490-10-8

Basic information

• Product Name: cis,trans-Nepetalactone
• Synonyms: cis,trans-Nepetalactone;(4aR)-5,6,7,7aβ-Tetrahydro-4,7α-dimethylcyclopenta[c]pyran-1(4aH)-one;(4aR)-5,6,7,7aβ-Tetrahydro-4,7α-dimethylcyclopenta[c]pyran-1(4aβH)-one;cis,cis-Nepetalactone;cis-cis-Nepetalactone;MD1-84;Tetrahydro-4,7-dimethylcyclopenta[c]pyranone
• CAS NO: 490-10-8
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22
• Mol File: 490-10-8.mol
• Article Data: 0

Chemical Properties

• Melting Point: 74°
• Boiling Point: bp0.05 71-72°
• Flash Point: 107.7°C
• Appearance: /
• Density: d425 1.0663
• Vapor Pressure: 0.00677mmHg at 25°C
• Refractive Index: nD25 1.4859
• Storage Temp.: Hygroscopic, Refrigerator, Under inert atmosphere
• Solubility: Chloroform (Sparingly), Diethyl Ether (Sparingly), Ethyl Acetate (Slightly), Met
• Stability: Hygroscopic
• CAS DataBase Reference: cis,trans-Nepetalactone(CAS DataBase Reference)
• NIST Chemistry Reference: cis,trans-Nepetalactone(490-10-8)
• EPA Substance Registry System: cis,trans-Nepetalactone(490-10-8)

Safety Data

• Hazardous Substances Data: 490-10-8(Hazardous Substances Data)

Usage

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/t6-,8+,9+/m0/s1

Synthetic route

nepetalactone (490-10-8) → 4,7-dimethyl-hexahydro-cyclopenta[c]pyran-1-one (490-09-5, 21950-33-4) + optically inactive 2-isopropyl-5-methyl-cyclopentanecarboxylic acid (528-23-4)

Conditions	Yield
With hydrogen; 5%-palladium/activated carbon In hexanes at 25℃; under 26852.7 Torr; for 0.17 - 4h; Product distribution / selectivity;	A 92.2% B 9%
With hydrogen; platinum on carbon In ethanol at 24 - 100℃; under 62706.3 Torr; for 0.5 - 3.82h; Product distribution / selectivity;	A 82.1% B 8.9%
With hydrogen; 5%-palladium/activated carbon In isopropyl alcohol at 25℃; under 26027.6 Torr; for 0.17 - 6h; Product distribution / selectivity;	A 44.8% B 2.7%

nepetalactone (490-10-8) → 4α,4aα,7α,7aα-dihydronepetalactone (24190-27-0) + (4S,4aR,7S,7aR)-4,7-dimethylhexahydrocyclopenta[c]pyran-1(3H)-one (24190-26-9)

Conditions	Yield
With hydrogen; 2% palladium on strontium carbonate In ethanol at 20℃; under 2311.54 Torr; for 48h;

nepetalactone (490-10-8) → 4aβ,7α,7aβ-Nepetalactone (21651-53-6) + nepetalactone (21651-62-7) + (4aS,7S,7aS)-nepetalactone (17257-15-7)

Conditions	Yield
Resolution of racemate;

nepetalactone (490-10-8) → (4aS,7S,7aS)-nepetalactone (17257-15-7)

Conditions	Yield
Resolution of racemate;

nepetalactone (490-10-8) → 4,7-dimethyl-hexahydro-cyclopenta[c]pyran-1-one (490-09-5, 21950-33-4)

Conditions	Yield
With hydrogen; 5%-palladium/activated carbon at 25℃; under 25877.6 Torr; Product distribution / selectivity;

nepetalactone (490-10-8) → nepetalic acid + 4,7-dimethyl-hexahydro-cyclopenta[c]pyran-1-one (490-09-5, 21950-33-4) + optically inactive 2-isopropyl-5-methyl-cyclopentanecarboxylic acid (528-23-4)

Conditions	Yield
With hydrogen; 5%-palladium/activated carbon at 15 - 25℃; under 1575.16 - 62031.2 Torr; Product distribution / selectivity;

Downstream Products

• 490-09-5 dihydronepetalactone 
• 528-23-4 optically inactive 2-isopropyl-5-methyl-cyclopentanecarboxylic acid 
• 21651-53-6 4aβ,7α,7aβ-Nepetalactone 
• 21651-62-7 nepetalactone 
• 17257-15-7 (4aS,7S,7aS)-nepetalactone