348 
The  Violet  Perfume. 
Am.  Jour.  Pbarm. 
July,  1395. 
two  products  are  obtained,  the  one  remaining  behind  being  a  slimy 
mass,  which,  on  treatment  with  alkali,  gives  myristic  acid,  ingenin, 
iridic  acid  and  a  brittle,  crystallisable  resin.  In  the  distillate  isthe 
volatile  portion  consisting  of  the  ethereal  oil  with  a  large  amount 
of  myristic  acid  and  its  methyl  salt,  oleic  acid  and  an  ester  of  the 
same,  oleic  aldehyde  and  other  substances  probably  in  the  nature  of 
alcohols  that  were  not  further  studied.  The  ethereal  solution  of 
this  mixture  is  shaken  with  a  two  per  cent.  KOH  solution  to  remove 
in  part  the  free  organic  acids.  The  remaining  organic  acids  with 
the  esters  are  further  removed  by  repeated  fractional  distillation  of 
the  oil  with  steam.  The  neutral  oil,  obtained  by  this  distillation 
treatment,  is  then  dissolved  in  alcohol,  and  at  the  ordinary  tempera- 
ture treated  with  alcoholic  KOH  to  saponify  any  organic  esters  re- 
maining. This  alcoholic  solution  is  then  poured  into  water,  and 
the  aqueous  solution  extracted  with  ether,  and  the  ethereal  extrac- 
tion again  distilled  with  steam.  The  "  Irisaroma"  goes  over  with 
the  first  distillate.  This  oil  is  then  boiled  with  water  -{-  Ag20  to 
oxidize  any  aldehydes  present,  and  so  remove  the  same.  The  "Iris- 
aroma" being  a  ketone,  is  purified  by  forming  a  phenylhydrazine 
compound  by  allowing  equal  molecules  of  the  "  Irisketone,"  and 
phenylhydrazine  to  remain  together  for  a  day  at  the  ordinary  tem- 
perature, and  then  distilling  this  hydrazone  mixture  with  steam. 
The  "  Irisketone"  remains  behind  in  combination  with  the  phenyl- 
hydrazine  as  a  brown  oil,  which  is  then  decomposed  with  dilute 
H2S04  into  phenylhydrazine  and  the  "  Irisketone  "  or  "  Irisaroma," 
called  Irone.  This  is  then  extracted  with  ether  from  the  aqueous 
distillate  and  rectified  under  diminished  pressure.  Irone  C13H20O  is 
an  oil  which  is  scarcely  soluble  in  water,  but  soluble  in  alcohol, 
ether,  chloroform,  benzol  and  ligroin.  B.  P.  1440  under  a  pressure 
of  16  mm.  Specific  gravity  o  939  at  200.  Index  of  refraction 
nD  =  1-50113.  It  polarizes  light  to  the  right  and  in  a  dcm.  tube  to 
the  extent  of  400.  The  smell  of  pure  irone  is  sharp  and  in  the 
concentrated  condition  quite  unlike  that  of  violets.  But  when  di- 
luted with  alcohol  and  exposed  to  the  air  the  odor  resembles  that  of 
the  natural  flowers. 
Ironoxime — C13H20NOH.  The  oxime  is  generally  obtained  as  an 
oil  soluble  in  alcohol  ether,  benzol,  chloroform  and  ligroin.  Once 
crystals  were  obtained,  and  some  of  these  were  subsequently  used 
in  obtaining,  with  great  difficulty,  however,  further  crystals  from  a 
ligroin  solution. 
