You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-02-23 11:52:29 UTC
Update Date2016-02-11 01:05:03 UTC
HMDB IDHMDB01871
Secondary Accession NumbersNone
Metabolite Identification
Common NameEpicatechin
DescriptionEpicatechin is an antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. Catechin is a tannin peculiar to green and white tea because the black tea oxidation process reduces catechins in black tea. Catechin is a powerful, water soluble polyphenol and antioxidant that is easily oxidized. Several thousand types are available in the plant world. As many as two thousand are known to have a flavon structure and are called flavonoids. Catechin is one of them. Green tea is manufactured from fresh, unfermented tea leaves; the oxidation of catechins is minimal, and hence they are able to serve as antioxidants. Researchers believe that catechin is effective because it easily sticks to proteins, blocking bacteria from adhering to cell walls and disrupting their ability to destroy them. Viruses have hooks on their surfaces and can attach to cell walls. The catechin in green tea prevents viruses from adhering and causing harm. Catechin reacts with toxins created by harmful bacteria (many of which belong to the protein family) and harmful metals such as lead, mercury, chrome, and cadmium. From its NMR espectra, there is a doubt on 2 and 3 atoms configuration. It seems to be that they are in trans position.
Structure
Thumb
Synonyms
ValueSource
EpicatechinMetaCyc
2,3-cis-EpicatechinMetaCyc
(-)-EpicatecholHMDB
(2R,3R)-(-)-EpicatechinHMDB
3,3',4',5,7-PentahydroxyflavaneHMDB
alpha-CatechinHMDB
EpicatecholHMDB
EpigallocatechinHMDB
L(-)-EpicatechinHMDB
L-AcacatechinHMDB
L-EpicatechinHMDB
L-EpicatecholHMDB
Chemical FormulaC15H14O6
Average Molecular Weight290.2681
Monoisotopic Molecular Weight290.07903818
IUPAC Name(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Nameent-epicatechin
CAS Registry Number490-46-0
SMILES
O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C=C1
InChI Identifier
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
InChI KeyInChIKey=PFTAWBLQPZVEMU-UKRRQHHQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as catechins. These are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentCatechins
Alternative Parents
Substituents
  • Catechin
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Resorcinol
  • 1,2-diphenol
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Plant
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point240 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.65 mg/mLALOGPS
logP1.02ALOGPS
logP1.8ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)9ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74 m3·mol-1ChemAxon
Polarizability28.13 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-014i-0649000000-e7a2620a4d8b1c243de3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000f-1690000000-16c536adc2a6e03c5b4fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-1910000000-92d64d3194a12735e531View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-5900000000-1ec541b64eecd72f3551View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-0006-0090000000-53e575c7acf970449e84View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0079-0900000000-1c23cf9e8aa258a986adView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-052r-1970000000-02212cd1c44e06d5add3View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Fibroblasts
  • Intestine
  • Platelet
  • Prostate
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.625 +/- 0.198 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 125
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 125
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 125
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 125
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 125
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 125
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 125
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 125
