ADoctober^9OT'm'}    Examination  of  Lippia  Scaberrima.  461 
sulphide  ;  but  on  concentrating  the  filtrate  only  a  dark-colored  tarry 
mass  was  obtained,  from  which  nothing  crystalline  could  be  isolated. 
The  filtrate  from  the  basic  lead  acetate  precipitate  was  freed  from 
lead  by  means  of  hydrogen  sulphide,  and,  after  filtering,  was  con- 
centrated under  diminished  pressure.  The  dark  brown  syrup  thus 
obtained  reduced  Fehling's  solution,  and  on  treatment  with  phenyl- 
hydrazine  acetate  gave  a  small  quantity  of  an  osazone  melting  at 
210°  C.  On  allowing  the  syrupy  liquid  to  stand  for  some  time,  a 
considerable  quantity  of  crystals  separated,  but  these  were  found  to 
consist  only  of  potassium  and  calcium  sulphates.  When  warmed 
with  potassium  hydroxide  it  evolved  ammonia,  but  did  not  give  any 
precipitate  with  alkaloidal  reagents.  The  syrup  was  therefore  mixed 
with  prepared  sawdust,  and  the  mixture  dried  in  a  vacuum  over 
sulphuric  acid,  after  which  it  was  extracted  in  a  Soxhlet  apparatus 
with  ethyl  acetate.  This  removed  a  quantity  of  an  uncrystallizable 
syrup,  which  did  not  reduce  Fehling's  solution  until  after  it  had 
been  boiled  with  a  dilute  mineral  acid,  a  behavior  which  indicated 
the  possible  presence  of  a  glucoside.  A  quantity  of  the  syrup  re- 
moved by  ethyl  acetate  was,  therefore,  diluted  with  an  equal  volume 
of  water,  10  per  cent,  sulphuric  acid  added,  and  the  mixture  gently 
heated.  When  the  temperature  reached  about  500  C.  a  dark-colored, 
flocculent  substance  was  precipitated,  which  soon  coalesced  to  a 
black  resin.  The  mixture  was  then  heated  to  the  boiling  point, 
diluted  with  water,  and  distilled  in  steam,  when  a  slightly  turbid 
distillate  was  obtained,  from  which  ether  removed  a  few  drops  of  a 
liquid  having  a  strongly  aromatic  odor.  The  distillation  flask  then 
contained  a  hard,  black  resin,  which  was  insoluble  in  all  the  usual 
solvents  and  in  alkalies,  together  with  a  brown  aqueous  liquid  con- 
taining sugar,  and  this,  after  the  removal  of  the  sulphuric  acid, 
afforded  an  osazone  melting  at  211°  C.  It  was  evident,  therefore, 
that  the  ethyl  acetate  extract  of  the  aqueous  liquid  contained  a 
glucoside  which  is  readily  hydrolyzed  by  sulphuric  acid;  but  the  only 
definite  hydrolytic  product  obtained  was  a  sugar,  which  appeared 
to  consist  chiefly  of  optically  inactive  glucose. 
SUMMARY. 
This  investigation  has  shown  that  Lippia  scaberrima,  Sonder, 
contains,  besides  resins  and  other  amorphous  products,  the  follow- 
ing substances  : 
