Catechin-5-O-glucoside

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 (Jmol)	Interactive image
PubChem	44257081
SMILES 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	452.41 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

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

↑ 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
↑ Flavanol glucosides from rhubarb and Rhaphiolepis umbellata. Gen-Ichiro Nonaka, Emiko Ezakia, Katsuya Hayashia and Itsuo Nishioka, Phytochemistry, Volume 22, Issue 7, 1983, Pages 1659–1661, doi:10.1016/0031-9422(83)80105-8
↑ Biotransformation of (+)-catechin by plant cultured cells of Eucalyptus perriniana. Shuichi Otani, Yoko Kondo, Yoshihisa Asada, Tsutomu Furuya, Hatsuyuki, Hamada, Nobuyoshi Nakajima, Kohji Ishihara and Hiroki Hamada, Plant Biotechnology, 2004, 21(5), pages 407–409 (article)

Flavan-3-ols and their glycosides

Flavan-3-ols	Afzelechin Catechin (Epicatechin) Epicatechin gallate Epigallocatechin Epigallocatechin gallate Fisetinidol Gallocatechin Gallocatechin gallate Guibourtinidol Mesquitol Robinetinidol

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 7-0-α-L-arabinoside) Symplocoside (3’-O-methyl-(-)-epicatechin 7-O-β-D-glucopyranoside)

Acetylated	Phylloflavan

Misc.	Thearubigins

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