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
- Heterocycles
- Pyrrole&Pyrrolidine&Pyrroline
- Chiral reagent
- Mol File:
- 618-27-9.mol
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
- form
- Powder
- pka
- 2.14±0.40(Predicted)
- color
- White to beige
- Water Solubility
- soluble
- Merck
- 14,4840
- BRN
- 81440
- InChIKey
- PMMYEEVYMWASQN-IMJSIDKUSA-N
- CAS DataBase Reference
- 618-27-9(CAS DataBase Reference)
- EPA Substance Registry System
- L-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
- Language:English Provider:cis-4-Hydroxy-L-proline
- Language:English Provider:SigmaAldrich
- Language:English Provider:ACROS
cis-4-Hydroxy-L-proline Usage And Synthesis
Chemical Properties
White to beige powder
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.
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.
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(618-27-9)Related Product Information
- CIS-4-HYDROXY-L-PROLINE METHYL ESTER HCL,CIS-4-HYDROXY-L-PROLINE METHYL ESTER HYDROCHLORIDE
- D-Proline
- L-PROLINE-(4-3H(N))
- L-Proline
- CHLOROPHOSPHONAZO III
- cis-4-Hydroxy-D-proline hydrochloride,CIS-4-HYDROXY-D-PROLINE HCL
- CIS-4-HYDROXY-D-PROLINE
- (4S)-4-hydroxy-L-proline hydrochloride
- cis-4-Hydroxycyclohexanecarboxylic acid
- Cyclohexanecarboxylic acid, 4-hydroxy-, Methyl ester, cis-
- cis-4-Methoxy-cyclohexylamine hydrochloride
- cis-4-AMinocyclohexaneMethanol hydrochloride
- 4-(Dimethylamino)cyclohexanol
- CIS-4-HYDROXY-D-PROLINE METHYL ESTER
- L-Hydroxyproline
- N-Boc-cis-4-Hydroxy-L-proline methyl ester
- N-ALPHA-BUTOXYCARBONYL-CIS-4-HYDROXY-L-PROLINE,N-BOC-CIS-4-HYDROXY-L-PROLINE,N-T-BOC-CIS-4-HYDROXY-L-PROLINE,BOC-CIS-4-HYDROXY-L-PROLINE
- N-Cbz-Hydroxy-L-proline