^'MaSim'""'}      Volatile  Oil  of  Monarda  Bundata.  117 
pyreumatic  odor.  Four  combustions  of  this  compound  gave  the  fol- 
lowing results : 
CALCULATEJJ  FOR  CioHigO  FOUND. 
1. 
2. 
3. 
4. 
c 
77-92 
77-47 
77-57 
77-89 
77-96. 
H 
11-69 
11-91 
11-55 
11-62 
11-73 
0 
10-39 
10-62 
10-88 
10-49 
10-31 
The  above  results  would  show  the  presence  of  a  higher  oxygenated 
compound  besides  thymol  in  the  oil.  The  formula  of  this  body  C^q 
HjgO,  was  also  established  by  taking  its  vapor  density. 
Sample  of  oil  No.  III.  was  submitted  to  partial  redivStillation  only^ 
the  object  being  to  obtain  a  larger  quantity  of  the  hydrocarbon.  After 
redistillation  a  similar  body  as  that  obtained  from  the  other  samples 
distilled  at  160°-175°,  and  upon  further  treatment  with  metallic  so- 
dium, two  fractions  were  obtained,  (I.)  at  160°-163°,  and  (II.)  at 
163°-165°  C.  Six  ultimate  analyses  of  these  compounds  gave  the 
following  results  : 
CALCULATED  FOR  C^*^H^^  FOUND. 
C  88-23 
H  11-77 
1.  160°-163°C. 
II.  163°-165°C. 
1. 
88-18 
11-52 
2. 
88-20 
11-68 
o 
O. 
88.27 
11-70 
1. 
87-85 
11-40 
87-97 
11-45 
3. 
88-02 
11-35 
100-00 
99-70 
99-88 
99-97 
99-25 
99-42 
99-37 
The  above  results  show  without  doubt  the  presence  of  a  hydrocar- 
bon in  oil  of  horsemint.  To  establish  the  correct  formula  of  this  body 
the  molecular  formula  was  arrived  at  by  taking  the  vapor  density  of 
this  compound. 
From  the  hydrocarbon  obtained  it  was  tried  to  form  a  substitutiort 
product  with  hydrochloric  acid.  The  terpene  was  treated  with  divj 
hydrochloric  acid  gas,  at  both  cold  and  warm  temperatures,  but  no 
crystalline  compound  separating.  The  resulting  liquid  though  as- 
sumed a  violet-red  color,  changing  to  dark-red. 
Vapor  Density.  The  vapor  densities  of  the  compounds  found  in  the- 
oil  were  ascertained.    The  method  used  was  that  of  V.  and  C.Meyer. 
