NEPETALACTON Chemical Properties

alpha 

D21 +3.7° (c = 27 in chloroform); D27.5 +11.11° (chloroform)

Boiling point:

270.6±19.0 °C(Predicted)

Density 

1.042±0.06 g/cm3(Predicted)

refractive index 

nD25 1.4878

storage temp. 

4°C, protect from light, stored under nitrogen

solubility 

DMSO : 100 mg/mL (601.61 mM; Need ultrasonic)

form 

Oil

color 

Colourless

Odor

Warm-spicy and very tenacious odor with an almost choking sweetness.

Stability:

Hygroscopic

EPA Substance Registry System

Cyclopenta[c]pyran-1(4aH)-one, 5,6,7,7a-tetrahydro-4,7-dimethyl-, (4aS,7S,7aR)- (21651-62-7)

NEPETALACTON Usage And Synthesis

Uses

cis-trans-Nepetalactone, is an organic compound, isolated from the plant catnip,which acts as a cat attractant. Nepetalactone can also be effective on some insects. It repels cockroaches and mosquitos.

Definition

ChEBI: Cis-trans-nepetalactone is a cyclopentapyran that is (4aS,7aR)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran substituted at position 1 by an oxo group and at positions 4 and 7 by methyl groups, respectively (the 4aS,7S,7aR-diastereomer). An iridoid monoterpenoid isolated from several Nepeta plant species. It is an aphid sex pheromone and cat attractant, and exhibits antibacterial, antifungal, and analgesic properties. It has a role as a pheromone, a plant metabolite, an insect attractant, an analgesic, an insect repellent, an antibacterial agent and an antifungal agent. It is an iridoid monoterpenoid and a cyclopentapyran.

Production Methods

Nepetalacton can be produced 1) by isolation from American catnip oil (about 45% lactone). 2) synthetic, from Ethyl-3-methyl-2-oxocyclopentane carboxylate with Bromo butyne.