My watch list
my.chemeurope.com  
Login  

Nepetalactone



Nepetalactone
IUPAC name 4,7-dimethyl-5,6,7,7a-tetrahydrocyclo--
penta[c]pyran-1(4aH)-one
Identifiers
CAS number 490-10-8
SMILES C\C2=C\OC(=O)C1C2CCC1C
InChI InChI=1/C10H14O2/c1-6-3-4-8-7(2)5-12-
10(11)9(6)8/h5-6,8-9H,3-4H2,1-2H3
Properties
Molecular formula C10H14O2
Molar mass 166.217
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Nepetalactone is an organic compound first isolated in the plant catnip, Nepeta cataria. The name is apparently derived from the Italian city Nepete. Nepetalactone is bicyclic terpenoid, i.e. it is a ten-carbon compound derived from isoprene with two fused rings, a cyclopentane and a cyclic ester. The structure and the effects of the compound are similar to those of valepotriates. A number of isomers of nepetalactone are known.

Additional recommended knowledge

Nepetalactone was first reported in 1941 after it was isolated by steam distillation of catnip.[1]

Effects on animals

As 4aα,7α,7aα-nepetalactone it is the active chemical in Nepeta cataria that causes its characteristic effect on cats. Around 75% of cats are affected; susceptibility is gene-linked. The chemical interacts as a vapour at the olfactory epithelium. The compound only mildly affects humans: it is a weak sedative, antispasmodic, febrifuge, and antibacterial. In high doses it also has an emetic effect. Nepetalactone also has an effect on some insects, repelling the cockroach and mosquito, but it is poisonous to some common flies and a sex pheromone to aphids.

References

  1. ^ S. M. McElvain, R. D. Bright and P. R. Johnson (1941). "The Constituents of the Volatile Oil of Catnip. I. Nepetalic Acid, Nepetalactone and Related Compounds". J. Am. Chem. Soc. 63 (6): 1558-1563. doi:10.1021/ja01851a019.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Nepetalactone". A list of authors is available in Wikipedia.
Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE