Afzelechin

Afzelechin

Chemical structure of Afzelechin (2R,3S)
Chemical structure of Epiafzelechin (2R,3R)
Names
IUPAC name Afzelechin - (2R,3S)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol Epiafzelechin - (2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
Other names 3,5,7,4'-Tetrahydroxyflavan 3,4',5,7-Flavantetrol
Identifiers
CAS Number	2545-00-8 Afzelechin N 24808-04-6 Epiafzelechin N 490-61-9 (Racemate) N
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:31028 Y
ChemSpider	391781 Y
KEGG	C12128 Y
PubChem CID	443639
InChI InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2/t13-,15-/m1/s1 Y Key: RSYUFYQTACJFML-UKRRQHHQSA-N Y InChI=1/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2/t13-,15-/m1/s1 Key: RSYUFYQTACJFML-UKRRQHHQBG
SMILES C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC=C(C=C3)O)O Oc1ccc(cc1)[C@H]3Oc2cc(O)cc(O)c2C[C@H]3O
Properties
Chemical formula	C15H14O5
Molar mass	274.26 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Afzelechin is a flavan-3-ol, a type of flavonoid. It can be found in Bergenia ligulata (a.k.a. Paashaanbhed in Ayurveda traditional Indian medicine). It exists as at least 2 major epimers (afzelechin and epi-afzelechin).

(2R,3S)-catechin:NADP+ 4-oxidoreductase transforms cis-3,4-leucopelargonidin into afzelechin.

Arthromerin A (afzelechin-3-O-β-D-xylopyranoside) and arthromerin B (afzelechin-3-O-β-D-glucopyranoside) are afzelechin glycosides isolated from the roots of the fern Arthromeris mairei.(+)-afzelechin-O-β-4'-D-glucopyranoside can be isolated from the rhizomes of the fern Selliguea feei.

Afzelechin-(4alpha→8)-afzelechin (molecular formula : C₃₀H₂₆O₁₀, molar mass : 546.52 g/mol, exact mass : 546.152597, CAS number : 101339-37-1, Pubchem CID : 12395) is a B type proanthocyanidin.
Ent-epiafzelechin-3-O-p-hydroxybenzoate-(4α→8,2α→O→7)-epiafzelechin) is an A-type proanthocyanidin found in apricots (Prunus armeniaca).

Selligueain A (epiafzelechin-(4β-8,2β-0-7)-epiafzelechin-(4β-8)-afzelechin) is an A type proanthocyanidin.