Caryophyllene

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Caryophyllene
Surname α-caryophyllene β-caryophyllene
Structural formula α-caryophyllene β-caryophyllene
other names Humulene E-BCP
CAS number 6753-98-6 87-44-5
PubChem 5281520 5281515
Molecular formula C 15 H 24
Molar mass 204.36 g mol −1
Physical state liquid
Brief description yellowish-green liquid Liquid with an odor similar
to clove to turpentine
boiling point 166-168 ° C 260-261 ° C
density 0.90-0.91 g cm -3 0.89 g cm −3
GHS
labeling
07 - Warning
Caution
no GHS pictograms

H and P phrases 315-319-335 no H-phrases
no EUH phrases no EUH phrases
261-305 + 351 + 338 no P-phrases

Caryophyllene (stress on the penultimate syllable: Caryophyll e ne ) are sesquiterpenes that are contained in essential oils . There are α-caryophyllene (humulene) and β-caryophyllene (abbreviated E-BCP for ( E ) - B eta C aryo p hyllen).

Occurrence

Black pepper

α-Caryophyllene has a monocyclic structure and occurs in cloves and many types of basil . β-Caryophyllene has a bicyclic structure; it is found in basil , cannabis , rosemary , cinnamon , oregano , caraway , hops and pepper .

effect

Sergio Rasmann from the University of Neuchâtel discovered in 2005 that E-BCP is secreted by maize plants when predators (e.g. corn rootworm ) eat their roots. This attracts predatory nematodes ( Heterorhabditis megidis ), which attack the predators .

β-caryophyllene oxidizes in the air to caryophyllene oxide , a substance with a weak allergenic effect; after five weeks about half of the caryophylline is converted.

pharmacology

β-caryophyllene is a CB 2 - cannabinoid and reduces inflammation. Since this active ingredient, unlike other known substances that act on the same CB 2 receptor but not on the CB 1 receptor , does not have an intoxicating effect, this natural substance can be used as a starting point for the development of new drugs.

Individual evidence

  1. ↑ a b c Data sheet α-Caryophyllene at Good Scents Company , accessed June 7, 2017.
  2. ↑ Entry on Caryophyllene. In: Römpp Online . Georg Thieme Verlag, accessed on December 25, 2014.
  3. ↑ a b Datasheet beta-Caryophyllene from Good Scents Company , accessed June 7, 2017.
  4. ↑ Data sheet a-Humulene from Sigma-Aldrich , accessed on April 27, 2011 ( PDF ).
  5. ↑ Data sheet (-) - trans-Caryophyllene from Sigma-Aldrich , accessed on April 27, 2011 ( PDF ).
  6. ↑ Jürg Gertsch, Marco Leonti, Stefan Raduner, Ildiko Racz, Jian-Zhong Chen: Beta-caryophyllene is a dietary cannabinoid . In: Proceedings of the National Academy of Sciences . tape 105 , no. July 26 , 2008, p. 9099-9104 , doi : 10.1073 / pnas.0803601105 , PMID 18574142 , PMC 2449371 (free full text).
  7. ↑ Spectrum of Science: Parasite Attractant Against Corn Pests . November 2009, pp. 20-22.
  8. ↑ M. Skold et al. (2006): The fragrance chemical beta-caryophyllene-air oxidation and skin sensitization. In: Food Chem. Toxicol. Vol. 44, No. 4, pp. 538-545; PMID 16226832 .
  9. ↑ Gertsch, J. et al. (2008): Beta-caryophyllene is a dietary cannabinoid. In: Proc. Natl. Acad. Sci. USA 105 (26): pp. 9099-9104; PMID 18574142 ; doi : 10.1073 / pnas.0803601105 .
  10. ↑ Deutsches Ärzteblatt : Oregano pizza spice helps against inflammation , June 24, 2008.