Ethyl caffeate Chemical structure of ethyl caffeate
Names Preferred IUPAC name Ethyl (2E )-3-(3,4-dihydroxyphenyl)prop-2-enoate
Other namesCaffeic 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
Properties C 11 H 12 O 4 Molar mass −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 ahydroxycinnamic acid , a naturally occurring organic compound.
Natural occurrences [ edit ] It can be found inBidens pilosa [ 1] Polygonum amplexicaule var. sinense
It is also found inHuáng bǎi , one of the fifty fundamental herbs of traditional Chinese medicine, also known also asCortex Phellodendri , the bark of one of two species of Phellodendron tree:Phellodendron amurense Phellodendron chinense [ 2]
It is also found in wines such asVerdicchio , a white wine from Marche, Italy.[ 3]
Ethyl caffeate suppressesNF-kappaB activation and its downstreaminflammatory mediators ,iNOS ,COX-2 andPGE2 in vitro or in mouse skin.[ 1]
Ethyl caffeate administered intraperitoneally in rats previously is able to prevent thedimethylnitrosamine -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 inchronic 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]
Ethyl caffeate reacts withmethylamine to producegreen pigments .[ 5]
^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 Dihydroxycinnamic acids Trihydroxycinnamic acids O -methylated formsothers
Esters
glycoside-likes
Esters of
Glycosides
Tartaric acid estersOther esters Caffeoyl phenylethanoid 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 withcoenzyme A (CoA)
