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17794

Sigma-Aldrich

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:
480-19-3
Molecular Weight:
316.26
Beilstein/REAXYS Number:
44723
EC Number:
207-545-5
MDL number:
MFCD00017310
UNSPSC Code:
12352205
PubChem Substance ID:
57647674
NACRES:
NA.47

Quality Level

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

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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 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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Gang Gong et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 128, 110301-110301 (2020-06-06)
Isorhamnetin is one of the most important active ingredients in the fruits of Hippophae rhamnoides L. and the leaves of Ginkgo biloba L., which possesses extensive pharmacological activities. At present, there have been numerous investigations on isorhamnetin, which has the
Ismail O Ishola et al.
Brain research, 1712, 188-196 (2019-02-18)
Isorhamnetin (IRN), a 3'-O-methylated metabolite of quercetin has antioxidant, anti-inflammatory and neuroprotective properties. In this study, we investigated the learning and memory enhancing effects of IRN on spatial and non-spatial learning and memory deficits induced by scopolamine (3 mg/kg, i.p; muscarinic
Mohamed Moalin et al.
Molecules (Basel, Switzerland), 16(11), 9636-9650 (2011-11-23)
The polyphenol quercetin (Q) that has a high antioxidant capacity is a lead compound in the design of antioxidants. We investigated the possibility of modifying quercetin while retaining its antioxidant capacity as much as possible. To this end, the antioxidant
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