Bongkrek acid

Bongkrek acid

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^N
PubChem	25463 (6R,17S) ^Y, 2423 () ^Y
ChemSpider	4938689 (2E,4E,8E,10E,14E,18E,20E)^Y, 4529223 (2E,4Z,8Z,10E,14E,18E,20Z) ^Y, 23764 (6R,17S) ^Y, 2329 () ^Y
MeSH	Bongkrekic+acid
Jmol-3D images	Image 1 Image 2
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
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)^N Key: SHCXABJSXUACKU-UHFFFAOYSA-N^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
Properties
Molecular formula	C₂₈H₃₈O₇
Molar mass	486.6 g mol⁻¹
Melting point	50-60 °C
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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

^ Peter J. F. Henderson and Henry A. Lardy (1970). "Bongkrekic acid: An Inhibitor of Adenine Nucleotide Translocase of Mitochondria". J. Biol. Chem. 245 (6): 1319. PMID 4245638. http://www.jbc.org/cgi/content/abstract/245/6/1319.
^ Garcia, RA; Hotchkiss, JH; Steinkraus, KH (1999). "The effect of lipids on bongkrekic (Bongkrek) acid toxin production by Burkholderia cocovenenans in coconut media". Food additives and contaminants 16 (2): 63–9. doi:10.1080/026520399284217. PMID 10435074.
^ 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.