N-Benzoyl-L-proline
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| Category | Others |
| Catalog number | BBF-05224 |
| CAS | 5874-58-8 |
| Molecular Weight | 219.24 |
| Molecular Formula | C12H13NO3 |
| Purity | ≥95% by HPLC |
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Specification
| Related CAS | 115795-02-3 (D-configuration) |
| Synonyms | Bz-L-Pro-OH; 1-benzoyl-L-proline; L-Proline, 1-benzoyl-; (S)-1-Benzoylpyrrolidine-2-carboxylic acid; L-N-benzoylproline; benzoyl-L-proline |
| Storage | Store at -20°C |
| IUPAC Name | (2S)-1-benzoylpyrrolidine-2-carboxylic acid |
| Canonical SMILES | C1CC(N(C1)C(=O)C2=CC=CC=C2)C(=O)O |
| InChI | InChI=1S/C12H13NO3/c14-11(9-5-2-1-3-6-9)13-8-4-7-10(13)12(15)16/h1-3,5-6,10H,4,7-8H2,(H,15,16)/t10-/m0/s1 |
| InChI Key | RQYKQWFHJOBBAO-JTQLQIEISA-N |
Properties
| Appearance | Crystal |
| Boiling Point | 428.9±38.0°C (Predicted) |
| Melting Point | 158-159°C |
| Density | 1.296±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol |
Reference Reading
1. Supramolecular architectures of N-acetyl-L-proline monohydrate and N-benzyl-L-proline
P Rajalakshmi, N Srinivasan, R V Krishnakumar, Ibrahim Abdul Razak, Mohd Mustaqim Rosli Acta Crystallogr C. 2013 Nov;69(Pt 11):1390-6. doi: 10.1107/S010827011302581X. Epub 2013 Oct 5.
The title compounds, N-acetyl-L-proline monohydrate, C7H11NO3·H2O, (I), and N-benzyl-L-proline, C12H15NO2, (II), crystallize in the monoclinic space group P21 with Z' = 1 and Z' = 2, respectively. The conformation of C(γ) with respect to the carboxylic acid group in (I) is C(γ)-exo or UP pucker, with the pyrrolidine ring twisted, while in (II), it is C(γ)-endo or DOWN, with the pyrrolidine ring assuming an envelope conformation. The crystal packing interactions in (I) are composed of two substructures, one characterized by an R6(6)(24) motif through O-H...O hydrogen bonds and the other by an R4(4)(23) ring through C-H...O interactions. In (II), the crystal packing interactions consist of N-H...O and C-H...O hydrogen bonds. Proline (Pro) exists in its neutral form in (I) and is zwitterionic in (II). This difference in the ionization states of Pro is manifested through the absence of N-H...O and presence of O-H...O interactions in (I), and the presence of N-H...O and absence of O-H...O hydrogen bonds in (II). While C-H...O interactions are present in both (I) and (II), the geometry of the synthons formed by them and their mode of participation in intermolecular interactions is different. Though the title compounds differ significantly in terms of modifications in the Pro skeleton, the differences in their supramolecular structures may also be viewed as a result of the molecular recognition facilitated by the presence of a solvent water molecule in (I) and the zwitterionic state of the amino acid in (II).
2. Potentiometric determination of the dissociation constants of an asymmetric sorbent containing l-proline, and the stability constants of its Cu(II) complexes
Y A Zolotarev, A A Kurganov, V A Davankov Talanta. 1978 Sep;25(9):493-8. doi: 10.1016/0039-9140(78)80082-4.
The dissociation constants of the carboxyl groups (pK(a1) = 2.2, n = 1.8) and amino groups (pK(a2) = 9.5, n(2) = 1.6) of a sorbent prepared by reacting l-proline with a cross-linked chloromethylated styrene polymer have been determined by potentiometric titration. The potentiometrically measured stability constants of the Cu(II) complexes of the resin (logbeta(1) = 6.9 and log beta(2) = 12.4) were found to be close to the values for the Cu(II) complexes of N-benzyl-l-proline. For complexed resins of alpha-amino-acid type the pH-values of decomplexation do not appear to be directly correlated with the stability constants.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
