Ethyl caffeate
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Ethyl caffeate is an ester of a
hydroxycinnamic acid Hydroxycinnamic acids (hydroxycinnamates) are a class of aromatic acids or phenylpropanoids having a C6–C3 skeleton. These compounds are hydroxy derivatives of cinnamic acid. In the category of phytochemicals that can be found in food, there ...
, a naturally occurring organic compound.


Natural occurrences

It can be found in ''
Bidens pilosa ''Bidens pilosa'' is an annual species of herbaceous flowering plant in the daisy family Asteraceae. Its many common names include hitch hikers, black-jack, beggarticks, farmer’s friends and Spanish needle, but most commonly referred to as ...
'', in '' Polygonum amplexicaule var. sinense''. It is also found in
Huáng bǎi Huáng bǎi ( 黃 栢 ''or'' 黃 栢, literally "yellow fir"), huáng bó ( 黃 柏) or huáng bò ( 黃 檗) is one of the fifty fundamental herbs of traditional Chinese medicine. Known also as Cortex Phellodendri, it is the bark of one of two ...
, 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 ''Phellodendron amurense'' is a species of tree in the family Rutaceae, commonly called the Amur cork tree. It is a major source of '' huáng bò'' ( or 黄 檗), one of the 50 fundamental herbs used in traditional Chinese medicine. The Ainu pe ...
'' or ''
Phellodendron chinense ''Phellodendron chinense'' is a plant species in the genus '' Phellodendron''. The isocoumarin derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output v ...
''. It is also found in wines such as
Verdicchio Verdicchio (, also , ) is a white Italian wine grape variety grown primarily in the Marche region of central Italy.J. Robinson ''Jancis Robinson's Guide to Wine Grapes'' pg 195 Oxford University Press 1996 The name ''Verdicchio'' derives from ' ...
, a white wine from Marche, Italy.


Health effects

Ethyl caffeate suppresses NF-kappaB activation and its downstream
inflammatory mediator Inflammation (from la, inflammatio) is part of the complex biological response of body tissues to harmful stimuli, such as pathogens, damaged cells, or irritants, and is a protective response involving immune cells, blood vessels, and molec ...
s, iNOS,
COX-2 Prostaglandin-endoperoxide synthase 2 (prostaglandin G/H synthase and cyclooxygenase) (The HUGO official symbol is PTGS2; HGNC ID, HGNC:9605), also known as cyclooxygenase-2 or COX-2, is an enzyme that in humans is encoded by the ''PTGS2'' gene ...
and
PGE2 Prostaglandin E2 (PGE2), also known as dinoprostone, is a naturally occurring prostaglandin with oxytocic properties that is used as a medication. Dinoprostone is used in labor induction, bleeding after delivery, termination of pregnancy, and ...
''in vitro'' or in mouse skin. 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 Chronic liver disease in the clinical context is a disease process of the liver that involves a process of progressive destruction and regeneration of the liver parenchyma leading to fibrosis and cirrhosis. "Chronic liver disease" refers to disease ...
. 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.


Chemistry

Ethyl caffeate reacts with methylamine to produce
green Green is the color between cyan and yellow on the visible spectrum. It is evoked by light which has a dominant wavelength of roughly 495570 nm. In subtractive color systems, used in painting and color printing, it is created by a combi ...
pigment A pigment is a colored material that is completely or nearly insoluble in water. In contrast, dyes are typically soluble, at least at some stage in their use. Generally dyes are often organic compounds whereas pigments are often inorganic compou ...
s.


See also

*
Phenolic compounds in wine The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include ...


References

{{DEFAULTSORT:Ethyl caffeate Hydroxycinnamic acid esters Ethyl esters Vinylogous carboxylic acids