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
Beilstein:
44723
EC Number:
MDL number:
UNSPSC Code:
12352205
PubChem Substance ID:
NACRES:
NA.47
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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 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
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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Quercetin and its metabolite isorhamnetin promote glucose uptake through different signalling pathways in myotubes
Jiang H, et al.,
Scientific Reports, 1-15 (2019)
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
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
Nida Jamali-Raeufy et al.
Journal of chemical neuroanatomy, 102, 101709-101709 (2019-11-08)
Isorhamnetin, a derivative of quercetin, exerts antioxidant and anti-inflammatory effects in different diseases, and we examined its protective effects against diabetes-related changes in the brain. A single dose of a freshly prepared solution of streptozotocin (STZ) (60 mg/kg body weight) was
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