Am.  Jour.  Pharm.  i 
November,  1907.  / 
Poison  Sumac. 
513 
not  be  acetylized  by  treatment  with  sodium  acetate  and  acetic  anhy- 
dride. It  reacts  with  bromine,  producing  a  black  compound  similar 
in  appearance  to  that  from  bromine  and  the  crude  resin.  It  did  not 
respond  to  the  Lieberman-Storch30  reaction  for  resins. 
BENZIN-SOLUBLE  RESIN. 
On  evaporation  the  solution  in  benzin  gave  a  beautiful,  clear, 
amber-red,  oily,  non- volatile  liquid,  amounting  to  79-5  percent,  of  the 
original  resin.  In  color  and  odor  it  resembles  the  original  resin,  but 
its  fluidity  is  greater  and  specific  gravity  less.    Sp.  gr.  at  25 0  C./ 
25 0  C.  —  0-9693- 
Its  color  is  much  lighter  and  its  fluidity  considerably  greater  than 
its  companion  resin,  the  benzin-insoluble  portion.  Its  specific 
gravity  is  also  considerably  less.  It  was  found  to  be  soluble  in 
aniline,  amyl  alcohol,  acetone,  acetic  ether,  benzol,  petroleum  ben- 
zin (b.  p.  below  500),  chloroform,  carbon  disulphide,  carbon  tetra- 
chloride, ethyl  alcohol,  methyl  alcohol,  ether  and  toluol.  Its  alco- 
holic solution  is  optically  inactive.  It  is  very  poisonous.  It 
blackens  with  alkalies,  like  its  companion  resin,  and  yields  a  brown- 
black,  soluble  soap  on  saponification,  without  the  liberation  of  gly- 
cerol. Its  saponification  number  could  not  be  obtained  with  exact- 
ness, as  the  same  difficulties  were  encountered  in  determining  the 
end  reaction  with  indicators  as  was  the  case  with  the  benzin- 
insoluble  portion.  Unlike  the  latter,  however,  it  does  not  dry  up 
appreciably  on  long  standing  or  moderate  heating.  It  unites  with  bro- 
mine and  iodine,  forming  black,  insoluble  compounds  with  evolution 
of  heat  and  liberation  of  the  corresponding  halogen  acids.  By  sub- 
jecting the  resin  to  the  Grignard  reaction,31  using  magnesium  methyl 
iodide,  it  yields  an  abundance  of  methane,  thus  indicating32  the 
presence  of  hydroxyl  groups.  The  resultant  magnesium  organic 
halide  blackens  on  exposure  to  air  and  is  not  poisonous.  The  resin 
contains  no  methoxyl  or  ethoxyl  groups,  as  shown  by  negative 
results  when  tested  by  Zeisel's  method.33  It  contains  neither  sul- 
phur nor  halogens.  All  attempts  to  crystallize  it  or  to  obtain  a 
crystalline  derivative  were  unsuccessful.     By  heating  with  acetic 
30  J.  S.  C.  I.,  1888,  136. 
31  Grignard:  Ann.  Chim.  Phys.  [7],  24,  433. 
32  Tschugarff :  Ber.  d.  chem.  Ges.,  35,  3912. 
33  Zeisel :  Monats.  f.  Chem.,  6,  989. 
