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
CAS Number	31456-71-0;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:6199;
ChemSpider	390175;
KEGG	C08268;
PubChem CID	441442;
CompTox Dashboard (EPA)	DTXSID20331580 ;
	InChI 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;
	SMILES C1C=CCN[C@@H]1C(=O)O;
Properties
Chemical formula	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). Infobox references

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.^[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

^ ^a ^b "Human Metabolome Database: Showing metabocard for Baikiain (HMDB0302856)".
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

[hmdb-1] "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.

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