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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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.9 μg/L
50 mg 2 times / day multiple, oral
dose: 50 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
EPICATECHIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
5.5 μg/L
50 mg 2 times / day multiple, oral
dose: 50 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
EPICATECHIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
34.5 μg/L
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPICATECHIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
10.3 μg × h/L
50 mg 2 times / day multiple, oral
dose: 50 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
EPICATECHIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
21.67 μg × h/L
50 mg 2 times / day multiple, oral
dose: 50 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
EPICATECHIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
122.4 μg × h/L
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPICATECHIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.5 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPICATECHIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
200 mg single, oral
Highest studied dose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources: Page: p.7
healthy, ADULT
n = 3
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Population Size: 3
Sources: Page: p.7
50 mg 2 times / day multiple, oral
Studied dose
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Sources: Page: p.7
healthy, ADULT
n = 8
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Population Size: 8
Sources: Page: p.7
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Green tea catechins and vitamin E inhibit angiogenesis of human microvascular endothelial cells through suppression of IL-8 production.
2001
Bioavailability of flavan-3-ols and procyanidins: gastrointestinal tract influences and their relevance to bioactive forms in vivo.
2001 Dec
Rapid conversion of tea catechins to monomethylated products by rat liver cytosolic catechol-O-methyltransferase.
2001 Dec
Proposed active constituents of Dipladenia martiana.
2001 Dec
Chemopreventive effects of cocoa polyphenols on chronic diseases.
2001 Nov
Contrasting influences of glucuronidation and O-methylation of epicatechin on hydrogen peroxide-induced cell death in neurons and fibroblasts.
2001 Nov 1
Chocolate: food as medicine/medicine as food.
2001 Oct
Dietary flavonoids: bioavailability, metabolic effects, and safety.
2002
Effects of epigallocatechin 3-O-gallate on cellular antioxidative system in HepG2 cells.
2002 Apr
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
On-line HPLC-DPPH screening method for evaluation of radical scavenging phenols extracted from apples (Malus domestica L.).
2002 Apr 24
Prolyl endopeptidase inhibitors from the roots of Lindera strychnifolia F. Vill.
2002 Aug
Fractionation of polymeric procyanidins from lowbush blueberry and quantification of procyanidins in selected foods with an optimized normal-phase HPLC-MS fluorescent detection method.
2002 Aug 14
Procyanidins protect Fao cells against hydrogen peroxide-induced oxidative stress.
2002 Aug 15
(-)epicatechin induces and modulates endothelium-dependent relaxation in isolated rat mesenteric artery rings.
2002 Dec
Uptake and metabolism of epicatechin and its access to the brain after oral ingestion.
2002 Dec 15
Antioxidant capacities of ten edible North American plants.
2002 Feb
Effects of dietary antioxidants on human DNA ex vivo.
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
Antiviral and antioxidant activity of flavonoids and proanthocyanidins from Crataegus sinaica.
2002 Jun
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
Vitamin C equivalent antioxidant capacity (VCEAC) of phenolic phytochemicals.
2002 Jun 19
Antioxidants from the bark of Burkea africana, an African medicinal plant.
2002 Mar
Principles of root bark of Hippocratea excelsa (Hippocrataceae) with gastroprotective activity.
2002 Mar
Hawthorn: pharmacology and therapeutic uses.
2002 Mar 1
Lower crop load for Cv. Jonagold apples (Malus x domestica Borkh.) increases polyphenol content and fruit quality.
2002 Mar 13
Study of catechin and xanthine tea profiles as geographical tracers.
2002 Mar 27
Hydrogen peroxide generation in caco-2 cell culture medium by addition of phenolic compounds: effect of ascorbic acid.
2002 May
Vasodilating procyanidins derived from grape seeds.
2002 May
Xanthones from the green fruit hulls of Garcinia mangostana.
2002 May
Inhibitory effects of cocoa flavanols and procyanidin oligomers on free radical-induced erythrocyte hemolysis.
2002 May
The effects of flavanol-rich cocoa and aspirin on ex vivo platelet function.
2002 May 15
Flavonoids uptake and their effect on cell cycle of human colon adenocarcinoma cells (Caco2).
2002 May 20
Contribution of presystemic hepatic extraction to the low oral bioavailability of green tea catechins in rats.
2002 Nov
Tea enhances insulin activity.
2002 Nov 20
Identification and biochemical characterization of mutants in the proanthocyanidin pathway in Arabidopsis.
2002 Oct
Procyanidin dimer B2 [epicatechin-(4beta-8)-epicatechin] in human plasma after the consumption of a flavanol-rich cocoa.
2002 Oct
Prevention of hepatic ischemia-reperfusion injury by green tea extract.
2002 Oct
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
Activity-guided fractionation of green tea extract with antiproliferative activity against human stomach cancer cells.
2002 Sep
Urinary tea polyphenols in relation to gastric and esophageal cancers: a prospective study of men in Shanghai, China.
2002 Sep
Elevation of P-glycoprotein function by a catechin in green tea.
2002 Sep 20
Interaction of designed sulfated flavanoids with antithrombin: lessons on the design of organic activators.
2002 Sep 26
Constituents and biological activities from Muehlenbeckia hastulata.
2002 Sep-Oct
Effect of a polyphenols-enriched chardonnay white wine in diabetic rats.
2003 Jan 1
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
  • Download
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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Secondary metabolite detected in developing cacao seeds.
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The compound was screened for it's antioxidant capacity in the DPPH assay, and displayed a high antioxidant activity, with an IC50 value of 49.0 uM.
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USP
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