Nepetalactone

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Structural formula
Structure of nepetalactone
Structure of cis , trans -nepetalactone
General
Surname Nepetalactone
other names

5,6,7,7a-Tetrahydro-4,7-dimethyl-cyclopenta [ c ] pyran-1- (4a H ) -one

Molecular formula C 10 H 14 O 2
External identifiers / databases
CAS number
  • 490-10-8 (unspec.)
  • 21651-62-7 ( cis , trans form, (4a S , 7 S , 7a R ) -Nepetalactone)
  • 21651-53-6 ( cis , cis form, (4a R , 7 S , 7a S ) -Nepetalactone)
PubChem 161367
Wikidata Q414257
properties
Molar mass 166.22 g mol −1
Physical state

liquid

boiling point

71–72 ° C (at 5 Pa )

Refractive index

1.4859 (25 ° C)

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Nepetalactone is a chemical compound and a natural product belonging to the group of iridoids .

Occurrence and effect

Nepetalactone was detected in the hind leg secretion of female aphids of the species Myoura vicia and is used here as a pheromone .

Real catnip ( Nepeta cataria )

It is also found in the catnip ( Nepeta cataria ) and is responsible for the fact that cats are attracted to the smell of this plant. The natural function of nepetalactone in the plant is likely to be that of a repellent against insect damage, which could at least be shown in experiments with the pure substance.

In mice, nepetalactone acted as an opioid on certain receptor subtypes.

Analytics

The reliable qualitative and quantitative determination of nepetalactone succeeds after appropriate sample preparation by using gas chromatography with mass spectrometry coupling . The use of HPLC in combination with mass spectrometry can also be used for reliable determination.

Individual evidence

  1. ↑ Entry on Iridodial. In: Römpp Online . Georg Thieme Verlag, accessed on November 12, 2014.
  2. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-386.
  3. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  4. ^ JB Harborne: Introduction to Ecological Biochemistry . 3rd edition, Academic Press, London 1988, pp. 244f., 263. ISBN 0-12-324684-9 .
  5. ↑ Aydin S, Beis R, Oztürk Y, Baser KH, Baser C: Nepetalactone: a new opioid analgesic from Nepeta caesarea Boiss . In: J. Pharm. Pharmacol. . 50, No. 7, July 1998, pp. 813-817. PMID 9720633 .
  6. ↑ Zomorodian K, Saharkhiz MJ, Shariati S, Pakshir K, Rahimi MJ, Khashei R: Chemical Composition and Antimicrobial Activities of Essential Oils from Nepeta cataria L. against Common Causes of Food-Borne Infections. , ISRN Pharm. 2012; 2012: 591953, PMID 22779012
  7. ↑ Bozari S, Agar G, Aksakal O, Erturk FA, Yanmis D: Determination of chemical composition and genotoxic effects of essential oil obtained from Nepeta nuda on Zea mays seedlings. , Toxicol Ind Health. 2013 May; 29 (4): 339-48, PMID 22312034
  8. ↑ Wang M, Cheng KW, Wu Q, Simon JE: Quantification of nepetalactones in catnip (Nepeta cataria L.) by HPLC coupled with ultraviolet and mass spectrometric detection. , Phytochem Anal. 2007 Mar-Apr; 18 (2): 157-60, PMID 17439017