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miquelianin
beta-D-glucopyranosiduronic acid, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl

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Name:(2S,3S,4S,5R)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Number: 22688-79-5Picture of molecule3D/inchi
Other(deleted CASRN):1463778-13-3
FDA UNII: RY36PD0CQ2
MDL:MFCD09752939
XlogP3-AA:0.60 (est)
Molecular Weight:478.36406000
Formula:C21 H18 O13
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 927.80 °C. @ 760.00 mm Hg (est)
Flash Point: 618.00 °F. TCC ( 325.80 °C. ) (est)
logP (o/w): 2.100 (est)
Soluble in:
 water, 6307 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Quercetin 3-O-?-D-Glucuronide 98%
BOC Sciences
For experimental / research use only.
Miquelianin
Carbosynth
For experimental / research use only.
Quercetin 3-O-b-D-glucuronide
ExtraSynthese
For experimental / research use only.
Quercetin-3-O-glucuronide (HPLC) ≥95%
Glentham Life Sciences
Quercetin 3-D-glucuronide
Sigma-Aldrich
For experimental / research use only.
Quercetin 3-glucuronide
analytical standard
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for miquelianin usage levels up to:
 not for fragrance use.
 
Recommendation for miquelianin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :13258914
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2S,3S,4S,5R)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
Chemidplus:0022688795
 
References:
 (2S,3S,4S,5R)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):13258914
Pubchem (sid):135263628
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
HMDB (The Human Metabolome Database):HMDB29212
FooDB:FDB017092
YMDB (Yeast Metabolome Database):YMDB01779
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 anise plant
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 anise seed
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 bean black bean leaf
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 bilberry leaf
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 caraway seed
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 chicory leaf
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 chicory plant
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 coriander fruit
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 cupuassu
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 dill leaf
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 dill seed
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 dill shoot
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 fennel
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 fennel plant
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 fennel seed
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 gaultheria miqueliana
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 grape leaf
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 guava
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 lotus indian lotus flower
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 raspberry red raspberry fruit
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 raspberry red raspberry juice
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 wine red wine
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Synonyms:
(2S,3S,4S,5R)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
beta-D-glucopyranosiduronic acid, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl
 quercetin-3-glucosiduronic acid
 quercetin-3-O-beta-D-glucuronide
 quercetin-3-O-glucuronide
 quercituron
 

Articles:

