Ch55 (Ch-55) is a synthetic retinoid acting as an inducer of teratocarcinoma cells by binding to RAR-α and RAR-β receptors with high affinity. Ch55 displays anticancer activity.
Physicochemical Properties
| Molecular Formula | C24H28O3 |
| Molecular Weight | 364.485 |
| Exact Mass | 364.204 |
| CAS # | 110368-33-7 |
| PubChem CID | 6184667 |
| Appearance | White to light yellow solid powder |
| Density | 1.085g/cm3 |
| Boiling Point | 509.5ºC at 760mmHg |
| Flash Point | 276ºC |
| Vapour Pressure | 3.33E-11mmHg at 25°C |
| Index of Refraction | 1.574 |
| LogP | 5.875 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 6 |
| Heavy Atom Count | 27 |
| Complexity | 531 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | CC(C)(C)C1=CC(=CC(=C1)C(=O)/C=C/C2=CC=C(C=C2)C(=O)O)C(C)(C)C |
| InChi Key | FOUVTBKPJRMLPE-FMIVXFBMSA-N |
| InChi Code | InChI=1S/C24H28O3/c1-23(2,3)19-13-18(14-20(15-19)24(4,5)6)21(25)12-9-16-7-10-17(11-8-16)22(26)27/h7-15H,1-6H3,(H,26,27)/b12-9+ |
| Chemical Name | 4-[(E)-3-(3,5-ditert-butylphenyl)-3-oxoprop-1-enyl]benzoic acid |
| Synonyms | Ch 55 Ch-55 Ch55 |
| 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 | Ch55 increases dissolved sulfate levels (EC50=0.03 nM) and inhibits type I transglutaminase activity (EC50=0.02 nM) to prevent squamous cell blanking of rabbit tracheal epithelial cells. Additionally, Ch55 suppresses the induction of avian dye decarboxylase activity in 3T6 fibroblasts (EC50 = 1 nM) and stimulates secretion from cancer F9 cells and melanoma S91 cells (EC50s=0.26 and 0.5 nM) [1]. |
| References |
[1]. New benzoic acid derivatives with retinoid activity: lack of direct correlation between biological activity and binding to cellular retinoic acid binding protein. Cancer Res. 1987 Jul 1;47(13):3523-7. [2]. Induction of differentiation and covalent binding to proteins by the synthetic retinoids Ch55 and Am80. Arch Biochem Biophys. 1994 Oct;314(1):82-9. |
| Additional Infomation | 4-[3-(3,5-ditert-butylphenyl)-3-oxoprop-1-enyl]benzoic acid is a member of chalcones. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~50 mg/mL (~137.18 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.86 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7436 mL | 13.7178 mL | 27.4356 mL | |
| 5 mM | 0.5487 mL | 2.7436 mL | 5.4871 mL | |
| 10 mM | 0.2744 mL | 1.3718 mL | 2.7436 mL |