11970

Sigma-Aldrich

1,3-Diphenyl-2-propenone

≥98.0% (GC)

Synonym(s):
Benzalacetophenone, Chalcone
Linear Formula:
C6H5CH=CHCOC6H5
CAS Number:
Molecular Weight:
208.26
Beilstein/REAXYS Number:
1210466
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

≥98.0% (GC)

solubility

dioxane: soluble 1 g/10 mL, clear, colorless

SMILES string

O=C(\C=C\c1ccccc1)c2ccccc2

InChI

1S/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H/b12-11+

InChI key

DQFBYFPFKXHELB-VAWYXSNFSA-N

Gene Information

rat ... Ar(24208)

Related Categories

Application

1,3-Diphenyl-2-propenone was used in the preparation of pharmacologically-interesting heterocyclic systems like pyrazolines and pyrimidines.

Packaging

100 g in poly bottle

Biochem/physiol Actions

1,3-Diphenyl-2-propenone (chalcone) inhibits the proliferation of human breast cancer cell lines, MCF-7 and MDA-MB-231 by inducing apoptosis and blocking cell cycle progression in the G2/M phase. It is an inhibitor of Plasmodium falciparum cyclin-dependent protein kinases.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 11970.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Certificate of Analysis
Certificate of Origin
Chaoyun Wang et al.
Toxicology and applied pharmacology, 273(1), 59-67 (2013-09-03)
Intracellular reactive oxygen species (ROS) are derived from nicotinamide adenine dinucleotide phosphate (NADPH) oxidase. Angiotensin II (Ang II) can cause endothelial dysfunction by promoting intracellular ROS generation. Safflor yellow B (SYB) effectively inhibits ROS generation by upregulating Bcl-2 expression. In...
André Sousa et al.
The journal of physical chemistry. B, 117(6), 1901-1910 (2013-01-17)
Two oaklins guaiacylcatechinpyrylium (GCP) and syringylcatechinpyrylium (SCP) and a model compound deoxypeonidin (DOP) were synthesized, and the rate and equilibrium constants of the respective pH dependent network of chemical reactions were calculated. In contrast to anthocyanins, the three compounds possess...
Jeanne A Geyer et al.
Bioorganic & medicinal chemistry letters, 19(7), 1982-1985 (2009-03-03)
The cyclin dependent protein kinases, Pfmrk and PfPK5, most likely play an essential role in cell cycle control and differentiation in Plasmodium falciparum and are thus an attractive target for antimalarial drug development. Various 1,3-diaryl-2-propenones (chalcone derivatives) which selectivity inhibit...
Zi-Ming Feng et al.
Journal of natural products, 76(2), 270-274 (2013-02-08)
Hydroxysafflor yellow A (HSYA), a representative component of Carthamus tinctorius, has attracted much attention because of its remarkable cardiovascular activities. Its structure was originally reported in 1993 and has been widely cited to date. In our experiments, its solution structure...
Jie Li et al.
Neuroscience letters, 535, 51-56 (2013-01-22)
Inflammation is a pivotal pathological progress in the development of ischemic stroke. Modulating inflammatory cytokines released by microglia is thought to be a potential strategy for the treatment of ischemic stroke. Hydroxy-safflor yellow A (HSYA), a chemical component of the...

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