Isorhamnetin
SIGMA/17794 - ≥95.0% (HPLC)
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
| assay | ≥95.0% (HPLC) |
| InChI | 1S/C16H12O7/c1-22-11-4-7( |
| InChI key | IZQSVPBOUDKVDZ-UHFFFAOYSA |
| Quality Level | 100  |
| SMILES string | COc1cc(ccc1O)C2=C(O)C(=O) |
| 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. |
| Other Notes: | Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 17794.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin. |
| 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 | 12352200 |