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Cyclosantalal and epicyclosantalal—new sesquiterpene aldehydes from east Indian sandalwood oil
Author(s) -
Brunke E.J.,
Vollhardt J.,
Schmaus G.
Publication year - 1995
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.2730100315
Subject(s) - sandalwood , sesquiterpene , chemistry , santalum album , essential oil , botany , organic chemistry , traditional medicine , chromatography , medicine , biology
Two new minor components of East Indian sandalwood oil have been isolated by chromatography. Structure elucidation using spectroscopical methods resulted in formulae 1 and 2 . The relative configurations of the epimeric sesquiterpene aldehydes 1 , 2 were determined by two‐dimensional NMR‐analysis (HETCOR‐, INADEQUATE‐, and NOE‐experiments) of the corresponding acids, cyclosantalic acid ( 3 ) and epicyclosantalic acid ( 4 ). The proposed structures of the aldehydes were confirmed by oxidative degradation reactions. Both aldehydes could be oxidized under normal conditions resulting in the known products acetyldihydroalbene ( 7 ) and albene ( 12 ) but also some new products such as the acids 3 , 4 and the formates 8 , 9 . Trace amounts of those oxidation products could also be detected as constituents of sandalwood oil. A possible biogenetic pathway leading from p‐santalane derivatives to the cyclosantalals is briefly discussed.