CAS Number22688-79-5
SynonymsQuerciturone; Quercetin-3-O-glucuronide; Quercetin-3-O-β-D-glucuronopyranoside; Miquelianin; quercetin 3-O-glucuronide; Quercetin 3-O-β-D-glucuronide; Quercetin-3-Glucuronide; 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl β-D-glucopyranosiduronic acid; Quercetin 3-glucuronide; Miquelianin (Quercetin 3-O-glucuronide)
Molecular FormulaC21H18O13
Molecular Weight478.36
Purity≥95 (LC/MS-ELSD)%
Density2.0±0.1 g/cm3
Boiling Point927.8±65.0 °C at 760 mmHg
Appearancesolid
Symbol
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| Chemical & Physical Properties | |
|---|---|
| CAS Number | 22688-79-5 |
| Catalog No. | 2A-9060874 |
| Chinese Name | 槲皮素3-O-葡萄糖酸苷 |
| Synonyms | Querciturone; Quercetin-3-O-glucuronide; Quercetin-3-O-β-D-glucuronopyranoside; Miquelianin; quercetin 3-O-glucuronide; Quercetin 3-O-β-D-glucuronide; Quercetin-3-Glucuronide; 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl β-D-glucopyranosiduronic acid; Quercetin 3-glucuronide; Miquelianin (Quercetin 3-O-glucuronide) |
| Molecular Formula | C21H18O13 |
| Molecular Weight | 478.36 |
| Purity | ≥95 (LC/MS-ELSD) |
| Density | 2.0±0.1 g/cm3 |
| Boiling Point | 927.8±65.0 °C at 760 mmHg |
| Appearance | solid |
| Storage Condition | ?20°C |
| Application | Miquelianin (Quercetin 3-O-glucuronide) is a metabolite of quercetin and a natural flavonoid. |
| PubChem ID | 329824823 |
| MDL Number | MFCD09752939 |
| SMILES | O[C@@H]1[C@@H](O)[C@@H](O[C@@H]([C@H]1O)C(O)=O)OC2=C(Oc3cc(O)cc(O)c3C2=O)c4ccc(O)c(O)c4 |
| 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 |
| NACRES Code | NA.25 |
| UNSPSC | 12352205 |
| Hazard Symbols | transportation |
| MSDS | msds/60874_1_22688_79_5.pdf |
| Bioactivity | Miquelianin (Quercetin 3-O-glucuronide) is a metabolite of quercetin and a type of natural flavonoid. Related Catalog Signaling Pathways >> Others >> Others Research Areas >> Cancer Natural Products >> Flavonoids In Vitro Miquelianin shows an antioxidant effect in human plasma. At 50 μM, miquelianin suppresses the consumption of the three antioxidants lycopene, β-carotene and α-tocopherol significantly[1]. In vitro studies indicate that miquelianin is able to reach the central nervous system from the small intestine[2]. Miquelianin significantly reduces the generation of β-amyloid (Aβ) peptides by primary neuron cultures generated from the Tg2576 AD mouse model. It is also capable of interfering with the initial protein-protein interaction of Aβ1-40 and Aβ1-42 that is necessary for the formation of neurotoxic oligomeric Aβ species[3]. Treatment with 0.1 μM miquelianin suppresses ROS generation, cAMP and RAS activation, phosphorylation of ERK1/2 and the expression of HMOX1, MMP2, and MMP9 genes. Miquelianin suppresses invasion of MDA-MB-231 breast cancer cells and MMP-9 induction, and inhibits the binding of [3H]-NA to b2-AR. Miquelianin may function to suppress invasion of breast cancer cells by controlling b2-adrenergic signaling, and may be a dietary chemopreventive factor for stress-related breast cancer[4]. In Vivo Miquelianin treatment, compared to vehicle-control treatment, significantly improves AD-type deficits in hippocampal formation basal synaptic transmission and long-term potentiation[3]. A flavonoid fraction obtained from a crude extract of Hypericum perforatum (St. John's wort) is remarkably active in the forced swimming test. Miquelianin is one of the compound separated from the fraction[5]. Animal Admin Rats: Miquelianin is administered orally using the gavage techniques. The rats