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
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About This Item
Empirical Formula (Hill Notation):
C16H12O7
CAS Number:
Molecular Weight:
316.26
UNSPSC Code:
12352205
NACRES:
NA.47
PubChem Substance ID:
EC Number:
207-545-5
Beilstein/REAXYS Number:
44723
MDL number:
Quality Segment
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
General description
Isorhamnetin is an O-methylated flavonol 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
- 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.
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.
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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
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