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Merck
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Documentos

17793

Sigma-Aldrich

Quercetin 3-β-D-glucoside

≥90% (HPLC)

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C21H20O12
Número CAS:
Peso molecular:
464.38
Beilstein:
100989
Número MDL:
Código UNSPSC:
12352205
ID de substância PubChem:
NACRES:
NA.25

Ensaio

≥90% (HPLC)

aplicação(ões)

metabolomics
vitamins, nutraceuticals, and natural products

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

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

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

chave InChI

OVSQVDMCBVZWGM-QSOFNFLRSA-N

Informações sobre genes

mouse ... Hexa(15211)

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Descrição geral

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.

Aplicação

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

Ações bioquímicas/fisiológicas

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.

Embalagem

Bottomless glass bottle. Contents are inside inserted fused cone.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)


Certificados de análise (COA)

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Quercitrin primary reference standard

00740580

Quercitrin

Quercetin 7-glucoside phyproof® Reference Substance

PHL82640

Quercetin 7-glucoside

Quercetina ≥95% (HPLC), solid

Sigma-Aldrich

Q4951

Quercetina

Hyperoside primary reference standard

00180585

Hyperoside

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)
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
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
Hyun Ju You et al.
Journal of agricultural and food chemistry, 58(20), 10886-10892 (2010-10-05)
The flavonol quercetin in plants and foods occurs predominantly in the form of glycoside whose sugar moiety affects the bioavailability and the mechanism of its biological activities. The antiproliferative activities of quercetin derivatives such as quercetin aglycone, quercetin-3-β-D-glucoside (Q3G), and

Protocolos

HPLC Analysis of Polyphenols in Nero d'Avola Red Wine on Discovery® HS C18 (UV 280 nm)

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