trans-3-hydroxy-L-proline
Basic information
- CAS
4298-08-2- Standard SMILES
O=C(O)[C@H]1NCC[C@@H]1O- InChIKey
BJBUEDPLEOHJGE-IMJSIDKUSA-N- Molecular formula
- C5H9NO3
- Average molar mass
- 131.13 g/mol
- Monoisotopic mass
- 131.05824315
Overview
Trans-3-hydroxy-L-proline is the (3S)-trans-diastereomer of 3-hydroxy-L-proline. It has a role as a metabolite. It is a tautomer of a trans-3-hydroxy-L-proline zwitterion.
Names & identifiers
- Preferred name
- trans-3-hydroxy-L-proline
- IUPAC
- (2S,3S)-3-hydroxypyrrolidine-2-carboxylic acid
- English name
- trans-3-Hydroxy-L-proline
- Molecular formula
- C5H9NO3
- Molecular weight
- 131.13
Names & synonyms
trans-3-hydroxy-L-proline(2S,3S)-3-Hydroxypyrrolidine-2-carboxylic acid(3S)-3-hydroxy-L-prolinetrans-L-3-HydroxyprolineCHEBI:16889DTXSID701009886L-threo-3-hydroxyproline3-trans-hydroxy-L-prolineRefChem:898794DTXCID601436321(2S,3S)-3-hydroxypyrrolidin-1-ium-2-carboxylate4298-08-2
Show more names
3-Hydroxy-L-prolineL-3-HYDROXYPROLINEH-3-HYP-OHH-HYP(3)-OHH-PRO(3-HYDROXY)-OHTRANS-3-HYDROXY-L-PRtrans-3-Hydroxy-prolintrans-3-Hydroxyproline.
trans-3-Hydroxyprolinetrans-3-Hydroxypyrrolidine-2-carboxylic acidMFCD00216471L-Proline, 3-hydroxy-, (3S)-4298-06-03-Hydroxy-L-proline, (3S)-H-trans-3-OH-Pro-OH(2S,3S)-(-)-3-Hydroxy-L-proline
Database identifiers
- CAS
4298-08-2- PubChem CID
- 440575
- DTXSID
DTXSID701009886- ChEMBL
CHEMBL1233466- ChEBI
CHEBI:16889- UNII
- 8ZWY97A2NG
- EC Number
- 639-470-2
- Nikkaji
- J191.774I
Properties
Computed structural properties
- XLogP
- -3.2
- 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
Experimental & physicochemical properties
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 235 °C · 235 °C
- Boiling point
- 242.42 °C · 242.42°C (rough estimate)
- Density
- 1.395 · 1.395
- refractive index
- 1.43 · 1.4300 (estimate)
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2–8 °C
- solubility
- soluble in No data available
- pka
- 2.03 · 2.03±0.40(Predicted)
- Appearance
- Off-white to light yellow Solid
- optical activity
- -15.667 ° · -15.667°(C=0.01g/ml H2O)
- InChI
- InChI=1S/C5H9NO3/c7-3-1-2-6-4(3)5(8)9/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m0/s1
- InChIKey
- BJBUEDPLEOHJGE-IMJSIDKUSA-N
- SMILES
- C(O)(=O)[C@@H]1[C@@H](O)CCN1
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS ClassificationNot Classified
Hazard information
Hazard Classes and CategoriesNot Classified
Safety data
- F
- 10
- wgk
- 3
- hs_code
- 29339980
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P301+P312-P302+P352-P304+P340-P305+P351+P338
Chemistry & industry
Applications
Usestrans-3-Hydroxyproline, is a versatile building block, used in the synthesis of various pharmaceutical and biologically active compounds. It is used as an intermediate in the synthesis of ferrocene-hydroxyproline amino acid conjugates.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: Trans-3-hydroxy-L-proline is the (3S)-trans-diastereomer of 3-hydroxy-L-proline. It has a role as a metabolite. It is a tautomer of a trans-3-hydroxy-L-proline zwitterion.
Related reactions
17 records
Compound notes
Loading…