Am.  Jour.  Pharm.  \ 
November,  1915.  j 
Chanlmoogra  Oil. 
499 
I.  Chaulmoogra  Oil  (from  the  seeds  of  Taraktogenos  Kurzii,  King). 
This  oil,  which  is  optically  active,  consists,  to  a  large  extent,  of 
the  glyceryl  esters  of  optically  active  acids  of  an  entirely  new  type. 
These  acids  are  represented  by  the  general  formula  CnH2n_402,  and 
have  a  cyclic  structure.  The"  acid  present  in  the  largest  pro- 
portion possesses  the  formula  C18H3202,  melts  at  68°  C,  has  \a\  D 
-f-  560,  and  has  been  designated  chaulmoogric  acid,  while  a  lower 
homologue,  C16H2802,  melting  at  6o°  C,  and  having  [af]D  +68°, 
has  been  termed  hydnocarpic  acid,  on  account  of  having  first 
been  isolated  from  a  Hydnocarpus  oil.10  Both  of  these  acids  are 
beautifully  crystalline  substances,  from  which  a  number  of  deriva- 
tives have  been  prepared,  and  their  constitution  has  also  been  defi- 
nitely established.11  Inasmuch  as  acids  of  the  above-described  type 
had  hitherto  not  been  known  to  occur  in  a  fatty  oil,  they  have  been 
classified  by  Lewkowitsch  ("  Chemical  Technology  and  Analysis  of 
Oils,  Fats,  and  Waxes  ")  under  the  heading  of  "  the  chaulmoogric 
acid  series." 
Chaulmoogra  oil  contains,  furthermore,  a  relatively  small  pro- 
portion of  palmitic  acid  and  a  phytosterol. 
II.  Gynocardia  Oil  (from  the  seeds  of  Gynocardia  odorata,  R.  Br.). 
This  oil  is  completely  devoid  of  optical  activity,  and  contains 
none  of  the  members  of  the  chaulmoogric  acid  series.  It  has  been 
shown  to  consist  of  the  glyceryl  esters  of  the  following  acids  12 :  (1) 
linolic  acid,  or  isomerides  of  the  same  series,  constituting  the  largest 
proportion  of  the  oil ;  (2)  palmitic  acid,  in  considerable  amount;  (3) 
linolenic  and  mdinolenic  acids,  the  latter  preponderating,  and  (4) 
oleic  acid,  in  relatively  small  amount.  A  phytosterol  (melting-point 
133  °)  was  also  isolated. 
Both  the  physical  properties  and  chemical  composition  of  the 
above-mentioned  oil  render  it  evident  that  the  chaulmoogra  oil  of 
European  commerce  could  never  have  been  obtained  from  Gyno- 
cardia seeds.  On  the  other  hand,  representative  samples  of  com- 
mercial chaulmoogra  oil  have  been  found  to  agree  closely  in  character 
with  the  oil  expressed  from  genuine  Taraktogenos  seed,  thus  com- 
pletely confirming,  from  the  chemical  side,  the  botanical  observations 
of  Sir  David  Prain  respecting  the  source  of  chaulmoogra  oil. 
In  connection  with  the  above  reference  to  Gynocardia  seeds 
10  Journ.  Chem.  Soc,  1905,  87,  p.  888. 
11  Ibid.,  1904,  85,  pp.  838-861;  1907,  91,  pp.  557-578. 
^lourn.  Chem.  Soc,  1905,  87,  pp.  896-900. 
