MOLECULE

trans-trans-alpha-Farnesene

Trans-trans-alpha-Farnesene, also known as (3E,6E)-alpha-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. There are four known Alpha-farnesene stereoisomers which differ about the geometry of two of its three internal double bonds (the stereoisomers of the third internal double bond are identical). (3E,6E)-alpha-Farnesene is one of the 4 isomers of Alpha-farnesene and is the most common isomer, Trans-trans-alpha-Farnesene is a hydrophobic, neutral molecule that is not water soluble. It has a woody, bergamot, green and citrus like aroma and a fresh, green, fruity taste. Trans-trans-alpha-Farnesene is used as a flavoring and perfuming agent. It is found in the coating of apples, and other fruits, and it is responsible for the characteristic green apple odour (doi:10.1038/2101260a0). (3E,6E)-alpha-Farnesene is found within a few different foods, such as gingers, cottonseeds, common oregano and sweet oranges. (3E,6E)-alpha-Farnesene has also been detected, but not quantified in, several different foods, such as apples, pears, spearmints, guava, and carrots. Trans-trans-alpha-farnesene 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).