Pyrrolidone carboxylic acid

HCID 499CAS 149-87-1
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Basic information

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 properties

XLogP
-0.8
Topological polar surface area
66.4 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
9

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

Safety & regulation

GHS classification

GHS Classification · 5 items

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 · 3 items

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

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

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
韶远科技（上海）有限公司021-50795510 4000665055 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]

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
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Linked notes

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