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Bongkrek acid

Bongkrek acid

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
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

Bongkrek acid is a respiratory toxin more deadly than cyanide.^[1]

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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.

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

Category: Toxicology