Catechin-7-O-glucoside

Catechin-7-O-glucoside is a flavan-3-ol glycoside formed from catechin.

Catechin-7-O-glucoside

Names
IUPAC name (2S,4S,5S)-2-[[(2R,3S)-2-(3,4-Dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2H-chromen-7-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Other names (2R,3S)-Catechin-7-O-β-D-glucopyranoside Catechin 7-O-β-glucopyranoside (+)-Catechin 7-O-β-glucoside (+)-Catechin 7-O-beta-D-glucopyranoside Catechin 7-glucoside C7G CA-G
Identifiers
CAS Number	65597-47-9 N
3D model (JSmol)	Interactive image
ChemSpider	8965102
PubChem CID	10789789
InChI InChI=1S/C21H24O11/c22-7-16-17(27)18(28)19(29)21(32-16)30-9-4-12(24)10-6-14(26)20(31-15(10)5-9)8-1-2-11(23)13(25)3-8/h1-5,14,16-29H,6-7H2/t14-,16+,17+,18-,19+,20+,21+/m0/s1 Key: VLFIBROLAXKPQK-DPRDWZRASA-N InChI=1/C21H24O11/c22-7-16-17(27)18(28)19(29)21(32-16)30-9-4-12(24)10-6-14(26)20(31-15(10)5-9)8-1-2-11(23)13(25)3-8/h1-5,14,16-29H,6-7H2/t14-,16+,17+,18-,19+,20+,21+/m0/s1 Key: VLFIBROLAXKPQK-DPRDWZRABG
SMILES O(c2cc3O[C@H](c1ccc(O)c(O)c1)[C@@H](O)Cc3c(O)c2)[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)CO
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

Natural occurrences

Catechin-7-O-glucoside can be isolated from the hemolymph of the European pine sawfly (Neodiprion sertifer).^[1] It also occurs in relatively large quantities in cowpea (Vigna unguiculata) as the dominant flavan-3-ol monomer, and actually accounts for up to 70% of cowpea proanthocyanidins (tannins).^[2]

It can also be produced by biotransformation of (+)-catechin by cultured cells of Eucalyptus perriniana.^[3]

Presence in natural traditional drugs

Catechin-7-O-glucoside can be found in paeoniae radix, the crude drug made from the roots of Chinese peony (Paeonia lactiflora),^[4] in red knotweed (Bistorta macrophylla, also known as Polygonum macrophyllum),^[5] in the stem barks of the Nepali hog plum (Choerospondias axillaris),^[6] in the Korean plum yew (Cephalotaxus koreana)^[7] and in Huanarpo Macho (Jatropha macrantha).^[8] (−)-Catechin 7-O-β-D-glucopyranoside is found in the bark of Rhaphiolepis umbellata.^[9]

Presence in food

It is found in buckwheat groats,^[10] in the red bean (the seed of Vigna umbellata, formerly known as Phaseolus calcaratus),^[11] in barley (Hordeum vulgare L.) and malt.^[12] (−)-Catechin 7-O-β-D-glucopyranoside is found in rhubarb.^[9]

Health effects

This compound has an antioxidant activity leading to a cytoprotective effect.^[11][13]