Farnesene

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Farnesene
Surname α-Farnese β-Farnese
other names (3 E , 6 E ) -3,7,11-trimethyl-
1,3,6,10-dodecatetraene 		(6 E ) -7,11-dimethyl-3-methylene-
1,6,10-dodecatriene
Structural formula Structural formula of α-Farnese Structural formula of β-Farnese
CAS number 26560-14-5 (Z, E-α) 502-60-3
18794-84-8 (trans-β)
502-61-4 (mixture of isomers)
PubChem 5281516 5281517
Molecular formula C 15 H 24
Molar mass 204.36 g mol −1
Physical state liquid
Brief description colorless liquid
density 0.844-0.879 g · cm -3
Refractive index 1.490–1.505 (at 20 ° C)
boiling point α- ( Z ) -isomer: 98-102 ° C (6.7 h Pa ) β- ( Z ) -isomer: 95-107 ° C (6.7 hPa)
solubility insoluble in water
GHS
labeling
no GHS pictograms
H and P phrases no H-phrases
no P-phrases

The Farnesene (stress on the third syllable: Farnes e ne ) form a group of substances that includes six closely related compounds from the class of sesquiterpenes . α-Farnese and β-Farnese are isomers with different positions of the double bond. Α-Farneses is 3,7,11-trimethyl-1,3,6,10-dodecatetraene, while β-Farneses has the formula 7,11-dimethyl-3-methylene-1,6,10-dodecatriene . There are four configuration isomers of the alpha form , which differ in terms of the geometry of the two inner double bonds (there is no possibility of isomerism at the terminal double bonds). There are two isomers of the beta isomer, which differ in the configuration of their middle double bond.

α-Farnese

Two of the configurational isomers of α-fernsene have been isolated as natural products .

alpha-farnese, isomer 3E6E
(3 E , 6 E ) -3,7,11-trimethyldodeca-1,3,6,10-tetraene

( E , E ) -α-Farnese is the more common of the two. It can be found in the skin of apples and other fruits , for example, and carries the characteristic “ green apple aroma ”. Oxidation by air leads to compounds that ultimately lead to the cell death of the outer cell layers of the fruit, as can be seen in the brown discoloration on bruises on apples.

alpha-farnese, isomer 3Z6E
(3 Z , 6 E ) -3,7,11-trimethyldodeca-1,3,6,10-tetraene

( Z , E ) -α-Farnese was isolated from the essential oil of Perilla . Both isomers act as messenger substances on insects ; they act as alarm pheromones for termites or as attractants for codling moth .

α-Farnese is still the main component of gardenia oil (from gardenia ) with a share of around 65% of the volatile components.

The other two isomers can be produced industrially.

alpha-farnese, isomer 3E6Z
(3 E , 6 Z ) -3,7,11-trimethyldodeca-1,3,6,10-tetraene
alpha-farnese, isomer 3Z6Z
(3 Z , 6 Z tetraen -3,7,11-trimethyldodeca-1,3,6,10-)

β-Farnese

An isomer of the β-farnesis has so far been detected in nature.

beta-farnese, isomer 6E
(6 E ) -7,11-dimethyl-3-methylidenedodeca-1,6,10-triene

The ( E ) isomer is a component of various essential oils. It is released by aphids as an alarm pheromone to warn other aphids. It has been shown that various plants such as some potato species use this pheromone as a natural repellent against insects.

The ( Z ) isomer has so far only been artificially represented.

beta-farnese, isomer 6Z
(6 Z ) -7,11-dimethyl-3-methylidenedodeca-1,6,10-triene

See also

Individual evidence

  1. ↑ a b c Entry on Farnese. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.
  2. ↑ a b c d e Data farnesene at Sigma-Aldrich , accessed on 29 March 2013 ( PDF ).Template: Sigma-Aldrich / name not given
  3. ↑ Šobotník, J., Hanus, R., Kalinová, B., Piskorski, R., Cvačka, J., Bourguignon, T., Roisin, Y .: ( E , E ) -α-Farnesene, an Alarm Pheromone of the termite Prorhinotermes canalifrons . In: Journal of Chemical Ecology . tape 34 , April 2008, p. 478-486 , doi : 10.1007 / s10886-008-9450-2 .
  4. ↑ Hern, A. & Dorn, S .: Sexual dimorphism in the olfactory orientation of adult Cydia pomonella in response to alpha-farnesene . In: Entomologia Experimentalis et Applicata . tape 92 , July 1999, p. 63-72 .
  5. ↑ Shau-Chun Wang, Ting-Yu Tseng, Chih-Min Huanga, Tung-Hu: Gardenia herbal active constituents: applicable separation procedures . In: Journal of Chromatography B . tape 812 , December 5, 2004, p. 193-202 .
  6. ↑ Gibson, RW & Pickett, JA: Wild potato repels aphids by release of aphid alarm pheromone . In: Nature . tape 302 , April 14, 1983, pp. 608-609 , doi : 10.1046 / j.1570-7458.1999.00525.x .
  7. ↑ Avé, DA, Gregory, P., Tingey, WM: Aphid repellent sesquiterpenes in glandular trichomes of Solanum berthaultii and S. tuberosum . In: Entomologia Experimentalis et Applicata . tape 44 , July 1987, pp. 131-138 , doi : 10.1111 / j.1570-7458.1987.tb01057.x .