Physicochemical Properties
| Molecular Formula | C23H18O5 |
| Molecular Weight | 374.39 |
| Exact Mass | 374.115 |
| CAS # | 1054549-73-3 |
| PubChem CID | 74762951 |
| Appearance | Light yellow to yellow solid powder |
| LogP | 4.7 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 28 |
| Complexity | 561 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | C1C=CC=CC=1/C=C/C1=C(C=C2C(=C1O)C(=O)CC(C1C=CC(O)=CC=1)O2)O |
| InChi Key | WBONVHMXTSZBAF-IZZDOVSWSA-N |
| InChi Code | InChI=1S/C23H18O5/c24-16-9-7-15(8-10-16)20-13-19(26)22-21(28-20)12-18(25)17(23(22)27)11-6-14-4-2-1-3-5-14/h1-12,20,24-25,27H,13H2/b11-6+ |
| Chemical Name | (E)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-styrylchroman-4-one |
| Synonyms | 6-CEPN 6 CEPN 6CEPN |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | 6-CEPN (10-100 μM, 24 h) can inhibit cell growth and decrease cell viability in SW620, SW480, HCT116, and HT29 cells in a concentration-dependent manner [1]. SW620 and HCT116 cells can have their cell cycle arrested in the G1 phase by 6-CEPN (10 μM, 24 h) [1]. In SW620 and HCT116 cells, 6-CEPN (2.5–10 μM, 24 h) activates cellular pathways [1]. |
| Cell Assay |
Cell cycle analysis[1] Cell Types: SW620, HCT116 Tested Concentrations: 10 μM Incubation Duration: 24 h) In SW620 and HCT116 cells, circular autophagy and cell death are exchanged by inhibiting RAS activation[1]. Experimental Results: p21 protein levels increased, and p-Rb and cyclin D1 protein levels diminished (P21, p-Rb, and cyclin D1 are cell cycle regulators related to the G1 phase). Autophagy detection [1] Cell Types: SW620, HCT116 Tested Concentrations: 2.5 μM, 5 μM, 10 μM Incubation Duration: 24 h Experimental Results: Formation of red fluorescent acidic vesicle organelles and MDC labeled particles (key characteristics of autophagy). The expression level of LC3 protein in cells increases and autophagy occurs. Western Blot Analysis[1] Cell Types: SW620, HCT116 Tested Concentrations: 2.5 μM, 5 μM, 10 μM Incubation Duration: 24 h Experimental Results: Dramatically inhibited the phosphorylation of C-raf, ERK, AKT and mTOR, while C-raf , ERK, AKT and mTOR phosphorylation had no significant effect. Levels of total C-raf, ERK, AKT, and mTOR. Inhibits RAS acti |
| References |
[1]. 6-C-(E-phenylethenyl)naringenin induces cell growth inhibition and cytoprotective autophagy in colon cancer cells.European journal of cancer: official journal for European Organization for Research and Treatment of Cancer (EORTC) [and] European Association for Cancer Research (EACR), 2016, 68(Null). |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.6710 mL | 13.3551 mL | 26.7101 mL | |
| 5 mM | 0.5342 mL | 2.6710 mL | 5.3420 mL | |
| 10 mM | 0.2671 mL | 1.3355 mL | 2.6710 mL |