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| | cis-4-Hydroxy-L-proline Basic information |
| | cis-4-Hydroxy-L-proline Chemical Properties |
| Melting point | 257 °C (dec.) (lit.) | | alpha | -59 º (c=2, H2O) | | Boiling point | 242.42°C (rough estimate) | | density | 1.3121 (rough estimate) | | refractive index | -59 ° (C=2, H2O) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | soluble | | pka | 2.14±0.40(Predicted) | | form | Powder | | color | White to beige | | Water Solubility | soluble | | Merck | 14,4840 | | BRN | 81440 | | Major Application | peptide synthesis | | InChI | 1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m0/s1 | | InChIKey | PMMYEEVYMWASQN-IMJSIDKUSA-N | | SMILES | O[C@@H]1CN[C@@H](C1)C(O)=O | | CAS DataBase Reference | 618-27-9(CAS DataBase Reference) | | EPA Substance Registry System | L-Proline, 4-hydroxy-, (4S)- (618-27-9) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 24/25-36/37/39-27-26 | | WGK Germany | 3 | | F | 10 | | TSCA | TSCA listed | | HS Code | 29339900 | | Storage Class | 11 - Combustible Solids |
| | cis-4-Hydroxy-L-proline Usage And Synthesis |
| Chemical Properties | White to beige powder | | Uses | Hydroxyprolines are valuable chiral building blocks for organic synthesis of pharmaceuticals. Several microorganisms producing proline trans-4- and cis-3-hydroxylase were discovered and these enzymes were applied to the industrial production of trans-4- and cis-3-hydroxy-L-proline. | | Uses | 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 line3 and rat pancreatic carcinoma cell line DSL6A. cis-4-Hydroxy-L-proline and other hydrosyl-L-prolines are important intermediates for chiral synthesis of potential drugs. | | Uses | 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. | | Definition | ChEBI: L-Proline in which a hydrogen at the 4-position of the pyrrolidine ring is substituted by a hydroxy group (S-configuration). | | 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. | | in vivo | cis-4-Hydroxy-L-proline (285-903 mg/kg; p.o.; 28 days) causes signs of liver damage in rats, showing elevated alanine aminotransferase (ALAT) and aspartate aminotransferase (ASAT)[3].
cis-4-Hydroxy-L-proline (200 mg/kg; s.c.; twice daily; 30 days) partially prevents the accumulation of collagen in the lungs and partially improves the decrease in lung compliance in the Bleomycin (HY-108345)-induced pulmonary fibrosis model experiment of hamsters[4].
cis-4-Hydroxy-L-proline (200 mg/kg; s.c.; injected alone for 3 days first and then co-injected with dihydrotestosterone for 10 days) significantly reduces the wet weight of the prostate, inhibits the proliferation and differentiation of prostatic glandular cells in response to androgen stimulation in Androgen-induced prostate growth model in prepubertal castrated guinea pigs[5].
CHOP-PEG (polymeric prodrug of cis-4-Hydroxy-L-proline, 0.8 mg by continuous s.c.; 10 mg by single s.c.; 40 mg by single i.v.; 90 mg by single intratracheal injection; 7 days) can prevent and reverse chronic hypoxic pulmonary hypertension in the rat hypoxic pulmonary hypertension model[6].
| Animal Model: | Rats[3] | | Dosage: | 285 mg/kg, 507 mg/kg, 903 mg/kg | | Administration: | Oral gavage (p.o.), 28 days | | Result: | Increased ALAT and ASAT at a dose of 903 mg/kg.
Increased albumin at 507 mg/kg.
Increased blood urea nitrogen at 903 mg/kg CHP.
Revealed a pale appearance of the liver due to drug-induced anemia.
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| | cis-4-Hydroxy-L-proline Preparation Products And Raw materials |
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