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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

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

  1. ^ 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
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Bongkrek_acid". A list of authors is available in Wikipedia.
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