cis-4-Hydroxy-L-proline
Synonym(s):(2S,4S)-(−)-4-Hydroxy-2-pyrrolidinecarboxylic acid;CHP
- CAS NO.:618-27-9
- Empirical Formula: C5H9NO3
- Molecular Weight: 131.13
- MDL number: MFCD00064319
- EINECS: 210-542-1
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-08 20:21:46
What is cis-4-Hydroxy-L-proline?
Chemical properties
White to beige powder
The Uses of cis-4-Hydroxy-L-proline
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.
The Uses of cis-4-Hydroxy-L-proline
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.
The Uses of cis-4-Hydroxy-L-proline
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.
What are the applications of Application
cis-4-Hydroxy-L-proline is a proline antagonist in collagen synthesis
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.
Properties of cis-4-Hydroxy-L-proline
Melting point: | 257 °C (dec.) (lit.) |
Boiling point: | 242.42°C (rough estimate) |
alpha | -59 º (c=2, H2O) |
Density | 1.3121 (rough estimate) |
refractive index | -59 ° (C=2, H2O) |
storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
solubility | soluble |
form | Powder |
pka | 2.14±0.40(Predicted) |
color | White to beige |
Water Solubility | soluble |
Merck | 14,4840 |
BRN | 81440 |
CAS DataBase Reference | 618-27-9(CAS DataBase Reference) |
EPA Substance Registry System | L-Proline, 4-hydroxy-, (4S)- (618-27-9) |
Safety information for cis-4-Hydroxy-L-proline
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for cis-4-Hydroxy-L-proline
InChIKey | PMMYEEVYMWASQN-IMJSIDKUSA-N |
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