Isomenthol acetate

Base Information

• Chemical Name: Isomenthol acetate
• CAS No.: 20777-45-1
• Molecular Formula: C₁₂H₂₂O₂
• Molecular Weight: 198.305
• DSSTox Substance ID: DTXSID901020799
• Nikkaji Number: J313.796A
• Mol file: 20777-45-1.mol

Synonyms:20777-45-1;rel-(1R,2S,5S)-2-Isopropyl-5-methylcyclohexyl acetate;Isomenthol acetate;SCHEMBL23722957;DTXSID901020799;(1S,4S)-p-Menthane-3beta-ol acetate

Chemical Property of Isomenthol acetate

Chemical Property:

• Boiling Point: 229.1±8.0 °C(Predicted)
• PSA: 26.30000
• Density: 0.92±0.1 g/cm3(Predicted)
• LogP: 3.01030
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 198.161979940
• Heavy Atom Count: 14
• Complexity: 199

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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 Isomenthol acetate

There total 46 articles about Isomenthol 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: 98.0%

menthol (89-78-1) + acetic anhydride (108-24-7) → 2-isopropyl-5-methylcyclohexyl acetate (89-48-5,2230-87-7,2552-91-2,2623-23-6,5157-89-1,16409-45-3,20777-36-0,20777-45-1,29066-34-0,42241-42-9,50539-17-8,55058-46-3,79199-84-1,146502-80-9)

Guidance literature:

With lithium perchlorate; at 25 ℃; for 22h;

DOI:10.1055/s-2001-17483

Reference yield: 97.0%

Isopropenyl acetate (108-22-5) + menthol (89-78-1) → 2-isopropyl-5-methylcyclohexyl acetate (89-48-5,2230-87-7,2552-91-2,2623-23-6,5157-89-1,16409-45-3,20777-36-0,20777-45-1,29066-34-0,42241-42-9,50539-17-8,55058-46-3,79199-84-1,146502-80-9)

Guidance literature:

With P(MeNCH₂CH₂)3N; In tetrahydrofuran; at 50 ℃; for 14h;

DOI:10.1021/jo981819m

Reference yield: 95.0%

menthol (89-78-1) + acetyl chloride (75-36-5) → 2-isopropyl-5-methylcyclohexyl acetate (89-48-5,2230-87-7,2552-91-2,2623-23-6,5157-89-1,16409-45-3,20777-36-0,20777-45-1,29066-34-0,42241-42-9,50539-17-8,55058-46-3,79199-84-1,146502-80-9)

Guidance literature:

With potassium fluoride on basic alumina; In toluene; for 2h;

DOI:10.1016/S0040-4020(01)00677-9

upstream raw materials:

acetic anhydride

menthol

[1-α]-5-methyl-2-[1-methylethyl]-cyclohexanol

vinyl acetate

Downstream raw materials:

(1S,2R,5S)-(+)-menthol

(-)-menthol

(+/-)-menthone

menthol

Refernces

• 1、 -. "A Method For Preparing (Meth)Acrylic Acid Ester Based Compound". Paragraph 0071-0072. . Retrieved 2021/05/07.
• 2、 Belkacemi, Fatima Zohra,Merabet-Khelassi, Mounia,Aribi-Zouioueche, Louisa,Riant, Olivier. "Production of l-menthyl acetate through kinetic resolution by?Candida cylindracea lipase: effects of alkaloids as additives". . p. 6847 - 6860. Retrieved 2018/07/15.