FL63ACNS0003

Latest revision as of 15:48, 18 December 2009

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
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:

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

IDs and Links
LipidBank	[1]
LipidMaps	[2]
CAS	35323-91-2
KEGG	{{{KEGG}}}
KNApSAcK	C00000957
CDX file
MOL file	FL63ACNS0003.mol

ent-Epicatechin
Structural Information
Systematic Name	(2S,3S) -2- (3,4-Dihydroxyphenyl) -3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Common Name	ent-Epicatechin (2S,3S) -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(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