390  Crystalline  Principle  of  Persimmon  Bark.  {AmAug.?i89oarm* 
THE  CRYSTALLINE  PRINCIPLE  OF  PERSIMMON  BARK. 
By  William  Schleif,  Jr.,  Ph.G. 
Contribution  from  the  Chemical  Laboratory  of  the  Philadelphia  College  of  Pharmacy. — 
No.  76. 
In  this  Journal,  February,  1888,  Mr.  F.  H.  Murphy  described  a 
proximate  analysis  of  the  bark  of  the  persimmon,  Dtospyros 
virginiana  ;  he  found  among  the  usual  constituents  a  peculiar  crys- 
talline principle.  This  appeared  in  the  ethereal  extract,  and  was 
in  one  instance  obtained  from  ether  in  cubical  masses,  soft  but  crys-. 
talline  ;  in  subsequent  experiments  a  granular  mass  resulted.  The 
principle  was  soluble  in  alcohol,  chloroform  and  ether,  but  insoluble 
in  water.  The  object  of  this  thesis  is  to  more  fully  determine  the 
characteristics  of  the  compound. 
Three  samples  of  bark  were  taken:  No.  1  was  collected  by  myself 
during  the  spring  in  New  Jersey;  No.  2  was  5  pounds  of  a  com- 
mercial sample,  and  No.  3  collected  during  the  autumn  in  Southern 
Illinois.  The  different  samples  in  No.  40  powder  were  completely 
exhausted  with  petroleum  ether,  the  extract  passing  off  with  a 
yellow  color,  and  leaving  only  a  waxy  residue  on  evaporation. 
The  next  treatment  was  with  commercial  ether,  the  extract  having 
a  deep  wine  red  color  in  the  case  of  Nos.  1  and  2  and  a  light  yel- 
low in  the  case  of  No.  3.  The  ether  was  recovered  by  distillation, 
and  the  remaining,  crystalline,  deep-red  extract  constituted  the 
crude  material. from  which  the  principle  was  prepared. 
The  following  methods  were  used  for  its  purification  : 
(1)  The  extract  was  repeatedly  crystallized  from  ether.  This 
yielded  a  light  brown  crystalline,  soft  substance,  very  bulky,  but 
drying  to  a  very  small  quantity  if  warmed  on  a  water  bath  at 
6o°  C,  or  over  sulphuric  acid  at  ordinary  temperatures.  The 
alcoholic  solution  was  slightly  precipitated  by  alcoholic  solution  of 
lead  acetate,  the  precipitate  being  of  a  light  brown  color. 
(2)  The  ethereal  extract  was  dissolved  in  hot  alcohol,  in  which  it 
was  completely  soluble,  and  precipitated  by  alcoholic  solution  of 
lead  acetate,  which  removed  coloring  matter,  but  did  not  affect  the 
principle,  which  was  separated  from  the  filtrate  by  evaporation, 
after  removal  of  the  excess  of  lead  by  hydrogen  sulphide. 
The  alcoholic  solution  still  retained  a  red-brown  color,  but  was 
much  lighter  than  at  first,  it  was  repeatedly  digested  with  animal 
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