Bongkrek acid

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Bongkrek acid
Bongkrekic acid.svg
IUPAC name
20-Carboxymethyl-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid
Other names
Bongkrekic acid

Bonqkrekik acid

Flavotoxin A
11076-19-0 N
ChemSpider 4938689 (2E,4E,8E,10E,14E,18E,20E) YesY
4529223 (2E,4Z,8Z,10E,14E,18E,20Z) YesY
23764 (6R,17S) YesY
2329 () YesY
Jmol 3D model Interactive image
Interactive image
MeSH Bongkrekic+acid
PubChem 25463 (6R,17S)
2423 ()
Molar mass 486.61 g·mol−1
Melting point 50 to 60 °C (122 to 140 °F; 323 to 333 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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]


  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.