MOLECULE

epi-beta-santalene

Epi-beta-Santalene, also known as epi-santalene, belongs to the class of organic compounds known as sesquiterpenoids. It is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpenoid. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Technically Epi-beta-santalene is a carbobicyclic compound that is bicyclo[2.2.1]heptane in which the hydrogens at position 3 are substituted by a methylidene group, while the 2-exo- and 2-endo- hydrogens are subsitituted by 2-methylpent-2-en-5-yl and methyl groups, respectively (the 1S,2R,4R enantiomer). Epi-beta-Santalene is a hydrophobic, neutral molecule that is insoluble in water. Epi-beta-Santalene is one of many terpenes that are found in cannabis plants (PMID: 6991645). It is also found in the essential oil of sandalwood which is a tropical tree (PMID: 24324844).