| Identification | Back Directory | [Name]
NARINGENIN CHALCONE | [CAS]
73692-50-9 | [Synonyms]
C06561
ISOSALIPURPOL
Naringein chalcone
NARINGENIN CHALCONE
4,2',4',6'-Tetrahydroxychalcone
2',4',6',4-TETRAHYDROXYCHALCONE
trans-2'4'6'4-tetrahydroxychalcone
NARINGENIN CHALCONE(cis and trans Mix)(RG)
2-Propen-1-one,3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-
(2E)-3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-2-propen-1-one | [Molecular Formula]
C15H12O5 | [MDL Number]
MFCD00016762 | [MOL File]
73692-50-9.mol | [Molecular Weight]
272.25 |
| Chemical Properties | Back Directory | [Melting point ]
173-174℃ | [Boiling point ]
538.7±50.0 °C(Predicted) | [density ]
1.483±0.06 g/cm3(Predicted) | [storage temp. ]
4°C, protect from light | [solubility ]
DMF:15.0(Max Conc. mg/mL);55.0(Max Conc. mM)
DMSO:10.0(Max Conc. mg/mL);36.0(Max Conc. mM)
Ethanol:1.0(Max Conc. mg/mL);3.6(Max Conc. mM) | [form ]
A solid | [pka]
6.82±0.40(Predicted) | [color ]
Light yellow to orange | [InChI]
InChI=1S/C15H12O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-8,16-17,19-20H | [InChIKey]
YQHMWTPYORBCMF-UHFFFAOYSA-N | [SMILES]
C(C1=C(O)C=C(O)C=C1O)(=O)C=CC1=CC=C(O)C=C1 | [LogP]
2.826 (est) |
| Hazard Information | Back Directory | [Chemical Properties]
Soluble in organic solvents such as methanol, ethanol, and DMSO. | [Uses]
Naringenin chalcone is an orally active intermediate in flavonol biosynthesis. Naringenin chalcone induces Apoptosis. Naringenin chalcone inhibits the production of MCP-1 and NO. Naringenin chalcone exhibits anticancer activity against glioblastoma. Naringenin chalcone has anti-inflammatory and anti-allergic properties[1][2][3][4][5][6]. | [Definition]
ChEBI: A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 2' ,4, 4', and 6' respectively. | [in vivo]
Naringenin chalcone (0.8 mg/kg; p.o.; daily) reduces eosinophilic airway inflammation, airway hyperresponsiveness, suppressed Th2 cytokine production by splenic CD4+ T cells, and slightly reduced mucus overproduction in allergic asthmatic BALB/c mice[2].
Naringenin chalcone (5-80 mg/kg; 24 days) reduced tumor volume and tumor weight in U87MG human glioblastoma xenograft Balb/c nude mice[3].
Naringenin chalcone (p.o.) increases plasma adiponectin levels in diabetic mice[4].
Naringenin chalcone (0.02%; i.v.) inhibits the anaphylactic response to IgE-mediated passive cutaneous anaphylaxis in CD-1 mice[5].
Naringenin chalcone (20 mg/kg; p.o.; once) resultes in the detection of naringenin chalcone -2'-O-β-D-glucuronide in the plasma of male Sprague-Dawley rats[6].
| [References]
[1] Hirai S, et al. Inhibitory effect of naringenin chalcone on inflammatory changes in the interaction between adipocytes and macrophages. Life Sci. 2007 Sep 29;81(16):1272-9. DOI:10.1016/j.lfs.2007.09.001
[2] Iwamura C, et al. Naringenin chalcone suppresses allergic asthma by inhibiting the type-2 function of CD4 T cells. Allergol Int. 2010 Mar;59(1):67-73. DOI:10.2332/allergolint.09-OA-0118
[3] Zhang S, et al. Anti-cancer effect of naringenin chalcone is mediated via the induction of autophagy, apoptosis and activation of PI3K/Akt signalling pathway. Bangladesh Journal of Pharmacology, 2016, 11(3): 684-690.
[4] Horiba T, et al. Naringenin chalcone improves adipocyte functions by enhancing adiponectin production. Mol Cell Endocrinol. 2010 Jul 29;323(2):208-14. DOI:10.1016/j.mce.2010.03.020
[5] Escribano-Ferrer E, et al. In Vivo Anti-inflammatory and Antiallergic Activity of Pure Naringenin, Naringenin Chalcone, and Quercetin in Mice. J Nat Prod. 2019 Feb 22;82(2):177-182. DOI:10.1021/acs.jnatprod.8b00366
[6] Yoshimura M, et al. Identification and quantification of metabolites of orally administered naringenin chalcone in rats. J Agric Food Chem. 2009 Jul 22;57(14):6432-7. DOI:10.1021/jf901137x |
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