CAS 614-47-1|(E)-Chalcone
| Common Name | (E)-Chalcone | ||
|---|---|---|---|
| CAS Number | 614-47-1 | Molecular Weight | 208.255 |
| Density | 1.1±0.1 g/cm3 | Boiling Point | 346.6±25.0 °C at 760 mmHg |
| Molecular Formula | C15H12O | Melting Point | 55-57ºC |
| MSDS | ChineseUSA | Flash Point | 150.1±18.1 °C |
| Symbol | GHS07 | Signal Word | Warning |
Names
| Name | trans-chalcone |
|---|---|
| Synonym | More Synonyms |
(E)-Chalcone BiologicalActivity
| 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 >>ApoptosisResearch Areas >>CancerSignaling Pathways >>Metabolic Enzyme/Protease >>Fatty Acid Synthase (FAS)Signaling Pathways >>Anti-infection >>FungalResearch 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 |
| InChIKey | DQFBYFPFKXHELB-VAWYXSNFSA-N |
| SMILES | O=C(C=Cc1ccccc1)c1ccccc1 |
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 |
Articles30
More 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... |
Synonyms
| 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 |
