306 
Asarone. 
Am.  Jour.  Pharm, 
Juue,  1888. 
hyde  is  also  proved  by  treating  it  with  phenylhydrazine  hydrochloride 
in  the  presence  of  sodium  acetate,  when  yellow  crystals  are  obtained, 
melting  at  120 — 121°,  and  having  the  formula  CigHigOgNa.  By  the 
action  of  sodium  amalgam  on  the  aldehyde,  two  new  compounds  are 
formed,  one  of  which  melts  at  62°,  the  other  at  102°.  One  of  them 
seems  to  be  the  alcohol  corresponding  with  the  aldehyde,  but  they 
were  not  further  investigated. 
Three  methoxyl-groups  exist  in  asarone,  and  these  are  also  present 
in  the  aldehyde  and  in  the  acid,  as  is  shown  by  heating  them  with  hy- 
drochloric or  hydrobromic  acid,  when  methyl  chloride  or  bromide  is 
formed.  It  is  best,  however,  to  first  heat  the  acid  or  aldehyde  with 
four  times  its  weight  of  slaked  lime,  whereby  it  is  converted  into  an 
oily  substance  of  the  formula  C9H12O3  boiling  at  245 — 247°  ;  this, 
when  heated  with  hydriodic  acid  in  a  sealed  tube  yields  methyl  iodide, 
corresponding  in  amount  with  three  methoxyl-groups,  from  which  it 
would  appear  that  the  constitution  of  this  oil  is  C6H3(OCH3)3 ;  that  is, 
the  trimethyl  ether  of  a  triatomic  phenol.  The  presence  of  the  ben- 
zene nucleus  in  asarone  was  proved  by  heating  it  with  zinc-dust,  and 
passing  the  products  of  distillation  into  strong  nitric  acid,  when  nitro- 
benzene was  obtained. 
The  authors  conclude  from  the  study  of  the  reactions  of  asarone  and 
the  allied  compounds  that  their  constitution  may  be  expressed  by  the 
following  formulae :  Asarone,  C6H2(OMe)3'CH:CH*CH3;  asarone  dibro- 
mide,CeH2(OMe)3-CHBr-CHBr-CH3;thealdehyde,C6H2(OMe)3-CHO; 
the  acid,  C6H2(OMe)3-COOH,  and  the  oily  substance  by  C6H3(OMe)3. 
Without  regard  to  the  position  of  the  single  group  in  the  benzene  nu- 
cleus, a  striking  analogy  exists  between  asarone,  the  aldehyde,  and  the 
acid  from  asarone,  and  anethoil,  OMe*C6H4*C3H5,  anisic  alde- 
hyde, OMe'C6H4-CHO,  and  anisic  acid,  OMeC6H4COOH,  on  one 
side,  and  eugenyl  methyl  ether,  (OMe)2*C6H3-C3H[5,  vanilyl  methyl 
ether,  (OMe)2C6H3*CHO,  and  veratric  or  dimethylresorcinic  acid, 
(OMe)2C6H3'COOH,  on  the  other.  The  authors  consider  it  a  com- 
plicated task  to  determine  the  relative  positions  of  the  substituting 
groups.  The  acid  and  the  trimethyl  ether  were  treated  with  phos- 
phorus pentachloride,  hydriodic  acid,  and,  lastly,  with  hydrochloric 
acid,  but  only  in  the  last  case  was  a  satisfactory  result  obtained.  The 
product  crystallized  from  hot  water  in  glistening  needles,  melting 
about  250°,  decomposition  and  sublimation  taking  place  at  a  much 
lower  temperature.    It  dissolves  in  sulphuric  acid,  forming  a  blue. 
