Am  Dec.ri8?2harm' }  Sesquiterpenes.  623 
crystallizable  compound.  This  hydrocarbon  exists  in  cubeb  oil,1 
savin  oil,2  cade  oil,3  betel  oil,4  camphor  oil,5  galbanum  oil,6 
patchouli  oil,7  juniper  oil,8  asafoetida,  coto  oil,9  and  olibanum 
oil.  It  appears  to  be  as  widely  distributed  as  limonene.  Of  the 
numerous  names  which  might  be  given  to  it  on  account  of  its  varied 
occurrence,  that  of  cadinene  is  suggested  by  Wallach  as  the  most 
convenient,  because  the  oil  of  cade,  juniper  tar  oil,  is  the  most 
accessible  and  the  cheapest  source  of  the  substance.10 
Caryophyllene  is  essentially  different  from  cadinene.  Its  physical 
constants  have  not  been  determined  precisely,  but  it  certainly  boils 
at  a  somewhat  lower  point  than  cadinene.  With  halogen  acids  it 
forms  only  liquid  addition  products.  By  addition  of  I  molecule  of 
water  it  yields  a  saturated  alcohol  C15H260.  But  it  must  be  remem- 
bered that  in  conversion  into  the  alcohol  caryophyllene  appears  to  be 
isomerized.  Well-defined  crystalline  halogen  compounds  can  be 
obtained  from  the  alcohol,  containing  only  one  atom  of  halogen  and 
presenting  the  characters  of  fully  saturated  stable  compounds.  But 
hitherto  it  has  not  been  possible  to  obtain  these  halogen  compounds 
directly  from  caryophyllene. 
By  separation  of  water  from  the  alcohol  a  different  sesquiterpene, 
clovene,  is  obtained.  This  differs  essentially  from  caryophyllene, 
since  it  is  not  convertible  into  the  alcohol  C15H260  by  warming  with 
dilute  sulphuric  acid,  and  since  it  apparently  does  not  form  a 
crystallizable  nitroso  chloride.  The  boiling  point  of  clovene  is  lower 
(261-2630)  and  the  specific  gravity  higher  (0-930)  than  that  of 
cadinene.  Apparently  clovene  has  only  one  ethylene  bond  in  its 
molecule.  This  cannot  be  affirmed  of  caryophyllene  until  its 
physical  constants  have  been  determined  with  greater  certainty. 
The  hydrocarbon  isomeric  with  caryophyllene,  which  is  generally 
associated  with  cadinene  in  ethereal  oils  and  differs  from  cadinene 
1  .Annalen,  238,  78. 
2  Ibid.,  238,  82. 
3  Ibid.,  238,  82. 
4  four.  p.  Chem.,  39,  355. 
5  Jour.  p.  Chem.,  39,  355  ;  and  Annalen,  114,  193. 
6  Annalen,  238,  81. 
1  Ibid.,  238,  81. 
8  Schimmel's  Berichte,  April,  1890. 
9  Arch.  f.  Pharm.,  229,  17. 
10  Annalen,  252,  150. 
