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

Description

C.I. 75710, also known as Quercetin-7-O-β-D-glucopyranoside, is a natural product derived from various organisms, including Dendroviguiera sphaerocephala and Dendroviguiera eriophora. It is a quercetin O-glucoside with a glucosyl residue attached at position 7 of quercetin via a beta-glycosidic linkage. C.I. 75710 possesses antioxidant properties and serves as a metabolite. It is classified as a beta-D-glucoside, a monosaccharide derivative, a member of flavonols, a tetrahydroxyflavone, and a quercetin O-glucoside.

Uses

Used in Pharmaceutical Industry:
C.I. 75710 is used as a pharmaceutical compound for its antioxidant properties and potential therapeutic applications. Its antioxidant activity can help protect cells from damage caused by reactive oxygen species, which are involved in various diseases and aging processes.
Used in Cosmetic Industry:
C.I. 75710 is used as an active ingredient in the cosmetic industry due to its antioxidant and anti-inflammatory properties. It can be incorporated into skincare products to help protect the skin from environmental stressors and promote a healthy, youthful appearance.
Used in Food Industry:
C.I. 75710 can be used in the food industry as a natural antioxidant additive to extend the shelf life of various products and protect them from oxidation, which can lead to spoilage and loss of nutritional value.
Used in Research:
C.I. 75710 is also used in scientific research as a model compound to study the bioavailability, metabolism, and biological activities of flavonoids, which are a group of naturally occurring compounds with diverse health benefits.

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.

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.

Characterization of flavonoid 7-O-glucosyltransferase from Arabidopsis thaliana

Most flavonoids found in plants exist as glycosides, and glycosylation status has a wide range of effects on flavonoid solubility, stability, and bioavailability. Glycosylation of flavonoids is mediated by Family 1 glycosyltransferases (UGTs), which use UDP-sugars, such as UDP-glucose, as the glycosyl donor. AtGT-2, a UGT from Arabidopsis thaliana, was cloned and expressed in Escherichia coli as a gluthatione S-transferase fusion protein. Several compounds, including flavonoids, were tested as potential substrates. HPLC analysis of the reaction products indicated that AtGT-2 transfers a glucose molecule into several different kinds of flavonoids, eriodictyol being the most effective substrate, followed by luteolin, kaempferol, and quercetin. Based on comparison of HPLC retention times with authentic flavonoid 7-O-glucosides and nuclear magnetic resonance spectroscopy, the glycosylation position in the reacted flavonoids was determined to be the C-7 hydroxyl group. These results indicate that AtGT-2 encodes a flavonoid 7-O-glucosyltransferase.