Quercetin-7-O-β-D-glucopyranoside

Product Name: Quercetin-7-O-β-D-glucopyranoside
CAS No.: 491-50-9
Chemical Name: Quercetin-7-O-β-D-glucopyranoside
Synonyms: Quercetin-7-O-beta-D-glucopyranoside;Quercetin 7-glucoside;quercetin 7-O-β-D-glucoside;Quercetin-7-O-b-D-glucopyranoside;C.I. 75710;QuerciMeritroside;Quercetin 7-glucoside-RM;quercetin7-O-β-D-glucoside;Quercimeritrin, 10 mM in DMSO;quercetin 7-O-beta-D-glucoside
CBNumber: CB51246345
Molecular Formula: C21H20O12
Formula Weight: 464.38
MOL File: 491-50-9.mol

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Quercetin-7-O-β-D-glucopyranoside Property

storage temp.: 2-8°C
solubility: DMF: 10 mg/ml; DMSO: 10 mg/ml; PBS (pH 7.2): 0.3 mg/ml
form: A crystalline solid
Boiling point:: 859.2±65.0 °C(Predicted)
Density: 1.809±0.06 g/cm3(Predicted)
Melting point:: 248 °C
pka: 5.92±0.40(Predicted)
color: White to yellow
InChIKey: BBFYUPYFXSSMNV-FJOWETSVNA-N
SMILES: O=C1C(=C(C2C=CC(O)=C(O)C=2)OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)=CC(O)=C12)O |&1:17,18,19,21,23,r|
LogP: -0.367 (est)

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 27641
Product name: Quercetin-7-O-β-D-Glucopyranoside
Packaging: 1mg
Price: $47
Updated: 2024/03/01

Cayman Chemical

Product number: 27641
Product name: Quercetin-7-O-β-D-Glucopyranoside
Packaging: 10mg
Price: $360
Updated: 2024/03/01

Cayman Chemical

Product number: 27641
Product name: Quercetin-7-O-β-D-Glucopyranoside
Packaging: 5mg
Price: $206
Updated: 2024/03/01

Usbiological

Product number: 300868
Product name: Quercetin-7-O-beta-D-glucopyranoside
Packaging: 10mg
Price: $490
Updated: 2021/12/16

AK Scientific

Product number: 8232AH
Product name: Quercetin-7-glucoside
Packaging: 10mg
Price: $499
Updated: 2021/12/16

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Quercetin-7-O-β-D-glucopyranoside Chemical Properties,Usage,Production

Chemical Properties

Yellow crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Ginkgo biloba L.

Occurrence

Quercimeritrin is a natural product found in Dendroviguiera sphaerocephala, Dendroviguiera eriophora, and other organisms with data available.

Uses

food and beverages

Definition

ChEBI: Quercetin-7-O-β-D-glucopyranoside is a quercetin O-glucoside in which a glucosyl residue is attached at position 7 of quercetin via a beta-glycosidic linkage. It has a role as an antioxidant and a metabolite. It is a beta-D-glucoside, a monosaccharide derivative, a member of flavonols, a tetrahydroxyflavone and a quercetin O-glucoside.

Antimicrobial activity

Quercetin-7-O-beta-D-glucopyranoside has antibacterial activity, it shows promising activity against Staphylococcus aureus. Quercetin 7-O-beta-D-glucopyranoside exhibits strong antioxidative, and anti-inflammatory activities, inhibiting expression of inducible nitric oxide synthase and release of nitric oxide by lipopolysaccharide-stimulated RAW 264.7 macrophages in a dose-dependent manner. It inhibits overexpression of cyclooxygenase-2 and granulocyte macrophage-colony-stimulating factor.

Biological Activity

Quercetin-7-O-β-D-glucopyranoside is a flavonoid originally isolated from G. hirsutum that has diverse biological activities, including antioxidant, anti-inflammatory, and anti-angiogenic properties. It has antioxidant activity in a oxygen radical absorbance capacity (ORAC) assay and decreases tert-butyl hydroperoxide-induced reactive oxygen species (ROS) production in L-929 cells when used at concentrations of 0.25 and 1 μg/ml. Quercetin-7-O-β-D-glucopyranoside (15 and 30 μg/ml) reduces protein levels of inducible nitric oxide synthase (iNOS) and COX-2 in LPS-stimulated RAW 264.7 cells. It decreases angiogenesis in isolated rat aortic rings and proliferation of human umbilical vein endothelial cells (HUVECs) but has no effect on tube formation or chemotaxis of HUVECs when used at a concentration of 100 μM.

Synthesis

1313191-79-5

491-50-9

The general procedure for the synthesis of 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-benzopyran-4-one was carried out in the following general steps, using the compound (CAS: 1313191-79-5) as starting material: compound 8 (50 mg, 0.06 mmol) was suspended in a mixed solvent of ethanol (EtOH, 20 mL) and tetrahydrofuran (THF, 20 mL), palladium hydroxide (30%, 30 mg) was added as a catalyst under hydrogen atmosphere, and the reaction lasted for 12 hours. Upon completion of the reaction, the reaction mixture was filtered through diatomaceous earth and the filter cake was washed with ethanol (EtOH, 30 mL). After the solvent was removed by evaporation, the resulting residue was purified by chromatography on a C18 reversed-phase column with the eluent being a solvent mixture of methanol (MeOH) and water (H2O) (30:70, v/v). The final target product was obtained as 20 mg in 72% yield.

References

[1] Tetrahedron, 2011, vol. 67, # 25, p. 4731 - 4741

Quercetin-7-O-β-D-glucopyranoside Preparation Products And Raw materials

Raw materials

Preparation Products

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Quercetin-7-O-β-D-glucopyranoside Suppliers

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View Lastest Price from Quercetin-7-O-β-D-glucopyranoside manufacturers

Shanghai Standard Technology Co., Ltd.

Product: Quercetin-7-O-β-D-glucopyranoside 491-50-9
Price: US $0.00/mg
Min. Order: 5mg
Purity: ≥98%(HPLC)
Supply Ability: 10 g
Release date: 2020-03-11

Career Henan Chemical Co

Product: C.I. 75710 491-50-9
Price: US $3.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 1kg,5kg,50kg
Release date: 2020-01-18

491-50-9, Quercetin-7-O-β-D-glucopyranosideRelated Search:

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Quercimeritrin, 10 mM in DMSO

Quercetin-7-O-β-D-glucopyranoside

491-50-9

chemical reagent

pharmaceutical intermediate

phytochemical

reference standards from Chinese medicinal herbs (TCM).

Flavanols

standardized herbal extract