MOLECULE

trans-beta-Farnesene

(E)-Beta-Farnesene, also known as EBF or trans-beta-Farnesene , belongs to the class of organic compounds known as sesquiterpenoids. Sesquiterpenes 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. The term farnesene refers to a set of six closely related chemical compounds (4 alpha-Farnesenes and 2 Beta-Farnesenes) which all are sesquiterpenes. α-Farnesene and β-Farnesene are isomers, differing by the location of one double bond. β-Farnesene is 7,11-dimethyl-3-methylene-1,6,10-dodecatriene while α-Farnesene is 3,7,11-trimethyl-1,3,6,10-dodecatetraene. The beta isomer exists as two stereoisomers (cis and trans) about the geometry of its central double bond. However, only the trans isomer exists in nature. Beta-Farnesene exists as a clear colorless liquid and is a hydrophobic, neutral compound that is insoluble in water. It has a woody, sweet, citrus aroma and is used as a masking or perfuming agent. Beta-Farnesene is found naturally in many plants and plant essential oils including basil, blood orange, carrots, celery, ginger, grapefruit, lavender, mint, orange peel, parsley, peppermint, pine, rosemary and thyme. It is one of several sesquiterpenes that are found in cannabis plants (PMID: 6991645). It is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). Beta-Farnesene is also released by aphids as an alarm pheremone upon death to warn away other aphids (PMID: 21092302)