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17794

Sigma-Aldrich

Isorhamnetin

≥95.0% (HPLC)

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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:
Molecular Weight:
316.26
Beilstein/REAXYS Number:
44723
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.47

Quality Level

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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This Item
38907PHL893141351800
Isorhamnetin ≥95.0% (HPLC)

17794

Isorhamnetin

Isorhamnetin analytical standard

38907

Isorhamnetin

Isorhamnetin phyproof® Reference Substance

PHL89314

Isorhamnetin

Isorhamnetin United States Pharmacopeia (USP) Reference Standard

1351800

Isorhamnetin

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

food and beverages

application(s)

-

application(s)

pharmaceutical (small molecule)

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


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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
Quercetin and its metabolite isorhamnetin promote glucose uptake through different signalling pathways in myotubes
Jiang H, et al.,
Scientific Reports, 1-15 (2019)
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
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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