A^r'iSr"'' }       Anthemis  Cotula — Chemical  Investigation.  ;^79 
distillate  possessed  a  disagreeable  smell,  differing  somewhat  from  that 
of  the  oil  when  pure  and  dry,  and  had  a  decided  acid  reaction. 
The  oil  thus  obtained  possessed  a  strong  ethereal  odor,  somewhat 
resembling  that  of  the  plant,  a  bitter,  acrid  taste,  an  acid  reaction  and 
the  sp.  gr.  0*858  at  26 °C.  A  portion  of  the  oil  was  distilled  alone, 
when  about  30  per  cent,  came  over  between  120^  and  200°C.,  about 
30  per  cent,  from  200°  to  280°C.,  the  remainder  decomposing  at  this 
point,  leaving  about  40  per  cent,  as  a  black,  tarry  residue.  A  saponi- 
fication of  the  oil  was  then  made,  using  the  process  adopted  by  Fittig 
m  his  analysis  of  the  oil  of  Anthemis  nobilis  Annalen  der  Ghemie, 
195,  p.  79).  The  oil  Avas  first  mixed  with  from  fifteen  to  twenty  times 
its  volume  of  alcohol  and  saturated  alcoholic  solution  of  potassium 
hydrate  added  until  the  solution  was  alkaline.  It  was  then  boiled  on 
a  return  cooler  for  about  ten  hours;  the  solution  was  then  of  a  dark 
brown  color  and  the  oil  seemed  to  be  entirely  decomposed.  The  alco- 
hol was  then  distilled  off,  and  the  residue  dissolved  in  distilled  water. 
This  aqueous  solution  smelled  very  much  like  rose-water  and  contained 
a  large  amount  of  flocculent  matter  which  would  not  dissolve  even  on 
heating.  Water  was  then  distilled  off,  oily  draps  coming  over  with 
the  distillate,  more  water  was  added  and  distilled  as  long  as  oily  drops 
came  over  (distillate  a).  The  residue  in  the  flask,  consisting  of  the 
potassium  salt  of  the  acids,  was  decomposed  by  adding  dilute  sulphuric 
acid  (sp.  gr.  1.25)  until  it  was  slightly  acid,  a  brown,  oily  substance 
separating  and  rising  to  the  surface,  where  it  solidified.  More  water 
was  then  added  and  distilled  off  as  long  as  an  acid  distillate  was 
obtained  (distillate  h).  A  brown  resinous  matter  remained  in  flask 
and  would  not  distil  over,  probably  due  to  a  portion  of  the  oil  being 
decomposed.  The  acid  distillate  5,  was  then  heated  to  boiling  and 
an  excess  of  calcium  carbonate  gradually  added  ;  the  liquid  was  well 
boiled,  filtered,  concentrated  and  set  aside,  when  a  small  amount  of 
fine  white  crystals  were  obtained.  These  were  purified  by  recrystalli- 
zation  and  dried,  decomposed  with  very  dilute  sulphuric  acid,  the  liquid 
extracted  with  ether  and  this  evaporated  to  crystallize.  Several  decom- 
positions were  made  both  of  the  oil  from  the  plant  as  well  as  that  from 
the  flowers,  giving  similar  results.  Considerable  difficulty  was  expe- 
rienced in  obtaining  the  acid  in  the  pure  state,  as  it  polymerized  easily 
and  a  great  deal  was  lost  by  recrystallizing  and  decomposing  the  cal- 
cium salt. 
Relatively  large  amounts  of  the  same  acid  crystallized  on  exposing 
