Mirch:fa-,'s.''''  }      Volatile  Oil  of  Mvnarda  Punctata.  119 
C^^  Hi6— Fraction  I.  (160°-163°)  gave  — 34°-50. 
II.  (163°-165°)    "  — 32°-40. 
C^^       O— Thymol  (230°-232°)    "  -f  -60. 
Cj^HigO—    '     (240^-242°)  -[-  1°-10. 
From  the  above  will  be  seen  that  the  hydrocarbon  tnrns  the  plane 
of  polarization  strongly  to  the  left,  while  with  the  oxygenated  com- 
poun(k  it  is  slightly  turned  to  the  right. 
Acids  obtained  hy  saponification. — 100  grams  of  the  oil  from  sam- 
ple No.  Ill  were  treated  with  a  solution  of  10  grams  of  caustic  pot- 
ash in  100  grams  of  water,  and  boiled  for  eight  hours  in  a  flask  with 
an  upright  condenser.  The  alkaline  liquid  was  separated  from  the 
oily  layer,  which  was  then  acidified  with  sulphuric  acid.  This  pro- 
duced two  layers,  (I)  a  yellowish  aqueous  liquid,  and  (II)  a  dark 
broAvn  oily  layer,  floating  on  the  surface  ;  the  former  was  separated 
from  the  latter  by  means  of  a  wet  filter. 
The  dark  brown  oily  liquid  (II)  was  exposed  to  a  temperature  of 
— 15°  C,  which  then  became  solidified.  This  was  dissolved  in  alcohol 
and  mostly  decolorized  by  means  of  animal  charcoal ;  but  on  expos- 
ure again  to  the  above  degree  of  cold  nothing  crystallized  out,  neither 
from  alcohol  nor  from  ether. 
The  aqueous  filtrate  (I)  from  this  oily  liquid  was  diluted  with  water 
and  distilled  as  long  as  the  distillate  had  an  acid  reaction.  The  distill- 
ate was  colorless,  of  peculiar  odor,  and  gave  the  following  reactions  : 
1.  With  cone.  II2SO4  and  ethyl  alcohol  produced  the  odor  of 
some  fruit  ethers,  prominently  that  of  butyric  ether. 
2.  With  HgClg  on  boiling  for  some  time  produced  white  precipi- 
tate of  Hg2Cl2,  which  was  blackened  by  ammonia. 
3.  On  addition  of  II2SO4,  a  rod  moistened  with  NH^OH,  pro- 
duced white  fumes  when  held  into  the  tube. 
4.  Fe2Cl6  caused  a  violet-pink  color  on  addition  of  a  few  drops, 
when  more  of  the  reagent  Avas  added  became  brownish,  and  on  boiling 
a  light-brown  precipitate  formed. 
5.  With  AgNOg  caused  a  reduction  of  the  salt  on  boiling  for  some 
lime. 
A  lead  salt  was  formed  from  this  acid  distillate  by  digestion  with 
lead  carbonate.  The  filtrate  was  evaporated  to  dryness  and  the  resi- 
due treated  with  95  per  cent,  alcohol. 
The  filtrate  (I)  from  this  was  then  tested  for  acetates,  the  residue 
(II)  not  soluble  in  alcohol  for  formates. 
