|PubChem||(6R,17S) , ()|
|ChemSpider||(2E,4E,8E,10E,14E,18E,20E) , (2E,4Z,8Z,10E,14E,18E,20Z) , (6R,17S) , ()|
|Jmol-3D images||Image 1
|Molar mass||486.60 g mol−1|
|Melting point||50-60 °C|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
Bongkrek acid is a respiratory toxin more deadly than other mitochondrial poisons cyanide or 2,4-dinitrophenol. There was some dispute regarding the actual structure of bongkrek acid (also known as bongkrekic acid) but this was resolved in 1973, which explains different structures appearing in the literature prior to this date.
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 the soybean and coconut-based product known as tempe bongkrèk, which is banned in Indonesia.
It is highly toxic because of its effect on the ATP/ADP translocation mechanism. It shuts this system down, preventing ATP from leaving the mitochondria and providing energy to the rest of the cell.
- 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.
- 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.
- 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.