Home Other Building Blocks Quercetin 3-O-glucuronide

Quercetin 3-O-glucuronide

CAS No.:
22688-79-5
Catalog Number:
AG0039UO
Molecular Formula:
C21H18O13
Molecular Weight:
478.3598
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥98%
1 week
United States
$161
- +
5mg
99%
1 week
United States
$423
- +
10mg
99%
1 week
United States
$590
- +
25mg
99%
1 week
United States
$1157
- +
50mg
99%
1 week
United States
$1890
- +
Product Description
Catalog Number:
AG0039UO
Chemical Name:
Quercetin 3-O-glucuronide
CAS Number:
22688-79-5
Molecular Formula:
C21H18O13
Molecular Weight:
478.3598
MDL Number:
MFCD09752939
IUPAC Name:
(2S,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI:
InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21-16(29)14(27)15(28)19(34-21)20(30)31/h1-5,14-16,19,21-25,27-29H,(H,30,31)/t14-,15-,16+,19-,21+/m0/s1
InChI Key:
DUBCCGAQYVUYEU-ZUGPOPFOSA-N
SMILES:
Oc1cc(O)c2c(c1)oc(c(c2=O)O[C@@H]1O[C@H](C(=O)O)[C@H]([C@@H]([C@H]1O)O)O)c1ccc(c(c1)O)O
UNII:
RY36PD0CQ2
Properties
Complexity:
830  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
0
Exact Mass:
478.075g/mol
Formal Charge:
0
Heavy Atom Count:
34  
Hydrogen Bond Acceptor Count:
13  
Hydrogen Bond Donor Count:
8  
Isotope Atom Count:
0
Molecular Weight:
478.362g/mol
Monoisotopic Mass:
478.075g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
224A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.6  
Literature
Title Journal
Quercetin-3-O-β-D-Glucuronide Suppresses Lipopolysaccharide-Induced JNK and ERK Phosphorylation in LPS-Challenged RAW264.7 Cells. Biomolecules & therapeutics 20161101
Effect of quercetin and its metabolite on caveolin-1 expression induced by oxidized LDL and lysophosphatidylcholine in endothelial cells. Journal of clinical biochemistry and nutrition 20160501
Amelioration of free fatty acid-induced fatty liver by quercetin-3-O-β-D-glucuronide through modulation of peroxisome proliferator-activated receptor-alpha/sterol regulatory element-binding protein-1c signaling. Hepatology research : the official journal of the Japan Society of Hepatology 20160201
Quercetin Metabolites Up-Regulate the Antioxidant Response in Osteoblasts Isolated From Fetal Rat Calvaria. Journal of cellular biochemistry 20150901
The effect of quercetin and kaempferol aglycones and glucuronides on peroxisome proliferator-activated receptor-gamma (PPAR-γ). Food & function 20150401
Quercetin-3-O-glucuronide inhibits noradrenaline-promoted invasion of MDA-MB-231 human breast cancer cells by blocking β₂-adrenergic signaling. Archives of biochemistry and biophysics 20140901
Quercetin and quercetin-3-O-glucuronide are equally effective in ameliorating endothelial insulin resistance through inhibition of reactive oxygen species-associated inflammation. Molecular nutrition & food research 20130601
Identification of brain-targeted bioactive dietary quercetin-3-O-glucuronide as a novel intervention for Alzheimer's disease. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20130201
Rapid dimerization of quercetin through an oxidative mechanism in the presence of serum albumin decreases its ability to induce cytotoxicity in MDA-MB-231 cells. Biochemical and biophysical research communications 20121019
Preparatory production of quercetin-3-β-D-glucopyranoside using alkali-tolerant thermostable α-L-rhamnosidase from Aspergillus terreus. Bioresource technology 20120701
Comparison of antioxidant activity of compounds isolated from guava leaves and a stability study of the most active compound. Drug discoveries & therapeutics 20120201
[Separation and purification of flavones from Nelumbo nucifera Gaertn. by silica gel chromatography and high-speed counter-current chromatography]. Se pu = Chinese journal of chromatography 20111201
Metabolism of quercetin by Cunninghamella elegans ATCC 9245. Journal of bioscience and bioengineering 20111001
Synthesis and evaluation of novel 2-butyl-4-chloro-1-methylimidazole embedded chalcones and pyrazoles as angiotensin converting enzyme (ACE) inhibitors. Bioorganic & medicinal chemistry 20110815
[Studies on the flavonoids from the flowers of Hylocereus undatus]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20110501
[Studies on the chemical constituents from Conyza canadensis]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20110501
Flavonoid conjugates interact with organic anion transporters (OATs) and attenuate cytotoxicity of adefovir mediated by organic anion transporter 1 (OAT1/SLC22A6). Biochemical pharmacology 20110401