PubMed:Biogenesis of C-Glycosyl Flavones and Profiling of Flavonoid Glycosides in Lotus (Nelumbo nucifera).
PubMed:Burdock root extracts limit quorum-sensing-controlled phenotypes and biofilm architecture in major urinary tract pathogens.
PubMed:The flavonoid quercetin induces acute vasodilator effects in healthy volunteers: Correlation with beta-glucuronidase activity.
PubMed:Evaluation of plant phenolic metabolites as a source of Alzheimer's drug leads.
PubMed:Quercetin-3-O-glucuronide inhibits noradrenaline-promoted invasion of MDA-MB-231 human breast cancer cells by blocking β₂-adrenergic signaling.
PubMed:Specific localization of quercetin-3-O-glucuronide in human brain.
PubMed:Modeling the effect of phase II conjugations on topoisomerase I poisoning: pilot study with luteolin and quercetin.
PubMed:Glucuronidation does not suppress the estrogenic activity of quercetin in yeast and human breast cancer cell model systems.
PubMed:Quercetin-3-O-glucronide inhibits noradrenaline binding to α2-adrenergic receptor, thus suppressing DNA damage induced by treatment with 4-hydroxyestradiol and noradrenaline in MCF-10A cells.
PubMed:Identification and quantitative analysis of polyphenolic compounds from the indigo plant (Polygonum tinctorium Lour).
PubMed:Mitochondrial dysfunction leads to deconjugation of quercetin glucuronides in inflammatory macrophages.
PubMed:Quercetin-3-O-glucuronide induces ABCA1 expression by LXRα activation in murine macrophages.
PubMed:Inhibition of hydroxycinnamic acid sulfation by flavonoids and their conjugated metabolites.
PubMed:A combined approach for characterisation of fresh and brined vine leaves by X-ray powder diffraction, NMR spectroscopy and direct infusion high resolution mass spectrometry.
PubMed:[Chemical constituents from aerial part of Rumex patientia].
PubMed:In vitro anthelmintic effect of Vicia pannonica var. purpurascens on trichostrongylosis in sheep.
PubMed:Quercetin and quercetin-3-O-glucuronide are equally effective in ameliorating endothelial insulin resistance through inhibition of reactive oxygen species-associated inflammation.
PubMed:Isolation of phenolic compounds from iceberg lettuce and impact on enzymatic browning.
PubMed:Extracts from Epilobium sp. herbs, their components and gut microbiota metabolites of Epilobium ellagitannins, urolithins, inhibit hormone-dependent prostate cancer cells-(LNCaP) proliferation and PSA secretion.
PubMed:Differential effects of grape powder and its extract on glucose tolerance and chronic inflammation in high-fat-fed obese mice.
PubMed:Identification of brain-targeted bioactive dietary quercetin-3-O-glucuronide as a novel intervention for Alzheimer's disease.
PubMed:Protective effect of extract from Rumex aquaticus herba on ethanol-induced gastric damage in rats.
PubMed:Quantitative determination of phenolic compounds in lotus (Nelumbo nucifera) leaves by capillary zone electrophoresis.
PubMed:Quercetin-3-O-glucuronide affects the gene expression profile of M1 and M2a human macrophages exhibiting anti-inflammatory effects.
PubMed:Quercetin and its metabolites improve vessel function by inducing eNOS activity via phosphorylation of AMPK.
PubMed:Comparison on phenolic compounds and antioxidant properties of cabernet sauvignon and merlot wines from four wine grape-growing regions in China.
PubMed:Carrier-mediated transport of quercetin conjugates: involvement of organic anion transporters and organic anion transporting polypeptides.
PubMed:A new lignan with anti-tumour activity from Polygonum perfoliatum L.
PubMed:Effect of quercetin and its glucuronide metabolite upon 6-hydroxydopamine-induced oxidative damage in Neuro-2a cells.
PubMed:Sanguisorba minor extract suppresses plasmin-mediated mechanisms of cancer cell migration.
PubMed:Flavonoid constituents and free radical scavenging activity of Alchemilla mollis.
PubMed:HPLC-DAD-ESI-MS analysis of flavonoid compounds in 5 seedless table grapes grown in Apulian Region.
PubMed:Screening of free radical scavengers from Erigeron breviscapus using on-line HPLC-ABTS/DPPH based assay and mass spectrometer detection.
PubMed:Effects of physiological quercetin metabolites on interleukin-1β-induced inducible NOS expression.
PubMed:Method development and validation for optimized separation of quercetin derivatives in selected Potentilla species using high-performance thin-layer chromatography photodensitometry method.
PubMed:Vascular deconjugation of quercetin glucuronide: the flavonoid paradox revealed?
PubMed:Interference of flavonoids with enzymatic assays for the determination of free fatty acid and triglyceride levels.
PubMed:Benzophenones and flavonoids from Hypericum maculatum and their antioxidant activities.
PubMed:The effect of quercetin-3-O-β-D-glucuronopyranoside on indomethacin-induced gastric damage in rats via induction of mucus secretion and down-regulation of ICAM-1 expression.
PubMed:Metabolic conversion of dietary flavonoids alters their anti-inflammatory and antioxidant properties.
PubMed:Anti-inflammatory, antiviral and quantitative study of quercetin-3-O-β-D-glucuronide in Polygonum perfoliatum L.
PubMed:Pharmacology in health food: metabolism of quercetin in vivo and its protective effect against arteriosclerosis.
PubMed:Quercetin and its principal metabolites, but not myricetin, oppose lipopolysaccharide-induced hyporesponsiveness of the porcine isolated coronary artery.
PubMed:Flavonoid conjugates interact with organic anion transporters (OATs) and attenuate cytotoxicity of adefovir mediated by organic anion transporter 1 (OAT1/SLC22A6).
