Am.  Jour.  Pharm. 
July.  1895. 
The  Violet  Perfume. 
349 
Constitution  of  Irone. — On  treatment  with  NaCIO  it  yields 
CHQ3,  showing  that  it  is  methylketone  of  the  formula 
CuHirCo.CHs. 
Irene  y  C13H18. — On  treatment  of  irone  with  HI  -j-  P  it  loses  a 
molecule  of  H20,  and  forms  a  colorless  oil  Irene,  B.P.  Ii3°-ii5° 
(9  mm).  Specific  gravity,  09402  at  20°.  Index  of  refraction, 
nD  =  1-5274.  It  dissolves  in  concentrated  H2S04,  decolorizes  a 
solution  of  Br  in  acetic  acid,  does  not  combine  with  picric  acid,  is 
gradually  converted  by  air  into  a  resin,  burns  with  a  sooty  ("  rus- 
sender  ")  flame.  When  carefully  oxidized,  Irene  yields  a  series  of 
compounds  which  throw  much  light  on  the  constitution  of  both 
Irene  and  Irone. 
(a)  Trioxydehydroirene : 
CH3  CH3 
r  X/ 
,C   CHOH 
CH3-C6H3/  I 
x  XC0  CHOH 
Produced  on  the  addition  of  Irene  to  a  chromic  acid  in  acetic 
acid  solution.  It  crystallizes  from  benzol  in  highly  refractive  rhom- 
bohedra  of  M.  P.,  I54°-I55°  and  possesses  feebly  acid  properties. 
(J?)  Iregenondicarboxylic  Acid : 
CH3  CH3 
\  / 
C  —COOH 
CH3-C6H  / 
XC0 • COOH 
This  acid  is  yielded  by  the  oxidation  of  trioxydehydroirene  by 
alkaline  K2Mn208.  It  crystallizes  from  hot  water  in  either  needles 
or  prisms  of  M.  P.  2270. 
(V)  Ire genontricar  boxy  lie  Acid : 
CH,  CH, 
,C  —COOH 
HOOC-C6H,/ 
XC0 • COOH 
This  is  formed  upon  the  further  oxidation  of  the  foregoing  acid, 
and  crystallizes  from  water  at  5  0  in  prisms  (granular)  holding  water 
of  crystallization,  which  it  loses  at  uo°,  and  on  heating  to  2270 
