Bongkrek acid
From Wikipedia, the free encyclopedia
| Bongkrek acid | |
|---|---|
 |
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| IUPAC name | 3-Carboxymethyl-17-methoxy-6,18,21-trimethyldocosa-2,4,8,12,18,20-heptaenedioic acid |
| Other names | Bongkrekic acid |
| Identifiers | |
| CAS number | [11076-19-0] |
| PubChem | |
| SMILES | O=C(O)/C=C(CC(O)=O)\C=C\[C@@H] (C)C/C=C/CC/C=C/C=C/C[C@@H] (OC)/C(C)=C/C=C(C)/C(O)=O |
| Properties | |
| Molecular formula | C28H35O7 |
| Melting point |
50-60 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Bongkrek acid is a respiratory toxin more deadly than cyanide.[1]
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 translocase mechanism. It shuts this system down, preventing ATP from leaving the mitochondria and providing energy to the rest of the cell.
[edit] References
- ^ Peter J. F. Henderson and Henry A. Lardy, "Bongkrekic acid: An Inhibitor of Adenine Nucleotide Translocase of Mitochondria", Journal of Biological Chemistry, (1970) 245, 6, 1319. Abstract, includes structure
