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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]

Additional recommended knowledge

Don't let static charges disrupt your weighing accuracy

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