CLASSIFICATION AND STRUCTURE OF FATTY ACIDS 31 



i\'orywood oil {Agonandra hrasiliensis)^^^ to the extent of 45%, argemone oil 

 from the prickle-poppy (Argemone mexicana)^^^ in the amount of 9.8%, 

 and also in seed oil from the Tonkinese "cay thu miic" {Wrighiia annamen- 

 sis).^^^ It also occurs in all seed fats of the Ricinus (castor bean) family. 



c. Hydroxy- Acids in Wool Fat. In addition to the normal aliphatic 

 fatty acids, wool fat contains a considerable proportion of hydroxy-acids. 

 As early as 1892, Lewkowitsch"^"^ called attention to the presence of 

 hydroxy-acids in wool fat; he observed that the acids form lactones on 

 heating, and also exhibit a reaction with acetic anhydride. Kuwata"^ 

 and Weitkamp^ have both identified 2-hydroxypalmitic acid in fat from 

 this source, and the latter investigator also demonstrated the presence of 2- 

 hydroxymyristic acid.^ Weitkamp is of the opinion that they are both 

 optical isomers, and Kuwata showed that the Cie member was levorotatory. 



(q) Lanoceri'c Acid. Lanoceric acid was one of the first acids to be 

 identified. DaiTnstaedter and Lifschiitz^-" found that it was a dihydroxy- 

 acid having an empirical formula of CjoH6o04, and melting at 104-105°C. 

 The presence of lanoceric acid was later confirmed by Abraham and Hil- 

 ditch'^^ and also by Kuwata. ^^^ 



(b) Lanopalmic Acid. A second acid identified by Darmstaedter and 

 Lifschiitz^-'* had an empirical formula of C16H32O3 and melted at 87-88 °C. 

 Its presence in wool fat was later confirmed. ^^^-^-^ Kuwata^^^ showed it to 

 be an isomer of 2-hydroxypalmitic acid, since it was converted to 2-keto- 

 palmitic acid on oxidation, and was ultimately degraded to pentadecanoic 

 acid on further oxidation. It is optically active ([a:]^ = —1.5°). 



d. Licanic Acid. Licanic acid was first called couepic acid by sev- 

 eral workers/'-^^'-^ because of its occurrence in the seeds of Couepia grandi- 

 flora (couflor). The structure was established by Brown and Farmer^-^ as 

 4-keto-9,ll,13-octadecatrienoic acid, CH3(CH2)3CH : CHCH : CHCH : CH- 

 (CH2)4CO(CH2)2COOH, on the basis of the identification of 4-ketostearic 

 acid when «-licanic acid was subjected to hydrogenation, and of the fact 

 that double bonds were conjugated. 



"^ L. Gurgel and T. F. de Amorin, Mem. inst. qiiim. Rio de .Taneiro, No. 2, 31-38 

 (1929); Chern. Abst., 24, 3668 (1930). 



"^S. N. Iyer, J. J. Sudborough and P. R. Avvar, ,/. Indian Irtst. Sci., A8, 29-38 

 (1925); Chern. AbsL, 19, 3607 (1925). 



ii« L. Margaillan, Compt. rend., 192, 373-374 (1931). 



"" J. Lewkowitsch, /. Soc. Chern. Ind., 11, 134-144 (1892). 



i'8 J. Lewkowitsch, /. Soc. Chern. Ind., 15, 14-15 (1896). 



1'=' T. Kuwata, /. .4m. Chern. Soc, 60, 559-560 (1938). 



'20 L. Darmstaedter, and J. Lifschutz, Ber., 29, 1474-1477; 2890-2900 (1896). 



'21 E. E. U. Abraham and T. P. Hilditch, J. Soc. Chern. Ind., 54, 398-404T (1935). 



'" F. Wilborn, Chem.-Ztg., 55, 434 (1931). 



'23 J. Van Loon and A. Steger, Chern. IJmschau, 24, 337-340 (1930); Chern. Abst., 25, 

 nil (1931). 



'2^ J. Van Loon and A. Steger, Rec. trav. chim., 50, 936-942 (1931). 



125 W. B. Brown and E. H. Farmer Biochem. J., 29, 631-639 (1935). 



