552  Derivatives  of  Benzoic  Sulphinide.  {Am'^f;1|J11arm" 
cooled  solution  of  pulegone  in  light  petroleum  ;  it  separates  from 
dilute  alcohol  in  well-defined,  colorless  crystals,  melts  at  40-5°,  arid 
is  readily  soluble  in  alcohol  and  ether.  It  gradually  decomposes 
on  keeping,  and  it  is  converted  into  pulegone  by  freshly-precipi- 
tated silver  oxide  and  lead  hydroxide,  but  it  is  not  acted  on  by  cold 
dilute  soda  or  by  warm  sodium  carbonate  ;  its  specific  rotatory 
power  is  [r/]D  =  — 33-88°.  When  treated  with  hydroxylamine,  as 
described  in  the  preparation  of  pulegoneoxime,  it  is  converted  into 
a  compound  which  crystallizes  in  quadratic  plates,  melts  at  38°,  and 
has  probably  the  composition  C10H18BrNO;  on  keeping  this  sub- 
stance for  some  time,  it  first  changes  into  a  mass  of  needles  melting 
at  iio°,  which  are  free  from  bromine,  but  contain  nitrogen,  and 
then  into  pulegoneoxime.  When  the  additive  compound  is  reduced 
with  zinc-dust  in  alcoholic  solution,  it  yields  very  small  quantities 
of  pulegone  and  a  considerable  quantity  of  an  oil,  which  has  the 
same  molecular  formula  as,  and  possesses  all  the  properties  of, 
the  levomenthone  described  by  Beckmann  ( 1 889),  except  that  its 
oxime  melts  at  a  higher  temperature,  namely,  at  84-85°  ;  when 
this  isomeride  of  menthone  is  treated  with  sodium  in  ethereal 
solution,  it  is  converted  into  a  mixture  of  isomeric  menthols,  from 
which  a  considerable  quantity  of  the  benzoyl  derivatives  of  natural 
laevomenthol  can  be  isolated  in  a  crystalline  condition.  Laevomen- 
thol  is  also  obtained,  together  with  resinous  products,  when  pule- 
gone is  reduced  with  sodium  under  the  same  conditions. 
The  author  gives  three  possible  formulae  for  pulegone. 
ON  SOME  DERIVATIVES  OF  BENZOIC  SULPHINIDE 
(SACCHARIN  OR  BENZOYL  SULPHONIC  IMIDE) 
AND  THE  CHANGES  CAUSED  IN  THEIR  TASTE  BY 
CHANGES  IN  COMPOSITION.1 
By  R.  De  Roode. 
The  most  characteristic  property  of  parabromosulphinide  is  that 
it  possesses  two  distinct  tastes,  a  bitter  and  a  sweet,  and  the  corre- 
sponding chlorine  compound  has  the  same  peculiarity  in  even  a 
more  marked  degree.  The  author  has,  therefore,  investigated  the 
other  para-halogen-sulphinides,  and  the  substances  from  which  they 
are  made,  and  observed  their  effect  upon  the  nerves  of  taste. 
1  From  the  Amer.  Chem.  Journ.,  xiii,  217-232.  Reprinted  from  the  Journ. 
of  the  Soc.  of  Chem.  Ind.,  July. 
