cis-4-Hydroxy-L-proline
SIGMA/H1637 - collagen synthesis inhibitor
Synonym: (2S,4S)-(−)-4-Hydroxy-2-pyrrolidinecarboxylic acid; CHP
CAS Number: 618-27-9
Empirical Formula (Hill Notation): C5H9NO3
Molecular Weight: 131.13
EC Number: 210-542-1
MDL Number: MFCD00064319
Linear Formula: C5H9NO3
Product Type: Chemical
ATR-IR Spectra for (2S,4S)-(−)-4-Hydroxy-2-pyrrolidinecarboxylic acid.
| application(s) | peptide synthesis |
| assay | ≥98% (TLC) |
| color | white to faint yellow |
| form | powder |
| InChI | 1S/C5H9NO3/c7-3-1-4(5(8)9 |
| InChI key | PMMYEEVYMWASQN-IMJSIDKUSA |
| mp | 257 °C (dec.) (lit.) |
| Quality Level | 100  |
| SMILES string | O[C@@H]1CN[C@@H](C1)C(O)= |
| technique(s) | ligand binding assay: suitable |
| Application: | cis-4-Hydroxy-L-proline (CHP) is a proline analog that inhibits collagen synthesis and has been used as an anticancer compound. CHP blocked myotube formation and expression of sarcomeric myosin heavy chain in C2C12 murine skeletal muscle cells. CHP inhibited proliferation of murine Panc02 pancreatic carcinoma cell line and rat pancreatic carcinoma cell line DSL6A. |
| Biochem/physiol Actions: | cis-4-Hydroxy-L-proline (CHP) and its derivatives may have anticancer activity. cis-4-Hydroxy-L-proline and other hydrosyl-L-prolines are important intermediates for chiral synthesis of potential drugs. |
| Other Notes: | Constituent of Amanita sp. peptide toxins but not of animal proteins like collagen. |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥98% (TLC) |
| mp | 257 °C (dec.) (lit.) |
| UNSPSC | 12352209 |