A1october,^907rm'}    Examination  of  Lippia  Scaberrima.  457 
As  already  stated,  lippianol  is  unaffected  by  aqueous  alkalies,  but, 
when  boiled  with  a  strong  solution  of  potassium  hydroxide  contain- 
ing some  alcohol,  it  forms  a  compound  with  the  alkali  which  does 
not  separate  even  after  the  removal  of  the  alcohol,  and,  on  acidify- 
ing this  liquid,  the  lippianol  is  precipitated  unchanged.  Although 
obtained  from  that  portion  of  the  resins  which  was  extracted  by 
light  petroleum,  lippianol  is  quite  insoluble  in  this  solvent,  and 
cannot,  therefore,  have  occurred  in  the  plant  in  a  free  state.  The 
fact  that  it  was  not  obtained  in  association  with  the  other  alcohols 
already  described,  is  owing  to  its  above-mentioned  property  of 
forming  a  compound  soluble  in  water  when  treated  with  alcoholic 
potash.  The  amount  of  lippianol  obtained  (3-5  grammes)  is  equiv- 
alent to  about  0  05  per  cent,  of  the  weight  of  the  air-dried  plant. 
Methyl  Lippianol,  C25H35PB  —  OCHz. — As  the  acetyl  derivative  of 
lippianol  was  unsuitable  for  the  purpose  of  ascertaining  the  number 
of  hydroxyl  groups  contained  in  this  alcohol,  and  as  a  determination 
by  ZeisePs  method  showed  the  absence  of  methoxyl  groups,  about 
1  gramme  of  the  lippianol  was  completely  methylated  by  treatment 
with  sodium  methoxide  and  methyl  iodide.  The  number  of  hydroxyl 
groups  present  in  the  original  substance  was  then  ascertained  by 
determining  the  percentage  of  methoxyl  in  the  resulting  derivative. 
Methyl  lippianol  crystallizes  from  dilute  alcohol  in  colorless 
needles,  which  melt,  with  decomposition,  at  about  2600  C.  An 
estimation  of  the  methoxyl  groups,  by  means  of  Perkin's  modification 
of  Zeisel's  method  (Jour.  Chem.  Soc.y  1903,  83,  p.  1367),  gave  the 
following  result : 
o-3034  gave  0-1725  Agl.     CH3O  =  7*5. 
C25H3503  —  OCH3  requires  CH30  =  7-5  per  cent. 
Lippianol  is  therefore  a  monohydric  alcohol. 
Examination  of  the  Non-volatile  Acids. 
The  light  petroleum  liquid  containing  the  non-volatile  fatty  acids, 
which  was  separated  from  the  product  from  which  the  lippianol  was 
obtained,  as  above  described,  was  washed,  dried  and  evaporated. 
The  residue,  which  weighed  50  grammes,  was  distilled  under  a 
pressure  of  1 5  mm.,  when  it  passed  over  between  2350  and  265°, 
and  crystallized  on  cooling.    It  was  then  dissolved  in  a  little  warm 
