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
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
| 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.
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.9 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25598082 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25598082 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25598082 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
10.3 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25598082 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25598082 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25598082 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25598082 |
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
| Dose | Population | Adverse 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
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| weak [IC50 >100 uM] | ||||
| weak [IC50 >100 uM] | ||||
| weak [IC50 >100 uM] | ||||
| weak [IC50 >100 uM] | ||||
| weak | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| yes [Km 1.8 uM] | ||||
| yes [Km 60 uM] | ||||
| yes [Km 961.8 uM] | ||||
| yes | ||||
| yes | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
|
| Polyphenols of cocoa: inhibition of mammalian 15-lipoxygenase. | 2001 Dec |
|
| 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 |
|
| Green tea polyphenols: DNA photodamage and photoimmunology. | 2001 Dec 31 |
|
| Dietary flavonoids: bioavailability, metabolic effects, and safety. | 2002 |
|
| Effects of epigallocatechin 3-O-gallate on cellular antioxidative system in HepG2 cells. | 2002 Apr |
|
| Procyanidins are not bioavailable in rats fed a single meal containing a grapeseed extract or the procyanidin dimer B3. | 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 |
|
| Polyphenols from alcoholic apple cider are absorbed, metabolized and excreted by humans. | 2002 Feb |
|
| 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 |
|
| Green tea catechins decrease apolipoprotein B-100 secretion from HepG2 cells. | 2002 Jan |
|
| 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 |
|
| 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 |
|
| Identification and in vitro biological activities of hop proanthocyanidins: inhibition of nNOS activity and scavenging of reactive nitrogen species. | 2002 Jun 5 |
|
| 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 |
|
| Stability of the flavan-3-ols epicatechin and catechin and related dimeric procyanidins derived from cocoa. | 2002 Mar 13 |
|
| Lower crop load for Cv. Jonagold apples (Malus x domestica Borkh.) increases polyphenol content and fruit quality. | 2002 Mar 13 |
|
| Designing small, nonsugar activators of antithrombin using hydropathic interaction analyses. | 2002 Mar 14 |
|
| Synthesis of theaflavin from epicatechin and epigallocatechin by plant homogenates and role of epicatechin quinone in the synthesis and degradation of theaflavin. | 2002 Mar 27 |
|
| 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 |
|
| Inhibition by wine polyphenols of peroxynitrite-initiated chemiluminescence and NADH oxidation. | 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 |
|
| Flavonoids uptake and their effect on cell cycle of human colon adenocarcinoma cells (Caco2). | 2002 May 20 |
|
| 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 |
|
| 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 |
|
| Effect of a polyphenols-enriched chardonnay white wine in diabetic rats. | 2003 Jan 1 |
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
Edited
Fri Dec 16 20:06:33 UTC 2022
by
admin
on
Fri Dec 16 20:06:33 UTC 2022
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| Record UNII |
34PHS7TU43
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| Record Status |
Validated (UNII)
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| Record Version |
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1379 (Number of products:24)
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90
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72276
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490-46-0
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DTXSID4045133
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207-710-1
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Epicatechin
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34PHS7TU43
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1236620
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DB12039
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81161
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Secondary metabolite detected in developing cacao seeds.
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PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT |
IN-VITRO
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METABOLIC ENZYME -> INHIBITOR |
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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 | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
