Bongkrek acid

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Bongkrek acid
Bongkrekic acid.svg
Identifiers
CAS number 11076-19-0 N
PubChem 25463 (6R,17SYesY, 2423 () YesY
ChemSpider 4938689 (2E,4E,8E,10E,14E,18E,20E) YesY, 4529223 (2E,4Z,8Z,10E,14E,18E,20ZYesY, 23764 (6R,17SYesY, 2329 () YesY
MeSH Bongkrekic+acid
ChEBI CHEBI:77742 N
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C28H38O7
Molar mass 486.60 g mol−1
Melting point 50-60 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Bongkrek acid is a respiratory toxin more deadly than other mitochondrial poisons cyanide or 2,4-dinitrophenol.[1] There was some dispute regarding the actual structure of bongkrek acid (also known as bongkrekic acid[2]) but this was resolved in 1973, which explains different structures appearing in the literature prior to this date.[3]

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,[citation needed] which is banned in Indonesia.[citation needed]

It is highly toxic because of its effect on the ATP/ADP translocation mechanism. It shuts this system down, preventing ATP from leaving the mitochondria and providing energy to the rest of the cell.[citation needed]

References[edit]

  1. ^ Henderson, P. J. F.; Lardy, H. A. (1970). "Bongkrekic Acid: An Inhibitor of Adenine Nucleotide Translocase of Mitochondria" (pdf). Journal of Biological Chemistry 245 (6): 1319–1326. PMID 4245638. 
  2. ^ Garcia, R. A.; Hotchkiss, J. H.; Steinkraus, K. H. (1999). "The Effect of Lipids on Bongkrekic (Bongkrek) Acid Toxin Production by Burkholderia cocovenenans in Coconut Media". Food Additives and Contaminants 16 (2): 63–69. doi:10.1080/026520399284217. PMID 10435074. 
  3. ^ De Bruijn, J.; Frost, D. J.; Nugteren, D. H.; Gaudemer, A.; Lijmbach, G. W. M.; Cox, H. C.; Berends, W. (1973). "Structure of Bongkrekic Acid". Tetrahedron 29 (11): 1541–1547. doi:10.1016/S0040-4020(01)83395-0.