ChemicalBook Product Catalog Biochemical Engineering Amino Acids and Derivatives Proline derivatives cis-4-Hydroxy-L-proline

cis-4-Hydroxy-L-proline

cis-4-Hydroxy-L-proline Basic information
Product Name:cis-4-Hydroxy-L-proline
Synonyms:L-ALLO-4-HYDROXY-2-PYRROLIDINECARBOXYLIC ACID;L-ALLO-4-HYDROXY-2-PYRROLIDINECARBOXYLLIC ACID;L-ALLO-HYDROXYPROLINE;CIS-4-HYDROXY-L-PROLINE;CIS-L-4-HYDROXYPROLINE;CIS-HYP-OH;CIS-HYDROXYPROLINE;CHYP
CAS:618-27-9
MF:C5H9NO3
MW:131.13
EINECS:210-542-1
Product Categories:Amino Acids;Biochemistry;Biological-modified Amino Acids;Chiral Compound;Amino Acids & Derivatives;Chiral Reagents;Pyrrole&Pyrrolidine&Pyrroline;Chiral reagent;Heterocycles
Mol File:618-27-9.mol
cis-4-Hydroxy-L-proline Structure
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
pka2.14±0.40(Predicted)
form Powder
color White to beige
Water Solubility soluble
Merck 14,4840
BRN 81440
InChIKeyPMMYEEVYMWASQN-IMJSIDKUSA-N
CAS DataBase Reference618-27-9(CAS DataBase Reference)
EPA Substance Registry SystemL-Proline, 4-hydroxy-, (4S)- (618-27-9)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 24/25-36/37/39-27-26
WGK Germany 3
F 10
TSCA Yes
HS Code 29339900
MSDS Information
ProviderLanguage
cis-4-Hydroxy-L-proline English
SigmaAldrich English
ACROS English
cis-4-Hydroxy-L-proline Usage And Synthesis
Chemical PropertiesWhite to beige powder
UsesHydroxyprolines 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.
Usescis-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.
Usescis-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.
DefinitionChEBI: L-Proline in which a hydrogen at the 4-position of the pyrrolidine ring is substituted by a hydroxy group (S-configuration).
Biochem/physiol Actionscis-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.
CIS-4-HYDROXY-L-PROLINE METHYL ESTER HCL,CIS-4-HYDROXY-L-PROLINE METHYL ESTER HYDROCHLORIDE (2S,4S)-4-(2-BENZYLPHENOXY)-1-(TERT-BUTOXY-CARBONYL)-2-PYRROLIDINECARBOXYLIC ACID (2S,4S)-4-(4-BROMO-2-CHLOROPHENOXY)-1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINECARBOXYLIC ACID N-Boc-cis-4-Hydroxy-L-proline methyl ester (2S,4S)-1-(TERT-BUTOXYCARBONYL)-4-(4-CHLORO-3,5-DIMETHYLPHENOXY)-2-PYRROLIDINECARBOXYLIC ACID D-Proline (2S,4S)-4-(2-BENZYL-4-CHLOROPHENOXY)-1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINECARBOXYLIC ACID (2S,4S)-4-(2-BROMO-4-CHLOROPHENOXY)-1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINECARBOXYLIC ACID BOC-CISHYP(BZL)-OH CIS-4-HYDROXY-L-PROLINE, [3H(G)] L-Proline cis-4-Hydroxy-L-proline (2S,4S)-4-[3-(ACETYLAMINO)PHENOXY]-1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINECARBOXYLIC ACID (2S,4S)-4-(2-ALLYLPHENOXY)-1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINECARBOXYLIC ACID (2S,4S)-4-[4-(BENZYLOXY)PHENOXY]-1-(TERT-BUTOXY-CARBONYL)-2-PYRROLIDINECARBOXYLIC ACID L-Hydroxyproline L-PROLINE-(4-3H(N)) CHLOROPHOSPHONAZO III
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