338  Lactic  Acid  Ester  of  Santalol,  etc.     { ^"\,;u";\9u*'''" 
line  nitrosochloride  at  122°  C,  and  is  insoluble  in  alcohol.  Beta- 
santalene  gives  two  isomeric  nitrosochlorides,  both  of  which  are 
soluble  in  alcohol.  The  two  santalols,  isolated  together  from  other 
constituents  of  the  oil  as  phthalic  esters,  can  only  be  separated  from 
each  other  after  saponification  by  fractional  distillation  under 
reduced  pressure.  Thus  obtained,  the  alpha-santalol  boils  at  300°- 
301°  C.  (as  pointed  out  by  Chapoteaut  in  his  first  paper  of  this 
subject),  has  a  density  of  0.9854  at  zero  centigrade  and  a  rotation 
of  —  1°  20'.  Beta-santalol  boils  at  309°-3io°  C,  and  has  a  density 
of  0.9868  at  0°  C.  and  the  rotation  is  — 56°.  Dehydrating  agents, 
such  as  acid  potassium  sulphate  or  phosphoric  anhydride,  remove  a 
molecule  of  water,  converting  them  into  their  respective  isosantalenes 
C^^Ho^.  Alpha-isosantalene  boils  at  259°-26o°  C,  so  that  the  alpha 
and  beta  compounds  approach  very  nearly  to  the  essences  of  copaiba 
and  cedar.  Hugo  and  Soden  have  also  given  considerable  time  to 
the  examination  of  sandalwood  oil.  F.  Muller  claims  to  have 
isolated  a  new  terpene  C,H]4,  which  lie  calls  santene.  This  has  a 
Sp.  gr.  of  0.871,  and  boils  between  ]39°-i4o°.  It  forms  two 
polymeric  crystalline  nitrosochlorides,  one  blue  and  the  other  color- 
less. It  also  gives  a  solid  hydrochloride  melting  at  80°  C,  thus 
conforming  with  the  reactions  of  other  terpenes.  This  terpene  is 
probably  derived  during  distillation  from  teresantalic  acid,  since 
when  that  acid  is  heated  under  a  reflux  condenser,  COo  is  found  to 
be  given  off  and  on  distilling,  santene  is  obtained.  Muller  also  found 
a  ketone,  santalone  Ci^H^f-O,  boiling  at  214° -21^°  C,  isomeric 
with  jasmone. 
To  summarize,  the  following  definite  compounds  have  been 
isolated  from  sandalwood  oil:  (per  kilogr.) 
Santalenes  "  a  "  and  "  I3  "    60 
Santalols  "  a  "  and  "  b  "    800 
Santalal   30 
Acids  in  the  state  of  esters  (formic,  acetic,  san- 
talic,  teresantalic)    30 
Undetermined  strongly  odorous  bodies  boiling 
at  i30°-220°  C   3 
Undetermined  products  boiling  about  320°  C. 
(hydro-carbons,   alcohols,   ethers,  resinous 
products)    77 
1000 
