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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:
Molecular Weight:
464.38
UNSPSC Code:
12352205
NACRES:
NA.25
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
100989
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Quality Segment

assay

≥90% (HPLC)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

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

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

InChI key

OVSQVDMCBVZWGM-QSOFNFLRSA-N

Gene Information

mouse ... Hexa(15211)

General description

Quercetin 3-β-D-glucoside (Q3G), also known as isoquercitrin, is one of the major glycosidic forms of quercetin.[1] 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.[1] Q3G has the basic chemical structure of a flavonoid, with a glucose molecule attached to the C-3 of quercetin.[1]

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)[2]
  • as an inhibitor for Escherichia coli adenosine triphosphate (ATP) synthase[3]
  • as an anti-aggregation agent to test its activity against β-amyloid, green fluorescent protein (GFP), and chymotrypsinogen proteins[4]

Biochem/physiol Actions

Quercetin 3-β-D-glucoside possesses strong antioxidant and anti-inflammatory activities.[1] 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[5] and MCF-7 human breast cancer cells in combination with apple extracts.[6]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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This Item
83388SMB0014916733
assay

≥90% (HPLC)

assay

≥97.0% (HPLC)

assay

≥95% (LC/MS-ELSD)

assay

≥85% (HPLC)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

-

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

-

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

100

storage temp.

−20°C

storage temp.

-

storage temp.

−20°C

storage temp.

−20°C

Gene Information

mouse ... Hexa(15211)

Gene Information

mouse ... Hexa(15211)

Gene Information

-

Gene Information

-


Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

Eyeshields, Gloves, type N95 (US)



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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)
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
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



Global Trade Item Number

SKUGTIN
17793-50MG-F04061838753557
17793-10MG-F04061838753540

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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