health effects
[edit | edit source]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.[3]
Pharmacophore modeling, molecular docking, and molecular dynamics simulation studies also indicate that ethyl caffeate is a potential inhibitor of the aldosterone synthase (CYP11B2), a key enzyme for the biosynthesis of aldosterone, which plays a significant role for the regulation of blood pressure.[4]
Chemistry
[edit | edit source]Ethyl caffeate reacts with methylamine to produce green pigments.[5]
See also
[edit | edit source]References
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