Bongkrek acid

Bongkrek acid

chembox new
ImageFile = Bongkrek acid.png ImageSize = 250px
IUPACName = 3-Carboxymethyl-17-methoxy-6,18,21-trimethyldocosa-2,4,8,12,18,20-heptaenedioic acid
OtherNames = Bongkrekic acid
Section1 = Chembox Identifiers
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CASNo = 11076-19-0
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PubChem = 6433556
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
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Section2 = Chembox Properties
Formula = C28H35O7
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MeltingPt = 50-60 °C
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Section7 = Chembox Hazards
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Bongkrek acid is a respiratory toxin more deadly than cyanide. [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. [http://www.jbc.org/cgi/content/abstract/245/6/1319 Abstract, includes structure] ]

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


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