PubMed:Oenothein B's contribution to the anti-inflammatory and antioxidant activity of Epilobium sp.
PubMed:Relationship between nonvolatile composition and sensory properties of premium Spanish red wines and their correlation to quality perception.
PubMed:Effect of quercetin and its metabolites isorhamnetin and quercetin-3-glucuronide on inflammatory gene expression: role of miR-155.
PubMed:Identification and quantification of flavonoids from Chuquiraga spinosa (Asteraceae).
PubMed:[HPLC-MS analysis of quercetin and its metabolites in portal vein after intragastrical administration of quercetin in rats].
PubMed:Quercetin-3-O-beta-d-glucuronopyranoside (QGC)-induced HO-1 expression through ERK and PI3K activation in cultured feline esophageal epithelial cells.
PubMed:Quercetin metabolites and protection against peroxynitrite-induced oxidative hepatic injury in rats.
PubMed:Antioxidative effect and active components from leaves of Lotus ( Nelumbo nucifera ).
PubMed:Dietary quercetin inhibits bone loss without effect on the uterus in ovariectomized mice.
PubMed:Phenolic compounds from Hypericum calycinum and their antioxidant activity.
PubMed:The kinetic basis for age-associated changes in quercetin and genistein glucuronidation by rat liver microsomes.
PubMed:Separation of epigallocatechin and flavonoids from Hypericum perforatum L. by high-speed counter-current chromatography and preparative high-performance liquid chromatography.
PubMed:Flavonol 3-O-glycosides series of Vitis vinifera Cv. Petit Verdot red wine grapes.
PubMed:[Study on aqueous chemical constituents from the flower buds of Eugenia caryophylla].
PubMed:Glucuronidated and sulfated metabolites of the flavonoid quercetin prevent endothelial dysfunction but lack direct vasorelaxant effects in rat aorta.
PubMed:A comparative study of the effects of quercetin and its glucuronide and sulfate metabolites on human neutrophil function in vitro.
PubMed:Flavonoid glucuronides with anti-leukaemic activity from Polygonum amphibium L.
PubMed:Physiologically relevant metabolites of quercetin have no effect on adhesion molecule or chemokine expression in human vascular smooth muscle cells.
PubMed:Metabolic transformation has a profound effect on anti-inflammatory activity of flavonoids such as quercetin: lack of association between antioxidant and lipoxygenase inhibitory activity.
PubMed:Evaluation of cytotoxic compounds from calligonum comosum L. growing in Egypt.
PubMed:Triterpenes and flavonol glucuronides from Oenothera cheiranthifolia.
PubMed:Effects of quercetin and quercetin 3-glucuronide on the expression of bone sialoprotein gene.
PubMed:Identification of the major constituents of Hypericum perforatum by LC/SPE/NMR and/or LC/MS.
PubMed:Effects of St. John's wort extract and single constituents on stress-induced hyperthermia in mice.
PubMed:Effect of a conjugated quercetin metabolite, quercetin 3-glucuronide, on lipid hydroperoxide-dependent formation of reactive oxygen species in differentiated PC-12 cells.
PubMed:Determination of phenolic compounds in fennel by HPLC and HPLC-MS using a monolithic reversed-phase column.
PubMed:Divergent effects of quercetin conjugates on angiogenesis.
PubMed:SIRT1 stimulation by polyphenols is affected by their stability and metabolism.
PubMed:Antioxidant flavonol glycosides from Schinus molle.
PubMed:Red wine alcohol promotes quercetin absorption and directs its metabolism towards isorhamnetin and tamarixetin in rat intestine in vitro.
PubMed:Modulatory effects of quercetin on proliferation and differentiation of the human colorectal cell line Caco-2.
PubMed:Evaluation of the phenolic content in the aerial parts of different varieties of Cichorium intybus L.
PubMed:Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera, and structure-activity correlations with related alkaloids.
PubMed:Flavonoids of St. John's Wort reduce HPA axis function in the rat.
PubMed:Bioguided isolation and identification of the nonvolatile antioxidant compounds from fennel (Foeniculum vulgare Mill.) waste.
PubMed:In vitro studies indicate that miquelianin (quercetin 3-O-beta-D-glucuronopyranoside) is able to reach the CNS from the small intestine.
PubMed:Constituents of Hypericum laricifolium and their cyclooxygenase (COX) enzyme activities.
PubMed:Quercetin glucuronide prevents VSMC hypertrophy by angiotensin II via the inhibition of JNK and AP-1 signaling pathway.
PubMed:Phenolic compounds from Hypericum perforatum.
PubMed:Protection by quercetin and quercetin 3-O-beta-D-glucuronide of peroxynitrite-induced antioxidant consumption in human plasma low-density lipoprotein.
PubMed:Inhibitory effect of a quercetin metabolite, quercetin 3-O-beta-D-glucuronide, on lipid peroxidation in liposomal membranes.
PubMed:Identification and determination of glucuronides and their aglycones in Erigeron breviscapus by liquid chromatography-tandem mass spectrometry.
PubMed:Identification of quercetin 3-O-beta-D-glucuronide as an antioxidative metabolite in rat plasma after oral administration of quercetin.
PubMed:Effect of variety, processing, and storage on the flavonoid glycoside content and composition of lettuce and endive.
PubMed:Flavonoids from Hypericum perforatum show antidepressant activity in the forced swimming test.
PubMed:Antioxidant properties of flavonol glycosides from green beans.
 
Notes:
Isol. from Gaultheria miqueliana and many other plant spp. Present in red wine [CCD]
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