Alpha-Farnesene

Alpha-Farnesene
Compound Structure:
Synonyms: alpha-Farnesene;Farnesene;(E,E)-alpha-farnesene;(3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene;1,3,6,10-Dodecatetraene, 3,7,11-trimethyl-, (3E,6E)-;(E)-alpha-Farnesene
Compound ID: NMPC-055
PubChem ID:

5281516

Molecular Formula: C15H24
Canonical SMILES: CC(=CCCC(=CCC=C(C)C=C)C)C
InChIKey: CXENHBSYCFFKJS-VDQVFBMKSA-N
About the compound:

α-Farnesene, also known as Alpha-Farnesene, is a sesquiterpene organic compound with notable roles in both aroma and biological interactions. It is a 1,3,6,10-tetraene substituted by methyl groups at positions 3, 7, and 11. This compound is naturally found in various organisms, including Eupatorium cannabinum and Lonicera japonica. α-Farnesene is most prominently recognized for its presence in the skin of apples, where it contributes to the characteristic green apple aroma. The concentration of α-Farnesene tends to increase as apples mature. It is not limited to apples and can be found in other plants such as pears, roses, and ginger. In some plants, α-Farnesene can undergo oxidation to form a polymer that results in brown spotting or scald on the skin of mature apples. Because of its distinctive aroma, α-Farnesene is utilized in the fragrance industry, particularly for replicating fruity or fresh scents. It can also be employed in flavor formulations. In certain plants, α-Farnesene serves as a natural pesticide by deterring herbivores. Additionally, it acts as a signaling molecule, enabling communication within and between plants. Given its involvement in the development of scald on mature apples, researchers in agriculture are interested in α-Farnesene to mitigate post-harvest damage and enhance the shelf-life of fruits.The term "farnesene" encompasses a group of closely related sesquiterpenes, with α-Farnesene and β-farnesene being isomers that differ in the location of a double bond. (E,E)-α-Farnesene is the most common isomer and is responsible for the green apple odor in fruits. On the other hand, β-Farnesene has one naturally occurring isomer. The E isomer is present in various essential oils and is released by aphids as an alarm pheromone to warn other aphids. Some plants, like potato species, produce this pheromone as a natural insect repellent.

https://en.wikipedia.org/wiki/Farnesene

GHS Hazard Statements

H304 (100%): May be fatal if swallowed and enters airways [Danger Aspiration hazard]


Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

204.35 g/mol

XLogP3-AA

6.1

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

0

Rotatable Bond Count

6

Exact Mass

204.187800766 g/mol

Monoisotopic Mass

204.187800766 g/mol

Topological Polar Surface Area

0²

Heavy Atom Count

15

Formal Charge

0

Complexity

270

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

2

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Boiling Point

260.00 to 262.00 °C. @ 760.00 mm Hg

Source: PubChem

Source Species: Crateva adansonii
Ficus asperifolia
Garcinia kola
Tetrapleura tetraptera
Cymbopogon citratus
Zingiber officinale
Centratherum punctatum
Plumeria alba
Tecoma stans
Download SDF