AmMJarcb.f8h9lrm•}    Volatile  Oil  from  Canada  Balsam.  137 
Since  the  bottle  in  which  this  fraction  was  contained  was  com- 
pletely rilled  and  well  stoppered,  it  did  not  appear  very  probable 
that  a  large  amount  of  oxygen  should  be  due  to  the  presence  of 
pinol-hydrate,  or  any  other  oxidation  product  of  pinene  that  might 
result  upon  standing. 
To  ascertain  whether  it  was  present  in  the  form  of  an  ester,  25 
c.c.  of  this  fraction  were  boiled  with  62  c.c.  of  a  6  68  per  cent, 
alcoholic  solution  of  potassa  for  four  hours.  Upon  titration  with 
decinormal  sulphuric  acid,  V.  S.,  it  was  ascertained  that  o  6978  gms. 
of  potassa  had  been  consumed  in  the  experiment,  corresponding  to 
2*442  gms.,  or  10-85  Per  cent,  of  bornyl  or  terpinyl  acetate.  Upon 
distillation  with  water,  a  camphoraceous  odor  was  very  perceptible, 
but  it  was  impossible  to  separate  crystals.  The  experiment  was 
repeated  on  a  larger  scale,  too  gms.  of  oil  being  used. 
After  saponification  and  distillation  with  water-vapor,  49  gms.  of 
oil  were  obtained.  A  black,  shining,  pitchy  residue  was  left  in  the 
distillation  flask.  The  oil  was  colorless,  and  possessed  a  mixed 
terebinthinate  and  camphoraceous  odor.  After  drying  with  anhy- 
drous copper  sulphate,  its  relative  density  was  found  to  be  0-864  at 
200  C.  In  a  100  mm.  tube,  it  deviated  the  plane  of  polarized  light 
30-18°  to  the  left,  hence  (a)  D  equals —  34'93°-  Upon  fractiona- 
tion, the  following  fractions  were  obtained  : 
Relative  Density 
Boiling  Point.  Percentage.  at  200  C.  (#)D. 
-155° 
1550  —  1610  about  25*00  0-8657  — 34*267° 
161°  —  164°  about  24*00  0*8728  — 34*254° 
164°  —  167°  about  23-6  0-8743  —  34*34° 
167°  —  170° 
1 70° 
Upon  exposure  to  cold  for  several  days,  no  crystals  separated. 
Fraction  1700  was  further  fractionated,  and  fractions  170  —  1800 
and  180°  -j-  were  obtained  ;  fraction  180°  -f  was  exposed  to  a  freez- 
ing mixture.  Crystals  resembling  borneol  were  obtained,  but  the 
yield  was  too  small  to  allow  isolation. 
FRACTION  III. 
The  bottle  containing  this  fraction  was  almost  filled  and  well 
stoppered.  The  oil  possessed  a  pale  straw  color  and  a  terebinthi- 
nate odor,  very  much  like  Fraction  I.  Its  relative  density  was 
found  to  be  0-903  at  200  C.    In  a  100  mm.  tube  it  deviated  the 
