Bongkrek acid
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Names | |
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IUPAC name
20-Carboxymethyl-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid
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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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CompTox Dashboard (EPA)
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Properties | |
C28H38O7 | |
Molar mass | 486.605 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).
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Bongkrek acid is a respiratory toxin more deadly than other mitochondrial poisons cyanide or 2,4-dinitrophenol.[1] There was some dispute regarding the actual structure of bongkrek acid (also known as bongkrekic acid[2]) 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 the soybean and coconut-based product known as tempe bongkrèk,[citation needed] which is banned in Indonesia.[citation needed]
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.[citation needed]
References
- ^ 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.