Am.  lour.  Pharm.  \ 
Sept.,  19  iS.  J 
Chemistry  of  Gossypol. 
659 
account  of  its  extreme  insolubility.  It  passes  through  the  digestive 
tract  unchanged. 
Presence  of  Gossypol  as  such  in  Commercial  Cottonseed  Prod- 
ucts.— Examination  of  a  number  of  cottonseed  products  with  a  view 
to  determining  the  fate  of  gossypol  has  given  results  which  are  of 
considerable  interest.  Very  little,  if  any,  gossypol  was  found  in 
samples  of  hot  pressed  meal.  In  one  case  a  small  amount  was 
found  where  the  seed  used  was  very  dry.  On  the  other  hand  in  the 
so-called  "  cold  pressing  "  process  at  least  three  fourths  of  the  gos- 
sypol of  the  seed  passed  into  the  oil.  Such  an  oil  was  found  to 
contain  1.5  per  cent,  gossypol.  On  treatment  with  alkali  any  gossy- 
pol in  the  crude  oil  is  quantitatively  removed  and  passes  into  the 
foots.  Since  crude  oil  is  always  treated  with  alkali  no  gossypol  or 
related  pigment  is  ever  found  in  the  refined  edible  oil.  Since  the 
non-occurrence  of  gossypol  in  hot  pressed  oil  is  contrary  to  what 
might  be  expected  and  since  it  does  not  occur  in  actually  cold  pressed 
oil  it  may  be  well  to  explain  the  difference.  Actual  cold  pressure 
squeezes  out  the  oil  from  the  oil  cells  without  allowing  it  to  dissolve 
gossypol  from  the  "  resin  glands."  Hence  the  gossypol  remains  in 
the  press  cake.  In  the  commercial  "  cold  pressing "  process  the 
seed  is  heated  to  a  considerable  extent  and  the  material  is  subjected 
to  a  grinding,  pulverizing  action  under  great  pressure  so  that  the 
glands  are  broken  up  and  the  contents  taken  up  by  the  hot  oil  and 
removed  mostly  from  the  cake. 
In  the  hot  pressing  process  as  ordinarily  conducted  under  the 
moist  cooking  conditions  the  gossypol  glands  are  disintegrated  by 
the  moisture  and  stirring  and  the  contents  stream  out  and  are 
spread  over  the  seed  tissue,  where  the  gossypol  is  subjected  to  oxi- 
dizing influences.  It  is  not  clear  why  so  little  passes  into  the  oil, 
but  perhaps  the  seed  tissue  holds  the  gossypol  and  its  oxidation 
product — "  D  "  gossypol — much  as  cloth  holds  a  dye,  or  possibly 
some  chemical  combination  may  take  place. 
If  rather  dry  seed  is  used  the  gossypol  is  apparently  not  so  read- 
ily converted  to  this  less  soluble,  less  toxic  oxidation  product  but 
remains  in  part  as  such  in  the  meal.  Such  a  meal  is  more  toxic 
than  a  properly  cooked  meal.  In  these  cases  gossypol  may  be  ex- 
tracted with  ether  and  the  amount  estimated  by  the  aniline  method. 
It  is  interesting  to  note  that  gossypol  in  crude  oil  behaves  much  the 
same  as  free  fatty  acid.    This  was  shown  by  dissolving  some  gossy- 
