Identification

PhytoHub ID
PHUB000262
Name
(-)-Epicatechin
Synonyms
  • 3,5,7,3',4'-Pentahydroxyflavane
CAS Number
490-46-0
Average Mass
290.271
Monoisotopic Mass
290.079038171
Chemical Formula
C15H14O6
IUPAC Name
(3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
InChI Key
PFTAWBLQPZVEMU-AFYYWNPRSA-N
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
SMILES
O[C@@H]1CC2=C(OC1C1=CC(O)=C(O)C=C1)C=C(O)C=C2O
Structure

Calculated Properties

Solubility (ALOGPS)
6.45e-01 g/l
LogS (ALOGPS)
-2.65
LogP (ALOGPS)
1.02
Hydrogen Acceptors
6
Hydrogen Donors
5
Rotatable Bond Count
1
Polar Surface Area
110.38000000000001
Refractivity
73.99970000000002
Polarizability
28.727443236736793
Formal Charge
0
Physiological Charge
0
pKa (strongest basic)
-3.289719332242856
pKa (strongest acidic)
9.004573813837975
FreewebChemaxon powered

Taxonomy

Family
Polyphenols
Class
Flavonoids
Sub-class
Flavanols

Spectra

Record IDSourceDescriptionView
BML00626MassBankLC-ESI-QTOF Spectrum - 10 ev, unspecifiedView Spectra
BML00630MassBankLC-ESI-QTOF Spectrum - 20 ev, unspecifiedView Spectra
BML00634MassBankLC-ESI-QTOF Spectrum - 40 ev, unspecifiedView Spectra
BML80050MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
BML80051MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
CE000088MassBankLC-ESI-ITFT Spectrum - 35eV, unspecifiedView Spectra
CE000089MassBankLC-ESI-ITFT Spectrum - 45eV, unspecifiedView Spectra
CE000090MassBankLC-ESI-ITFT Spectrum - 55eV, unspecifiedView Spectra
CE000091MassBankLC-ESI-ITFT Spectrum - 70eV, unspecifiedView Spectra
CE000092MassBankLC-ESI-ITFT Spectrum - -, unspecifiedView Spectra
FIO00067MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
FIO00068MassBankLC-ESI-QTOF Spectrum - 20 eV, unspecifiedView Spectra
FIO00069MassBankLC-ESI-QTOF Spectrum - 30 eV, unspecifiedView Spectra
FIO00070MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
FIO00071MassBankLC-ESI-QTOF Spectrum - 50 eV, unspecifiedView Spectra
FIO00072MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
FIO00073MassBankLC-ESI-QTOF Spectrum - 20 eV, unspecifiedView Spectra
FIO00074MassBankLC-ESI-QTOF Spectrum - 30 eV, unspecifiedView Spectra
FIO00075MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
FIO00076MassBankLC-ESI-QTOF Spectrum - 50 eV, unspecifiedView Spectra
OUF00223MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
PB001329MassBankLC-ESI-QTOF Spectrum - 15 eV, unspecifiedView Spectra
PB001330MassBankLC-ESI-QTOF Spectrum - 25 eV, unspecifiedView Spectra
PB001331MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
PB001332MassBankLC-ESI-QTOF Spectrum - 55 eV, unspecifiedView Spectra
PB001337MassBankLC-ESI-QTOF Spectrum - 15 eV, unspecifiedView Spectra
PB001338MassBankLC-ESI-QTOF Spectrum - 25 eV, unspecifiedView Spectra
PB001339MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
PB001340MassBankLC-ESI-QTOF Spectrum - 55 eV, unspecifiedView Spectra
PB002429MassBankLC-ESI-QTOF Spectrum - 15 eV, unspecifiedView Spectra
PB002430MassBankLC-ESI-QTOF Spectrum - 25 eV, unspecifiedView Spectra
PB002431MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
PB002432MassBankLC-ESI-QTOF Spectrum - 55 eV, unspecifiedView Spectra
PB006281MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
PB006301MassBankLC-ESI-QTOF Spectrum - 15 eV, unspecifiedView Spectra
PB006302MassBankLC-ESI-QTOF Spectrum - 20 eV, unspecifiedView Spectra
PR100262MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100263MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100264MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100687MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100688MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100689MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra

