Isopulegyl acetate

Base Information

• Chemical Name: Isopulegyl acetate
• CAS No.: 57576-09-7
• Molecular Formula: C12H20 O2
• Molecular Weight: 196.29
• European Community (EC) Number: 260-820-1
• NSC Number: 403868,71930
• UNII: R3C4VQ5WQM
• DSSTox Substance ID: DTXSID60904398
• Nikkaji Number: J296.736G
• Wikidata: Q27287738
• Metabolomics Workbench ID: 48919
• ChEMBL ID: CHEMBL3120645
• Mol file: 57576-09-7.mol

Synonyms:isopulegyl acetate

Chemical Property of Isopulegyl acetate

Chemical Property:

• Vapor Pressure: 0.0248mmHg at 25°C
• Melting Point: 85°C
• Refractive Index: 1.4566 (estimate)
• Boiling Point: 248°Cat760mmHg
• Flash Point: 85.6°C
• PSA: 26.30000
• Density: 0.94g/cm³
• LogP: 2.93040
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 196.146329876
• Heavy Atom Count: 14
• Complexity: 233

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C(C1)OC(=O)C)C(=C)C
• Isomeric SMILES: C[C@@H]1CC[C@H]([C@@H](C1)OC(=O)C)C(=C)C

Technology Process of Isopulegyl acetate

There total 12 articles about Isopulegyl acetate 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: 96.0%

[(1R,2R,5R)-2-(1-hydroxy-1-methyl-ethyl)-5-methylcyclohexyl] acetate (91667-08-2) → (1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexyl acetate (57576-09-7)

Guidance literature:

With pyridine; thionyl chloride; at 0 ℃; for 0.5h;

Reference yield: 92.0%

acetic anhydride (108-24-7) + isopulegol (7786-67-6,18674-65-2,20549-46-6,21290-09-5,29141-10-4,50373-36-9,59905-53-2,59905-54-3,96612-21-4,104870-56-6,121468-66-4,122517-60-6,122517-61-7,144541-38-8,89-79-2) → (1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexyl acetate (57576-09-7)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/acs.orglett.5b01711

Reference yield: 71.0%

Ketene (463-51-4) + isopulegol (7786-67-6,18674-65-2,20549-46-6,21290-09-5,29141-10-4,50373-36-9,59905-53-2,59905-54-3,96612-21-4,104870-56-6,121468-66-4,122517-60-6,122517-61-7,144541-38-8,89-79-2) → (1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexyl acetate (57576-09-7)

Guidance literature:

at 80 ℃; for 4.5h;

upstream raw materials:

acetic anhydride

(rac)-neo-isopulegol

3,7-dimethyl-oct-6-enal

p-menth-8-en-3-one

Downstream raw materials:

2-((1R,2R,4S)-2-Hydroxy-4-methyl-cyclohexyl)-propenal

2-((1R,2S,4S)-2-Hydroxy-4-methyl-cyclohexyl)-propenal

isopulegol

L-menthyl acetate

Refernces

• 1、 Arora, Amandeep,Teegardin, Kip A.,Weaver, Jimmie D.. "Reductive Alkylation of 2-Bromoazoles via Photoinduced Electron Transfer: A Versatile Strategy to Csp2-Csp3 Coupled Products". supporting information. p. 3722 - 3725. Retrieved 2015/08/18.
• 2、 Serra, Stefano,Brenna, Elisabetta,Fuganti, Claudio,Maggioni, Francesco. "Lipase-catalyzed resolution of p-menthan-3-ols monoterpenes: Preparation of the enantiomer-enriched forms of menthol, isopulegol, trans- and cis-piperitol, and cis-isopiperitenol". . p. 3313 - 3319. Retrieved 2007/10/03.