Am.  Tour.  Pharm.  \ 
Sept.,  19 18.  J 
Chemistry  of  Gossypol. 
649 
CONTRIBUTION  TO  THE  CHEMISTRY  OF  GOSSYPOL, 
THE  TOXIC  PRINCIPLE  OF  COTTONSEED.1 
By  Frank  E.  Carruth. 
(Contribution  from  the  Chemical  Division  of  the  North  Carolina  Experiment 
Station.) 
Gossypol  is  a  peculiar  coloring  matter  present  in  the  cotton  plant. 
Apparently  it  does  not  belong  to  any  known  class  of  plant  pigments. 
Its  relation  to  cottonseed  poisoning  has  been  shown  by  Withers  and 
Carruth2  in  separate  publications  on  the  subject.  At  present  gossy- 
pol is  of  negative  economic  value,  but  it  is  possible  that  it  may  prove 
useful  in  the  future. 
Historical. — The  first  published  work  on  this  substance  seems  to 
"be  by  F.  Kuhlmann.3  Kuhlmann  was  attempting  to  recover  fatty 
acids  from  the  "  degras  "  or  "  foots  "  of  cottonseed-oil  purification. 
After  distilling  off  most  of  the  fatty  acids  by  superheated  steam,  a 
greenish-blue  mass  was  left  behind,  from  which  he  obtained  a  sub- 
stance later  called  "  cottonseed  blue "  by  dissolving  out  the  fatty 
acids  with  naphtha,  to  which  he  gave  the  formula  C17H2404.  This 
substance  prepared  by  Kuhlmann  differs  considerably  from  pure 
gossypol  in  composition  and  properties  and  perhaps  consisted  of  a 
mixture  of  gossypol  with  its  oxidation  products  and  fatty  acids. 
A  substance  known  as  "  gossypin  "  has  been  prepared  from  the 
foots  of  cottonseed  oil.  This  substance  is  described4  as  a  light 
"brown  pungent  powder  and  evidently  consisted  of  gossypol  with 
certain  odorous  impurities.  Probably  this  description  is  based  on 
the  work  of  J.  Longmore5  who,  however,  does  not  give  his  sub- 
stance any  name. 
Under  the  title  of  "  Cottonseed  Oil,  Its  Coloring  Matter  and 
Mucilage,"  J.  Longmore  describes  the  preparation  of  the  coloring 
matter  from  crude  cotton  oil: 
1  Abstract  of  paper  in  The  Journal  of  the  American  Chemical  Society, 
April,  1918. 
2  J.  Agr.  Research,  5,  261  (1915)  ;  /.  Biol.  Chem.,  32,  245  (1917)  ;  /.  Agr. 
Research,  12,  83  (1918),  and  a  fourth  paper  to  appear  soon. 
3  Compt.  rend.,  53,  444  (1861). 
4  Cf.  Julius  Wiesner,  "  Die  Rohstoffe  des  Pflanzenreiches,"  1903,  2d  edi- 
tion, p.  754. 
5 J.  Soc.  Chem.  Ind.,  5,  200-6  (1886). 
