Am.  Jour.  P^la^^i. 
Jan.,  iS8o. 
Goto  Barks. 
25 
and  benzol.  Warnn  nitric  acid  acquires  with  oxyleucotin  a  blue  green 
color,  and  forms  a  resin  of  a  similar  color.  Bromine  produces  two 
crystallizable  substitution  products,  and  fusing  potassa  decomposes  oxy- 
leucotin into  hydrocoton,  cotogenin  and  benzoic,  protocatechuic  and 
formic  acids. 
DiBENzoYLHYDROCOTON,  C32H320y,  is  Contained  in  the  crude  leucotin, 
and  prepared  by  washing  it  with  little  glacial  acetic  acid,  and  recrystalliz- 
ing  the  undissolved  portion  from  the  same  solvent.  It  is  readily  soluble 
in  hot  alcohol  and  glacial  acetic  acid,  and  in  cold  chloroform,  ether  and 
aceton,  and  is  insoluble  in  petroleum  naphtha.  Nitric  acid  produces  a 
blue-green  resin  and  liquid.  With  fusing  potassa,  hydrocoton  and  ben- 
zoic acid  are  formed,  together  with  a  little  cotogenin  and  protocate- 
chuic acid.    Bromine  yields  two  substitution  compounds. 
Hydrocotoin,  Ci5Hi^04,  remains  in  the  resinous  mother-liquor 
separated  from  the  mixture  of  paracotoin  and  other  constituents.  It 
is  dissolved  in  dilute  solution  of  soda,  the  liquid  supersaturated  with 
hydrochloric  acid  and  the  precipitate  recrystallized  from  boiling  alco- 
hol. It  forms  large  pale-yellow  prisms  or  long  thin  needles,  is  spar- 
ingly soluble  in  petroleum  naphtha,  more  so  in  ether,  and  freely  soluble 
in  chloroform  and  aceton.  It  has  a  neutral  reaction,  melts  at  gS^C, 
and  yields  with  ferric  chloride  a  deep  brown-red  color,  and  with  sul- 
phuric acid  a  dark  yellow  solution.  It  yields  substitution  products  with 
bromine  and  acetyl,  and  with  fusing  potassa  is  decomposed  into  hydro- 
coton and  benzoic  acid,  probably  with  a  little  methylic  alcohol. 
PiPERONYLic  Acid,  CgHgO^ — Paracoto  bark,  exhausted  with  ether, 
is  treated  with  lime  and  water,  the  alkaline  liquid  supersaturated  with 
hydrochloric  acid,  agitated  with  ether,  and  this  solution  evaporated  ; 
the  semi-crystalline  mass  is  dissolved  in  boiling  alcohol,  when,  on  cool- 
ing, piperonylic  acid  ^  crystallizes.  Goto  bark,  treated  in  the  same 
manner  yields  the  same  acid,  but  in  much  smaller  quantity.  It  is  net 
altered  by  melting  it  with  potassa,  or  by  treatment  with  potassium  per- 
manganate. Its  salts  are  mostly  crystallizable  ;  those  with  the  alkalies 
are  freely  soluble  in  water,  those  with  other  metals  are  mostly  sparingly 
soluble  in  cold  water.  The  quinia  piperonylate,  C2oH4oN202-  CgHgO^ 
-j-  H2O,  crystallizes  in  white  needles,  is  rather  freely  soluble  in  hot 
^  This  acid  was  discovered  by  Fittig  and  Mieick  (1869)  on  treating  piperic  acid 
with  potassium  permanganate,  when  piperonal,  having  a  coumarin-like  odor,  and 
piperonylic  acid  are  produced,  which  sublimes  at  228^0. — Editor. 
