baikiain
{{Chembox
| ImageFile = Baikiain.svg
| ImageSize = 150px
| ImageAlt =
| IUPACName = (2S)-1,2,3,6-Tetrahydropyridine-2-carboxylic acid
| OtherNames = (-)-(S)-Baikiain; L-Baikiain; (S)-4,5-Didehydropipecolic acid
| Section1 = {{Chembox Identifiers
| CASNo = 31456-71-0
| ChEBI = 6199
| ChemSpiderID = 390175
| KEGG = C08268
| PubChem = 441442
| StdInChI=1S/C6H9NO2/c8-6(9)5-3-1-2-4-7-5/h1-2,5,7H,3-4H2,(H,8,9)/t5-/m0/s1
| StdInChIKey = YCQPUTODZKESPK-YFKPBYRVSA-N
| SMILES = C1C=CCN[C@@H]1C(=O)O
}}
| Section2 = {{Chembox Properties
| C = 6 | H = 9 | N = 1 | O = 2
| Appearance =
| Density =
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| Section3 = {{Chembox Hazards
| MainHazards =
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Baikiain is an organic compound with the molecular formula {{chem2|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.{{Cite web | url = https://hmdb.ca/metabolites/HMDB0302856 | title = Human Metabolome Database: Showing metabocard for Baikiain (HMDB0302856) }} 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,{{cite journal | doi = 10.1039/JR9500003590 | title = 709. The chemistry of extractives from hardwoods. Part III. Baikiain, an amino-acid present in Baikiaea plurijuga | year = 1950 | last1 = King | first1 = F. E. | last2 = King | first2 = T. J. | last3 = Warwick | first3 = A. J. | journal = Journal of the Chemical Society (Resumed) | page = 3590 }} and the red algae Serraticardia maxima.{{cite journal | doi = 10.1080/00021369.1980.10864393 | title = Identification ofl-Baikiain from Calcareous Red Algae Serraticardia maxima(Yendo) Silva and Its Distribution in Some Rhodophyta | year = 1980 | last1 = Maeda | first1 = Masaakira | last2 = Hasegawa | first2 = Yoshikazu | last3 = Hashimoto | first3 = Hisanobu | journal = Agricultural and Biological Chemistry | volume = 44 | issue = 11 | pages = 2725–2737 }}
Several laboratory syntheses of baikiain and its racemic form have been reported.{{cite journal | doi = 10.1021/jo01074a001 | title = A Direct Synthesis of DL-Baikiain | year = 1960 | last1 = Burgstahler | first1 = Albert W. | last2 = Aiman | first2 = Charles E. | journal = The Journal of Organic Chemistry | volume = 25 | issue = 4 | pages = 489–492 }}{{cite journal | doi = 10.1016/S0040-4039(01)02271-7 | title = Straightforward entry to the pipecolic acid nucleus. Enantioselective synthesis of baikiain | year = 2002 | last1 = Ginesta | first1 = Xavier | last2 = Pericàs | first2 = Miquel A. | last3 = Riera | first3 = Antoni | journal = Tetrahedron Letters | volume = 43 | issue = 5 | pages = 779–782 }}{{cite journal | doi = 10.3987/COM-06-10874 | title = Synthesis of Pipecolic Acid and Baikiain | year = 2006 | last1 = Chang | first1 = Meng-Yang | last2 = Kung | first2 = Yung-Hua | last3 = Wu | first3 = Tsun-Cheng | journal = Heterocycles | volume = 68 | issue = 11 | page = 2365 | doi-access = free }}{{cite journal | doi = 10.1002/jhet.4648 | title = Synthesis of cyclic amino acid baikiain via asymmetric phase transfer catalysis | year = 2023 | last1 = Espinoza-Hicks | first1 = José C. | last2 = Chávez-Flores | first2 = David | last3 = Galán | first3 = Gerardo Zaragoza | last4 = Camacho-Dávila | first4 = Alejandro A. | journal = Journal of Heterocyclic Chemistry | volume = 60 | issue = 6 | pages = 1027–1031 | s2cid = 257784165 }}
Effects
Baikiain is hypothesized to be the causative agent of illnesses resulting from consumption of food products containing tara flour.{{cite journal | doi = 10.1021/acs.chemrestox.3c00100 | title = 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 | year = 2023 | last1 = Chittiboyina | first1 = Amar G. | last2 = Ali | first2 = Zulfiqar | last3 = Avula | first3 = Bharathi | last4 = Khan | first4 = Shabana I. | last5 = Mir | first5 = Tahir M. | last6 = Zhang | first6 = Jin | last7 = Aydoğan | first7 = Fadime | last8 = Zulfiqar | first8 = Fazila | last9 = Techen | first9 = Natascha | last10 = Parveen | first10 = Iffat | last11 = Pandey | first11 = Pankaj | last12 = Adams | first12 = Sebastian J. | last13 = Wang | first13 = Yan-Hong | last14 = Zhao | first14 = Jianping | last15 = Marshall | first15 = Gailen D. | last16 = Pugh | first16 = Nirmal D. | last17 = Khan | first17 = Ikhlas A. | journal = Chemical Research in Toxicology | volume = 36 | issue = 6 | pages = 818–821 | pmid = 37255213 | s2cid = 258988288 | pmc = 10283043 }}