Physicochemical Properties
| Molecular Formula | C13H15NO4 |
| Molecular Weight | 249.26 |
| Exact Mass | 249.1 |
| CAS # | 1148-11-4 |
| PubChem CID | 101987 |
| Appearance | White to off-white solid powder |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 432.3±45.0 °C at 760 mmHg |
| Melting Point | 76-78ºC |
| Flash Point | 215.3±28.7 °C |
| Vapour Pressure | 0.0±1.1 mmHg at 25°C |
| Index of Refraction | 1.582 |
| LogP | 1.17 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 18 |
| Complexity | 312 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | O=C(O)[C@H]1N(C(OCC2=CC=CC=C2)=O)CCC1 |
| InChi Key | JXGVXCZADZNAMJ-NSHDSACASA-N |
| InChi Code | InChI=1S/C13H15NO4/c15-12(16)11-7-4-8-14(11)13(17)18-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,15,16)/t11-/m0/s1 |
| Chemical Name | (2S)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid |
| Synonyms | EINECS 214-557-4; Benzyloxycarbonylproline; Carbobenzoxyproline |
| 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 | Carphenoxyproline (6 mM; 0–10 days; pH=6.0) has been shown in long-term culturing of fibroblasts from patients with prolinase deficiency (PD) 33% to promote mitochondrial depolarization and accelerate cell death[1]. Fibroblast prolinase (FBP) is hydrolyzed by carphenoxyproline (0, 1, 3, 6 mM; 1 min; pH=6.0), exhibiting linear competitive inhibition [1]. |
| ln Vivo | In a mouse model, carphenoxyproline (60 mg/kg; injection; once daily; 3 weeks) inhibits erythrocyte prolinase in vivo [1]. |
| Animal Protocol |
Animal/Disease Models: C57Bl/6J mice (4 weeks old) [1] Doses: 60 mg/kg Route of Administration: injection; one time/day for 3 weeks. Experimental Results: Result in a significant decrease in erythrocyte prolinase activity. |
| References | [1]. Lupi A, et al. N-benzyloxycarbonyl-L-proline: an in vitro and in vivo inhibitor of prolidase. Biochim Biophys Acta. 2005 Jun 30;1744(2):157-63. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~401.19 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.03 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (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 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (10.03 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (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 20% SBE-β-CD physiological saline solution and mix evenly. 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (10.03 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 | 4.0119 mL | 20.0594 mL | 40.1188 mL | |
| 5 mM | 0.8024 mL | 4.0119 mL | 8.0238 mL | |
| 10 mM | 0.4012 mL | 2.0059 mL | 4.0119 mL |