Basic information
- CAS
618-27-9- Standard SMILES
O=C(O)[C@@H]1CC(O)CN1- InChIKey
PMMYEEVYMWASQN-IMJSIDKUSA-N- Molecular formula
- C5H9NO3
- Average molar mass
- 131.13 g/mol
Overview
4-hydroxy-L-proline is the L-stereoisomer of 4-hydroxyproline. It is a 4-hydroxyproline, a non-proteinogenic L-alpha-amino acid and a L-proline derivative. It is a conjugate acid of a 4-hydroxy-L-prolinate. It is an enantiomer of a 4-hydroxy-D-proline. It is a tautomer of a 4-hydroxy-L-proline zwitterion.
Names & identifiers
- Preferred name
- L-Proline, 4-hydroxy-, cis-
- IUPAC
- (2S)-4-hydroxypyrrolidine-2-carboxylic acid
- English name
- cis-4-Hydroxy-L-proline
- Molecular formula
- C5H9NO3
- Molecular weight
- 131.13
Names & synonyms
L-Proline, 4-hydroxy-, cis-RefChem:797378L-Proline, 4-hydroxy-, cis-(9CI)(2S)-4-hydroxypyrrolidine-2-carboxylic acid4-Hydroxy-L-proline1599456-27-5Proline, 4-hydroxy-The (R)-4-hydroxy L-isomer has been assumedunless otherwise specified or implied in the original document and is indexed at L-Proline,4-hydroxy-,(4R)- [51-35-4]. When synthetichydroxyproline has been clearly indicated in theoriginal document,the 4-hydroxyL-Allohydroxyprolineallo-L-Hydroxyproline4-Hydroxy-proline4hydroxy-l-proline
Show more names
(2S,4S)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACIDH-CIS-HYP-OHCIS-4-HYDROXYPROLINECIS-HYP-OHCIS-HYDROXYPROLINEcis-Hydroxy-L-proline(4S)-4-hydroxypyrrolidine-2-carboxylic acidCHYPcis Lcis-L-Hyp-OH
(2S)-4-hydroxy-2-pyrrolidinecarboxylic acidcis-4-hydroxy-l-pro4-Hydroxy-(L)-prolineSCHEMBL211844-Hydroxy-L-proline, (Z)-SCHEMBL1302842SCHEMBL1662290L-Proline, allo-hydroxy-, cis
Database identifiers
- CAS
618-27-9、6912-67-0- PubChem CID
- 69248
- ChEBI
CHEBI:18240- Nikkaji
- J94.857H
Properties
Computed structural properties
- XLogP
- -3.3
- Topological polar surface area
- 69.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 125
Physicochemical properties
- Melting point
- 257 °C · 257 °C (dec.) (lit.)
- alpha
- -59 · -59 º (c=2, H2O)
- Boiling point
- 242.42 °C · 242.42°C (rough estimate)
- Density
- 1.3121 · 1.3121 (rough estimate)
- refractive index
- -59 ° · -59 ° (C=2, H2O)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- soluble
- form
- Powder
- pka
- 2.14 · 2.14±0.40(Predicted)
- color
- White to beige
- Water Solubility
- soluble
- Merck
- 14 · 14,4840
- BRN
- 81440 · 81440
- Major Application
- peptide synthesis
- 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
- InChIKey
- PMMYEEVYMWASQN-IMJSIDKUSA-N
- SMILES
- O[C@@H]1CN[C@@H](C1)C(O)=O
- CAS DataBase Reference
- 618 · 618-27-9(CAS DataBase Reference)
- FDA UNII
- 43 V78B6A3B · 43V78B6A3B
- EPA Substance Registry System
- 4 · L-Proline, 4-hydroxy-, (4S)- (618-27-9)
- UNSPSC Code
- 12352209 · 12352209
- NACRES
- 26 · NA.26
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 24 · 24/25-36/37/39-27-26
- WGK Germany
- 3 · 3
- F
- 10 · 10
- TSCA
- TSCA listed
- HS Code
- 29339900 · 29339900
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Hazard information
Regulatory InformationChemical: L-Proline, 4-hydroxy-, cis-
Other Safety InformationIMAP assessments - L-Proline, 4-hydroxy-, cis-: Environment tier I assessment
Safety data
- F
- 10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29339900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 24/25-36/37/39-27-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
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.
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.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: L-Proline in which a hydrogen at the 4-position of the pyrrolidine ring is substituted by a hydroxy group (S-configuration).
Related reactions
16 records
Compound notes
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