FL63ACNS0004

From Metabolomics.JP
Revision as of 16:14, 18 December 2009 by Adm (Talk | contribs)

Jump to: navigation, search


Flavonoid Top Molecule Index Author Index Journals Structure Search Food New Input

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.


ent-Catechin
FL63ACNS0004.png
Structural Information
Systematic Name (2S,3R) -2- (3,4-Dihydroxyphenyl) -3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Common Name
  • ent-Catechin
  • (2S,3R) -2- (3,4-Dihydroxyphenyl) -3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Symbol
Formula C15H14O6
Exact Mass 290.07903818
Average Mass 290.26806
SMILES Oc(c1)cc(O2)c(CC(O)C2c(c3)cc(O)c(O)c3)c(O)1
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

Personal tools
Namespaces

Variants
Actions
Navigation
metabolites
Toolbox