Miquelianin (quercetin 3-O-glucuronide) is a flavonol glucuronide, a type of phenolic compound present in wine,[1] in species of St John's wort,[2] like Hypericum hirsutum,[3] in Nelumbo nucifera (Indian lotus)[4] or in green beans.[5]
Quick facts Names, Identifiers ...
Miquelianin
 Chemical structure of miquelianin |
| Names |
| IUPAC name
3′,4′,5,7-Tetrahydroxy-4-oxoflav-2-en-3-yl β-D-glucopyranosiduronic acid |
Systematic IUPAC name
(2S,3S,4S,5R,6S)-6-{[2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid |
Other names
Quercetin 3- O-glucuronide Quercetol glucuronideQuercetin 3-glucuronide Quercetol 3- O-glucuronide quercetin 3- O-β- D-glucuronopyranoside Querciturone |
| Identifiers |
|
|
|
|
| ChEBI |
|
| ChEMBL |
|
| ChemSpider |
|
|
|
| UNII |
|
|
|
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 Key: DUBCCGAQYVUYEU-ZUGPOPFOSA-N
|
C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)C(=O)O)O)O)O)O)O
|
| Properties |
|
C21H18O13 |
| Molar mass |
478.362 g·mol−1 |
| Density |
1.961 g/mL |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Close
It is also a rat plasma quercetin metabolite.[6] It shows an antioxidant effect in human plasma.[7]
In vitro studies indicate that miquelianin is able to reach the central nervous system from the small intestine.[8]
