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 List of phytochemicals in food, phytochemicals tha ...

, 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 co ...

'', 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 ''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 wiktionary:黄, 黄wiktionary:檗, 檗), one of the 50 fundamental herbs used in traditional Ch ...

'' or '' Phellodendron chinense''. 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 fro ...

, a white wine from Marche, Italy.

Health effects

Ethyl caffeate suppresses NF-kappaB activation and its downstream

inflammatory mediator Inflammation (from ) is part of the biological response of body tissues to harmful stimuli, such as pathogens, damaged cells, or irritants. The five cardinal signs are heat, pain, redness, swelling, and loss of function (Latin ''calor'', ''d ...

iNOS Nitric oxide synthases (NOSs) are a family of enzymes catalyzing the production of nitric oxide (NO) from L-arginine. NO is an important cellular signaling molecule. It helps modulate vascular tone, insulin secretion, airway tone, and perist ...

COX-2 Cyclooxygenase-2 (COX-2), also known as prostaglandin-endoperoxide synthase 2 ( HUGO PTGS2), is an enzyme that in humans is encoded by the ''PTGS2'' gene. In humans it is one of three cyclooxygenases. It is involved in the conversion of arachid ...

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, ...

''in vitro'' or in mouse skin. Ethyl caffeate administered intraperitoneally in rats previously is able to prevent the

dimethylnitrosamine ''N''-Nitrosodimethylamine (NDMA), also known as dimethylnitrosamine (DMN), is an organic compound with the formula (CH3)2NNO. It is one of the simplest members of a large class of nitrosamines. It is a volatile yellow oil. NDMA has attracted wi ...

-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 diseas ...

. 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 Methylamine, also known as methanamine, is an organic compound with a formula of . This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine. Methylamine is sold ...

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 com ...

pigment A pigment is a powder used to add or alter color or change visual appearance. Pigments are completely or nearly solubility, insoluble and reactivity (chemistry), chemically unreactive in water or another medium; in contrast, dyes are colored sub ...

References

{{DEFAULTSORT:Ethyl caffeate Hydroxycinnamic acid esters Ethyl esters

Natural occurrences

Health effects

Chemistry

See also

References