are treated with 0.6 mg/kg miquelianin for 12 days. Antidepressant activity is performed using the Forced Swimming Test[5]. References [1]. Terao J, e al. Protection by quercetin and quercetin 3-O-beta-D-glucuronide of peroxynitrite-induced antioxidant consumption in human plasma low-density lipoprotein. Free Radic Res. 2001 Dec;35(6):925-31. [2]. Juergenliemk G, et al. In vitro studies indicate that miquelianin (quercetin 3-O-beta-D-glucuronopyranoside) is able to reach the CNS from the small intestine. Planta Med. 2003 Nov;69(11):1013-7. [3]. Butterweck V, et al. Flavonoids from Hypericum perforatum show antidepressant activity in the forced swimming test. Planta Med. 2000 Feb;66(1):3-6. [4]. Yamazaki S, et al. Quercetin-3-O-glucuronide inhibits noradrenaline-promoted invasion of MDA-MB-231 human breast cancer cells by blocking β₂-adrenergic signaling. Arch Biochem Biophys. 2014 Sep 1;557:18-27. [5]. Ho L, et al. Identification of brain-targeted bioactive dietary quercetin-3-O-glucuronide as a novel intervention for Alzheimer's disease. FASEB J. 2013 Feb;27(2):769-81. Chemical & Physical Properties Density 2.0±0.1 g/cm3 Boiling Point 927.8±65.0 °C at 760 mmHg Molecular Formula C21H18O13 Molecular Weight 478.360 Flash Point 325.8±27.8 °C Exact Mass 478.074738 PSA 227.58000 LogP 2.10 Vapour Pressure 0.0±0.3 mmHg at 25°C Index of Refraction 1.819 InChIKey DUBCCGAQYVUYEU-ZUGPOPFOSA-N SMILES O=C(O)C1OC(Oc2c(-c3ccc(O)c(O)c3)oc3cc(O)cc(O)c3c2=O)C(O)C(O)C1O Storage condition ?20°C |
| Use of | Miquelianin (Quercetin 3-O-glucuronide) is a metabolite of quercetin and a type of natural flavonoid. Properties Name miquelianin Synonym More Synonyms Quercetin-3-O-glucuronide Biological Activity Description Miquelianin (Quercetin 3-O-glucuronide) is a metabolite of quercetin and a type of natural flavonoid. Related Catalog Signaling Pathways >> Others >> Others Research Areas >> Cancer Natural Products >> Flavonoids In Vivo Miquelianin treatment, compared to vehicle-control treatment, significantly improves AD-type deficits in hippocampal formation basal synaptic transmission and long-term potentiation[3]. A flavonoid fraction obtained from a crude extract of Hypericum perforatum (St. John's wort) is remarkably active in the forced swimming test. Miquelianin is one of the compound separated from the fraction[5]. References [1]. Terao J, e al. Protection by quercetin and quercetin 3-O-beta-D-glucuronide of peroxynitrite-induced antioxidant consumption in human plasma low-density lipoprotein. Free Radic Res. 2001 Dec;35(6):925-31. [2]. Juergenliemk G, et al. In vitro studies indicate that miquelianin (quercetin 3-O-beta-D-glucuronopyranoside) is able to reach the CNS from the small intestine. Planta Med. 2003 Nov;69(11):1013-7. [3]. Butterweck V, et al. Flavonoids from Hypericum perforatum show antidepressant activity in the forced swimming test. Planta Med. 2000 Feb;66(1):3-6. [4]. Yamazaki S, et al. Quercetin-3-O-glucuronide inhibits noradrenaline-promoted invasion of MDA-MB-231 human breast cancer cells by blocking β₂-adrenergic signaling. Arch Biochem Biophys. 2014 Sep 1;557:18-27. [5]. Ho L, et al. Identification of brain-targeted bioactive dietary quercetin-3-O-glucuronide as a novel intervention for Alzheimer's disease. FASEB J. 2013 Feb;27(2):769-81. Chemical & Physical Properties Molecular Formula C21H18O13 Exact Mass 478.074738 PSA 227.58000 Index of Refraction 1.819 InChIKey DUBCCGAQYVUYEU-ZUGPOPFOSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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