Back نپتالاکتون AZB Nepetalakton Czech Nepetalacton German Nepetalactona Spanish نپتالاکتون Persian Nepetalaktoni Finnish Népétalactone French Nepetalakton Hungarian Nepetalattone Italian ネペタラクトン Japanese

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 checkY
    Key: ZDKZHVNKFOXMND-NBEYISGCSA-N checkY
  • 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).
checkY verify (what is checkY☒N ?)

Nepetalactone is a name for multiple iridoid analog stereoisomers. Nepetalactones are produced by Nepeta cataria (catnip) and many other plants belonging to the genus Nepeta, in which they protect these plants from herbivorous insects by functioning as insect repellents. They are also produced by many aphids, in which they are sex pheromones.[1] 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.[2] In 1941, the research group of Samuel M. McElvain was the first to determine the structures of nepetalactones and several related compounds.[3][4]

  1. ^ Lichman BR, et al. (2020). "The evolutionary origins of the cat attractant nepetalactone in catnip". Science Advances. 6 (20): eaba0721. Bibcode:2020SciA....6..721L. doi:10.1126/sciadv.aba0721. PMC 7220310. PMID 32426505.
  2. ^ Espín-Iturbe LT, et al. (2017). "Active and passive responses to catnip (Nepeta cataria) are affected by age, sex and early gonadectomy in male and female cats". Behavioural Processes. 142: 110–115. doi:10.1016/j.beproc.2017.06.008. PMID 28698045. S2CID 37487390.
  3. ^ McElvain SM, Bright RD, Johnson PR (1941). "The constituents of the volatile oil of catnip. I. Nepetalic acid, nepetalactone and related compounds". Journal of the American Chemical Society. 63 (6): 1558–1563. doi:10.1021/ja01851a019.
  4. ^ Zimmermann N, et al. (2012). "Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones". Beilstein Journal of Organic Chemistry. 8 (1): 1246–1255. doi:10.3762/bjoc.8.140. PMC 3458745. PMID 23019455.

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