Title: Bongkrekic Acid
CAS Registry Number: 11076-19-0
CAS Name: (2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)-20-(Carboxymethyl)-6-methoxy-2,5,17-trimethyl-2,4,8,10,14,18,20-docosaheptaenedioic acid
Additional Names: 3-carboxymethyl-17-methoxy-6,18,21-trimethyldocosa-2,4,8,12,14,18,20-heptaenedioic acid; BA
Molecular Formula: C28H38O7
Molecular Weight: 486.60
Percent Composition: C 69.11%, H 7.87%, O 23.02%
Literature References: One of the 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. Isoln: van Veen, Mertens, Rec. Trav. Chim. 53, 257 (1934); 54, 373 (1935); Nugteren, Berends, ibid. 76, 13 (1957). Purification and properties: Lijmbach et al., Tetrahedron 26, 5993 (1970). Structural studies: eidem, ibid. 27, 1839 (1971). Revised structure: De Bruijn et al., ibid. 29, 1541 (1973). Absolute configuration: Zylber et al., Experientia 29, 387, 648 (1973). Influence on carbohydrate metabolism: van Veen, Mertens, Arch. Neerl. Physiol. 21, 73 (1936), C.A. 30, 38809 (1936); inhibition of adenine nucleotide translocation: Henderson, Lardy, J. Biol. Chem. 245, 1319 (1970); Klingenberg et al., Biochem. Biophys. Res. Commun. 39, 363 (1970).
Properties: White, amorphous solid, mp 50-60°. uv max (methanol): 237, 267 nm (e 32000, 36700). [a]D25 +162.5°. LD50 i.v. in mice: 1.41 mg/kg (Lijmbach).
Melting point: mp 50-60°
Optical Rotation: [a]D25 +162.5°
Absorption maximum: uv max (methanol): 237, 267 nm (e 32000, 36700)
Toxicity data: LD50 i.v. in mice: 1.41 mg/kg (Lijmbach) |