584 
Color-  Compounds. 
f  Am.  Jour.  Pharm. 
I   December,  1902. 
THE  COLOR  -  COMPOUND  OF  STYLOPHORUM 
DIPHYLLUM  AND  CHELIDONIUM  MAJUS. 
BY  J.  O.  SCHI,OTTBRBKCK. 
The  two  plants,  Stylophorum  diphyllum  and  Chelidonium  majus, 
Family  Papaveraceae,  are  so  closely  related  botanically  that  a 
cursory  glance  would  scarcely  distinguishes  them.  In  fact,  they  are 
properly  species  of  the  same  genus.  A  remarkable  similarity  in 
chemical  constituents  is  also  evident,  since  both  plants  contain  the 
alkaloids  chelidonine,  protopine  and  sanguinarine,  yellow  coloring 
matter  of  an  alkaloidal  nature  and  chelidonic  acid.  The  yellow  color- 
ing matter  was  first  found  in  Chelidonium  by  Probst  and  given  the 
descriptive  name  chelidoxanthin.  In  a  paper1  entitled,  "  Contribu- 
tion to  the  Chemistry  of  Stylophorum  Diphyllum,"  the  statement 
was  made  that  a  yellow  color  body  was  separated  which  from  anal- 
ogy was  believed  to  be  identical  with  the  chelidoxanthin  of  Probst. 
The  properties  of  chelidoxanthin  are  described  by  Probst  as  follows: 
"  Short,  yellow  needles,  very  difficultly  soluble  in  cold  water,  more 
easily  soluble  in  hot  water,  more  soluble  in  dilute  alcohol  than 
strong  alcohol,  and  insoluble  in  ether.  Extremely  bitter,  solutions 
intensely  yellow,  one  part  coloring  over  1,000  parts  of  water  yellow. 
Acid  and  alkalies  do  not  alter  the  color  materially ;  concentrated 
sulphuric  acid  dissolves  it  easily  with  evolution  of  gas.  The  water 
solution  is  precipitated  with  tincture  of  nutgalls." 
Chelidoxanthin  was  originally  separated  from  both  fresh  and 
dried  material  as  follows :  The  drug  was  extracted  with  water  con- 
taining a  little  sulphuric  acid  for  the  purpose  of  removing  alka- 
loids. The  dregs  were  then  exhausted  with  hot  water,  or  until  the 
percolate  was  no  longer  yellow.  To  the  concentrated  aqueous 
extract,  lead-acetate  solution  was  added  until  no  further  precipitate 
was  formed,  and  then  filtered.  To  the  filtrate  more  lead  acetate 
was  added  and  the  lead  sulphate  decomposed  with  hydrogen  sul- 
phide. The  lead  sulphide  was  washed  with  cold  water  until  the 
filtrate  became  colorless  and  did  not  possess  a  bitter  taste.  Then 
the  sulphide  precipitate  was  boiled  repeatedly  with  water  until  it  was 
exhausted  of  yellow  color.  The  combined  filtrates  were  evaporated 
to  dryness,  digested  with  ammonia,  then  with  ether  and  lastly  with 
dilute  alcohol,  from  which  the  compound  crystallized  in  crusts. 
1  Proc.  A.  Ph.  A.,  49,  251. 
