Baikiain

Baikiain
Names
IUPAC name
(2S)-1,2,3,6-Tetrahydropyridine-2-carboxylic acid
Other names
(-)-(S)-Baikiain; L-Baikiain; (S)-4,5-Didehydropipecolic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C6H9NO2/c8-6(9)5-3-1-2-4-7-5/h1-2,5,7H,3-4H2,(H,8,9)/t5-/m0/s1
    Key: YCQPUTODZKESPK-YFKPBYRVSA-N
  • C1C=CCN[C@@H]1C(=O)O
Properties
C6H9NO2
Molar mass 127.143 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Baikiain is an organic compound with the molecular formula C6H9NO2. Chemically, it is classified as a tetrahydropyridine substituted with a carboxylic acid. Because it contains both this carboxylic acid and an adjacent amine group, it is also an alpha-amino acid. Baikiain is one of the two enantiomers of the chiral compound 4,5-didehydropipecolic acid.

Sources

Baikiain has been found in diverse natural sources including dates, African teak (Baikiaea plurijuga) wood, and the red algae Serraticardia maxima.

Several laboratory syntheses of baikiain and its racemic form have been reported.

Effects

Baikiain is hypothesized to be the causative agent of illnesses resulting from consumption of food products containing tara flour. In several cases documented in 2022 people became ill after consuming meals containing tara flour with high concentrations of Baikian (3% dry weight). People experienced acute gastrointestinal and liver disease with clinical signs of hepatotoxicity. Baikiain was found not to harm mammalian or human cells in culture but did cause liver injury and depletion of glutathione in rodent models.

References

  1. 1 2 "Human Metabolome Database: Showing metabocard for Baikiain (HMDB0302856)".
  2. ↑ King, F. E.; King, T. J.; Warwick, A. J. (1950). "709. The chemistry of extractives from hardwoods. Part III. Baikiain, an amino-acid present in Baikiaea plurijuga". Journal of the Chemical Society (Resumed): 3590. doi:10.1039/JR9500003590.
  3. ↑ Maeda, Masaakira; Hasegawa, Yoshikazu; Hashimoto, Hisanobu (1980). "Identification ofl-Baikiain from Calcareous Red Algae Serraticardia maxima(Yendo) Silva and Its Distribution in Some Rhodophyta". Agricultural and Biological Chemistry. 44 (11): 2725–2737. doi:10.1080/00021369.1980.10864393.
  4. ↑ Burgstahler, Albert W.; Aiman, Charles E. (1960). "A Direct Synthesis of DL-Baikiain". The Journal of Organic Chemistry. 25 (4): 489–492. doi:10.1021/jo01074a001.
  5. ↑ Ginesta, Xavier; Pericàs, Miquel A.; Riera, Antoni (2002). "Straightforward entry to the pipecolic acid nucleus. Enantioselective synthesis of baikiain". Tetrahedron Letters. 43 (5): 779–782. doi:10.1016/S0040-4039(01)02271-7.
  6. ↑ Chang, Meng-Yang; Kung, Yung-Hua; Wu, Tsun-Cheng (2006). "Synthesis of Pipecolic Acid and Baikiain". Heterocycles. 68 (11): 2365. doi:10.3987/COM-06-10874.
  7. ↑ Espinoza-Hicks, José C.; Chávez-Flores, David; Galán, Gerardo Zaragoza; Camacho-Dávila, Alejandro A. (2023). "Synthesis of cyclic amino acid baikiain via asymmetric phase transfer catalysis". Journal of Heterocyclic Chemistry. 60 (6): 1027–1031. doi:10.1002/jhet.4648. S2CID 257784165.
  8. ↑ Chittiboyina, Amar G.; Ali, Zulfiqar; Avula, Bharathi; Khan, Shabana I.; Mir, Tahir M.; Zhang, Jin; Aydoğan, Fadime; Zulfiqar, Fazila; Techen, Natascha; Parveen, Iffat; Pandey, Pankaj; Adams, Sebastian J.; Wang, Yan-Hong; Zhao, Jianping; Marshall, Gailen D.; Pugh, Nirmal D.; Khan, Ikhlas A. (2023). "Is Baikiain in Tara Flour a Causative Agent for the Adverse Events Associated with the Recalled Frozen French Lentil & Leek Crumbles Food Product? - A Working Hypothesis". Chemical Research in Toxicology. 36 (6): 818–821. doi:10.1021/acs.chemrestox.3c00100. PMC 10283043. PMID 37255213. S2CID 258988288.
  9. 1 2 3 "Tara Flour", LiverTox: Clinical and Research Information on Drug-Induced Liver Injury, Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases, 2012, PMID 38985927, retrieved 2026-07-12