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HomeProduct name listcis-4-Hydroxy-L-proline

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: 2024-11-19 15:53:33
cis-4-Hydroxy-L-proline Structural

What is cis-4-Hydroxy-L-proline?

Chemical properties

White to beige powder

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

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 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)
ghs
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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