144 
Aspidium  Fdix  Mas,  L. 
( Am.  Jour.  Phariift. 
I      March,  1889. 
ASPIDIUM  FILIX  MAS,  L.1 
By  G.  Daccomo. 
If  the  ether  extract  residue  of  the  rootstock  of  aspidium  (male  fern) 
is  treated  with  two  volumes  of  95  per  cent,  alcohol  and  one  volume  of 
ether,  a  brown  residue  is  left  which  is  partially  soluble  in  one  per  cent, 
aqueous  potash.  The  soluble  portion  is  the  filicin  or  filicic  acid  of 
Trommsdorff ;  the  insoluble  part  separates  from  an  alcoholic  solution 
as  a  white,  floccular,  waxy  substance,  (C13H260)tt ,  melting  at  80°,  it  is 
insoluble  in  water,  sparingly  soluble  in  ether  and  cold  alcohol,  but 
soluble  in  hot  alcohol ;  it  is  not  decomposed  by  boiling  alcoholic 
potash,  and  gives  no  coloration  with  sulphuric  acid  and  chloro- 
form. 
The  residue  obtained  by  evaporating  the  alcohol-ether  solution  of 
the  original  extract,  when  extracted  with  water,  furnishes  glucose 
and  tannin,  and  with  95  per  cent,  alcohol  a  black  resin  which  is 
almost  completely  soluble  in  2  per  cent,  aqueous  potash.  The  residue 
of  the  extract,  insoluble  both  in  water  and  alcohol,  is  a  green  oil  diffi- 
cult to  saponify. 
The  blood-red  alkaline  solution  when  agitated  with  ether  parts 
with  some  of  the  red  coloring  matter  (filix  red).  The  residue  of  this 
ether  extract  when  distilled  with  steam  furnishes  the  essential  oil  of 
filix ;  this  essential  oil  appears  not  to  pre-exist  in  the  plant.  The 
residue  from  this  distillation,  when  extracted  with  ether,  gives,  when 
the  ether  is  evaporated,  a  red  liquid  and  a  precipitate,  which,  after 
crystallizing  from  hot  alcohol,  forms  plates  melting  at  136"5°,  having 
the  composition  C20H34O.  This  compound  has  received  the  name  of 
aspidol.  It  is  insoluble  in  alkalis,  easily  soluble  in  ether,  benzene, 
chloroform,  light  petroleum,  and  hot  alcohol.  It  is  optically  active 
in  a  3  per  cent,  chloroform  solution  [a]D  =  — 24.08.  The  filtrate 
from  this  precipitate  of  aspidol  was  fractionated  into  three  parts.  The 
first  fraction,  130 — 190°,  was  a  yellow  oil  with  a  strong  odor  and 
acid  reaction,  which  did  not  reduce  silver  nitrate.  The  second  frac- 
tion, 220 — 290°,  was  a  beautiful  green  oil,  which  gradually  became 
brown ;  it  has  the  empirical  formula  (C27H4602)W .    The  third  fraction 
1Eeprinted  from  Journal  of  the  Chemical  Society,  1888,  p.  521,  and  1889,  p.  54. 
The  first  part  of  the  paper  appeared  originally  in  Annali  di  Chimica  e  Farmaco- 
logia,  1887,  p.  69 ;  and  the  second  part  relating  to  the  chemistry  of  filicic  acid  in 
Berichte  d.  D.  Chem.  Ges.,  1888,  p.  2962.  Compare  also  the  preliminary  report  in 
American  Journal  of  Pharmacy,  1886,  p.  378. 
