(E)-Chalcone

Names

[ CAS No. ]:
614-47-1

[ Name ]:
(E)-Chalcone

[Synonym ]:
Phenyl (E)-2-phenylethenyl ketone
RV1U1R &&E Form
Phenyl styryl ketone
2-Propen-1-one, 1,3-diphenyl-, (E)-
a-Benzylideneacetophenone
b-Phenylacrylophenone
β-Phenylacrylophenone
1-Benzoyl-2-phenylethylene
chalcone
trans-benzylideneacetophenone
EINECS 202-330-2
(2E)-1,3-diphenylprop-2-en-1-one
(E)-benzylideneacetophenone
phenyl trans-styryl ketone
trans-benzalacetophenone
(E)-1-Benzoyl-2-phenylethylene
2-Propen-1-one, 1,3-diphenyl-, (2E)-
trans-Chalcone
MFCD00003082
(2E)-1,3-Diphenyl-2-propen-1-one
β-Benzoylstyrene
b-Benzoylstyrene

Biological Activity

[Description]:

trans-Chalcone, isolated from Aronia melanocarpa skin, is a biphenolic core structure of flavonoids precursor. trans-Chalcone is a potent fatty acid synthase (FAS) and α-amylase inhibitor. trans-Chalcone causes cellcycle arrest and induces apoptosis in the breastcancer cell line MCF-7. trans-Chalcone has antifungal and anticancer activity[1][2][3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Signaling Pathways >> Metabolic Enzyme/Protease >> Fatty Acid Synthase (FAS)

Signaling Pathways >> Anti-infection >> Fungal

Research Areas >> Inflammation/Immunology

[In Vitro]

trans-Chalcone competitively inhibits porcine pancreatic α-amylase with a Ki of 48 μM[2]. trans-Chalcone (30.23-98.03 μM; 24 hours) induces cell cycle arrest and apoptosis in MCF-7 cells[1]. trans-Chalcone (30.23-98.03 μM; 24 hours) reduces the expression of the apoptosis-related protein Bcl-2 and induces the expression of the CIDEA gene[1]. trans-Chalcone (58.25 μM; 6, 24 hours) has greater inhibition of Bcl-2, induction of APAF1 and BAX, and strong induction of CIDEA in 24 hours[1]. trans-Chalcone (24 hours) inhibits MCF-7 cell viability (IC20=30.23 μM; IC50=58.25 μM; IC80=98.03 μM). trans-Chalcone (48 h) has IC50s of 41.53 μM and 48.41 μM for MCF-7 and 3T3 cell lines, respectively. trans-Chalcone exhibits a pronounced cytotoxicity activity[1]. Apoptosis Analysis[1] Cell Line: MCF-7 cell Concentration: 30.23, 58.25, 98.03 μM Incubation Time: 24 hours Result: Induced apoptosis of the breast cancer cell line. Cell Cycle Analysis[1] Cell Line: MCF-7 cell Concentration: 30.23, 58.25, 98.03 μM Incubation Time: 24 hours Result: Caused cell cycle arrest in G1. Western Blot Analysis[1] Cell Line: MCF-7 cell Concentration: 20, 40, 80 μM Incubation Time: 24, 48 hours Result: Reduced the expression of the apoptosis-related protein Bcl-2 and induced the expression of the CIDEA gene. There was marked degradation of cyclin D1 at 48 h. RT-PCR[1] Cell Line: MCF-7 cell Concentration: 58.25 μM Incubation Time: 6, 24 hours Result: Had greater inhibition of Bcl-2, induction of APAF1 and BAX, and strong induction of CIDEA in 24 hours.

[References]

[1]. Luis Felipe Buso Bortolotto, et al. Cytotoxicity of trans-chalcone and licochalcone A against breast cancer cells is due to apoptosis induction and cell cycle arrest. Biomed Pharmacother. 2017 Jan;85:425-433.

[2]. Mahmoud Najafian, et al. Trans-chalcone: a novel small molecule inhibitor of mammalian alpha-amylase. Mol Biol Rep. 2011 Mar;38(3):1617-20.

[3]. Tamires Aparecida Bitencourt, et al. Trans-chalcone and quercetin down-regulate fatty acid synthase gene expression and reduce ergosterol content in the human pathogenic dermatophyte Trichophyton rubrum. BMC Complement Altern Med. 2013 Sep 17;13:229.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
346.6±25.0 °C at 760 mmHg

[ Melting Point ]:
55-57ºC

[ Molecular Formula ]:
C₁₅H₁₂O

[ Molecular Weight ]:
208.255

[ Flash Point ]:
150.1±18.1 °C

[ Exact Mass ]:
208.088821

[ PSA ]:
17.07000

[ LogP ]:
4.01

[ Vapour Pressure ]:
0.0±0.8 mmHg at 25°C

[ Index of Refraction ]:
1.625

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22;R36/37

[ Safety Phrases ]:
S22-S36/37/39-S45

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UD5576750

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Impact of induced fit on ligand binding to the androgen receptor: a multidimensional QSAR study to predict endocrine-disrupting effects of environmental chemicals.

J. Med. Chem. 48 , 5666-74, (2005)

We investigated the influence of induced fit of the androgen receptor binding pocket on free energies of ligand binding. On the basis of a novel alignment procedure using flexible docking, molecular d...

A chemical screening approach reveals that indole fluorescence is quenched by pre-fibrillar but not fibrillar amyloid-beta.

Bioorg. Med. Chem. Lett. 19 , 4952-7, (2009)

Aggregated amyloid-beta (Abeta) peptide is implicated in the pathology of Alzheimer's disease. In vitro and in vivo, these aggregates are found in a variety of morphologies, including globular oligome...

Novel chalcone derivatives as potent Nrf2 activators in mice and human lung epithelial cells.

J. Med. Chem. 54 , 4147-59, (2011)

Nrf2-mediated activation of antioxidant response element is a central part of molecular mechanisms governing the protective function of phase II detoxification and antioxidant enzymes against carcinog...