FL63ACNS0004

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{{Metabolite
 
{{Metabolite
|Sysname=(2S,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
+
|SysName= (2S,3R) -2- (3,4-Dihydroxyphenyl) -3,4-dihydro-2H-1-benzopyran-3,5,7-triol
|Common Name=&&ent-Catechin&&
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|Common Name=&&(-) -Catechin&&ent-Catechin&&
 
|CAS=18829-70-4
 
|CAS=18829-70-4
 
|KNApSAcK=C00008808
 
|KNApSAcK=C00008808
 
}}
 
}}

Latest revision as of 14:52, 22 November 2012


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.


(-) -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
  • (-) -Catechin
  • ent-Catechin
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
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Spectral Information
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