[Chemical constituents in herb of Polygonum orientale II]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20110201
Inhibitory effects of phenolic compounds from needles of Pinus densiflora on nitric oxide and PGE2 production. Archives of pharmacal research 20101201
Flavonoids from Halostachys caspica and their antimicrobial and antioxidant activities. Molecules (Basel, Switzerland) 20101105
The synthesis and angiotensin converting enzyme (ACE) inhibitory activity of chalcones and their pyrazole derivatives. Bioorganic & medicinal chemistry letters 20100315
Fast counter current chromatography of n-butanolic fraction from Senecio giganteus (Asteraceae). Natural product communications 20091001
[Study on chemical constituents of Herba Cirsii]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20090101
Dietary quercetin inhibits bone loss without effect on the uterus in ovariectomized mice. Journal of bone and mineral metabolism 20090101
Regioselective synthesis of plant (iso)flavone glycosides in Escherichia coli. Applied microbiology and biotechnology 20080801
[Studies on chemical constituents of Syringa veutina]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20080501
Macrophage as a target of quercetin glucuronides in human atherosclerotic arteries: implication in the anti-atherosclerotic mechanism of dietary flavonoids. The Journal of biological chemistry 20080404
Comparative effects of quercetin and its predominant human metabolites on adhesion molecule expression in activated human vascular endothelial cells. Atherosclerosis 20080301
Metabolic transformation has a profound effect on anti-inflammatory activity of flavonoids such as quercetin: lack of association between antioxidant and lipoxygenase inhibitory activity. Biochemical pharmacology 20080301
Interaction of quercetin and its conjugate quercetin 3-O-beta-D-glucopyranoside with albumin as determined by NMR relaxation data. Journal of natural products 20080201
Flavonoid glucuronides with anti-leukaemic activity from Polygonum amphibium L. Phytochemical analysis : PCA 20080101
Flavonoid glycosides are not transported by the human Na+/glucose transporter when expressed in Xenopus laevis oocytes, but effectively inhibit electrogenic glucose uptake. The Journal of pharmacology and experimental therapeutics 20070801
Ethnoveterinary medicines used for ruminants in British Columbia, Canada. Journal of ethnobiology and ethnomedicine 20070101
Divergent effects of quercetin conjugates on angiogenesis. The British journal of nutrition 20060501
[Non-alkaloid constituents from a Tibetan medicine Meconopsis quintuplinervia]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20060301
Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera, and structure-activity correlations with related alkaloids. Bioorganic & medicinal chemistry 20050117
[Studies on the chemical constituents of Knoxia corymbosa]. Yao xue xue bao = Acta pharmaceutica Sinica 20040601
New bioactive polyphenols from Theobroma grandiflorum ('cupuaçu'). Journal of natural products 20031101
In vitro studies indicate that miquelianin (quercetin 3-O-beta-D-glucuronopyranoside) is able to reach the CNS from the small intestine. Planta medica 20031101
Polyphenols from some foodstuffs as inhibitors of ovalbumin permeation through caco-2 cell monolayers. Bioscience, biotechnology, and biochemistry 20030601
Oedema protective properties of the red vine leaf extract AS 195 (Folia vitis viniferae) in the treatment of chronic venous insufficiency. A 6-week observational clinical trial. Arzneimittel-Forschung 20030101
Protective effects of flavonoids contained in the red vine leaf on venular endothelium against the attack of activated blood components in vitro. Arzneimittel-Forschung 20030101
Quercetin glucuronide prevents VSMC hypertrophy by angiotensin II via the inhibition of JNK and AP-1 signaling pathway. Biochemical and biophysical research communications 20020524
In vitro antimicrobial activity of extracts and isolated constituents of Rubus ulmifolius. Journal of ethnopharmacology 20020201
Alkaloids and flavonoids from peanut skins. Planta medica 20010601
Inhibition of mammalian 15-lipoxygenase-dependent lipid peroxidation in low-density lipoprotein by quercetin and quercetin monoglucosides. Archives of biochemistry and biophysics 19980115
Properties