324 
Car  vol. 
Am  Jour.  Pharm. 
June,  1884. 
colloids  are  analogous  to  the  nitrogenous  colloids  of  the  animal  organ- 
ism.— Jour.  Chem.  Soc,  May,  1884,  p.  573  ;  Compt.  Rend.,  vol.  98. 
CARVOL. 
By  A.  Beyer. 
Gladstone  has  shown  that  the  carvol  obtained  from  dill-oil  agrees  in 
its  principal  physical  properties  with  the  carvol  from  caraway  oil. 
Fliickiger  found  that  the  carvol  obtained  from  German  mint-oil,  Men- 
tha crisjia,  differed  from  the  carvol  from  the  other  two  sources  in  being 
strongly  Isevorotatory.  The  author  has  re-examined  the  carvol  obtained 
from  these  three  oils.  To  obtain  it,  the  crude  oils  were  distilled,  the 
portion  of  the  caraway  oil  distilling  at  223°,  those  of  the  German 
mint-oil  at  215  to  230°,  and  200  to  215°  being  employed.  The  crude 
dill-oil  was  used  without  distillation.  The  hydrogen  sulphide  com- 
pounds, (C]6H140)2,SH2,  were  first  obtained  in  the  crystalline  state  and 
recrystallized  from  a  mixture  of  three  parts  of  chloroform  and  one  of 
alcohol.  The  yield  from  caraway  oil  was  8  per  cent.,  that  from  dill- 
oil  40  per  cent.,  whilst  the  first  fraction  of  the  mint-oil  yielded  50  per 
cent.,  the  second  fraction  30  per  cent.  All  the  hydrogen  sulphide  com- 
pounds melted  at  187°.  The  specific  rotatory  power  [«]D  at  20°  of 
the  compound  from  caraway  oil  was  5*53,  from  dill-oil  -f-  5  44, 
from  mint-oil  — 5*55.  No  crystal lographic  difference  in  the  com- 
pounds could  be  detected.  By  the  action  of  hydrogen  sulphide  on  an 
alcoholic  solution,  all  the  three  compounds  were  converted  into  the 
amorphous  thiocarvol  (C10H14S)2,SH2.  The  carvol  obtained  from  all 
the  hydrogen  sulphide  compounds  agreed  in  boiling  point  and  density  ; 
and  the  specific  rotatory  power  of  carvol  from  caraway  oil  and  dill- 
oil  was  nearly  the  same,  being  dextrorotatory ;  the  carvol  from  mint- 
oil,  however,  was  lsevorotatory  =  — 62*46  at  2Q). 
The  carvol  from  mint-oil  was  distilled  from  metaphosphoric  acid, 
the  resulting  carvacrol  dissolved  in  potash  solution,  filtered,  decom- 
posed with  sulphuric  acid,  and  the  carvacrol,  C10HuO,  was  dried  over 
calcium  chloride.  It  solidified  at  — 20°  to  a  crystalline  mass.  The 
boiling  point  was  230  to  231°,  sp.  gr.  at  4°  0*975,  specific  rotatory 
power  0.  The  crystalline  barium  salt  of  carvacrolsulphonic  acid  was 
also  prepared.  It  was  thus  shown  that  the  carvacrol  from  lsevorota- 
tory  carvol  is  identical  with  the  carvacrol  from  dextrorotatory  carvol. 
A  small  quantity  of  a  hydrocarbon  boiling  at  168  to  171°  was 
obtained  from  the  mint-oil.  It  was  lsevorotatory,  and  appeared  to  be 
a  terpene.—  Jour.  Chem.  Soe.,  March,  1884,  p.  331  ;  Arch.  Phar.,  [3] 
vol.  21. 
