Pyrrole-2-carboxylic acid

Pyrrole-2-carboxylic acid is an organic compound with the formula HNC4H3CO2H. It is one of two monocarboxylic acids of pyrrole. It is a white solid. It arises in nature by dehydrogenation of the amino acid proline.[1] It also arises by carboxylation of pyrrole.[2] The ethyl ester of this acid is readily prepared from pyrrole.[3]

Pyrrole-2-carboxylic acid
Names
Other names
2-Mialine, 2-Minaline, Minalin, Minaline
Identifiers
3D model (JSmol)
80825
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.010.202 Edit this at Wikidata
EC Number
  • 211-221-9
101562
KEGG
  • InChI=1S/C5H5NO2/c7-5(8)4-2-1-3-6-4/h1-3,6H,(H,7,8)
    Key: WRHZVMBBRYBTKZ-UHFFFAOYSA-N
  • C1=CNC(=C1)C(=O)O
Properties
C5H5NO2
Molar mass 111.100 g·mol−1
Appearance white solid
Melting point 206 °C (403 °F; 479 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

References

edit
  1. ^ Thomas, Michael G.; Burkart, Michael D.; Walsh, Christopher T. (2002). "Conversion of L-Proline to Pyrrolyl-2-Carboxyl-S-PCP during Undecylprodigiosin and Pyoluteorin Biosynthesis". Chemistry & Biology. 9 (2): 171–184. doi:10.1016/S1074-5521(02)00100-X. PMID 11880032.
  2. ^ Wieser, Marco; Yoshida, Toyokazu; Nagasawa, Toru (2001). "Carbon dioxide fixation by reversible pyrrole-2-carboxylate decarboxylase and its application". Journal of Molecular Catalysis B: Enzymatic. 11 (4–6): 179–184. doi:10.1016/S1381-1177(00)00038-2.
  3. ^ Denis M. Bailey, Robert E. Johnson, and Noel F. Albertson (1971). "Ethyl Pyrrole-2-Carboxylate". Organic Syntheses. 51: 100. doi:10.15227/orgsyn.051.0100.{{cite journal}}: CS1 maint: multiple names: authors list (link)