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 125
  • Not Applicable
details
UrineDetected and Quantified0.13 +/- 0.20 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified7.445 +/- 5.022 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified3.571 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID125
Phenol Explorer Metabolite ID125
FoodDB IDFDB002576
KNApSAcK IDC00000956
Chemspider ID65230
KEGG Compound IDC09727
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEpicatechin
NuGOwiki LinkHMDB01871
Metagene LinkHMDB01871
METLIN ID3420
PubChem Compound72276
PDB IDNot Available
ChEBI ID671201
References
Synthesis ReferenceLaw, Khoon Huat; Das, Nagaratnam P. Production of (-)-epicatechin by Uncaria elliptica callus cultures. Phytochemistry (1989), 28(4), 1099-100.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Li C, Meng X, Winnik B, Lee MJ, Lu H, Sheng S, Buckley B, Yang CS: Analysis of urinary metabolites of tea catechins by liquid chromatography/electrospray ionization mass spectrometry. Chem Res Toxicol. 2001 Jun;14(6):702-7. [11409941 ]
  2. Yang CS, Lee MJ, Chen L: Human salivary tea catechin levels and catechin esterase activities: implication in human cancer prevention studies. Cancer Epidemiol Biomarkers Prev. 1999 Jan;8(1):83-9. [9950244 ]
  3. Henning SM, Aronson W, Niu Y, Conde F, Lee NH, Seeram NP, Lee RP, Lu J, Harris DM, Moro A, Hong J, Pak-Shan L, Barnard RJ, Ziaee HG, Csathy G, Go VL, Wang H, Heber D: Tea polyphenols and theaflavins are present in prostate tissue of humans and mice after green and black tea consumption. J Nutr. 2006 Jul;136(7):1839-43. [16772446 ]
  4. Lill G, Voit S, Schror K, Weber AA: Complex effects of different green tea catechins on human platelets. FEBS Lett. 2003 Jul 10;546(2-3):265-70. [12832052 ]
  5. Murphy KJ, Chronopoulos AK, Singh I, Francis MA, Moriarty H, Pike MJ, Turner AH, Mann NJ, Sinclair AJ: Dietary flavanols and procyanidin oligomers from cocoa (Theobroma cacao) inhibit platelet function. Am J Clin Nutr. 2003 Jun;77(6):1466-73. [12791625 ]
  6. Meng X, Lee MJ, Li C, Sheng S, Zhu N, Sang S, Ho CT, Yang CS: Formation and identification of 4'-O-methyl-(-)-epigallocatechin in humans. Drug Metab Dispos. 2001 Jun;29(6):789-93. [11353745 ]
  7. Sano A, Yamakoshi J, Tokutake S, Tobe K, Kubota Y, Kikuchi M: Procyanidin B1 is detected in human serum after intake of proanthocyanidin-rich grape seed extract. Biosci Biotechnol Biochem. 2003 May;67(5):1140-3. [12834296 ]
  8. Babich H, Krupka ME, Nissim HA, Zuckerbraun HL: Differential in vitro cytotoxicity of (-)-epicatechin gallate (ECG) to cancer and normal cells from the human oral cavity. Toxicol In Vitro. 2005 Mar;19(2):231-42. [15649637 ]
  9. Holt RR, Lazarus SA, Sullards MC, Zhu QY, Schramm DD, Hammerstone JF, Fraga CG, Schmitz HH, Keen CL: Procyanidin dimer B2 [epicatechin-(4beta-8)-epicatechin] in human plasma after the consumption of a flavanol-rich cocoa. Am J Clin Nutr. 2002 Oct;76(4):798-804. [12324293 ]
  10. Spencer JP, Schroeter H, Crossthwaithe AJ, Kuhnle G, Williams RJ, Rice-Evans C: Contrasting influences of glucuronidation and O-methylation of epicatechin on hydrogen peroxide-induced cell death in neurons and fibroblasts. Free Radic Biol Med. 2001 Nov 1;31(9):1139-46. [11677047 ]
  11. DuPont MS, Bennett RN, Mellon FA, Williamson G: Polyphenols from alcoholic apple cider are absorbed, metabolized and excreted by humans. J Nutr. 2002 Feb;132(2):172-5. [11823574 ]
  12. Vinson JA, Proch J, Bose P: MegaNatural((R)) Gold Grapeseed Extract: In Vitro Antioxidant and In Vivo Human Supplementation Studies. J Med Food. 2001 Spring;4(1):17-26. [12639284 ]
  13. Lhoste EF, Ouriet V, Bruel S, Flinois JP, Brezillon C, Magdalou J, Cheze C, Nugon-Baudon L: The human colonic microflora influences the alterations of xenobiotic-metabolizing enzymes by catechins in male F344 rats. Food Chem Toxicol. 2003 May;41(5):695-702. [12659723 ]
  14. Keen CL: Chocolate: food as medicine/medicine as food. J Am Coll Nutr. 2001 Oct;20(5 Suppl):436S-439S; discussion 440S-442S. [11603654 ]