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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H14O6
Molecular Weight 290.2686
Optical Activity ( - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPICATECHIN

SMILES

c1cc(c(cc1[C@]2([H])[C@@]([H])(Cc3c(cc(cc3O2)O)O)O)O)O

InChI

InChIKey=PFTAWBLQPZVEMU-UKRRQHHQSA-N
InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1

HIDE SMILES / InChI

Molecular Formula C15H14O6
Molecular Weight 290.2686
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Epichatechin is one of the 4 catechin diastereoisomers. It can be isolated from a number of species of Palmae, as well as Dryas octopetala and guarana seeds. Epicatechin has been widely studied as a potential therapeutic compound in a wide variety of conditions including cancers, diabetes, heart conditions, and neurological conditions. Epicatechin is available as a natural health supplement and marketed for bodybuilding and the treatment of high blood pressure, high cholesterol, immune support, low testosterone, high blood sugar, and improved memory.

CNS Activity

Curator's Comment:: referenced study was conducted on mice

Approval Year

PubMed

PubMed

TitleDatePubMed
Biological evaluation of proanthocyanidin dimers and related polyphenols.
1999 Jul
Green tea catechins and vitamin E inhibit angiogenesis of human microvascular endothelial cells through suppression of IL-8 production.
2001
Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures.
2001
Erythrocyte sodium/hydrogen exchange inhibition by (-) epicatechin.
2001
Measurement of copper-binding sites on low density lipoprotein.
2001 Apr
Separation of phenolic compounds by high-performance liquid chromatography with absorbance and fluorimetric detection.
2001 Apr 6
Inhibition by green tea catechins of metabolic activation of procarcinogens by human cytochrome P450.
2001 Aug 8
Green tea polyphenols: DNA photodamage and photoimmunology.
2001 Dec 31
Studies in polyphenol chemistry and bioactivity. 3.(1,2) stereocontrolled synthesis of epicatechin-4alpha,8-epicatechin, an unnatural isomer of the B-type procyanidins.
2001 Feb 23
Daily cocoa intake reduces the susceptibility of low-density lipoprotein to oxidation as demonstrated in healthy human volunteers.
2001 Jan
Efficiency and mechanism of the antioxidant action of trans-resveratrol and its analogues in the radical liposome oxidation.
2001 Jul 1
The antioxidant properties of zinc: interactions with iron and antioxidants.
2001 Jul 15
Stability of phenolic compounds during extraction with superheated solvents.
2001 Jul 6
Metabolism of phenolic compounds during loquat fruit development.
2001 Jun
Furanocoumarins from the aerial parts of Dorstenia contrajerva.
2001 May
Water-soluble antioxidants inhibit macrophage recognition of oxidized erythrocytes.
2001 May
Chemopreventive effects of cocoa polyphenols on chronic diseases.
2001 Nov
Chocolate: food as medicine/medicine as food.
2001 Oct
A review of the French maritime pine bark extract (Pycnogenol), a herbal medication with a diverse clinical pharmacology.
2002 Apr
Immunomodulatory proanthocyanidins from Ecdysanthera utilis.
2002 Apr
Phenolic compounds and antioxidant capacity of Georgia-grown blueberries and blackberries.
2002 Apr 10
Changes in proanthocyanidin chain length in winelike model solutions.
2002 Apr 10
(-)epicatechin induces and modulates endothelium-dependent relaxation in isolated rat mesenteric artery rings.
2002 Dec
Polyphenols from alcoholic apple cider are absorbed, metabolized and excreted by humans.
2002 Feb
The contribution of the pyrogallol moiety to the superoxide radical scavenging activity of flavonoids.
2002 Jan
Chemical studies on antioxidant mechanism of tea catechins: analysis of radical reaction products of catechin and epicatechin with 2,2-diphenyl-1-picrylhydrazyl.
2002 Jul
Preparative isolation of polyphenolic compounds from Vitis vinifera by centrifugal partition chromatography.
2002 Jul 26
Inhibition of the PDGF beta-receptor tyrosine phosphorylation and its downstream intracellular signal transduction pathway in rat and human vascular smooth muscle cells by different catechins.
2002 Jun
Hawthorn: pharmacology and therapeutic uses.
2002 Mar 1
Inhibition by wine polyphenols of peroxynitrite-initiated chemiluminescence and NADH oxidation.
2002 May
Contribution of presystemic hepatic extraction to the low oral bioavailability of green tea catechins in rats.
2002 Nov
Identification and biochemical characterization of mutants in the proanthocyanidin pathway in Arabidopsis.
2002 Oct
Prevention of hepatic ischemia-reperfusion injury by green tea extract.
2002 Oct
Cocoa extract protects against early alcohol-induced liver injury in the rat.
2002 Oct 1
Influence of flavan-3-ols and procyanidins on UVC-mediated formation of 8-oxo-7,8-dihydro-2'-deoxyguanosine in isolated DNA.
2002 Oct 15
Analysis of flavonoids in Ginkgo biloba L. and its phytopharmaceuticals by capillary electrophoresis with electrochemical detection.
2002 Sep
Patents

