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Introduction:
Farnesene, a member of the sesquiterpene family, encompasses a group of closely related chemical compounds. This page provides an overview of farnesene, including its chemical properties, natural sources, uses, cultivars with farnesene dominance, and cautions to consider.
Chemical Properties:
Farnesene is classified as a sesquiterpene hydrocarbon and consists of 15 carbon atoms. It can exist in different isomeric forms, with α-farnesene and β-farnesene being the most common. α-Farnesene has four stereoisomers, while β-farnesene has two. Farnesene exhibits a pleasant, fruity, and slightly spicy aroma.
Sources:
Farnesene is naturally present in various plants, including fruits, vegetables, and herbs. Notably, it is found in significant quantities in apples, hops, chamomile, ylang-ylang, and other botanical sources. Extraction methods such as steam distillation or solvent-based extraction are commonly used to obtain farnesene.
Nitty Gritty:
In nature, (E,E)-α-farnesene is the most prevalent isomer of α-farnesene and is responsible for the green apple odor found in apple coatings. It serves as an alarm pheromone in termites and as a food attractant for the codling moth. Another isomer, (Z,E)-α-farnesene, has been isolated from perilla oil. β-Farnesene, consisting of the E isomer, is found in various essential oils and is released by aphids as an alarm pheromone.
Benefits of Farnesene Terpenes:
Farnesene terpenes offer various benefits and applications. They contribute to the aroma and flavor profiles of plants, making them valuable in perfumes, cosmetics, and food and beverage flavors. Certain farnesene terpenes, such as β-farnesene, act as natural insect repellents. Additionally, farnesene is being explored for potential therapeutic properties, including anti-inflammatory, antimicrobial, and antioxidant effects.
Smell of Farnesene:
The smell of farnesene depends on the specific isomer and its context. α-Farnesene, particularly the (E,E)-α-farnesene isomer, is associated with the distinct aroma of green apples. β-Farnesene and other isomers may have different odor characteristics, described as woody, floral, or slightly spicy.
Difference Between alpha-Farnesene and beta-farnesene:
α-Farnesene and β-farnesene differ in their chemical structures. α-Farnesene has three internal double bonds and four stereoisomers, while β-farnesene has one internal double bond and two stereoisomers based on its central double bond. These structural distinctions result in unique chemical and sensory properties for each isomer.
CAS Number of Farnesene:
The CAS number for Farnesene is 18794-84-8, providing a specific identifier for this compound.
Cultivars (strains) with Farnesene Dominance:
Cautions:
While Farnesene is generally regarded as safe for approved uses, caution should be exercised by individuals with known fragrance allergies or sensitivities. Following recommended usage guidelines and consulting professionals in relevant fields is advisable.
Overall, Farnesene and its isomers play diverse roles in nature, from influencing fruit aromas to serving as semiochemicals for communication and defense mechanisms in insects.
Farnesene is a term used to describe a group of six closely related sesquiterpene compounds. Among them, α-farnesene and β-farnesene are isomers that differ in the position of one double bond. α-Farnesene is known as 3,7,11-trimethyl-1,3,6,10-dodecatetraene, while β-farnesene is referred to as 7,11-dimethyl-3-methylene-1,6,10-dodecatriene. α-Farnesene has four stereoisomers, distinguished by the arrangement of two of its three internal double bonds, while β-farnesene has two stereoisomers based on the configuration of its central double bond.
Formula: C15H24e
Molar Mass: 204.35g/mol
PubChem CID:
5281516 alpha,(E,E)
5362889 alpha,(Z,E)
5317320 alpha,(Z,Z)
5317319 beta,Z
5281517 beta,E
Density: 0.813g/cm3
Boiling Point:
α-(Z): 125 at 12 mmHg (1.6 kPa)
β-(E): 124 °C
β-(Z): 95-107 at 3 mmHg (0.40 kPa)