Pfizer Handbook of Microbial Metabolites 72 



Obtained together with palmitic, tuberculostearic and 

 mycoceranic acids. 



R. J. Anderson, J. Biol. Chem. 83 505-519 (1929). 



Karl Bernhard and Hans Albrecht, Helv. Chim. Acta 31 977 

 (1948). 



Jean Asselineau, Compt. rend. 237 1804 (1953). 



1 25 Mycolipenic Acid ( ( + )-2,4L,6L-Trimethyltetracos-2-enoic Acid ) , 



CotH^-^.Oo, low melting solid [a]i,-" +7.9° (c 25.2 in ether), 

 n^"' 1.'4600. 



CH3(CH2)i7— CH— CH,— CH— CH=C— COOH 

 CH3 CH3 CH3 



Mycobacterium tuberculosis var. hominis 



J. D. Chanley and N. Polgar, /. Chem. Soc, 1003 (1954). 



(Isolation) 



D. J. Millin and N. Polgar, Proc. Chem. Soc, 122 (1957). 



( Synthesis ) 



126 Csv-Phthienoic Acid (trans-2,4-Dimethyl-13-n-amyl-2-eicosenoic 



Acid), CoyH^oOo, soft white crystals, m.p. 26° and 39° 

 ( polymorphic ),"[ a] d'' +17.8° ±0.2°, n,,^' 1.4666. 

 Tentative structure : 



CHACHoU 



\ 



CH— (CH,)8— CH— CH=C— COOH 



/ I 1 



CH3(CH2)4 CH3 CH3 



The author emphasizes the difference of this compound 



from mycolipenic acid. 



Mycobacterium tuberculosis var. hoviinis 



James Cason, Hans-Ruedi Urscheler and C. Freeman Allen, 



J. Org. Chem. 22 1284 (1957). (Structure) and earher papers 



in this series. 



127 Ustilagic Acids. 



The corn smut fungus produces a group of related 

 glycolipides. As originally isolated, the properties of the 

 partially purified mixture were given as : CayH^o-eeOiy, color- 

 less, needle-like crystals, m.p. 144-147°, [x]rr' +7° (c 1.0 



