Nepetalactone

Nepetalactone
(cis,trans)-nepetalactone
(cis,trans)-nepetalactone
Names
IUPAC name
4,7-Dimethyl-5,6,7,7a-tetrahydrocyclopenta[c]pyran-1(4aH)-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C10H14O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h5-6,8-9H,3-4H2,1-2H3/t6-,8+,9+/m0/s1 Y
    Key: ZDKZHVNKFOXMND-NBEYISGCSA-N Y
  • 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
  • Key: ZDKZHVNKFOXMND-NBEYISGCBC
  • O=C1O\C=C(/[C@H]2CC[C@@H]([C@@H]12)C)C
Properties
C10H14O2
Molar mass 166.220 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Nepetalactones are a group of iridoid analog stereoisomers produced by Nepeta cataria (catnip) and certain other plants in the genus Nepeta in order to repel insects. They are also produced by many aphids, in which they are sex pheromones. Nepetalactones are cat attractants, and cause the behavioral effects that catnip induces in domestic cats. However, they affect visibly only about two thirds of adult cats. They produce similar behavioral effects in many other felids, especially in lions and jaguars. In 1941, the research group of Samuel M. McElvain was the first to determine the structures of nepetalactones and several related compounds.