Sample Use Guides

Ten adults with genetically-confirmed Becker muscular dystrophy received (-)-epicatechin 100 mg/day orally for 8 weeks.
Route of Administration: Oral
HCAEC cells were obtained from 14-, 40, and 60-year old healthy male donors. Cells were maintained in HCAEC growth medium at 37 deg-C under a 5% CO2 atmosphere. Sixteen hours prior to experiments, HCAECs were washed with phenol red-free Hank’s salts solution and kept in phenol red-free M-199 supplemented with 200 mmol/L of L-glutamine and 1% antibiotic mix. To develop time response curves, cells were treated with 1 micromol/L epicatechin diluted in water. Culture media samples were collected at 0, 5, 10, 20, 30, 60, 120, 180 and 240 min. To develop concentration-response curves, cells were treated with epicatechin (0.1 nmol/L–100 μmol/L) for 10 min. Increases in NO were detected as early as 5 min after treatment, with a maximal effect occurring at 10–30 minutes and a maximal effect was obtained with 1 μmol/L epicatechin.
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:57:43 UTC 2021
Edited
by admin
on Sat Jun 26 05:57:43 UTC 2021
Record UNII
34PHS7TU43
Record Status Validated (UNII)
Record Version
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Name Type Language
EPICATECHIN
Common Name English
L-EPICATECHIN [WHO-DD]
Common Name English
(-)-EPI CATECHIN
Common Name English
2H-1-BENZOPYRAN-3,5,7-TRIOL, 2-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-, (2R,3R)-
Systematic Name English
EPICATECHOL
Common Name English
L-ACACATECHIN
Common Name English
EPI-CATECHOL
Common Name English
(-)-EPICATECHIN (CONSTITUENT OF MARITIME PINE) [DSC]
Common Name English
(-)-(2R:3R)-5,7,3',4'-TETRAHYDROXYFLAVAN-3-OL
Common Name English
(-)-EPICATECHIN
Common Name English
(-)-EPICATECHIN(EG) (CONSTITUENT OF POWDERED DECAFFEINATED GREEN TEA EXTRACT) [DSC]
Common Name English
(-)-EPICATECHIN [USP-RS]
Common Name English
L-EPICATECHIN
Common Name English
EPI-CATECHIN
Common Name English
(-)-EPICATECHIN (CONSTITUENT OF GRAPE SEEDS OLIGOMERIC PROANTHOCYANIDINS) [DSC]
Common Name English
(-)-EPICATECHOL
Common Name English
NSC-81161
Code English
Classification Tree Code System Code
DSLD 1379 (Number of products:24)
Created by admin on Sat Jun 26 05:57:43 UTC 2021 , Edited by admin on Sat Jun 26 05:57:43 UTC 2021
Code System Code Type Description
USP_CATALOG
1236620
Created by admin on Sat Jun 26 05:57:43 UTC 2021 , Edited by admin on Sat Jun 26 05:57:43 UTC 2021
PRIMARY USP-RS
PUBCHEM
72276
Created by admin on Sat Jun 26 05:57:43 UTC 2021 , Edited by admin on Sat Jun 26 05:57:43 UTC 2021
PRIMARY
CAS
490-46-0
Created by admin on Sat Jun 26 05:57:43 UTC 2021 , Edited by admin on Sat Jun 26 05:57:43 UTC 2021
PRIMARY
EPA CompTox
490-46-0
Created by admin on Sat Jun 26 05:57:43 UTC 2021 , Edited by admin on Sat Jun 26 05:57:43 UTC 2021
PRIMARY
ECHA (EC/EINECS)
207-710-1
Created by admin on Sat Jun 26 05:57:43 UTC 2021 , Edited by admin on Sat Jun 26 05:57:43 UTC 2021
PRIMARY
WIKIPEDIA
Epicatechin
Created by admin on Sat Jun 26 05:57:43 UTC 2021 , Edited by admin on Sat Jun 26 05:57:43 UTC 2021
PRIMARY
FDA UNII
34PHS7TU43
Created by admin on Sat Jun 26 05:57:43 UTC 2021 , Edited by admin on Sat Jun 26 05:57:43 UTC 2021
PRIMARY
DRUG BANK
DB12039
Created by admin on Sat Jun 26 05:57:43 UTC 2021 , Edited by admin on Sat Jun 26 05:57:43 UTC 2021
PRIMARY
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