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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)
  • 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 a chemical compound with the molecular formula C6H9NO2.

Chemistry

Chemically, it is a tetrahydropyridine substituted with a carboxylic acid. Because it contains both this carboxylic acid and an adjacent amine group, it is an alpha-amino acid.[1] 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,[1] African teak (Baikiaea plurijuga) wood,[2] and the red algae Serraticardia maxima.[3]

Several laboratory syntheses of baikiain and its racemic form have been reported.[4][5][6][7]

Effects

Baikiain is hypothesized to be the causative agent of illnesses resulting from consumption of food products containing tara flour.[8]

References

  1. ^ a b https://hmdb.ca/metabolites/HMDB0302856. {{cite web}}: Missing or empty |title= (help)
  2. ^ . doi:10.1039/JR9500003590. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)
  3. ^ . doi:10.1080/00021369.1980.10864393. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)
  4. ^ . doi:10.1021/jo01074a001. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)
  5. ^ . doi:10.1016/S0040-4039(01)02271-7. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)
  6. ^ . doi:10.3987/COM-06-10874. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)
  7. ^ . doi:10.1002/jhet.4648. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)
  8. ^ . doi:10.1021/acs.chemrestox.3c00100. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)