NARINGENIN CHALCONE CAS#: 73692-50-9

NARINGENIN CHALCONE Basic information

Product Name:

NARINGENIN CHALCONE

Synonyms:

ISOSALIPURPOL
2',4',6',4-TETRAHYDROXYCHALCONE
NARINGENIN CHALCONE
C06561
NARINGENIN CHALCONE(cis and trans Mix)(RG)
Naringein chalcone
(2E)-3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-2-propen-1-one
4,2',4',6'-Tetrahydroxychalcone

CAS:

73692-50-9

MF:

C15H12O5

MW:

272.25

Mol File:

73692-50-9.mol

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NARINGENIN CHALCONE Chemical Properties

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)

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NARINGENIN CHALCONE Usage And Synthesis

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

NARINGENIN CHALCONESupplier

ChengDu Yijierui Biotechnology CO., Ltd Gold

Tel: 18224018291 18224018291
Email: yirui307@163.com

ShangHai YuanYe Biotechnology Co., Ltd.

Tel: 021-61312847 13636370518
Email: shyysw007@163.com

Chengdu Biopurify Phytochemicals Ltd.

Tel: +86-028-82633397 18982077548
Email: cwb1@biopurify.cn

Shanghai Tauto Biotech Co., Ltd.

Tel: 021-51320588
Email: tauto@tautobiotech.com

TargetMol Chemicals Inc.

Tel: 021-021-33632979 15002134094
Email: marketing@targetmol.com

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