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: 2024-11-19 23:02:33
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) |
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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