114  Volatile  Oil  of  Monar da  Punctata.  {^'^MirchJm!'"'' 
was  presented  some  six  years  ago.  It  was  contained  in  a  ten  pint 
bottle  and  about  one-quarter  of  its  volume  was  a  crystalline  deposit  of 
thymol,  having  formed  gradually  by  age.  It  was  of  reddish-yellow 
color,  sp.  gr.  .926,  strong  mint-like  odor  and  neutral  reaction. 
Samples  Nos.  II.  and  III.,  were  procured  from  reliable  sources,  had 
both  a  brownish-red  color,  sp.  gr.,  .920  and  .922  respectively,  some- 
what fragrant  and  minty  odor,  and  neutral  to  test  paper.  These  were 
subjected  several  times  to  a  temperature  of — 15^  to — 20°  C.  for 
several  hours,  but  no  separation  of  thymol  occurred.  The  process  de- 
scribed in  the  National  Dispensatory  was  then  tried  as  follows  : — The 
oils  were  subjected  to  fractional  distillation  ;  portions  of  the  distillates 
obtained  at  above  200°  C.  were  treated  with  solution  of  soda,  the 
sodium  compound  separated  and  treated  with  HCl,  but  no  thymol  was 
obtained.  The  higher  fractions  obtained  by  fractional  distillation 
from  all  three  samples  (225°-245°  C),  wwealso  subjected  to  a  tempera- 
ture of  below — 15°  C,  but  all  without  yielding  crystals  of  thymol. 
It  was  concluded  that  samples  Nos.  II  and  III  had  either  previously 
been  treated  for  thymol  and  separated,  or  else  being  freshly  distilled 
oils,  had  not  become  sufficiently  changed  to  allow  of  the  crystallization 
of  that  compound.  This  latter  view,  from  further  investigations,  is 
probably  the  correct  one. 
Sample  of  oil  No.  I  assumed  with  solution  of  ferric  chloride  a 
bright-red  color,  changing  on  long  standing  to  near  black.  Samples 
Nos.  II  and  III  gave  no  reaction  with  this  reagent.  Solution  of 
bisulphite  of  sodium  gave  no  reaction  with  either  of  the  samples  of  oil, 
indicating  the  absence  of  any  aldehyde-like  bodies. 
Sample  of  oil  No.  I,  after  partial  drying  with  calcium  chloride,  was 
subjected  to  fractional  distillation.  On  redistillation  6  fractions  were 
obtained  as  follows : 
I.  170°-185°  C.    III.  200°-230°.    V.  245°-255°. 
II.  185°-200°.    IV.  230°-245°.    VI.  255°+ 
Fractions  V  and  VI  had  low  boiling  points,  showing  decomposition 
products.  Fractions  I  and  IV  were  the  largest,  and  therefore 
were  investigated.  The  former  constituted  about  25  per  cent.,  and 
the  latter  15  per  cent.  Fraction  I  (170°-185°)  was  redistilled  over 
zinc  dust,  the  largest  portion  distilling  at  170°-173°  C.  This 
having  a  quite  constant  boiling  point,  several  ultimate  analyses  were 
made  of  same.  The  results,  however,  showed  from  2-4  per  cent, 
still  lacking  to  assume  this  body  a  hydrocarbon.    The  same  portion 
