38 
New  Essential  Oils. 
f  Am.  Jour.  Pharrn. 
1     January,  1907. 
NEW  ESSENTIAL  OILS.1 
Two  oils  which  had  not  been  produced  up  to  the  present  were 
sent  to  us  for  approval  by  the  Syndicat  du  Geranium  Bourbon. 
They  are  the  oils  from  Evodia  simplex  Cordem.,  and  from  Pile  a 
spec.  nov.  Both  plants  are  indigenous  to  Reunion  and  grow  there 
in  the  wild  state. 
Oil  of  Evodia  simplex. — This  plant  belonging  to  the  family  Ruta- 
ceae  is  closely  allied  to  Toddalia  aculeata  Pers.,  which  has  essential 
oil2  both  in  the  leaves  and  in  the  bark  of  the  roots.  The  yellow- 
green,  mobile  oil  has  a  pleasant,  not  obtrusive  odor.  The  fact  that 
the  oil  strongly  reminds  of  Reunion  geranium  oil,  is,  according  to 
the  manufacturer,  due  to  the  use  of  stills  employed  in  the  geranium 
oil  production.  d150  0-9737;  aB — I3°4/5  acid  no.  21;  ester 
no.  16*4;  ester  no.  after  acetylation  63-3.  The  oil  forms  a  clear 
solution  in  0-9  vol.  80  per  cent,  alcohol,  with  a  slight  separation  of 
paraffin,  but  does  not  completely  dissolve  in  10  vol.  70  per  cent, 
alcohol.  In  a  freezing  mixture  it  becomes  cloudy  with  separation 
of  a  very  few  colorless  scales,  but  does  not  solidify.  After  it  had 
been  seen  that  up  to  about  1900  (ordinary  pressure)  nothing  distilled 
over,  the  oil  was  fractionated  in  vacuo  (3  mm.  pressure),  when  it 
boiled  between  90  and  1400.  The  portion  passing  over  on  repeated 
distillation  from  97  to  100°  (2-5  mm.  pressure)  (d15C  1-006;  aD  —  40) 
had  a  pronounced  odor  of  eugenol  methyl  ether.  The  further  ex. 
amination  showed  that  this  body  was  actually  present.  The  oxida- 
tion of  6  g.  of  this  oil  with  a  solution  of  18  g.  permanganate  in 
about  400  c.c.  water  gave  a  fair  yield  of  veratric  acid,  colorless  thin 
small  needles  of  the  m.  p.  177*5°.  Repeated  recrystallization  did 
not  raise  the  melting  point  further. 
From  the  last  fraction  of  the  oil  a  body  crystallized  out  which 
after  recrystallization  from  90  per  cent,  alcohol  formed  long  colorless 
needles,  which  proved  to  be  a  paraffin  by  their  difficult  solubility  in 
alcohol,  and  their  indifference  towards  concentrated  nitric  acid.  Its 
melting  point  lay  between  80  and  8i°. 
Eugenol  methyl  ether  and  a  paraffin  melting  at  80  to  81 0  have, 
therefore,  been  found  by  us  in  the  oil  of  Evodia  simplex  Cordem. 
1  Abstract  from  the  Semi-annual  Report  of  Sehimmel  &  Co.,  October,  T906. 
2  Gildemeister  and  Hoffmann,  "The  Volatile  Oils,"  p.  460. 
