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Ethyl caffeate
Chemical structure of ethyl caffeate
Names
Preferred IUPAC name
Ethyl (2E )-3-(3,4-dihydroxyphenyl)prop-2-enoate
Other names
Caffeic acid ethyl ester
Identifiers
ChEBI
ChemSpider
UNII
InChI=1S/C11H12O4/c1-2-15-11(14)6-4-8-3-5-9(12)10(13)7-8/h3-7,12-13H,2H2,1H3/b6-4+
Key: WDKYDMULARNCIS-GQCTYLIASA-N
InChI=1S/C11H12O4/c1-2-15-11(14)6-4-8-3-5-9(12)10(13)7-8/h3-7,12-13H,2H2,1H3/b6-4+
Key: WDKYDMULARNCIS-GQCTYLIASA-N
CCOC(=O)/C=C/C1=CC(=C(C=C1)O)O
Properties
C 11 H 12 O 4
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
Caffeic acid
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
UV spectrum of ethyl caffeate.
Ethyl caffeate is an ester of a
hydroxycinnamic acid , a naturally occurring organic compound.
Natural occurrences
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
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
Ethyl caffeate reacts with
methylamine to produce
green
pigments .
[5]
See also
References
^
a
b 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 .
^ Wang, M; Ji, TF; Yang, JB; Su, YL (2009). "Studies on the chemical constituents of Phellodendron chinense". Zhong Yao Cai . 32 (2): 208–10.
PMID
19504962 .
^
a
b Boselli, Emanuele; Bendia, Emanuele; Di Lecce, Giuseppe; Benedetti, Antonio; Frega, Natale G. (2009).
"Ethyl caffeate from Verdicchio wine: Chromatographic purification and in vivo evaluation of its antifibrotic activity" . Journal of Separation Science . 32 (21): 3585–90.
doi :
10.1002/jssc.200900304 .
PMID
19813225 .
^ Luo, Ganggang; Lu, Fang; Qiao, Liansheng; Chen, Xi; Li, Gongyu; Zhang, Yanling (2016).
"Discovery of Potential Inhibitors of Aldosterone Synthase from Chinese Herbs Using Pharmacophore Modeling, Molecular Docking, and Molecular Dynamics Simulation Studies" . BioMed Research International . 2016 : 1–8.
doi :
10.1155/2016/4182595 .
ISSN
2314-6133 .
PMC
5065998 .
PMID
27781210 .
^ Matsui, T (1981).
"Greening pigments produced reaction of ethyl caffeate with methylamine" . Journal of Nutritional Science and Vitaminology . 27 (6): 573–82.
doi :
10.3177/jnsv.27.573 .
PMID
7334427 .
Aglycones
Precursor Monohydroxycinnamic acids (Coumaric acids)
Dihydroxycinnamic acids Trihydroxycinnamic acids O -methylated formsothers
Esters
glycoside-likes
Esters of caffeic acid with cyclitols
Glycosides
Tartaric acid esters Other esters with caffeic acid Caffeoyl phenylethanoid glycoside (CPG)
Echinacoside
Calceolarioside A ,
B ,
C ,
F
Chiritoside A ,
B ,
C
Cistanoside A ,
B ,
C ,
D ,
E ,
F ,
G ,
H
Conandroside
Myconoside
Pauoifloside
Plantainoside A
Plantamajoside
Tubuloside B
Verbascoside (
Isoverbascoside ,
2′-Acetylverbascoside )
Oligomeric forms
Dimers
Diferulic acids (DiFA) :
5,5′-Diferulic acid ,
8-O -4′-Diferulic acid ,
8,5′-Diferulic acid ,
8,5′-DiFA (DC) ,
8,5′-DiFA (BF) ,
8,8′-Diferulic acid
Trimers Tetramers
Conjugates with
coenzyme A (CoA)