Pyrrolidone carboxylic acid
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Basic information
- CAS
149-87-1- Standard SMILES
O=C1CCC(C(=O)O)N1- InChIKey
ODHCTXKNWHHXJC-UHFFFAOYSA-N- Molecular formula
- C5H7NO3
- Average molar mass
- 129.11 g/mol
- Monoisotopic mass
- 129.04259308
Overview
5-oxoproline is an oxoproline having the oxo group placed at the 5-position. It is an intermediate metabolite in the glutathione cycle. It has a role as a human metabolite. It is an oxoproline, a pyrrolidinemonocarboxylic acid and a member of pyrrolidin-2-ones. It is a conjugate acid of a 5-oxoprolinate.
Names & identifiers
- Preferred name
- Pyrrolidone carboxylic acid
- IUPAC
- 5-oxopyrrolidine-2-carboxylic acid
- English name
- DL-Pyroglutamic acid
- Molecular formula
- C5H7NO3
- Molecular weight
- 129.11
Names & synonyms
DL-Pyroglutamic acid149-87-15-Oxo-DL-prolineDL-Proline, 5-oxo-DL-2-Pyrrolidone-5-carboxylic aciddl-pyrrolidonecarboxylic acid6VT1YZM21HNSC-40887DL-2-Pyrrolidinone-5-carboxylic acidRefChem:871105DTXCID50382626205-748-3
Show more names
2-PYRROLIDONE-5-CARBOXYLIC ACIDH-DL-PYR-OHDL-Pyr-OHDL-PYRDL- pGlu-OHDL-5-OxoprolineDL-PyroglutamicDL- pyroglutaMate
DTXSID20431796PYRROLIDONE CARBOXYLIC ACID5-Oxopyrrolidine-2-carboxylic acid5-OXOPROLINE5-Oxo-D-prolinPyr-OH2-L-Pyrrolidone-5-carboxylicacidOXOPROLINE
Database identifiers
- CAS
149-87-1、16891-48-8- PubChem CID
- 499
- DTXSID
DTXSID80859174- ChEBI
CHEBI:16010- UNII
- 6VT1YZM21H
- EC Number
- 205-748-3
- Nikkaji
- J36.868G
Properties
Computed structural propertiesFilling in
- XLogP
- -0.8
- Topological polar surface area
- 66.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 154
Physicochemical properties
- Melting point
- 183 · 183-185 °C(lit.)
- Boiling point
- 239.15 °C · 239.15°C (rough estimate)
- Density
- 1.3816 · 1.3816 (rough estimate)
- vapor pressure
- 0 Pa · 0Pa at 25℃
- refractive index
- 1.422 · 1.4220 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- 52 g/l · 52g/l
- pka
- 3.48 · 3.48±0.20(Predicted)
- form
- Crystalline Powder
- color
- White
- PH
- 1.7 · 1.7 (50g/l, H2O, 20℃)
- Water Solubility
- 5.67 g/100 · 5.67 g/100 mL (20 ºC)
- BRN
- 82131 · 82131
- Major Application
- peptide synthesis
- InChI
- 1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)
- InChIKey
- ODHCTXKNWHHXJC-UHFFFAOYSA-N
- SMILES
- OC(=O)C1CCC(=O)N1
- LogP
- 0.065 at · 0.065 at 21.1℃
- CAS DataBase Reference
- 149 · 149-87-1(CAS DataBase Reference)
- FDA UNII
- 6 VT1YZM21H · 6VT1YZM21H
- NIST Chemistry Reference
- -5 · DL-5-Oxoproline(149-87-1)
- UNSPSC Code
- 12352106 · 12352106
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Warning
- Hazard statements
- 318 · H318-H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338-P280a-P304+P340-P405-P501a
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/37/38
- Safety Statements
- 26 · 26-37/39
- WGK Germany
- 3 · 3
- HazardClass
- IRRITANT
- HS Code
- 29337900 · 29337900
- Storage Class
- 11 · 11 - Combustible Solids
- REACH Registrations
- Active
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 Classification
This chemical does not meet GHS hazard criteria for 54.5% (60 of 110) of all reports.
Warning
H302 (36.4%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 110 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: DL-Proline, 5-oxo-
Status: Active Update: 19-11-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/23377
Proline, 5-oxo-: Non hazardous
Other Safety InformationIMAP assessments - DL-Proline, 5-oxo-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (36.4%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 29337900
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- Xn,Xi
- safety_code
- 26-37/39
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H318-H302-H315-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P305+P351+P338-P280a-P304+P340-P405-P501a
Chemistry & industry
Applications
UsesDL-Pyroglutamic acid is used in the preparation of AZT steroid conjugates as potent anti-HIV agents.
UsesDL-2-Pyrrolidone-5-carboxylic Acid is used in the preparation of AZT steroid conjugates as potent anti-HIV agents.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: An oxoproline having the oxo group placed at the 5-position. It is an intermediate metabolite in the glutathione cycle.
Related reactions
57 records
Compound notes
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