BONGKREKIC ACID

Description

BONGKREKIC ACID · CAS 11076-19-0 · C28H38O7. UNII L7V4I673D2. Melting Point: 50-60 °C.

Identification

CAS Registry Number	11076-19-0
PubChem CID	6433556
Molecular formula	C28H38O7
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
UNII (FDA)	L7V4I673D2

Computed Descriptors

Molecular Weight	486.6
XLogP3	5.7
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	17
Exact Mass	486.26175355
Monoisotopic Mass	486.26175355
Topological Polar Surface Area	121
Heavy Atom Count	35
Formal Charge	0

Physical & Chemical Properties

Melting Point	50-60 °C

Physical description & handling notes

• White amorphous solid
• Stable under recommended storage conditions.
• Specific optical rotation = +162.5 deg at 25 °C

GHS Hazard Classification

Reported hazard statements	H301 (100%)

Documented Uses

• Laboratory chemicals, synthesis of substances.
• Bongkrekic (or bongkrek) acid, produced in fermented coconut by a pathovar of the bacterium Burkholderia gladioli, is a more potent respiratory toxin than cyanide. Its first total synthesis was reported by E. J. Corey and A. Tramontano in 1984, and M. Shindo and co-workers described improved syntheses in 2004 and 2009. Most recently, S. V. Ley used three stereospecific palladium cross-coupling reactions to accomplish an even better synthesis.
• An antibiotic produced by Pseudomonas cocovenenans. It is an inhibitor of mitochondrial ADP, ATP translocases. Specifically, it blocks adenine nucleotide efflux from mitochondria by enhancing membrane binding.
• Natural product; Anti-Bacterial Agent; Anti-Infective Agent; Drug/Therapeutic Agent
• One of two toxic antibiotic principles produced by Pseudomonas cocovenenans on partially defatted coconut; the other being toxoflavin, q.v. Name derived from "bongkrek", a molded coconut product from Indonesia which becomes highly poisonous when P. cocovenenans outgrows the mold.
• Substances that inhibit the growth or reproduction of BACTERIA.

Synonyms

BONGKREKIC ACID; 11076-19-0; Bongkrek acid; L7V4I673D2; (-)-BONGKREKIC ACID; CHEBI:77742; DTXSID00894840; 3-Carboxymethyl-17-methoxy-6,18,21-trimethyldocosa-2,4,8,12,14,18,20-heptaenedioic acid; RefChem:569813; DTXCID301324402; 998-673-7; Flavotoxin A; Bongkrekate; Bongkreksaure; UNII-L7V4I673D2; Isobongkrekic acid,

Frequently Asked Questions

What are the CAS number and molecular formula of BONGKREKIC ACID?

CAS 11076-19-0; molecular formula C28H38O7; molecular weight — g/mol.

What other names is BONGKREKIC ACID known by?

BONGKREKIC ACID, 11076-19-0, Bongkrek acid, L7V4I673D2, (-)-BONGKREKIC ACID, CHEBI:77742.

Is BONGKREKIC ACID classified as hazardous?

Hazard statements reported: H301.

What are the key physical properties of BONGKREKIC ACID?

Melting Point: 50-60 °C.

Facts on this page are taken from PubChem (US National Library of Medicine) and Wikidata. Grade-specific data — assay, moisture, particle size, packaging, shelf life — is issued per batch on the COA and is not published here.