Food Sources

Metabolism

PrecursorMetaboliteSpeciesBiofluidsFormulaMonoisotopic mass
(-)-Epicatechin 4'-Hydroxyphenylacetic acidhumanNot AvailableC8H8O3152.047344122 Publications
(-)-Epicatechin (-)-Epicatechin 3'-O-glucuronidehumanplasma (major), urine (major)C21H22O12466.111126148 Publications
(-)-Epicatechin (-)-Epicatechin 3'-O-sulfatehumanplasma (major), urine (major)C15H14O9S370.035853205 Publications
(-)-Epicatechin (-)-Epicatechin 4'-O-glucuronidehumanplasma, urine (minor)C21H22O12466.111126148 Publications
(-)-Epicatechin (-)-Epicatechin 4'-O-sulfatehumanplasma (minor), urine (minor)C15H14O9S370.035853205 Publications
(-)-Epicatechin (-)-Epicatechin 5-O-sulfatehumanurine (minor)C15H14O9S370.035853205 Publications
(-)-Epicatechin (-)-Epicatechin 7-O-glucuronidehuman ratplasma, urine (major)C21H22O12466.111126148 Publications
(-)-Epicatechin (-)-Epicatechin glucuronidehumanplasmaC21H22O12466.3989068 Publications
(-)-Epicatechin (-)-Epicatechin sulfatehumanplasma, urineC15H14O9S370.335352 Publications
(-)-Epicatechin (-)-Epicatechin sulfoglucuronidehumanplasma, urineC21H22O15S546.4612115 Publications
(-)-Epicatechin (Epi)catechin O-glucuronidehumanileal fluid, plasma, urineC21H22O12466.3989068 Publications
(-)-Epicatechin (Epi)catechin O-sulfatehumanileal fluid, plasma, urineC15H14O9S370.335352 Publications
(-)-Epicatechin 1-(3',4'-Dihydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-olin vitro (human)Not AvailableC15H16O6292.094688235 Publications
(-)-Epicatechin 1-(Hydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-olin vitro (human)Not AvailableC15H16O5276.2896941 Publications
(-)-Epicatechin 3-(3',4'-Dihydroxyphenyl)propionic acidin vitro (human)Not AvailableC9H10O4182.057908808 Publications
(-)-Epicatechin 3-(3'-Hydroxyphenyl)propionic acidin vitro (human)Not AvailableC9H10O3166.062994186 Publications
(-)-Epicatechin 3'-Hydroxyphenylacetic acidin vitro (human)Not AvailableC8H8O3152.047344122 Publications
(-)-Epicatechin 3'-O-Methyl-(-)-epicatechin 4'-O-sulfatehumanplasma, urine (minor)C16H16O9S384.051503269 Publications
(-)-Epicatechin 3'-O-Methyl-(-)-epicatechin 5-O-sulfatehuman ratplasma (major), urine (major)C16H16O9S384.051503269 Publications
(-)-Epicatechin 3'-O-Methyl-(-)-epicatechin 7-O-sulfatehumanplasma, urine (minor)C16H16O9S384.051503269 Publications
(-)-Epicatechin 3'-O-Methyl-(-)-epicatechin glucuronidehumanurine (minor)C22H24O12480.4258956 Publications
(-)-Epicatechin 3'-O-Methyl(epi)catechin O-sulfatehumanileal fluid, plasma, urineC16H16O9S384.3623408 Publications
(-)-Epicatechin 4'-O-Methyl-(-)-epicatechin 5-O-sulfatehumanplasma (minor), urine (minor)C16H16O9S384.051503269 Publications
(-)-Epicatechin 4'-O-Methyl-(-)-epicatechin 7-O-sulfatehumanplasma (major), urine (major)C16H16O9S384.051503269 Publications
(-)-Epicatechin 4'-O-Methyl-(-)-epicatechin glucuronidehumanurine (minor)C22H24O12480.4258956 Publications
