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17794

Sigma-Aldrich

Isorhamnetin

≥95.0% (HPLC)

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C16H12O7
Numero CAS:
Peso molecolare:
316.26
Beilstein:
44723
Numero CE:
Numero MDL:
Codice UNSPSC:
12352205
ID PubChem:
NACRES:
NA.47

Saggio

≥95.0% (HPLC)

applicazioni

metabolomics
vitamins, nutraceuticals, and natural products

Stringa SMILE

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
IZQSVPBOUDKVDZ-UHFFFAOYSA-N

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Descrizione generale

Isorhamnetin is an O-methylated flavonol found in fruits, plants, and medicinal herbs. It is a metabolite of quercetin.

Applicazioni

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)

Azioni biochim/fisiol

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.

Confezionamento

Bottomless glass bottle. Contents are inside inserted fused cone.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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


Certificati d'analisi (COA)

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Quercetin ≥95% (HPLC), solid

Sigma-Aldrich

Q4951

Quercetin

Kaempferide analytical standard

Supelco

69545

Kaempferide

Narcissoside ≥95% (HPLC)

Sigma-Aldrich

SMB00581

Narcissoside

Kaempferol analytical standard

Supelco

96353

Kaempferol

Kaempferol United States Pharmacopeia (USP) Reference Standard

USP

1354900

Kaempferol

Myricetin ≥96.0%, crystalline

Sigma-Aldrich

M6760

Myricetin

Myricetin ≥96.0% (HPLC)

Sigma-Aldrich

70050

Myricetin

Quercetin and its metabolite isorhamnetin promote glucose uptake through different signalling pathways in myotubes
Jiang H, et al.,
Scientific Reports, 1-15 (2019)
Juraj Majtan et al.
Archives of dermatological research, 305(7), 619-627 (2013-07-03)
Matrix metalloproteinase-9 (MMP-9) appears to be a major protease responsible for the degradation of matrix and growth-promoting agents in chronic wounds. Honey has been successfully used for treating non-healing wounds associated with infections. However, the mechanisms of its action at
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
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

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