Bongkrek acid

Bongkrek acid
Names
	Preferred IUPAC name (2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)-20-(Carboxymethyl)-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid
	Other names Bongkrekic acid; Bongkrekik acid
Identifiers
CAS Number	11076-19-0 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:77742 ;
ChemSpider	4938689 (2E,4E,8E,10E,14E,18E,20E) ; 4529223 (2E,4Z,8Z,10E,14E,18E,20Z) ; 23764 (6R,17S) ; 2329 () ;
MeSH	Bongkrekic+acid
PubChem CID	25463 (6R,17S); 2423 ();
UNII	L7V4I673D2 ;
CompTox Dashboard (EPA)	DTXSID00894840 ;
	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	486.605 g·mol−1
Appearance	Odorless and colorless
Melting point	50 to 60 °C (122 to 140 °F; 323 to 333 K)
Hazards
NFPA 704 (fire diamond)	4 0 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Bongkrek acid (also known as bongkrekic acid) is a respiratory toxin produced in fermented coconut or maize contaminated by the bacterium Burkholderia gladioli pathovar cocovenenans. It is a highly toxic, heat-stable, colorless, odorless, and highly unsaturated tricarboxylic acid that inhibits the mitochondrial ADP/ATP carrier, preventing ATP from leaving the mitochondria to provide metabolic energy to the rest of the cell. Food poisoning by bongkrek acid mainly targets the liver, brain, and kidneys. Early symptoms include vomiting, diarrhea, urinary retention, abdominal pain, and excessive sweating. Most of the outbreaks are found in Indonesia and China where fermented coconut and maize-based foods are consumed.