cis-4-Hydroxy-L-proline

• CAS: 618-27-9
• Catalog Number: ACM618279
• Category: Amino Acids
• Molecular Weight: 131.13
• Synonyms: (2S,4S)-(-)-4-Hydroxy-2-pyrrolidinecarboxylic acid, CHP
• Canonical SMILES: O[C@@H]1CN[C@@H](C1)C(O)=O
• 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
• InChI Key: PMMYEEVYMWASQN-IMJSIDKUSA-N
• Melting Point: 257 ℃(dec.) (lit.)
• Application: 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.
• Assay: ≥98% (TLC)
• Beilstein: 81440
• 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.
• Color: white to faint yellow
• EC Number: 210-542-1
• Form: powder
• MDL Number: MFCD00064319
• NACRES: NA.26
• PubChem ID: 24895470
• Quality Level: 100
• Storage Temperature: 2-8℃
• Technique: ligand binding assay: suitable

Synthetic Use

Upstream Synthesis Route 1

• 129431-03-4

• 618-27-9

Reference: [1]Acta Chemica Scandinavica,1990,vol. 44,p. 243 - 251

Downstream Synthesis Route 1

• 501-53-1
• 618-27-9

• 13504-86-4

Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 3, p. 451 - 454
[2] Archives of Biochemistry, 1955, vol. 57, p. 301,303
[3] Tetrahedron Letters, 1993, vol. 34, # 23, p. 3671 - 3674
[4] Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S234 - S237
[5] Patent: US5962660, 1999, A,

Downstream Synthesis Route 2

• 618-27-9

• 2438-57-5

Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 1999, vol. 42, # 12, p. 1135 - 1144

Downstream Synthesis Route 3

• 618-27-9

• 16217-15-5

Reference: [1] Patent: WO2014/82380, 2014, A1,

* For details of the synthesis route, please refer to the original source to ensure accuracy.