• }  Chemistry  of  Gossypol.  657 
Pure  "Free"  Gossypol,  Prepared  from  the  Gossypol  "Acetate"  (Re- 
crystallized  4  Times)  by  Removal  of  Acetic  Acid  and 
Crystallization  from  Diluted  Alcohol. 
0-5573 
0.1097 
67.67 
5-47 
  0.2381 
0.5929 
0.1165 
67.90 
5-48 
3  
 |  0.2361 
0.5861 
0.1167 
67.70 
5-53 
Free  Gossypol,  Earlier  Preparations,  Possibly  Less  Pure. 
0.1953 
0.4878 
0.C969 
68.11 
5-55 
0.2079 
0.5183 
0.1032 
67.98 
5-55 
Calc.  for  C30H28O9: 
67.64 
5-30 
Calc.  for  C30H30O9: 
67-39 
5-66 
Salts  of  Gossypol. — Gossypol  readily  forms  salts  with  alkalies. 
It  dissolves  easily  in  aqueous  sodium  hydroxide,  carbonate  and  very 
slowly  in  bicarbonate  and  disodium  phosphate.  Gossypol  may  be 
titrated  as  a  dibasic  acid  with  dilute  alkali,  using  phenolphthalein 
as  an  indicator.  The  alkali  salts  are  very  soluble  in  water  and  alco- 
hol and  are  extremely  sensitive  to  oxidizing  agents.  The  yellow 
color  of  their  solution  soon  turns  greenish  brown  and  then  slowly 
to  a  beautiful  blue  which  in  turn  gradually  disappears.  The  alkali 
salts  may  be  precipitated  by  saturated  salt  solution  and  a  similar 
salting  out  action  of  the  alkali  is  noted  when  attempts  are  made  to 
break  up  gossypol  with  fused  alkali. 
Lime  water  and  baryta  water  do  not  dissolve  gossypol  as  readily 
as  do  alkali  hydroxides,  which  seems  to  be  due  to  the  lesser  solu- 
bility of  these  salts.  Neutral  salts  of  the  alkaline  earths  do  not 
precipitate  gossypol  from  its  alcoholic  solutions,  neither  do  silver 
mercury  or  copper  salts.  Iron  sulphate  and  lead  acetate  give  amor- 
phous brownish  and  yellow  lake-like  precipitates,  respectively,  from 
alcoholic  solutions  of  gossypol.  Gossypol  does  not  readily  dissolve 
in  strong  or  dilute  ammonia  water.  The  ammonium  salt  is  proba- 
bly formed  but  as  an  insoluble  compound.  After  warming  gossypol 
with  dilute  ammonia  and  cooling,  the  liquid  formed  a  gelatinous 
mass,  evidently  due  to  the  physical  properties  of  the  ammonium  salt. 
Compound  of  Gossypol  with  Aniline. — Gossypol  dissolves  read- 
ily in  warm  aniline  with  which  it  combines  to  form  a  bright  orange- 
yellow  substance,11  which  is  possibly  the  dianiline  salt  of  gossypol 
11  This  substance  heated  to  1000  was  found  to  contain  3.97  per  cent, 
nitrogen,  which  agreed  sufficiently  well  with  the  3.90  per  cent,  required  for  a 
substance  of  the  formula  CsoHasOg  •  2C6H5NH2.    This  seemed  at  the  time  to  be 
