Chemistry:Pipecolic acid

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Pipecolic acid
Structural formula of pipecolic acid.svg
Preferred IUPAC name
Piperidine-2-carboxylic acid
3D model (JSmol)
EC Number
  • 217-024-4
MeSH C031345
Molar mass 129.15704
Appearance white or colorless solid
Melting point 268 °C (514 °F; 541 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pipecolic acid (piperidine-2-carboxylic acid) is an organic compound with the formula HNC5H9CO2H. It is a carboxylic acid derivative of piperidine and, as such, an amino acid, although not one encoded genetically. Like many other α-amino acids, pipecolic acid is chiral, although the S-stereoisomer is more common. It is a colorless solid.

Its biosynthesis starts from lysine.[1] CRYM, a taxon-specific protein that also binds thyroid hormones, is involved in the pipecolic acid pathway.


It accumulates in pipecolic acidemia. Pipecolic acid can be associated with some forms of epilepsy.[2]

Occurrence and reactions

Like most amino acids, pipecolic acid is a chelating agent. One complex is Cu(HNC5H9CO2)2(H2O)2.[3]

Pipecolic acid was identified in the Murchison meteorite.[4] It also occurs in the leaves of the genus Myroxylon, a tree from South America.[5]

See also


  1. Gatto, Gregory J.; Boyne, Michael T.; Kelleher, Neil L.; Walsh, Christopher T. (2006). "Biosynthesis of Pipecolic Acid by RapL, a Lysine Cyclodeaminase Encoded in the Rapamycin Gene Cluster". Journal of the American Chemical Society 128 (11): 3838–3847. doi:10.1021/ja0587603. PMID 16536560. 
  2. "Pipecolic acid as a diagnostic marker of pyridoxine-dependent epilepsy". Neuropediatrics 36 (3): 200–5. 2005. doi:10.1055/s-2005-865727. PMID 15944906. 
  3. Hockless, David C.R.; Mayadunne, Renuka C.; Wild, S.Bruce (1995). "Convenient resolution of (±)-piperidine-2-carboxylic acid ((±)-pipecolic acid) by separation of palladium(II) diastereomers containing orthometallated (S)-(−)-1-[1-(dimethylamino)ethyl]naphthalene". Tetrahedron: Asymmetry 6 (12): 3031–3037. doi:10.1016/0957-4166(95)00400-9. 
  4. Kvenholden, Keith A.; Lawless, James G.; Ponnamperuma, Cyril (February 1971). "Nonprotein Amino Acids in the Murchison Meteorite". Proceedings of the National Academy of Sciences 68 (2): 486–490. doi:10.1073/pnas.68.2.486. PMID 16591908. Bibcode1971PNAS...68..486K. 
  5. Kite, GC; Cardoso, D; Lewis, GP; Zartman, CE; de Queiroz, LP; Veitch, NC (2015). "Monomethyl ethers of 4,5-dihydroxypipecolic acid from Petaladenium urceoliferum: Enigmatic chemistry of an enigmatic legume". Phytochemistry 116: 198–202. doi:10.1016/j.phytochem.2015.02.026. PMID 25817832.