^^'^FcC^ljg!"''}  Behavior  of  Cymene  in  the  Animal  Organism.  \o\ 
ever,  dissolves  it  with  difficulty.  From  water  it  crystallizes — (i),  on 
addition  of  an  acid,  in  nacreous  scales,  and  (2)  on  slow  evaporation,  in 
large  iridescent  rhombic  plates,  without  water  of  crystallization,  and 
from  alcohol,  on  evaporation,  in  radiated  crystals. 
The  W/Wz  W/,  Ba(Ci2Hi^N03)2.H20,  dissolves  with  some  difficulty, 
and  crystallizes  from  its  hot  solution  in  long  right-angled  plates  or  in 
flat  needles,  arranged  in  a  fan-shaped  form.  The  calcium  salt^  Cz.(C^f{^^ 
N03)2.3H20,  crystallizes  in  thin  needles,  and  is  also  soluble  with  diffi- 
culty. The  ammonium  and  potassium  salts  are  very  easily  soluble,  and 
crystallize  in  needles.  The  two  latter  salts  give  precipitates  with  salts 
of  zinc,  manganese,  cadmium,  magnesium,  ferrous  and  ferric  salts, 
copper,  lead  and  silver;  with  mercuric  chloride,  it  gives  no  precipitate, 
and  with  mercuric  nitrate,  a  flocculent  insoluble  precipitate. 
This  cuminuric  acid  probably  differs  from  that  which  Cahours  pre- 
pared from  cuminic  chloride  and  glycolyl  silver. 
In  order  further  to  confirm  the  relations  of  this  acid,  it  was  decom- 
iposed  by  heating  with  hydrochloric  acid  ;  it  split  up  into  glycocine  and 
cuminic  acid,  melting  at  1 16-1 17°,  and  agreeing  in  all  its  properties 
with  that  described  by  others.  It  thus  appears  that  cuminic  acid  is 
really  a  product  of  oxidation  of  cymene  in  the  animal  organism,  but  to 
remove  all  doubt,  and  further  to  connect  cuminic  and  cuminuric  acids, 
the  latter  acid  was  synthetically  prepared  from  cymyl  alcohol  and  gly- 
cocol  silver.  The  product  was  identical  in  all  respects  with  that  sepa- 
rated from  the  urine. 
If,  then,  there  is  conclusive  proof  that  cumene  contains  normal 
propyl,  and  that  cuminic  acid  contains  isopropyl,  then  the  preparation 
of  cumene  from  cymyl  alcohol  with  zinc  dust  involves  the  transform- 
ation j  of  ^isopropyl  into  normal  propyl,  and,  on  the  other  hand,  the 
formation  of  cuminic  acid  from  cymene  implies  the  opposite  change. 
In  conclusion,  the  author  draws  attention  to  the  fact  that  in  his 
experiments  the  chief  product  was  cuminuric  acid,  whilst  in  those  of 
Nencki^  and  Ziegler  cuminic  acid  was  formed.  He  also  found  the 
latter  acid,  but  in  very  small  amount. — Jour.  Chem.  Jan.  1879,  fr. 
Jour.  Phar.  [4],  xxx,  ps.  30-35,  1 39-141. 
