Bongkrek acid

Bongkrek acid

Names
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
Identifiers
CAS Number	11076-19-0
ChEBI	CHEBI:77742
ChemSpider	4938689 (2E,4E,8E,10E,14E,18E,20E) 4529223 (2E,4Z,8Z,10E,14E,18E,20Z) 23764 (6R,17S) 2329 ()
Jmol interactive 3D	Image Image
MeSH	Bongkrekic+acid
PubChem	25463 (6R,17S) 2423 ()
InChI InChI=1S/C28H38O7/c1-21(15-18-24(19-26(29)30)20-27(31)32)13-11-9-7-5-6-8-10-12-14-25(35-4)22(2)16-17-23(3)28(33)34/h6,8-12,15-19,21,25H,5,7,13-14,20H2,1-4H3,(H,29,30)(H,31,32)(H,33,34) Key: SHCXABJSXUACKU-UHFFFAOYSA-N InChI=1/C28H38O7/c1-21(15-18-24(19-26(29)30)20-27(31)32)13-11-9-7-5-6-8-10-12-14-25(35-4)22(2)16-17-23(3)28(33)34/h6,8-12,15-19,21,25H,5,7,13-14,20H2,1-4H3,(H,29,30)(H,31,32)(H,33,34)/b8-6+,11-9+,12-10-,18-15+,22-16-,23-17+,24-19+/t21-,25+/m0/s1 Key: SHCXABJSXUACKU-WUTQZGRKBG InChI=1S/C28H38O7/c1-21(15-18-24(19-26(29)30)20-27(31)32)13-11-9-7-5-6-8-10-12-14-25(35-4)22(2)16-17-23(3)28(33)34/h6,8-12,15-19,21,25H,5,7,13-14,20H2,1-4H3,(H,29,30)(H,31,32)(H,33,34)/b8-6+,11-9+,12-10-,18-15+,22-16-,23-17+,24-19+/t21-,25+/m0/s1 Key: SHCXABJSXUACKU-WUTQZGRKSA-N
SMILES COC(CC=CC=CCCC=CCC(C)C=CC(CC(O)=O)=CC(O)=O)C(C)=CC=C(C)C(O)=O O=C(O)\C(=C\C=C(\C)[C@H](OC)C/C=C\C=C\CC/C=C/C[C@@H](/C=C/C(=C\C(=O)O)CC(=O)O)C)C
Properties
Chemical formula	C28H38O7
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).
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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, which is banned in Indonesia.

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.

References

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.