NARINGENIN CHALCONE

NARINGENIN CHALCONE Property

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 and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

NARINGENIN CHALCONE Chemical Properties,Usage,Production

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

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