Nepetalactone cis-trans-form

Base Information

• Chemical Name: Nepetalactone cis-trans-form
• CAS No.: 21651-62-7
• Deprecated CAS: 123357-09-5
• Molecular Formula: C10H14 O2
• Molecular Weight: 166.22
• UNII: 7TM7PE24UW
• DSSTox Substance ID: DTXSID6075198
• Nikkaji Number: J15.869K
• Wikipedia: Nepetalactone
• Wikidata: Q414257
• Metabolomics Workbench ID: 28065
• Mol file: 21651-62-7.mol

Synonyms:(4aS,7S,7aR)-nepetalactone;nepetalactone;nepetalactone, (4aalpha,7alpha,7abeta)-isomer;nepetalactone, (4aR-(4aalpha,7beta,7aalpha))-isomer

Chemical Property of Nepetalactone cis-trans-form

Chemical Property:

• Vapor Pressure: 0.00677mmHg at 25°C
• Refractive Index: nD25 1.4878
• Boiling Point: 270.6°Cat760mmHg
• Flash Point: 107.7°C
• PSA: 26.30000
• Density: 1.042g/cm³
• LogP: 2.10930
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 166.099379685
• Heavy Atom Count: 12
• Complexity: 242

Purity/Quality:

99% ^*data from raw suppliers

cis-transNepetalactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2C1C(=O)OC=C2C
• Isomeric SMILES: C[C@H]1CC[C@H]2[C@@H]1C(=O)OC=C2C
• 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.

Technology Process of Nepetalactone cis-trans-form

There total 49 articles about Nepetalactone cis-trans-form which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

(4aS,7S,7aS)-nepetalactone (17257-15-7) → nepetalactone (21651-62-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In xylene; for 2h; Heating;

DOI:10.1021/np049647d

Reference yield: 84.0%

(S)-10-oxocitronellal (67978-93-2,73127-93-2,105660-79-5,121962-36-5) → nepetalactone (21651-62-7)

Guidance literature:

With 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; 1-(2,4,6-trimethyl-3-nitrophenyl)-4-(2,4,6-trimethylphenyl)-3-phenyl-1H-1,2,4-triazol-4-ium chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 16h; Reagent/catalyst; Solvent; enantioselective reaction; Catalytic behavior; Inert atmosphere; Molecular sieve;

DOI:10.1021/acs.orglett.9b04034

Reference yield: 76.0%

C13H20OS2 → nepetalactone (21651-62-7)

Guidance literature:

With boron trifluoride diethyl etherate; mercury(II) oxide; In tetrahydrofuran; water;

DOI:10.1021/ja00286a035

upstream raw materials:

(+)-Nepetalic acid

bis-((4aR)-4c,7c-dimethyl-1-oxo-(4ar,7ac)-octahydro-cyclopenta[c]pyran-3ξ-yl)-ether

Citronellol

Nerol

Downstream raw materials:

p-bromophenacyl formate

α- and δ-skytanthines

iridomyrmecin

isoiridomyrmecin

Refernces

• 1、 Denmark, Scott E.,Sternberg, Jeffrey A.. "Intramolecular Cycloadditions of (Z)-α,β-Unsaturated Aldehydes with Vinyl Sulfides and Ketene Dithioacetals". . p. 8277 - 8279. Retrieved 1986.
• 2、 McElvain,Bright,Johnson. "-". . p. 1558,1561. Retrieved 1941.
• 3、 -. "Methods of separating ZE-nepetalactone and EZ-nepetalactone from catnip oil". Page/Page column 3; sheet 2. . Retrieved 2008/06/13.