(-)-Epicatechin 4'-O-methyl(epi)catechin O-sulfatehumanileal fluid, plasma, urineC16H16O9S384.3623408 Publications
(-)-Epicatechin 5-(3',4'-dihydroxyphenyl)-gamma-valerolactonein vitro (human) raturineC11H12O4208.073558872 Publications
(-)-Epicatechin 5-(3',4'-dihydroxyphenyl)valeric acidin vitro (human)Not AvailableC11H14O4210.089208936 Publications
(-)-Epicatechin 5-(3'-hydroxyphenyl)-gama-valerolactonein vitro (human)Not AvailableC11H12O3192.078644246 Publications
(-)-Epicatechin 5-(3'-hydroxyphenyl)valeric acidin vitro (human)Not AvailableC11H14O3194.094294314 Publications
(-)-Epicatechin Methyl-(-)-epicatechin sulfatehumanplasma, urineC16H16O9S384.3623408 Publications
(-)-Epicatechin Methyl-(-)-epicatechin sulfoglucuronidehumanplasma, urineC22H24O15S560.4882003 Publications
(-)-Epicatechin Phenylacetic acidin vitro (human)Not AvailableC8H8O2136.0524295 Publications
(-)-Epicatechin 3-Hydroxyhippuric acidhumanurineC9H9NO4195.053157781 Publications
(-)-Epicatechin Hippuric acidhuman raturineC9H9NO3179.058243159 Publications
(-)-Epicatechin (-)-Epicatechin-5-O-glucuronidehuman ratplasma (minor), urine (minor)C21H22O12466.111126148 Publications
(-)-Epicatechin 3'-O-Methyl-epicatechin-5-O-glucuronidehuman ratplasma, urineC22H26O12482.142426277 Publications
(-)-Epicatechin 5-(3'-hydroxyphenyl)-gamma-hydroxyvaleric acid -4'-O-glucuronideratplasma, urineC17H22O11402.116211528 Publications
(-)-Epicatechin (-)-Epicatechin-7-O-glucuronidehumanurineC21H22O12466.111126148 Publications
(-)-Epicatechin 3'-O-Methyl-epicatechinraturineC16H16O6304.094688244 Publications
(-)-Epicatechin 5-(3'-Methoxyphenyl)-gamma-hydroxyvaleric acid-4'-O-glucuronideraturineC18H24O11416.131861593 Publications
(-)-Epicatechin 5-(3'-Hydroxyphenyl)-gamma-hydroxyvaleric acidraturineC11H14O4210.089208931 Publications
(-)-Epicatechin 5-(Phenyl)-gamma-hydroxyvaleric acid-3'-sulfateraturineC11H13O7S289.038747513 Publications
(-)-Epicatechin 5-(Phenyl)-gamma-valerolactone-3'-sulfateraturineC11H11O6S271.028182828 Publications
(-)-Epicatechin 4-Hydroxybenzoic acid -3-sulfateraturineC7H5O7S232.976147255 Publications
(-)-Epicatechin 3-(4'-Hydroxyphenyl)propionic acid-3'-sulfateraturineC9H9O7S261.007447384 Publications
(-)-Epicatechin 5-(3'-hydroxyphenyl)-gamma-valerolactone-4'-O-beta-D-glucuronideraturineC17H20O10384.105646844 Publications
(-)-Epicatechin 5-(4'-hydroxyphenyl)-gamma-valerolactone-3'-sulfateraturineC11H11O7S287.023097448 Publications
(-)-Epicatechin 5-(4’-hydroxyphenyl)-gamma-valerolactonehumanNot AvailableC11H12O3192.078644246 Publications
(-)-Epicatechin 3'-Methyl-epicatechin-7-O-glucuronidehumanNot AvailableC22H24O12480.126776213 Publications
Procyanidin dimer B2 (-)-Epicatechinin vitro (human)Not AvailableC15H14O6290.079038171 Publications
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