17794

Isorhamnetin

≥95.0% (HPLC)

• Synonym(s): 3′-Methoxy-3,4′,5,7-tetrahydroxyflavone, 3′-Methylquercetin, 3,4′,5,7-Tetrahydroxy 3′-methoxyflavone, Isorhamnetol, Quercetin 3′-methyl ether
• Empirical Formula (Hill Notation): C₁₆H₁₂O₇
• CAS Number: 480-19-3
• Molecular Weight: 316.26
• UNSPSC Code: 12352205
• NACRES: NA.47
• PubChem Substance ID: 57647674
• EC Number: 207-545-5
• Beilstein/REAXYS Number: 44723
• MDL number: MFCD00017310

Properties

• Quality Segment: 100
• assay: ≥95.0% (HPLC)
• application(s): metabolomics; vitamins, nutraceuticals, and natural products
• SMILES string: COc1cc(ccc1O)C2=C(O)C(=O)c3c(O)cc(O)cc3O2
• 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

Description

General description

Isorhamnetin is an O-methylated flavonol [1] found in fruits, plants, and medicinal herbs. It is a metabolite of quercetin.

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[2]
• as a reference standard in quadrupole time-of-flight mass spectrometry (QTOF MS) to analyze and quantify the phenolic compounds present in honey extract[3]
• 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)[4]

Biochem/physiol Actions

Isorhamnetin exerts antioxidant, anti-inflammatory, anti-cancer, anti-bacterial, and anti-viral effects.[5] It has shown to be a potential neuroprotective agent by inhibiting neurodegeneration in the hippocampus under Diabetes mellitus (DM) conditions.[1] 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.[5] Isorhamnetin elicits protective and therapeutic effects on atherosclerosis and cardiovascular diseases.[5]

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges