FL63ACNS0002

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Upper classes : FL Flavonoid : FL6 Flavan : FL63 Flavan 3-ol :  FL63AC Catechin and Epicatechin (75 pages) :  FL63ACNS Simple substitution (24 pages)


Catechins refer to a subgroup of flavan 3-ol derivatives (FL63AC). The two chiral center at C2 and C3 of the flavan 3-ols produces 4 isomers, and (+)-Catechin and its stereoisomer (-)-Epicatechin are naturally abundant. Less abundant are (-)-Catechin and (+)-Epicatechin.

  • afzelechin ... catechin minus 1 hydroxyl group in ring B
  • gallocatechin ... catechin plus 1 hydroxyl group in ring B

Structure FL63ACNS0001.png FL63ACNS0002.png FL63ACNS0004.png FL63ACNS0003.png
Name (+)-Catechin or
D-Catechin
(-)-Epicatechin or
L-Epicatechin
ent-Catechin or
(-)-Catechin
ent-Epicatechin or
(+)-Epicatechin
B-ring stereo
3-Hydroxyl stereo
Afzelechins (+)-Afzelechin (-)-Epiafzelechin ent-Epiafzelechin
Gallocatechins (+)-Gallocatechin (-)-Epigallocatechin ent-Gallocatechin

Among the stereoisomers, the bioavailability in human follows the order:

(-)-epicatechin > (+)-catechin = (+)-epicatechin > (-)-catechin

The circulation level of (-)-epicatechin is 6 times higher than that of (-)-catechin. Naturally abundant species are more bioavailable than less abundant ones.


(-)-Epicatechin
FL63ACNS0002.png
Structural Information
Systematic Name (2R,3R) -2- (3,4-Dihydroxyphenyl) 3,4-dihydro-2H-chromene-3,5,7-triol
Common Name
  • (-)-Epicatechin
  • EC
  • (2R) -2alpha- (3,4-Dihydroxyphenyl) -3,4-dihydro-2H-1-benzopyran-3alpha,5,7-triol
Symbol
Formula C15H14O6
Exact Mass 290.07903818
Average Mass 290.26806
SMILES Oc(c3)cc(O1)c(c(O)3)CC([H])(O)C([H])1c(c2)cc(O)c(O)c2
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Reflactive Index
Solubility
Spectral Information
Mass Spectra
UV Spectra
IR Spectra
NMR Spectra
Chromatograms



Species Information

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