491-50-9

Basic information

• Product Name: C.I. 75710
• Synonyms: C.I. 75710;7-(β-D-Glucopyranosyloxy)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4H-1-benzopyran-4-one;7-(β-D-Glucopyranosyloxy)-3,3',4',5-tetrahydroxyflavone;7-(β-D-Glucopyranosyloxy)-5,3',4'-trihydroxyflavonol;Quercetin 7-glucoside;Quercetin-7-O-beta-D-glucopyranoside;Quercetin-7-O-β-D-glucopyranoside;QuerciMeritroside
• CAS NO: 491-50-9
• Molecular Formula: C₂₁H₂₀O₁₂
• Molecular Weight: 464.38
• Product Categories: Flavanols;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 491-50-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 248 °C
• Boiling Point: 859.2 °C at 760 mmHg
• Flash Point: 302.8 °C
• Appearance: /
• Density: 1.809 g/cm³
• Vapor Pressure: 1.85E-31mmHg at 25°C
• Refractive Index: 1.774
• Storage Temp.: 2-8°C
• PKA: 5.92±0.40(Predicted)
• CAS DataBase Reference: C.I. 75710(CAS DataBase Reference)
• NIST Chemistry Reference: C.I. 75710(491-50-9)
• EPA Substance Registry System: C.I. 75710(491-50-9)

Safety Data

• Hazardous Substances Data: 491-50-9(Hazardous Substances Data)

Usage

Occurrence

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

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.

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

Upstream product

• 133-89-1 UDP-glucose 
• 117-39-5 quercetol 
• 498548-17-7 3-(benzyloxy)-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5,7-dihydroxy-4H-chromen-4-one 
• 1313191-78-4 2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-3,5-bisbenzyloxy-7-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-4H-chromen-4-one 
• 1313191-77-3 2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-3-benzyloxy-5-hydroxyl-7-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-4H-chromen-4-one 
• 357194-11-7 2-(2,2-diphenyl-1,3-benzodioxol-5-yl)-3,5-dihydroxy-7-[tetra-O-acetyl-β-D-glucopyranosyloxy]-4H-1-benzopyran-4-one 
• 357194-03-7 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-trihydroxychromen-4-one 
• 339276-12-9 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate 
• 1064-06-8 3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one 
• 143631-95-2 acetic acid 2-acetoxy-4-(3,5-diacetoxy-7-hydroxy-4-oxo-4H-chromen-2-yl)-phenyl ester 
• 357194-04-8 2-(2,2-diphenyl-1,3-benzodioxol-5-yl)-3,5-dihydroxy-7-(β-D-glucopyranosyloxy)-4H-1-benzopyran-4-one 

Downstream Products

• 50-99-7 D-glucose 
• 117-39-5 quercetol 
• 492-61-5 β-D-glucose 
• 2280-44-6 D-Glucose 

Relevant articles and documents

Exploring the catalytic promiscuity of a new glycosyltransferase from Carthamus tinctorius

The catalytic promiscuity of a new glycosyltransferase (UGT73AE1) from Carthamus tinctorius was explored. UGT73AE1 showed the capability to glucosylate a total of 19 structurally diverse types of acceptors and to generate O-, S-, and N-glycosides, making it the first reported trifunctional plant glycosyltransferase. The catalytic reversibility and regioselectivity were observed and modeled in a one-pot reaction transferring a glucose moiety from icariin to emodin. These findings demonstrate the potential versatility of UGT73AE1 in the glycosylation of bioactive natural products.

Cloning and functional characterisation of two regioselective flavonoid glucosyltransferases from Beta vulgaris

Two full-length cDNAs encoding flavonoid-specific glucosyltransferases, UGT73A4 and UGT71F1, were isolated from a cDNA library of Beta vulgaris (Amaranthaceae) cell suspension cultures. They displayed high identity to position-specific betanidin and flavonoid glucosyltransferases from Dorotheanthus bellidiformis (Aizoaceae) and to enzymes with similar substrate specificities from various plant families. The open reading frame of the sequences encode proteins of 476 (UGT73A4) and 492 (UGT71F1) amino acids with calculated molecular masses of 54.07 kDa and 54.39 kDa, and isoelectric points of 5.8 and 5.6, respectively. Both enzymes were functionally expressed in Escherichia coli as His- and GST-tagged proteins, respectively. They exhibited a broad substrate specificity, but a distinct regioselectivity, glucosylating a variety of flavonols, flavones, flavanones, and coumarins. UGT73A4 showed a preference for the 4′- and 7-OH position in the flavonoids, whereas UGT71F1 preferentially glucosylated the 3- or the 7-OH position. Glucosylation of betanidin, the aglycone of the major betacyanin, betanin, in B. vulgaris was also observed to a low extent by both enzymes. Several O-glycosylated vitexin derivatives isolated from leaves of young B. vulgaris plants and rutin obtained from B. vulgaris tissue culture are discussed as potential endogenous products of UGT73A4 and UGT71F1. The results are analyzed with regard to evolution and specificity of plant natural product glucosyltransferases.

Flavonoids from Cephalaria gigantea flowers

Luteolin, quercetin, cinaroside, quercimeritrin, and the new flavonol bioside gigantoside A were isolated from Cephalaria gigantea (Ledeb.) Bobr. (Dipsacaceae) flowers. Spectral properties and chemical transformations established that gigantoside A had the structure quercetin-7-O-[α-L- arabinopyranosyl(1→6)]-β-D-glucopyranoside.