Synonym: 3′-Methoxy-3,4′,5,7-tetrahydroxyflavone; 3′-Methylquercetin; 3,4′,5,7-Tetrahydroxy 3′-methoxyflavone; Isorhamnetol; Quercetin 3′-methyl ether
CAS Number: 480-19-3
Empirical Formula (Hill Notation): C16H12O7
Molecular Weight: 316.26
EC Number: 207-545-5
MDL Number: MFCD00017310
Linear Formula: C16H12O7
Product Type: Chemical
| application(s) |
metabolomics
vitamins, nutraceuticals, and natural products |
| assay |
≥95.0% (HPLC) |
| InChI |
1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3 |
| InChI key |
IZQSVPBOUDKVDZ-UHFFFAOYSA-N |
| Quality Level |
100  |
| SMILES string |
COc1cc(ccc1O)C2=C(O)C(=O)c3c(O)cc(O)cc3O2 |
| Application: |
Isorhamnetin (IRN) has been used:
• as a neuroprotective agent to test its effect on scopolamine-induced cortico-hippocampal learning and memory deficiency in mice
• as a reference standard in quadrupole time-of-flight mass spectrometry (QTOF MS) to analyze and quantify the phenolic compounds present in honey extract
• as a reference standard to determine the phenolic profile of Artemisia species using Reversed-phase high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry (RP-HPLC-DAD-ESI-TQ-MS/MS)
|
| Biochem/physiol Actions: |
Isorhamnetin exerts antioxidant, anti-inflammatory, anti-cancer, anti-bacterial, and anti-viral effects. It has shown to be a potential neuroprotective agent by inhibiting neurodegeneration in the hippocampus under Diabetes mellitus (DM) conditions. Isorhamnetin at low levels may serve as an anti-diabetic agent by promoting glucose uptake in skeletal muscle cells and maintaining glucose homeostasis in hyperglycemic conditions. It regulates cell signaling pathways such as Nuclear factor kappa B (NF-κB), phosphatidylinositol 3-kinase (PI3K)/protein kinase B (AKT), mitogen-activated protein kinase (MAPK) etc. Isorhamnetin elicits protective and therapeutic effects on atherosclerosis and cardiovascular diseases. |
| Biochem/physiol Actions: |
Isorhamnetin inhibits adipogenesis by interfering with differentiation of adipose stem cells, by a mechanism involving stabilization of β-catenin and up-regulating the Wnt signaling pathway. |
| General description: |
Isorhamnetin is an O-methylated flavonol found in fruits, plants, and medicinal herbs. It is a metabolite of quercetin. |
| Packaging: |
Bottomless glass bottle. Contents are inside inserted fused cone. |
| Hazard Codes |
Xn |
| Risk Statements |
40 |
| Safety Statements |
36/37 |
| RIDADR |
NONH for all modes of transport |
| WGK Germany |
WGK 3 |
| Flash Point(F) |
Not applicable |
| Flash Point(C) |
Not applicable |
| Purity |
≥95.0% (HPLC) |
| UNSPSC |
12352205 |
