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 |
|---|---|---|
| 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 |
|
| 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 |
|
| 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 |
|
| Daily cocoa intake reduces the susceptibility of low-density lipoprotein to oxidation as demonstrated in healthy human volunteers. | 2001 Jan |
|
| Epicatechin is the primary bioavailable form of the procyanidin dimers B2 and B5 after transfer across the small intestine. | 2001 Jul 20 |
|
| Procyanidins from the herb of Hypericum perforatum. | 2001 Jun |
|
| Formation and identification of 4'-O-methyl-(-)-epigallocatechin in humans. | 2001 Jun |
|
| Resveratrol and a novel tyrosinase in Carignan grape juice. | 2001 Mar |
|
| Epicatechin and its in vivo metabolite, 3'-O-methyl epicatechin, protect human fibroblasts from oxidative-stress-induced cell death involving caspase-3 activation. | 2001 Mar 15 |
|
| Furanocoumarins from the aerial parts of Dorstenia contrajerva. | 2001 May |
|
| Simplified catechin-gallate inhibitors of HIV-1 reverse transcriptase. | 2001 Oct 22 |
|
| (-)epicatechin induces and modulates endothelium-dependent relaxation in isolated rat mesenteric artery rings. | 2002 Dec |
|
| 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 |
|
| Antiviral and antioxidant activity of flavonoids and proanthocyanidins from Crataegus sinaica. | 2002 Jun |
|
| 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 |
|
| The effects of flavanol-rich cocoa and aspirin on ex vivo platelet function. | 2002 May 15 |
|
| Identification and biochemical characterization of mutants in the proanthocyanidin pathway in Arabidopsis. | 2002 Oct |
|
| Elevation of P-glycoprotein function by a catechin in green tea. | 2002 Sep 20 |
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 15 16:25:12 GMT 2023
by
admin
on
Fri Dec 15 16:25:12 GMT 2023
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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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490-46-0
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Epicatechin
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DB12039
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81161
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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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USP
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT |
IN-VITRO
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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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METABOLIC ENZYME -> INHIBITOR |
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