^'"jine'isso"''"'}  Ethereal  Oil  of  California  Bay  Tree.  317 
pound  analyzed  is  not  unlike  that  of  spirits  of  camphor,  though  not 
quite  identical. 
It  is  not  readily  affected  by  metallic  sodium,  even  when  heated  with 
it.  The  water  is  therefore  in  intimate  combination,  possibly  as  an 
ether  {C^^H^>j\0. 
A  vapor  density  determination  was  made  by  Mr.  J.  B.  Wilcutt 
according  to  Victor  Meyer's  method,  in  diphenylamine  vapor.  The 
result  in  one  case  gave  4*7,  whereas  the  vapor  density  calculated  for 
CgoHg^O  would  give  io*o.  If,  however,  dissociation  should  take  place^ 
splitting  up  the  molecule  into  C20H32+H2O,  the  vapor  density  of  the 
mixture  would  be  5*0,  not  so  far  from  the  result  obtained.  That  dis- 
sociation would  take  place  was  to  be  foreseen  from  the  behavior  oa 
distillation,  and  was  confirmed  by  the  fact  that  after  the  operation  the 
contents  of  the  apparatus  no  longer  had  the  original  camphor-like  odor,, 
but  possessed  a  distinct,  rank  odor  of  turpentme.  It  was  also  noticed 
that  the  compound  itself  by  long  standing  bleached  the  cork  of  the  test 
tube,  probably  due  to  traces  of  the  free  C20H32  resulting  from  the 
distillation. 
An  analysis  was  made  of  a  fraction  boiling  at  171  to  172°,  which  gave 
C=8i*39;  H=ii*40.  Evidently,  therefore,  a  mixture  of  the  above 
with  the  more  oxygenated,  higher-boiling  constituent,  umbeliol,CgHj20- 
The  higher  fraction  (210  to  225°)  was  also  subjected  to  fractional  dis- 
tillation and  a  compound  obtained  in  considerable  quantity,  boiling: 
without  decomposition  at  215  to  216°  (uncorrected).  This  substance  is 
also  a  colorless  mobile  liquid  of  aromatic  but  powerful  odor,  which,, 
too  strongly  inhaled,  attacks  the  mucous  surfaces  and  causes  headache. 
It  is  but  slightly  volatile,  a  quantity  in  an  open  watch  glass  losing  one 
mg.  in  an  hour  and  a  half.  With  concentrated  sulphuric  acid  it  gives 
a  blood-red  color,  turning  to  brown  and  black.  Water  separates  it 
from  its  solution  in  the  acid.  It  is  acted  on  violently  by  sodium,  form- 
ing a  blood-red,  brittle,  resinous  substance  ;  it  is  also  acted  on  violently 
and  decomposed  by  strong  nitric  acid.    Elementary  analvsis  gave 
T  TT  TTi  Calculated  for 
C  ...  77  28  77"27  77"i7  77*42  ' 
H  ...  9  74  9-53  9-57  9-67 
The  vapor  density  determined,  with  the  assistance  of  Mr.  F.  Slate^ 
according  to  Victor  Meyer,  in  diphenylamine  vapor  gave  4*3 9;  calcu- 
lated for  C8Hi20=4*29.    The  formula  is,  therefore,  C8Hj20. 
It  is  isomeric,  as  far  as  I  know,  with  no  other  known  compound. 
