q?6  Chemical  Examination  of  Nutmeg.     \ A™-  Joy- p^™- 
'     .  o         (   December,  1908. 
The  substance  afforded  a  color  reaction  similar  to  that  character- 
istic of  the  phytosterols.  Thus,  when  dissolved  in  chloroform  with 
a  little  acetic  anhydride,  and  a  drop  of  concentrated  sulphuric  acid 
added,  a  pink  color  was  produced  which  rapidly  changed  to  blue 
and  finally  to  green. 
The  composition  and  character  of  the  above-described  substance 
render  it  evident  that  it  is  diacetylipuranol,  C23H3804  (CO.CH3)2. 
The  dihydric  alcohol,  ipuranol,  C23H3802  (OH)2,  was  first  isolated 
in  these  laboratories  from  the  resin  of  Ipomoea  purpurea,  Roth 
(Amer.  Journ.  Pharm.,  1908,  80,  p.  264),  and  subsequently  from 
olive  bark  (Journ.  Chem.  Soc.,  1908,  93,  p.  907). 
The  above-mentioned  ethereal  solution  of  the  more  readily  soluble 
portion  of  the  ether  resin  was  extracted,  first  with  small  successive 
portions  of  a  saturated  solution  of  sodium  carbonate,  and  subse- 
quently with  a  10  per  cent,  solution  of  sodium  hydroxide.  The 
first  sodium  carbonate  extract  formed  a  thick,  dark  brown  emulsion 
of  an  insoluble  sodium  compound  which  could  not  be  filtered.  It 
was,  therefore,  directly  acidified,  when  a  yellow  solid  was  obtained, 
which  was  collected  and  washed  with  water.  The  attempts  to  obtain 
it  in  a  crystalline  form  were  unsuccessful,  and  it  also  yielded  noth- 
ing crystalline  on  acetylation.  The  subsequent  sodium  carbonate 
extracts  were  similar  in  character  and  behavior  to  that  above 
described.  The  sodium  hydrate  extracts  were  dark  in  color,  and, 
on  acidification,  yielded  brown,  amorphous  products.  After  extract- 
ing the  ethereal  solution  with  the  above-mentioned  alkalies,  it  was 
washed,  dried,  and  the  ether  removed,  but  only  a  small  amount  of 
a  pale  yellow,  amorphous  product  was  obtained. 
Chloroform,  Ethyl  Acetate,  and  Alcohol  Extracts  of  the  Resin. 
The  portion  of  resin  extracted  by  chloroform  was  a  reddish-brown 
solid,  while  the  portions  removed  by  ethyl  acetate  and  by  alcohol 
respectively  were  soft,  black  masses.  Nothing  of  a  crystalline  char- 
acter could  be  obtained  from  any  of  these  products.  In  order  to 
ascertain  whether  the  alcohol  extract  of  the  resin  contained  anything 
of  a  glucosidic  nature,  a  quantity  (50  grammes)  of  it  was  heated 
for  several  hours  in  alcoholic  solution  with  such  an  amount  of 
sulphuric  acid  that  the  latter  represented  5  per  cent,  of  the  mixture. 
After  the  removal  of  the  greater  portion  of  the  alcohol,  water  was 
added,  and  the  mixture  distilled  with  steam.  A  small  amount  of  a 
volatile  oily  product  was  thus  obtained,  which  was  found  to  contain 
