Chemistry:Baikiain
From HandWiki
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| Names | |
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| IUPAC name
(2S)-1,2,3,6-Tetrahydropyridine-2-carboxylic acid
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| Other names
(-)-(S)-Baikiain; L-Baikiain; (S)-4,5-Didehydropipecolic acid
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| 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). | |
| Infobox references | |
Tracking categories (test):
Baikiain is an organic compound with the molecular formula C
6H
9NO
2. 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
- ↑ 1.0 1.1 "Human Metabolome Database: Showing metabocard for Baikiain (HMDB0302856)". https://hmdb.ca/metabolites/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.
- ↑ Chittiboyina, Amar G.; Ali, Zulfiqar; Avula, Bharathi; Khan, Shabana I.; Mir, Tahir M.; Zhang, Jin; Aydoğan, Fadime; Zulfiqar, Fazila et al. (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. doi:10.1021/acs.chemrestox.3c00100. PMID 37255213.
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