Ethyl caffeate

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
CAS Number
  • 102-37-4 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:132714
ChemSpider
  • 4476132
PubChem CID
  • 5317238
UNII
  • 76GBB1JU5Y checkY
CompTox Dashboard (EPA)
  • DTXSID70876375 Edit this at Wikidata
InChI
  • 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
Chemical formula
 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
 Caffeic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  • v
  • t
  • e
Aglycones
Precursor
Monohydroxycinnamic acids
(Coumaric acids)
  • p-Coumaric acid
  • o-Coumaric acid
  • m-Coumaric acid
Dihydroxycinnamic acids
Trihydroxycinnamic acids
O-methylated forms
others
Esters
glycoside-likes
Esters of
caffeic acid
with cyclitols
esters of
quinic acid
  • Chlorogenic acid (3-caffeoylquinic acid)
  • Cryptochlorogenic acid (4-O-caffeoylquinic acid)
  • Neochlorogenic acid (5-O-Caffeoylquinic acid)
  • Cynarine (1,5-dicaffeoylquinic acid)
  • 3,4-dicaffeoylquinic acid
  • 3,5-dicaffeoylquinic acid
esters of
shikimic acid
Glycosides
  • Ferulic acid glucoside
  • p-Coumaric acid glucoside
  • 1-Sinapoyl-D-glucose
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
Trimers
Tetramers
  • Tetraferulic acids
Conjugates with
coenzyme A (CoA)