(E)-β-Famesene

(E)-β-Famesene
Compound Structure:
Synonyms: (E)-beta-farnesene;7,11-dimethyl-3-methylidenedodeca-1,6,10-triene;BETA-FARNESENE;(E)-.beta.-Farnesene;7,11-Dimethyl-3-methylene-1,6,10-dodecatriene
Compound ID: NMPC-049
PubChem ID:

10407

Molecular Formula: C15H24
Canonical SMILES: CC(=CCCC(=CCCC(=C)C=C)C)C
InChIKey: JSNRRGGBADWTMC-UHFFFAOYSA-N
About the compound:

(E)-beta-farnesene is a natural compound found in various organisms, including Dipteryx lacunifera and Grindelia hirsutula. The term "farnesene" refers to a group of closely related sesquiterpenes. Within this group, both α-farnesene and β-farnesene are significant members, differing in the location of a double bond: α-Farnesene (3,7,11-trimethyl-1,3,6,10-dodecatetraene): This compound can exist as four stereoisomers, differing in the geometry of two of its three internal double bonds. The α-farnesene isomers play various roles in nature, including being found in the coating of apples and other fruits. They are responsible for the distinctive green apple odor. However, their oxidation by air can lead to fruit damage, causing a storage disorder known as scald. These isomers also serve as insect semiochemicals, acting as alarm pheromones in termites or food attractants for pests like the codling moth. α-Farnesene is a significant contributor to the scent of gardenia, making up a considerable portion of its headspace constituents. β-Farnesene (7,11-dimethyl-3-methylene-1,6,10-dodecatriene): This compound exists in a single naturally occurring isomer. The E isomer of β-farnesene is found in various essential oils and is also released by aphids as an alarm pheromone upon their death to warn away other aphids. Some plants, including certain potato species, synthesize β-farnesene as a natural insect repellent.

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

204.35 g/mol

XLogP3-AA

6.2

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

0

Rotatable Bond Count

7

Exact Mass

204.187800766 g/mol

Monoisotopic Mass

204.187800766 g/mol

Topological Polar Surface Area

0Ų

Heavy Atom Count

15

Formal Charge

0

Complexity

260

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

1

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Source: PubChem

Source Species: Greenwayodendron suaveolens
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