Bongkrek acid
Names | |
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IUPAC name
20-Carboxymethyl-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid | |
Other names
Bongkrekic acid Bonqkrekik acid | |
Identifiers | |
3D model (JSmol) |
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ChEBI | |
ChemSpider | |
MeSH | Bongkrekic+acid |
PubChem CID |
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Properties | |
C28H38O7 | |
Molar mass | 486.61 g·mol−1 |
Melting point | 50 to 60 °C (122 to 140 °F; 323 to 333 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
Bongkrek acid (also known as bongkrekic acid[1]) is a respiratory toxin more deadly than other mitochondrial poisons such as cyanide or 2,4-dinitrophenol.[2] There was some dispute regarding the actual structure of bongkrek acid, but this was resolved in 1973, which explains different structures appearing in the literature prior to this date.[3]
It is produced in fermented coconut contaminated by the bacterium Burkholderia gladioli pathovar cocovenenans. In particular, it has been implicated in deaths resulting from eating coconut-based product known as tempe bongkrèk, which is banned in Indonesia.[4]
It is highly toxic because it inhibits the ADP/ATP translocase, preventing ATP from leaving the mitochondria and providing energy to the rest of the cell.[5]
References
- ↑ Garcia, R. A.; Hotchkiss, J. H.; Steinkraus, K. H. (1999). "The Effect of Lipids on Bongkrekic (Bongkrek) Acid Toxin Production by Burkholderia cocovenenans in Coconut Media". Food Additives and Contaminants. 16 (2): 63–69. doi:10.1080/026520399284217. PMID 10435074.
- ↑ Henderson, P. J. F.; Lardy, H. A. (1970). "Bongkrekic Acid: An Inhibitor of Adenine Nucleotide Translocase of Mitochondria" (pdf). Journal of Biological Chemistry. 245 (6): 1319–1326. PMID 4245638.
- ↑ De Bruijn, J.; Frost, D. J.; Nugteren, D. H.; Gaudemer, A.; Lijmbach, G. W. M.; Cox, H. C.; Berends, W. (1973). "Structure of Bongkrekic Acid". Tetrahedron. 29 (11): 1541–1547. doi:10.1016/S0040-4020(01)83395-0.
- ↑ Bhavbhuti M. Mehta, Afaf Kamal-Eldin and Robert Z. Iwanski, ed. (2012). Chapter 9. Fermented Cereal and Legume Products. Fermentation: Effects on Food Properties. CRC Press. doi:10.1201/b11876-10. ISBN 978-1-4398-5334-4.
- ↑ Toxicants Occurring Naturally in Foods. National Academy of Sciences. 1973. p. 472.