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
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;
	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	452.412 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

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
^ 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.
^ 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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v t e Flavan-3-ols and their glycosides
Flavan-3-ols	Afzelechin Catechin (Epicatechin) Epicatechin gallate Epigallocatechin Fisetinidol Gallocatechin Guibourtinidol Mesquitol Oritin 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-O-α-L-arabinoside) Symplocoside (3’-O-methyl-(-)-epicatechin 7-O-β-D-glucopyranoside)
Acetylated	Phylloflavan
Gallate esters	Epigallocatechin gallate Gallocatechin gallate
Misc.	Thearubigins