(2R)-pyrrolidinium-2-carboxylate
Basic information
- CAS
344-25-2- Standard SMILES
O=C([O-])[C@H]1CCC[NH2+]1- InChIKey
ONIBWKKTOPOVIA-SCSAIBSYSA-N- Molecular formula
- C5H9NO2
- Average molar mass
- 115.13 g/mol
- Monoisotopic mass
- 115.06332853
Overview
D-proline zwitterion is a D-alpha-amino acid zwitterion that is D-proline in which a proton has been transferred from the carboxy group to the amino group. It is the major species at pH 7.3. It is a tautomer of a D-proline.
Names & identifiers
- Preferred name
- (2R)-pyrrolidinium-2-carboxylate
- IUPAC
- (2R)-pyrrolidin-1-ium-2-carboxylate
- English name
- D-Proline
- Molecular formula
- C5H9NO2
- Molecular weight
- 115.13
Names & synonyms
D-proline zwitterionCHEBI:57726(2R)-pyrrolidinium-2-carboxylateProlineD-PROH-D-PRO-OHD-Pro-OH(R)-PYRROLIDINE-2-CARBOXYLIC ACID(2R)-Pyrrolidine-2-carboxylic acidD-PYRROLIDINE-2-CARBOXYLIC ACIDD-PyrroLD-PROLINE
Show more names
D(+)-PROLINE
Database identifiers
- CAS
344-25-2- PubChem CID
- 6971012
- ChEBI
CHEBI:57726
Properties
Computed structural properties
- XLogP
- -1.9
- Topological polar surface area
- 56.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 97.1
Experimental & physicochemical properties
Melting Point221 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 223 °C · 223 °C (dec.) (lit.)
- alpha
- 84.75 · 84.75 º (c=4, H2O)
- Boiling point
- 215.41 °C · 215.41°C (rough estimate)
- Density
- 1.36 · 1.36
- refractive index
- 85 ° · 85 ° (C=4, H2O)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Methanol (Slightly), Water (Sparingly)
- form
- Powder
- pka
- 1.952 · 1.952(at 25℃)
- color
- White to yellow to pale brown
- optical activity
- 22 · [α]22/D +85.0°, c = 4 in H2O
- Water Solubility
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 3-10
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29339990
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- hazard_note
- Irritant
- safety_code
- 22-24/25-36/37/39-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P271-P280
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Metabolite PathwaysArginine and proline metabolism
Applications
OccurrenceD-proline is an isomer of the naturally occurring amino acid, L-Proline. D-amino acids have been found in relatively high abundance in human plasma and saliva. These amino acids may be of bacterial origin, but there is also evidence that they are endogenously produced through amino acid racemase activity.
UsesUsed in the synthesis of (R)-(+)-N-Boc-Pipecolic Acid, (S)-(-)-Coniine, (S)-(+)-Pelletierine, (+)-.beta.-Conhydrine, and (S)-(-)-Ropivacaine and formal synthesis of (-)-Lasubine II and (+)-Cermizine C.
UsesLabelled D-Proline Lasubine II and (+)-Cermizine C.
Usesproline is a skin-conditioning agent. An amino acid found in the collagen molecule.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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