21651-62-7

Basic information

• Product Name: NEPETALACTON
• Synonyms: NEPETALACTON;nepetalactone;Nepetalacton cis-trans-forM;NEPETALACTON (cis-transisoMer);(4aS,7S,7aR)-4,7-diMethyl-5,6,7,7a-tetrahydrocyclopenta[c]pyran-1(4aH)-one;Cyclopenta[c]pyran-1(4aH)-one,5,6,7,7a-tetrahydro-4,7-diMethyl-, (4aS,7S,7aR)-;Nepetalactone cis-trans-form
• CAS NO: 21651-62-7
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.21696
• EINECS: 1532714-185-1
• Mol File: 21651-62-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 270.6°Cat760mmHg
• Flash Point: 107.7°C
• Appearance: /
• Density: 1.042g/cm³
• Vapor Pressure: 0.00677mmHg at 25°C
• Refractive Index: nD25 1.4878
• CAS DataBase Reference: NEPETALACTON(CAS DataBase Reference)
• NIST Chemistry Reference: NEPETALACTON(21651-62-7)
• EPA Substance Registry System: NEPETALACTON(21651-62-7)

Safety Data

• Hazardous Substances Data: 21651-62-7(Hazardous Substances Data)

Usage

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.

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

Upstream product

• 524-06-1 (+)-Nepetalic acid 
• 1127-66-8 dolichodial 
• 23062-07-9 (E)-2,6-dimethyl-oct-2-ene-1,8-diol 
• 5949-05-3 (S)-Citronellal 
• 7540-51-4 (S)-3,7-dimethyl-6-octen-1-ol 
• 89822-36-6 (1S,4R,5R)-4,8-dimethylbicyclo<3.3.0>oct-7-en-2-one 
• 120657-91-2 (1S,4R,5R)-4,8-dimethyl-2,2-ethylenedioxybicyclo<3.3.0>oct-7-ene 
• 120709-97-9 (1R,4R,5R,8S)-4,8-dimethylbicyclo<3.3.0>octan-2-one 
• 120657-92-3 (1S,4R,5R,7S,8S)-4,8-dimethyl-2,2-ethylenedioxy-7-hydroxybicyclo<3.3.0>octane 
• 120709-96-8 (1S,4R,5R,7R,8R)-4,8-dimethyl-2,2-ethylenedioxy-7-hydroxybicyclo<3.3.0>octane 
• 120709-99-1 (1R,4S,5R,8S)-4,8-dimethyl-2-trimethylsilyloxybicyclo<3.3.0>oct-2-ene 
• 120657-93-4 (1S,4R,5R,8R)-4,8-dimethyl-2,2-ethylenedioxybicyclo<3.3.0>octan-7-one 
• 120709-95-7 (1S,4R,5R,8S)-4,8-dimethyl-2,2-ethylenedioxybicyclo<3.3.0>octan-7-one 
• 361438-06-4 gastrolactone 

Downstream Products

• 10536-76-2 p-bromophenacyl formate 
• 485-43-8 iridomyrmecin 
• 485-43-8 isoiridomyrmecin 
• 2065-32-9 α- and δ-skytanthines 

Relevant articles and documents

Divergent synthetic route to new cyclopenta[c]pyran iridoids: Syntheses of jatamanin A, F, G and J, gastrolactone and nepetalactone

Six natural iridoids including jatamanin A, F, G and J, gastrolactone and nepetalactone have been synthesized via the efficient transformation of a core cyclopenta[c]pyran intermediate. Key features of the syntheses include the stereoselective construction of the core cyclopenta[c]pyran skeleton of the iridoid lactones via a Pd(0)-catalyzed intramolecular allylic alkylation, and the facile transformation of the common intermediate into natural iridoids.

Simplified isolation procedure and interconversion of the diastereomers of nepetalactone and nepetalactol

Three nepetalactones were isolated from Nepeta racemosa (mussinii) by traditional methods. An improved method was developed to isolate nepetalactones from N. faassenii. An epimerization procedure was used to prepare the fourth 7S-nepetalactone diastereomer. The cis-fused nepetalactols were prepared by reduction of the corresponding nepetalactones, while the trans-fused nepetalactols were unstable and found to undergo ring-opening reactions yielding iridodials. The characterizations and structural assignments by means of NMR agree with quantum chemical density functional calculations.

Enantiospecific Synthesis of Nepetalactones by One-Step Oxidative NHC Catalysis

An efficient oxidative NHC-catalyzed one-step transformation of (S)-or (R)-8-oxocitronellal to nepetalactone (NL) in enantio- A nd diastereomerically pure form has been developed. Several new and "easy to make" N-Mes-or N-Dipp-substituted 1,2,4-triazolium salts carrying nitroaromatic groups on N1 were synthesized and evaluated as precatalysts in combination with base and stoichiometric organic oxidant. Under optimized conditions, NLs are accessible in very good yields and diastereomerically pure under mild conditions. The oxidant used could be recovered and recycled under operationally simple conditions.

INSECT REPELLENT COMPOSITIONS COMPRISING DIHYDRONEPETALACTONE

Dihydronepetalactone, a minor natural constituent of the essential oil of catmints (Nepeta spp.) such as Nepeta cataria, has been identified as an effective insect repellent compound. Synthesis of dihydronepetalactone may be achieved by hydrogenation of nepetalactone, the major constituent of catmint essential oils. This compound, which also has fragrance properties, may be used commercially for its insect repellent properties.