As^ptSerPhi896ra'}        Oil  from  Moiicirda  Punctata.  471 
Non-Phenol  Constituents. — That  portion  of  the  oil  which  was  not 
dissolved  by  shaking  with  10  per  cent,  soda  solution  was  distilled 
with  water  vapor ;  79*3  grammes  of  oily  distillate  were  obtained; 
this  was  dried.  Inasmuch  as  the  original  oil  had  been  shaken  only 
once  with  caustic  soda,  the  oily  distillate  still  gave  a  reaction  for 
thymol,  when  tested  according  to  Fliickiger,  with  chloroform  and 
caustic  soda  solution.  This  reaction,  however,  is  very  delicate  and 
would  indicate  traces  of  phenol.  The  oil,  deprived  practically  of 
thymol,  had  a  specific  gravity  of  0-887.  In  a  100-mm.  tube  it  turned 
the  plane  of  polarized  light  1  71 66°  to  the  right.  Upon  fractiona- 
tion, the  following  fractions  were  obtained  : 
C.c. 
78°-  88°  3*5 
88°-  98°  175 
98°-i66°  (about)  yo 
i66°-i72°  4-0 
i72°-i78°   .  .     .  .  V  •:•':*  13*0 
i78°-i86°  05 
i86°-202°  6*o 
202°   — 
Fraction  Ij2°-ij8° . — It  was  shown  by  Mr.  Brennan.  a  year  ago, 
that  the  oil  of  Monarda  fistulosa  contained  cymene.  A  large  yield 
of  this  fraction  suggested  the  possibility  of  the  presence  of  this 
hydrocarbon  in  this  closely  related  oil.  In  order  to  ascertain  its 
presence  or  absence,  7  c.c.  of  this  fraction  were  tested  with  a  dilute 
solution  of  30  grammes  of  potassium  permanganate  until  the  color 
disappeared.  The  solution  was  then  filtered  and  evaporated  to  dry- 
ness, the  residue  then  dissolved  in  water  and  acidulated  with  sul- 
phuric acid.  A  dense,  whitish  precipitate  was  formed.  After 
recrystallization  from  alcohol,  the  melting  point  was  found  to  be 
1 5  50  to  1560,  which  is  that  of  oxycumic  acid,  thus  proving  the 
presence  of  cymene. 
Fraction  i86°-202°. — On  account  of  the  small  amount  of  this 
fraction,  the  combustion  only  could  be  made  in  order  to  ascertain 
the  probable  presence  of  linalool  or  a  similar  body. 
(1)  0*1372  gr.  of  substance  gave  0*1340  gr.  H20  =  0*01488  gr.  H, 
and  o  4145  gr.  C02  =  0*11304  gr.  C. 
(2)  0*13089  gr.  of  substance  gave  0*1285  gr.  H20  —  0*01427  gr.  H, 
and  0*3749  gr.  C02  =  o*iioi   gr.  C. 
(3)  0*1289  gr-  of  substance  gave  0*1322  gr.  H.20  =  0*0149  gr- 
and  0*3809  gr.  C02  =  0*10388  gr.  C. 
