Quercetin-7-O-β-D-glucopyranoside Chemical Properties

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)

Quercetin-7-O-β-D-glucopyranoside Usage And Synthesis

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

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(491-50-9)Related Product Information

• Thiophanate-methyl
• N-Ethyl-N-(2-hydroxy-3-sulfopropyl)-3,5-dimethoxyaniline sodium salt
• Sophoricoside
• 4',5-DIHYDROXY-7-METHOXYFLAVONE
• kaempferol 3-O-sophoroside
• Naringenin 7-O-β-D-Glucuronide (Mixture of Diastereomers)
• GARDENIN B
• MEDICAGOL
• hydroxygenkwanin
• KAEMPFEROL-3-O-RUTINOSIDE
• Naringenin
• Rutin
• 2-(3,4-Dihydroxyphenyl)-8-(2-O-beta-L-galactopyranosyl-beta-D-glucopyranosyl)-5,7-dihydroxy-4H-1-Benzopyran-4-one
• PONCIRIN
• KAEMPFEROL-3-GLUCURONIDE
• MOSLOFLAVONE
• Quercetin dihydrate
• Quercetin