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Naringenin chalcone

CAT: 0804-HY-N3007-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N3007-01Size:1 mg
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Description
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].
CAS Number
73692-50-9
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Apoptosis; Drug Intermediate; NO Synthase
Type
Natural Products
Related Pathways
Apoptosis; Immunology/Inflammation; Others
Applications
COVID-19-immunoregulation
Field of Research
Cancer; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/naringenin-chalcone.html
Concentration
10mM
Purity
99.29
Solubility
DMSO : 50 mg/mL (ultrasonic) |Methanol : ≥ 25 mg/mL
Smiles
OC(C=C1)=CC=C1/C=C/C(C2=C(C=C(O)C=C2O)O)=O
Molecular Formula
C15H12O5
Molecular Weight
272.25
Precautions
H302, H315, H319, H335
References & Citations
[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. |[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.|[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. |[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. |[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.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

2',4,4',6'-Tetrahydroxychalcone

2',4,4',6'-tetrahydroxychalcone is a member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 2' ,4, 4', and 6' respectively. It has a role as a metabolite, an anti-allergic agent and an anti-inflammatory agent. It is a member of chalcones, a member of (E)-2'-hydroxy-chalcones and a polyphenol. It is functionally related to a trans-chalcone.

CAS Number73692-50-9
PubChem CID5280960
IUPAC Name(E)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
Molecular FormulaC15H12O5
Molecular Weight272.25
XLogP2.8
Topological Polar Surface Area98
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Heavy Atom Count20
Formal Charge0
Complexity347
SMILES
C1=CC(=CC=C1/C=C/C(=O)C2=C(C=C(C=C2O)O)O)O
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/b6-3+
InChIKey
YQHMWTPYORBCMF-ZZXKWVIFSA-N
Chemical Structure
2D Structure
2D structure of 2',4,4',6'-Tetrahydroxychalcone
CAS: 73692-50-9
CID: 5280960
Formula: C15H12O5
MW: 272.25
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight272.25
XLogP32.8
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass272.06847348
Monoisotopic Mass272.06847348
Topological Polar Surface Area98 Ų
Heavy Atom Count20
Formal Charge0
Complexity347
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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