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Category: natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00 %
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| Food Chemicals Codex Listed: | No |
| Boiling Point: | 927.80 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 618.00 °F. TCC ( 325.80 °C. ) (est)
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| logP (o/w): | 2.100 (est) |
| Soluble in: |
| | water, 6307 mg/L @ 25 °C (est) |
Organoleptic Properties:
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| Odor and/or flavor descriptions from others (if found). |
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Cosmetic Information:
Suppliers:
Safety Information:
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | natural substances and extractives |
| Recommendation for miquelianin usage levels up to: | | | not for fragrance use.
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| Recommendation for miquelianin flavor usage levels up to: |
| | not for flavor use.
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Safety References:
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:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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. |
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