73 Aliphatic Acids and Glycolipides 



in pyridine). Two of the component structures have been 

 characterized as shown: 



CH2OH H OH 



R = — OOC— CH— (CH2)io— CH-CHoOH (Ustilic Acid A) 



OH 



and 

 R = — OOC— CH— (CH2)i2— CH— CHoOH (Ustilic Acid B) 



OH OH 



Ustilago zeae, other Ustilaginales spp. 



Yields of 12-33% of the glucose supplied were reported. 



R. H. Haskins and J. A. Thorn, Can. J. Botany 29 585 

 (1951). 



R. U. Lemieux, J. A. Thorn, Carol Brice and R. H. Haskins, 

 Can. J. Chem. 29 409 (1951). (Isolation) 



R. U. Lemieux, ibid. 29 415 (1951). 



R. U. Lemieux, J. A. Thorn and H. F. Bauer, ibid. 31 1054 

 (1953). 



128 Bongkrekic Acid, C29H40OY, unstable, resinous, [ajo" +165° (c 

 2.0inNaHCd3). 



The stabler hydrogenated compound, C29H54O7, was 

 given the following partial structure. 



C2H5(±CH2) 



HOOCl I 



(C17H33 ± 2CH2)— CH2— C— CH2— CH— CH-COOH 



HOOCj I I , ^ 1 



OCH3 V 



CH3,H 



Pseudomonas cocovenenans (on a special copra-con- 

 taining medium) 



Bongkrekic acid is a toxin and has antibiotic properties. 



D. H. Nugteren and W. Berends, Rec. trav. chim. 76 13 

 (1957). 



