ChemicalBook Product Catalog Natural Products Flavonoids TAMARIXETIN

TAMARIXETIN

Product NameTAMARIXETIN
CAS603-61-2
MFC16H12O7
MW316.26
EINECS210-050-7
MOL File603-61-2.mol

Chemical Properties

Melting point	265-268°C
Boiling point	601.8±55.0 °C(Predicted)
Density	1.634±0.06 g/cm3(Predicted)
storage temp.	Store at -20°C
solubility	DMSO: Slightly Soluble; Methanol: Slightly Soluble
form	A solid
pka	6.31±0.40(Predicted)
color	Yellow to brown
InChI	1S/C16H12O7/c1-22-11-3-2-7(4-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3
InChIKey	FPLMIPQZHHQWHN-UHFFFAOYSA-N
SMILES	[o]1c2c([c](c(c1c3cc(c(cc3)OC)O)O)=O)c(cc(c2)O)O
LogP	2.420 (est)

Safety Information

Risk Statements	22
Safety Statements	22-45
WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

4''-O-methyl Quercetin is a flavonoid isolated from C. ordata with anticancer and antiplasmodial activity. 4''-O-methyl Quercetin is a major metabolite of quercetin (Item No. 10005169) that inhibits the viability of HL-60, U937, MOLT-3, Raji, K562, MCF-7, SK-MEL-1, and A549 human tumor cell lines with IC₅₀ values ranging from 5.5-24.1 μM. It induces G₂-M arrest and inhibits tubulin polymerization in vitro in a dose-dependent manner. 4''-O-methyl Quercetin inhibits breast cancer resistance protein (BCRP/ABCG2; IC₅₀ = 40 nM in a vesicular transport assay) with no cellular toxicity indicating potential for use in overcoming multidrug resistance in chemotherapy. 4''-O-methyl Quercetin also reduces in vitro proliferation of chloroquine-resistant P. falciparum (IC₅₀ = 4.8 μM) and suppresses infection in mice (65-81% suppression at 2.5-5 mg/kg dose).

Uses

A major metabolite of the flavanoid Quercetin (Q509500) 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.

Definition

ChEBI: A monomethoxyflavone that is quercetin methylated at position O-4'. Isolated from Cyperus teneriffae.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

in vivo

Tamarixetin (0.2% feed management; 6 weeks) improves the myocardial hypertrophy model ^[2].
Tamarixetin (intraperitoneal injection; 1 mg/kg; single dose) has better anti-inflammatory properties, which is related to the increase of the immune cell population secreting IL-10 in mouse models of bacterial septicemia^[3].

Animal Model:	Transverse aortic constriction (TAC) mouse model^[2]
Dosage:	0.2%
Administration:	Feed management; 6 weeks
Result:	Alleviated pressureoverloadinduced cardiac hypertrophy in mice. Attenuated cardiac fibrosis and apoptosis in pressureoverloaded hearts. Suppressed oxidative stress. Negatively regulated NFAT nuclear translocation level. Was able to the down-regulate the activation of PI3K/AKT signaling pathway in the heart after pressure overload.

References

[1] FABIO NICOLINI. Induction of G2/M phase arrest and apoptosis by the flavonoid tamarixetin on human leukemia cells.[J]. Molecular Carcinogenesis, 2014, 53 12: 939-950. DOI: 10.1002/mc.22055
[2] KEE W. TAN . Identification of novel dietary phytochemicals inhibiting the efflux transporter breast cancer resistance protein (BCRP/ABCG2)[J]. Food Chemistry, 2013, 138 4: Pages 2267-2274. DOI: 10.1016/j.foodchem.2012.12.021
[3] I C EZENYI. Antiplasmodial activity-aided isolation and identification of quercetin-4’-methyl ether in Chromolaena odorata leaf fraction with high activity against chloroquine-resistant Plasmodium falciparum.[J]. Parasitology Research, 2014, 113 12: 4415-4422. DOI: 10.1007/s00436-014-4119-y

TAMARIXETIN

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