| Identification | Back Directory | [Name]
TAMARIXETIN | [CAS]
603-61-2 | [Synonyms]
Aids098167
amarixetin
Aids-098167
Chiosmethin
TAMARIXETIN
tamaraxetin
TAMARIEXETIN
4’-methylquercetin
4’-methoxyquercetin
4’-o-methylquercetin
TAMARIXETIN WITH HPLC
QUERCETIN-4'-METHYL ETHER
QUERCETIN-4''-METHYL ETHER hplc
4'-METHOXY-3,5,7,3'-TETRAHYDROFLAVONE
3,3',5,7 TETRAHYDROXY-4'-METHOXYFLAVONE
4’-methoxy-3,3’,5,7-tetrahydroxy-flavon
3,3’,5,7-tetrahydroxy-4’-methoxy-flavon
4'-METHOXY-3,3',5,7-TETRAHYDROXYFLAVONE
3,5,7-trihydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one
3,5,7-trihydroxy-2-(3-hydroxy-4-methoxy-phenyl)chroman-4-one
3,5,7-trihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone
3,5,7-trihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4h-1-benzopyran-4-on
3,5,7-Trihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(3-hydroxy-4-methoxyphenyl)- | [EINECS(EC#)]
210-050-7 | [Molecular Formula]
C16H12O7 | [MDL Number]
MFCD00017308 | [MOL File]
603-61-2.mol | [Molecular Weight]
316.26 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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.1 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.2 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).3 | [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 pressure?overload?induced cardiac hypertrophy in mice.
Attenuated cardiac fibrosis and apoptosis in pressure?overloaded 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.
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| [storage]
Store at -20°C | [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 |
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