Catechin-5-O-glucoside

Catechin-5-O-glucoside
Chemical structure of catechin 5-O-glucoside.
Names
IUPAC name
(2S,3R,4S,5S,6R)-2-{[(2R,3S)-2-(3,4-Dihydroxyphenyl)-3,7-dihydroxydihydro-2H-1-benzopyran-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Other names
Catechin 5-O-beta-D-glucopyranoside
C5G[1]
Identifiers
3D model (JSmol)
  • Interactive image
ChemSpider
  • 8519294
PubChem CID
  • 44257081
InChI
  • InChI=1S/C21H24O11/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-5-9(23)4-14-10(15)6-13(26)20(30-14)8-1-2-11(24)12(25)3-8/h1-5,13,16-29H,6-7H2/t13-,16-,17-,18+,19-,20-,21-/m1/s1
    Key: ZESJTWVSXGZYTD-NJOLZHPTSA-N
  • OC[C@H]1O[C@@H](OC2=C3C[C@H](O)[C@H](OC3=CC(O)=C2)C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O
Properties
Chemical formula
 C21H24O11
Molar mass 452.412 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

Catechin 5-O-glucoside is a flavanol glucoside. It can be found in rhubarb and in the bark of Rhaphiolepis umbellata.[2] It can also be formed from (+)-catechin by plant-cultured cells of Eucalyptus perriniana.[3]

References

  1. ^ Catechin glucosides: occurrence, synthesis, and stability. Raab T, Barron D, Vera FA, Crespy V, Oliveira M and Williamson G, J Agric Food Chem., 2010 Feb 24, 58(4), pages 2138-2149, doi:10.1021/jf9034095
  2. ^ Nonaka, Gen-Ichiro; Ezaki, Emiko; Hayashi, Katsuya; Nishioka, Itsuo (1983). "Flavanol glucosides from rhubarb and Rhaphiolepis umbellata". Phytochemistry. 22 (7): 1659–1661. Bibcode:1983PChem..22.1659N. doi:10.1016/0031-9422(83)80105-8.
  3. ^ Otani, Shuichi; Kondo, Yoko; Asada, Yoshihisa; Furuya, Tsutomu; Hamada, Hatsuyuki; Nakajima, Nobuyoshi; Ishihara, Kohji; Hamada, Hiroki (2004). "Biotransformation of (+)-catechin by plant cultured cells of Eucalyptus perriniana" (PDF). Plant Biotechnology. 21 (5): 407–409. doi:10.5511/plantbiotechnology.21.407. Archived 2015-09-23 at the Wayback Machine)
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Flavan-3-ols and their glycosides
Flavan-3-ols
O-methylated flavan-3ols
  • Meciadanol (3-O-methylcatechin)
  • Ourateacatechin (4′-O-methyl-(−)-epigallocatechin)
Glycosides
  • Arthromerin A (Afzelechin-3-O-β-D-xylopyranoside)
  • Arthromerin B (Afzelechin-3-O-β-D-glucopyranoside)
  • Catechin-3-O-glucoside
  • Catechin-3'-O-glucoside
  • Catechin-4'-O-glucoside
  • Catechin-5-O-glucoside
  • Catechin-7-O-glucoside
  • (+)-Catechin 7-O-β-D-xylopyranoside
  • Epicatechin-3′-O-glucoside
  • Glochiflavanoside A, B, C D
  • Polydine ((+)-catechin 7-O-α-L-arabinoside)
  • Symplocoside (3’-O-methyl-(-)-epicatechin 7-O-β-D-glucopyranoside)
AcetylatedGallate estersMisc.
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