574 
Chemical  Examination  of  Nutmeg. 
Petroleum 
Ether 
Chloroform 
Ethyl  Acetate 
Alcohol 
extracted  47  grammes  or   9.6  per  cent. 
66  "  "  13.5 
33  "  "  6.7 
55  "  "  n-2 
170  "  "  34-7 
371  grammes  or  75.7  per  cent. 
It  is  evident  that  by  this  treatment  a  considerable  proportion  of 
the  original  resin  had  been  rendered  insoluble. 
This  was  a  soft,  dark  brown  mass.  It  was  dissolved  in  ether 
and  the  ethereal  solution  extracted,  first  with  small  successive  por- 
tions of  aqueous  sodium  carbonate,  and  afterwards  with  a  solution 
of  sodium  hydroxide.  The  sodium  carbonate  extracts  were  of  a 
dark  brown  color,  and,  when  acidified,  yielded  soft,  resinous  solids. 
The  latter  were  distilled  under  diminished  pressure,  when  a  small 
fraction  was  collected  between  210  and  2300  C./20  mm.,  which 
became  crystalline  on  cooling.  After  recrystallization  from  alcohol, 
it  melted  at  52-53 0  C,  and  proved  to  be  myristic  acid.  The  sodium 
hydrate  extract,  when  acidified,  yielded  a  light  yellow  solid,  which 
was  readily  soluble  in  hot,  but  not  in  cold  alcohol,  and  was  deposited 
from  its  hot  solution  in  an  amorphous  state. 
The  portion  of  the  petroleum  extract  which  was  not  soluble  in 
alkalies  amounted  to  about  30  grammes.  It  was  hydrolized  by  heat- 
ing on  a  water-bath  with  an  alcoholic  solution  of  12  grammes  .of 
potassium  hydroxide.  After  the  removal  of  the  alcohol,  water  was 
added,  and  the  alkaline  mixture  extracted  with  ether,  the  ethereal 
solution  being  washed,  dried,  and  the  ether  removed.  A  quantity 
(about  5  grammes)  of  unsaponifiable  material  was  thus  obtained, 
which  was  distilled  under  diminished  pressure,  and  the  following 
fractions  collected  :  1 60-1 75 0  ;  1 75-280 0  ;  280-3 io°  C./15  mm.  Only 
the  highest  fraction,  280-3100  C./15  mm.,  was  sufficient  in  amount 
for  further  examination.  This  was  a  yellow,  viscid  product  which, 
on  digesting  with  dilute  alcohol,  yielded  a  very  small  amount  of 
solid  substance.  The  latter,  after  crystallization  from  a  mixture  of 
alcohol  and  ethyl  acetate,  melted  at  1350,  and  yielded  the  color  reac- 
tions characteristic  of  the  phytosterols. 
Petroleum  Extract  of  the  Resin. 
