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HomeProduct name listIsorhamnetin

Isorhamnetin

Synonym(s):3′-Methoxy-3,4′,5,7-tetrahydroxyflavone;3′-Methylquercetin;3,4′,5,7-Tetrahydroxy 3′-methoxyflavone;Isorhamnetol;Quercetin 3′-methyl ether

  • CAS NO.:480-19-3
  • Empirical Formula: C16H12O7
  • Molecular Weight: 316.26
  • MDL number: MFCD00017310
  • EINECS: 207-545-5
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-05 11:59:05
Isorhamnetin Structural

What is Isorhamnetin?

Chemical properties

Beige to lighet yellow powder

The Uses of Isorhamnetin

Isorhamnetin is a natural flavonol aglycone that is the 3-methyl metabolite of quercetin . It has antioxidant activity and inhibits xanthine oxidase (IC50 = 0.40 μM). Isorhamnetin also competitively inhibits the human multidrug and toxic compounds extrusion transporter 1 (Ki = 0.32 μM), which has an important role in the excretion of xenobiotics at the kidney and liver. It has also been reported to potentiate the neurological actions of nerve growth factor, diminish the cardiotoxic impact of doxorubicin, and have beneficial anti-cancer effects.

What are the applications of Application

Isorhamnetin is an antiviral, antioxidant apoptosis inducer

Definition

ChEBI: Isorhamnetin is a monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group. It has a role as an EC 1.14.18.1 (tyrosinase) inhibitor, an anticoagulant and a metabolite. It is a 7-hydroxyflavonol, a tetrahydroxyflavone and a monomethoxyflavone. It derives from a quercetin. It is a conjugate acid of an isorhamnetin(1-).

What are the applications of Application

Isorhamnetin is a metabolite of the flavanoid Quercetin with antioxidant properties. It helps to protect H9c2 cardiomyoblasts against H2O2-induced oxidative stress via the modulation of PI3K/Akt and ERK1/2 signaling pathways.

Benefits

Isorhamnetin may have potential benefits in inhibiting the onset and treatment of neuroinflammatory diseases. Isorhamnetin is not that much studied than quercetin. However, the few that exist indicate that isorhamnetin has similar health benefits: it may reduce the risk of cancer, improve heart health and ease diabetes complications.

General Description

Isorhamnetin is one of the important flavanols found in G.biloba leaf extracts. Isorhamnetin is also found in parsley, and thereby it is a common dietary flavonoid as the metabolite of quercetin.Generally, it is well known as antagonist of peroxisome proliferator-activated receptor Y (PPARy), which inhibits adipocyte differentiation induced by the PPARy agonist rosiglitazone. Isorhamnetin is a naturally occurring compound in fruits and vegetables; recent study showed that isorhamnetin could significantly inhibit the invasion of MDA-MB-231 cells by downregulating matrix metalloproteinases(MMP-2 and MMP-9) through inhibiting p38 MAPK and STAT3. Similar results were also obtained in another study, which showed that isorhamnetin inhibited cell proliferation and led to apoptosis. In addition, isorhamnetin was found effective on Akt/mTOR/MAPKs signaling axis. It was established that isorhamnetin-induced autophagy can be reversed by the co-treatment of 3-methyl-adenine in lung cancer cells. The results indicated that isorhamnetin exerts antitumor effect in breast cancer through targeting multiple molecular targets.

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.

Properties of Isorhamnetin

Melting point: 307°C
Boiling point: 599.4±50.0 °C(Predicted)
Density  1.634±0.06 g/cm3(Predicted)
storage temp.  2-8°C
solubility  DMF: 10 mg/ml; DMSO: 20 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml
pka 6.31±0.40(Predicted)
form  Solid
form  neat
color  Light yellow to Amber to Dark green
BRN  44723
Stability: Hygroscopic
CAS DataBase Reference 480-19-3(CAS DataBase Reference)

Safety information for Isorhamnetin

Signal word Warning
Pictogram(s)
ghs
Health Hazard
GHS08
GHS Hazard Statements H351:Carcinogenicity
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P281:Use personal protective equipment as required.

Computed Descriptors for Isorhamnetin

InChIKey IZQSVPBOUDKVDZ-UHFFFAOYSA-N

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