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Merck

17793

Quercetin 3-β-D-glucoside

≥90% (HPLC)

Synonym(s):

3,3′,4′,5,7-Pentahydroxyflavone 3-β-glucoside, Isoquercitrin

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About This Item

Empirical Formula (Hill Notation):
C21H20O12
CAS Number:
482-35-9
Molecular Weight:
464.38
UNSPSC Code:
12352205
NACRES:
NA.25
PubChem Substance ID:
57647673
MDL number:
MFCD00017746
Beilstein/REAXYS Number:
100989

Product Name

Quercetin 3-β-D-glucoside, ≥90% (HPLC)

InChI

1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m1/s1

SMILES string

OC[C@H]1O[C@@H](OC2=C(Oc3cc(O)cc(O)c3C2=O)c4ccc(O)c(O)c4)[C@H](O)[C@@H](O)[C@@H]1O

InChI key

OVSQVDMCBVZWGM-QSOFNFLRSA-N

assay

≥90% (HPLC)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

Quality Level

100

Gene Information

mouse ... Hexa(15211)

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Application

Quercetin 3-β-D-glucoside has been used:
  • as a dietary flavonoid supplement to check its binding capacity with human small ubiquitin-related modifier 1 (SUMO1) protein using surface plasmon resonance (SPR)
  • as an inhibitor for Escherichia coli adenosine triphosphate (ATP) synthase
  • as an anti-aggregation agent to test its activity against β-amyloid, green fluorescent protein (GFP), and chymotrypsinogen proteins

Biochem/physiol Actions

Quercetin 3-β-D-glucoside possesses strong antioxidant and anti-inflammatory activities. Being a potent oxygen-radical scavenger, it is a neuroprotective agent that improves Alzheimer′s disease (AD) condition in mice models. It has shown antiproliferative activity against colon, lung, and hepatocellular cell lines and MCF-7 human breast cancer cells in combination with apple extracts.

General description

Quercetin 3-β-D-glucoside (Q3G), also known as isoquercitrin, is one of the major glycosidic forms of quercetin. It is a mono-glucoside, first isolated from the seed pods of Cercis canadensis L., it is also found in various plants, vegetables, and fruits. Q3G has the basic chemical structure of a flavonoid, with a glucose molecule attached to the C-3 of quercetin.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM9418
BCCM5016
BCCK0046
BCCK9939
BCCH7422

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Jun Yang et al.
Journal of agricultural and food chemistry, 57(18), 8581-8586 (2009-08-22)
Breast cancer is the most frequently diagnosed cancer in women. An alternative strategy to reduce the risk of cancer is through dietary modification. Although phytochemicals naturally occur as complex mixtures, little information is available regarding possible additive, synergistic, or antagonistic
Prasanna K Dadi et al.
International journal of biological macromolecules, 45(1), 72-79 (2009-04-21)
We have studied the inhibitory effect of five polyphenols namely, resveratrol, piceatannol, quercetin, quercetrin, and quercetin-3-beta-D glucoside on Escherichia coli ATP synthase. Recently published X-ray crystal structures of bovine mitochondrial ATP synthase inhibited by resveratrol, piceatannol, and quercetin, suggest that
Quercetin and quercetin-3-beta-d-glucoside improve cognitive and memory function in Alzheimer?s disease mouse
Kim J H, et al.,
Applied Biological Chemistry, 721-728 (2016)
Kateřina Valentová et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 68, 267-282 (2014-04-01)
The flavonoid isoquercitrin (quercetin-3-O-β-d-glucopyranoside) is commonly found in medicinal herbs, fruits, vegetables and plant-derived foods and beverages. This article reviews the occurrence, preparation, bioavailability, pharmacokinetics, toxicology and biological activity of isoquercitrin and "enzymatically modified (α-glucosylated) isoquercitrin" (EMIQ). Pure isoquercitrin can
Ali Reza A Ladiwala et al.
Biotechnology and bioengineering, 109(7), 1869-1874 (2012-02-15)
Protein aggregation is a common problem during the purification and formulation of therapeutic proteins. Here we report that polyphenolic disaccharides are unusually effective at preventing protein aggregation. We find that two polyphenolic glycosides-naringin and rutin-endow diverse proteins with the ability
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