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17794

Sigma-Aldrich

Isorhamnetin

≥95.0% (HPLC)

Synonym(s):
3′-Methylquercetin, Isorhamnetol, 3,4′,5,7-Tetrahydroxy 3′-methoxyflavone, 3′-Methoxy-3,4′,5,7-tetrahydroxyflavone, Quercetin 3′-methyl ether
Empirical Formula (Hill Notation):
C16H12O7
CAS Number:
Molecular Weight:
316.26
Beilstein:
44723
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.47

Quality Level

assay

≥95.0% (HPLC)

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

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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 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.
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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Lutz Franke et al.
Journal of medicinal chemistry, 50(11), 2640-2646 (2007-04-28)
A natural product collection and natural-product-derived combinatorial libraries were virtually screened for potential inhibitors of human 5-lipoxygenase (5-LO) activity. We followed a sequential ligand-based approach in two steps. First, similarity searching with a topological pharmacophore descriptor (CATS 2D method) was
Rongsheng E Wang et al.
Journal of medicinal chemistry, 52(7), 1912-1921 (2009-03-20)
Inhibitors of heat-induced heat shock protein 70 (HSP70) expression have the potential to enhance the therapeutic effectiveness of heat-induced radiosensitization of tumors. Among known small molecule inhibitors, quercetin has the advantage of being easily modified for structure-activity studies. Herein, we
Jong-Eun Kim et al.
Cancer prevention research (Philadelphia, Pa.), 4(4), 582-591 (2011-02-19)
3'-Methoxy-3,4',5,7-tetrahydroxyflavone (isorhamnetin) is a plant flavonoid that occurs in fruits and medicinal herbs. Isorhamnetin exerts anticancer effects, but the underlying molecular mechanism for the chemopreventive potential of isorhamnetin remains unknown. Here, we report anti-skin cancer effects of isorhamnetin, which inhibited
Felipe Surco-Laos et al.
Food & function, 2(8), 445-456 (2011-07-22)
Quercetin is a major flavonoid in the human diet and the most commonly used in studies of biological activity. Most of the knowledge about its biological effects has originated from in vitro studies while in vivo data are scarce. Quercetin
Elise F Hoek-van den Hil et al.
Analytical and bioanalytical chemistry, 402(3), 1389-1392 (2011-11-29)
Flavonoids are bioactive food compounds with potential lipid-lowering effects. Commercially available enzymatic assays are widely used to determine free fatty acid (FFA) and triglyceride (TG) levels both in vivo in plasma or serum and in vitro in cell culture medium

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