FL63ACNS0004

Revision as of 16:14, 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	18829-70-4
KEGG	{{{KEGG}}}
KNApSAcK	C00008808
CDX file
MOL file	FL63ACNS0004.mol

ent-Catechin
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