Praeruptorin C (Pra-C) is a natural product that has been widely used as an antioxidant and a calcium antagonist for the treatment of various diseases. Pra-C partially protects cortical neurons by inhibiting the expression of GluN2B-containing NMDA receptors and regulating the Bcl-2 family.
Physicochemical Properties
| Molecular Formula | C24H28O7 |
| Molecular Weight | 428.4749 |
| Exact Mass | 428.183 |
| CAS # | 72463-77-5 |
| PubChem CID | 5320692 |
| Appearance | White to off-white solid powder |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 516.5±50.0 °C at 760 mmHg |
| Melting Point | 132-134ºC |
| Flash Point | 221.4±30.2 °C |
| Vapour Pressure | 0.0±1.3 mmHg at 25°C |
| Index of Refraction | 1.560 |
| Source | Chrysanthemum × morifolium (Ramat.) Hemsl.; Musineon divaricatum |
| LogP | 5.59 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 7 |
| Heavy Atom Count | 31 |
| Complexity | 779 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | C/C=C(/C)\C(=O)O[C@@H]1[C@@H](C2=C(C=CC3=C2OC(=O)C=C3)OC1(C)C)OC(=O)CC(C)C |
| InChi Key | UFUVJROSOIXJGR-IULGZIFLSA-N |
| InChi Code | InChI=1S/C24H28O7/c1-7-14(4)23(27)30-22-21(29-18(26)12-13(2)3)19-16(31-24(22,5)6)10-8-15-9-11-17(25)28-20(15)19/h7-11,13,21-22H,12H2,1-6H3/b14-7-/t21-,22-/m1/s1 |
| Chemical Name | [(9R,10R)-8,8-dimethyl-10-(3-methylbutanoyloxy)-2-oxo-9,10-dihydropyrano[2,3-f]chromen-9-yl] (Z)-2-methylbut-2-enoate |
| Synonyms | Praeruptorin C; 72463-77-5; 83382-71-2; [(9R,10R)-8,8-dimethyl-10-(3-methylbutanoyloxy)-2-oxo-9,10-dihydropyrano[2,3-f]chromen-9-yl] (Z)-2-methylbut-2-enoate; praeruptorine C; Praeruptorin-C; |
| 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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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
| Targets | Natural product from Peucedanum praeruptorum |
| ln Vitro | Praeruptorin C and E isolated from Peucedanum praeruptorum Dunn. decreased the maximum contractile effect of Ca2+ in potassium-depolarized swine coronary strips and shifted the concentration-response curve to the right in a non-parallel manner. The calcium antagonistic activity of praeruptorin C and E expressed as pD'2 value was 5.7 and 5.2, respectively. Nifedipine, with a pD'2 value of 6.88, was used as a known calcium antagonistic drug to compare the potency of the drugs studied. The relaxation induced by praeruptorin C was concentration-dependent and the IC50 value was 79 microM. Praeruptorin C also reduced the maximum contractile response and shifted the concentration-response curve for calcium to the right in a non-parallel manner in potassium-depolarized guinea-pig left atria (pD'2 = 5.52) but its potency was much less than that of nifedipine (pD'2 = 7.19). The results suggest that praeruptorin C and E relaxed swine coronary artery and decreased contractility in guinea-pig left atria. These effects are similar in many respects to those displayed by drugs that have calcium entry blocking activity [1]. |
| References |
[1]. Effects of praeruptorin C and E isolated from 'Qian-Hu' on swine coronary artery and guinea-pig atria. Eur J Pharmacol. 1988 Oct 18;155(3):293-6. |
| Additional Infomation | Praeruptorin C has been reported in Musineon divaricatum with data available. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~25 mg/mL (~58.35 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.83 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 | 2.3339 mL | 11.6694 mL | 23.3389 mL | |
| 5 mM | 0.4668 mL | 2.3339 mL | 4.6678 mL | |
| 10 mM | 0.2334 mL | 1.1669 mL | 2.3339 mL |