Am.  Jour.  Pharni. ") 
April,  1909.  j 
Alpha-  and  Beta-Iononcs. 
183 
From  this  comparison  of  physical  properties  of  the  two  ionones 
and  their  compounds  it  will  be  seen  that  a  perfect  separation  of  the 
two  when  occurring-  in  admixture  is  not  an  easy  task. 
Fractional  crystallization  of  the  mixed  semicarbazones  and 
/?-bromphenylhydrazones  has  been  used  and  differences  of  solubility 
of  the  same,  but  the  methods  that  are  most  satisfactory  are  both 
upon  the  different  behavior  of  the  bisulphite  compounds  of  the  two 
ionones.  The  firm  of  Haarmann  &  Reimer,  the  holders  of  the  Tie- 
mann  and  DeLaire  patent  in  Germany,  published  the  first  of  these 
methods,  which  is  to  boil  the  mixture  of  a-  and  /^-ionones  with  a 
concentrated  aqueous  alkaline  bisulphite  solution  until  they  both  go 
into  solution.  On  distilling  the  solution  with  steam,  /?-ionone  is 
set  free  from  its  combination  and  can  be  distilled  over,  while  a-ionone 
is  only  set  free  after  making  the  solution  alkaline  with  sodium 
hydroxide. 
The  other  process  is  that  of  Chuit,  Naef  &  Co.,  and  depends  upon 
the  saturation  of  the  mixed  bisulphite  solutions  of  the  two  ionones 
with  salt,  when  the  a-ionone  compound  separates  out  insoluble  in 
the  salt  solution  while  the  /3-compound  remains  dissolved.  Both 
hydrosulphonates  may  then  be  decomposed  with  alkalies  and  the 
respective  ionones  set  free.  ■ 
The  difference  in  odor  between  the  pure  a-  and  /^-ionones  is 
sufficient  to  enable  a  person  with  some  little  practice  not  to  mistake 
one  for  the  other ;  when  the  oils  themselves  are  smelled,  the  a-ionone 
is  possessed  of  a  sweeter  and  at  the  same  time  more  penetrating  odor, 
reminding  one  more  of  the  orris  than  the  /3-ionone,  but  if  a  drop 
of  each  of  these  products  is  allowed  to  evaporate  spontaneously  on 
a  slip  of  paper,  it  is  noticed  that  the  /?-ionone  yields  a  perfume  which 
is  quite  as  strong  and  which  has  perhaps  more  resemblance  to  the 
true  odor  of  the  flower. 
Both  the  product  of  the  Tiemann  patent  No.  556943  and  the 
DeLaire  patent  No.  600429  are  mixtures,  although  in  the  former  the 
a-ionone  predominates,  and  in  the  latter  the  /3-ionone  is  the  chief 
ingredient.  As  these  mixtures  differ  from  each  other  in  odor,  and 
both  differ  from  the  pure  ionones  separated  by  one  of  the  methods 
mentioned  above,  it  is  obvious  that  the  perfumer  has  a  variety  of 
slightly  different  violet  perfumes,  made  possible  by  varying  his 
choice  of  the  basic  substance  used. 
Violet  extract,  or  violet  perfume,  as  sold,  however,  always  con- 
tains other  essential  oil  extracts,  as  "  adjuncts  "  or  "  auxiliaries  "  to 
