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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H14O6
Molecular Weight 290.2681
Optical Activity ( - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPICATECHIN

SMILES

O[C@@H]1CC2=C(O[C@@H]1C3=CC(O)=C(O)C=C3)C=C(O)C=C2O

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 290.2681
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
Biological evaluation of proanthocyanidin dimers and related polyphenols.
1999 Jul
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
Protective effect of phenolic compounds isolated from the hooks and stems of Uncaria sinensis on glutamate-induced neuronal death.
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
Polyphenols of cocoa: inhibition of mammalian 15-lipoxygenase.
2001 Dec
Rapid conversion of tea catechins to monomethylated products by rat liver cytosolic catechol-O-methyltransferase.
2001 Dec
Comparative contents of dietary fiber, total phenolics, and minerals in persimmons and apples.
2001 Feb
Polyphyenolics increase t-PA and u-PA gene transcription in cultured human endothelial cells.
2001 Feb
Degradation of green tea catechins in tea drinks.
2001 Jan
Efficiency and mechanism of the antioxidant action of trans-resveratrol and its analogues in the radical liposome oxidation.
2001 Jul 1
Simultaneous determination of twelve tea catechins by high-performance liquid chromatography with electrochemical detection.
2001 Jun
Antioxidant mechanism of flavonoids. Solvent effect on rate constant for chain-breaking reaction of quercetin and epicatechin in autoxidation of methyl linoleate.
2001 Jun
Metabolism of phenolic compounds during loquat fruit development.
2001 Jun
Analysis of urinary metabolites of tea catechins by liquid chromatography/electrospray ionization mass spectrometry.
2001 Jun
Stereospecificity in membrane effects of catechins.
2001 Mar 14
Furanocoumarins from the aerial parts of Dorstenia contrajerva.
2001 May
Water-soluble antioxidants inhibit macrophage recognition of oxidized erythrocytes.
2001 May
Contrasting influences of glucuronidation and O-methylation of epicatechin on hydrogen peroxide-induced cell death in neurons and fibroblasts.
2001 Nov 1
Regulation of phenobarbital-mediated induction of CYP102 (cytochrome P450(BM-3)) in Bacillus megaterium by phytochemicals from soy and green tea.
2001 Oct
Simplified catechin-gallate inhibitors of HIV-1 reverse transcriptase.
2001 Oct 22
Flavonoids protect neurons from oxidized low-density-lipoprotein-induced apoptosis involving c-Jun N-terminal kinase (JNK), c-Jun and caspase-3.
2001 Sep 15
High-performance liquid chromatographic method for simultaneous determination of hawthorn active components in rat plasma.
2001 Sep 5
A review of the French maritime pine bark extract (Pycnogenol), a herbal medication with a diverse clinical pharmacology.
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
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
(-)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
Differential inhibition of polymerase and strand-transfer activities of HIV-1 reverse transcriptase.
2002 Feb 25
Effects of dietary antioxidants on human DNA ex vivo.
2002 Jan
Preparative isolation of polyphenolic compounds from Vitis vinifera by centrifugal partition chromatography.
2002 Jul 26
Identification and in vitro biological activities of hop proanthocyanidins: inhibition of nNOS activity and scavenging of reactive nitrogen species.
2002 Jun 5
Lower crop load for Cv. Jonagold apples (Malus x domestica Borkh.) increases polyphenol content and fruit quality.
2002 Mar 13
Inhibition by wine polyphenols of peroxynitrite-initiated chemiluminescence and NADH oxidation.
2002 May
The effects of flavanol-rich cocoa and aspirin on ex vivo platelet function.
2002 May 15
Contribution of presystemic hepatic extraction to the low oral bioavailability of green tea catechins in rats.
2002 Nov
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
Activity-guided fractionation of green tea extract with antiproliferative activity against human stomach cancer cells.
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
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 Wed Jul 05 23:51:28 UTC 2023
Edited
by admin
on Wed Jul 05 23:51:28 UTC 2023
Record UNII
34PHS7TU43
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPICATECHIN
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
L-Epicatechin [WHO-DD]
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 Wed Jul 05 23:51:28 UTC 2023 , Edited by admin on Wed Jul 05 23:51:28 UTC 2023
Code System Code Type Description
CHEBI
90
Created by admin on Wed Jul 05 23:51:28 UTC 2023 , Edited by admin on Wed Jul 05 23:51:28 UTC 2023
PRIMARY
PUBCHEM
72276
Created by admin on Wed Jul 05 23:51:28 UTC 2023 , Edited by admin on Wed Jul 05 23:51:28 UTC 2023
PRIMARY
CAS
490-46-0
Created by admin on Wed Jul 05 23:51:28 UTC 2023 , Edited by admin on Wed Jul 05 23:51:28 UTC 2023
PRIMARY
SMS_ID
300000013075
Created by admin on Wed Jul 05 23:51:28 UTC 2023 , Edited by admin on Wed Jul 05 23:51:28 UTC 2023
PRIMARY
EPA CompTox
DTXSID4045133
Created by admin on Wed Jul 05 23:51:28 UTC 2023 , Edited by admin on Wed Jul 05 23:51:28 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-710-1
Created by admin on Wed Jul 05 23:51:28 UTC 2023 , Edited by admin on Wed Jul 05 23:51:28 UTC 2023
PRIMARY
WIKIPEDIA
Epicatechin
Created by admin on Wed Jul 05 23:51:28 UTC 2023 , Edited by admin on Wed Jul 05 23:51:28 UTC 2023
PRIMARY
FDA UNII
34PHS7TU43
Created by admin on Wed Jul 05 23:51:28 UTC 2023 , Edited by admin on Wed Jul 05 23:51:28 UTC 2023
PRIMARY
RS_ITEM_NUM
1236620
Created by admin on Wed Jul 05 23:51:28 UTC 2023 , Edited by admin on Wed Jul 05 23:51:28 UTC 2023
PRIMARY
DRUG BANK
DB12039
Created by admin on Wed Jul 05 23:51:28 UTC 2023 , Edited by admin on Wed Jul 05 23:51:28 UTC 2023
PRIMARY
NSC
81161
Created by admin on Wed Jul 05 23:51:28 UTC 2023 , Edited by admin on Wed Jul 05 23:51:28 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
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USP
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Secondary metabolite detected in developing cacao seeds.
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IN-VITRO
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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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PARENT -> CONSTITUENT ALWAYS PRESENT