358 



IV. WAXES, HIGHER ALCOHOLS, ETC. 



Some bacteria, such as Bacillus hutyricus^^^ and Staphylococcus albus,^^^ 

 contain ergosterol, although the mycobacteria which most closely resemble 

 the molds do not include it. Mycobacterium tuberculosis and certain other 

 bacteria have no sterol whatsoever, ^"o 



It is, therefore, apparent that the presence of ergosterol is not an invari- 

 able occurrence in the lower forms, nor is it confined exclusively to the 

 cryptogams. Bills^^^ suggests that Gerard's rule should rather state that 

 ergosterol predominates in the lower orders of cryptogams. 



(1') Structure of Ergosterol: Chuang^"' showed that the same tetra- 

 cyclic nucleus is present in ergosterol as occurs in cholesterol, as evidenced 

 by degradation in both cases to 3 (j3) -hydroxy norallocholanic acid. Ergos- 

 terol contains three double bonds, since six hydrogen atoms are absorbed 

 in forming the saturated alcohol ergostanol,^"- C28H49OH. The original 

 Rosenheim and King formula ^"^ for ergosterol agrees with the present con- 

 ception except that the hydroxyl group was placed on C4 instead of on Cj. 

 The positions of the double bonds and of the hydroxyl group were correctly 

 postulated by Windaus et aZ.,*°* who criticized the Heilbron formula because 

 the double bonds were not in conjugate position as the reactions indi- 

 cated.^"^ The position of the third double bond in the side chain between 

 C22 and C23, as well as of the methyl group at C24, was readily deducible by 

 the isolation of methyl isopropylacetaldehyde after ozonization.^°^-^°^ 



OH 



I ' 



=CHC-CH-CH, 



" in. 



Ergosterol 



(2') Properties of Ergosterol: Ergosterol crystallizes from alcohol in 

 small, white, glistening platelets; these platelets contain one to one and 

 one-half molecules of water of crystallization, which can be removed only 

 with difl&culty. When ergosterol is crystallized from an ether-acetic acid 

 mixture, needle-like crystals are fonned which are anhydrous. It is soluble 



«9 A. Heiduschka and H. Lindner, Z. physiol. Chem., 181, 15-23 (1929). 



^ R. J. Anderson and E. Chargaff, J. Biol. Chem., 84, 703-717 (1929). 



s"! C. K. Chuang, Ann., 500, 270-280 (1933); Chem. AbsL, 27, 2157 (1933). 



»2 A. Windaus, H. H. Inhoffen, and S. v. Reichel, Ann., 510, 248-259 (1934). 



»3 O. Rosenheim and H. King, J. Sue. Chem. Ind., 63, 19r)-200T (1934). 



»»^ A. Windaus and O. Linsert, Ann., 465, 148-166 (1928). 



305 F. Reindel and H. Kipphan, Ann., 493, 181-190 (1932). 



SOS A. Guiteras, Z. Nakamiva, and H. H. Inhoffen, Ann., 494, 116-126 (1932). 



