Menthyl acetate

Base Information

• Chemical Name: Menthyl acetate
• CAS No.: 16409-45-3
• Molecular Formula: C12H22O2
• Molecular Weight: 198.305
• Hs Code.: 2915390090
• European Community (EC) Number: 201-911-8,220-076-0,219-856-3,218-767-7,249-409-8,240-459-6
• NSC Number: 122112,7350
• DSSTox Substance ID: DTXSID20859153
• Nikkaji Number: J156.147B
• Wikipedia: Menthyl_acetate
• Wikidata: Q72488412
• Metabolomics Workbench ID: 129697
• ChEMBL ID: CHEMBL254585
• Mol file: 16409-45-3.mol

Synonyms:Menthyl acetate;16409-45-3;89-48-5;Menthol, acetate;Menthyl acetate racemic;29066-34-0;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate;2230-87-7;FEMA Number 2668;Neomenthyl acetate;(5-methyl-2-propan-2-ylcyclohexyl) acetate;2623-23-6;HSDB 824;EINECS 240-459-6;5-Methyl-2-(1-methylethyl)cyclohexanol acetate;2-Isopropyl-5-methylcyclohexyl acetate;Acetic acid, p-menth-3-yl ester, dl-;AI3-36197;(+/-)-Menthyl acetate;EINECS 218-767-7;d-Neomenthyl acetate;(+)-Neomenthyl acetate;l-Menthyl acetate (natural);Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1R,2S,5R)-rel-;FEMA No. 2668;Neomenthol acetate;NSC 3722;EINECS 220-076-0;NSC 52970;L - menthyl acetate;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1R,2R,5R)-rel-;L-Menthyl acetate;(-)-Menthyl acetate;BRN 2208505;(+-)-Menthol acetate;(+-)-Menthyl acetate;Menthol, acetate, (1R,3R,4S)-(-)-;UNII-LF3LEI45OH;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1R,2S,5R)-;ACETIC ACID, p-MENTH-3-YL ESTER, l-;(.+/-.)-Menthol acetate;Cyclohexan-1-ol, 2-isopropyl-5-methyl-, acetate, L-;enthyl acetate;Menthol, neo-;CYCLOHEXANOL, 5-METHYL-2-(1-METHYLETHYL)-, ACETATE, (1.ALPHA.,2.BETA.,5.ALPHA.)-;20777-36-0;l-Menthyl acetate (1alpha,2beta,5alpha);(5R)-2-Isopropyl-5-methylcyclohexyl acetate;EC 201-911-8;starbld0011430;Menthyl acetate, 97%;MENTHYLACETATE97;(2-isopropyl-5-methyl-cyclohexyl) acetate;acetic acid menthyl ester;SCHEMBL57396;Menthol, acetate, (.+.)-;CHEMBL254585;2-Isopropyl-5-methylcyclohexyl acetate, (1.alpha.,2.beta.,5.alpha.)-;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 1-acetate, (1R,2R,5R)-rel-;DTXSID20859153;NSC7350;Acetic acid, p-menth-3-yl ester;CHEBI:191550;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1R-(1alpha,2beta,5alpha))-;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1theta-(1alpha,2beta,5alpha))-;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, [1R-(1.alpha.,2.beta.,5.alpha.)]-;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, [1S-(1.alpha.,2.alpha.,5.beta.)]-;(1S)-(+)-MENTHYLACETATE;NSC-7350;DL-Menthyl acetate, >=97%, FG;L-enthyl acetate;(-)-enthyl acetate;NSC122112;AKOS015837885;cis-1,3,trans-1,4- menthol acetate;( .PLUS/MINUS.) - menthyl acetate;Menthyl acetate (1alpha,2beta,5alpha);NSC 122112;NSC-122112;SB44841;SB46743;Menthol, acetate, cis-1,3,cis-1,4-;AS-83629;FT-0604526;FT-0604554;FT-0628207;FT-0631427;FT-0690234;FT-0694110;W-100373;Cyclohexanol, acetate, (1.alpha.,2.alpha.,5.beta.)-;Menthyl acetate, primary pharmaceutical reference standard;Cyclohexanol, acetate, [1S-(1.alpha.,2.alpha.,5.beta.)]-;Ciclohexanol, 5-metil-2-(1-metiletil)-, 1-acetato, (1r, 2s, 5r)-rel-;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1.alpha.,2.alpha.,5.alpha.)-;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1.alpha.,2.beta.,5.alpha.)-(.+.)-;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1alpha,2alpha,5beta)-;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1.alpha.,2.beta.,5.alpha.)-(.+/-.)-

Chemical Property of Menthyl acetate

Chemical Property:

• Vapor Pressure: 0.0707mmHg at 25°C
• Melting Point: <25 °C
• Refractive Index: n20/D 1.447(lit.)
• Boiling Point: 229.124 °C at 760 mmHg
• Flash Point: 92.222 °C
• PSA: 26.30000
• Density: 0.927 g/cm³
• 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:

98%,99%, ^*data from raw suppliers

DL-Menthyl acetate ≥97%,FG ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CC1CCC(C(C1)OC(=O)C)C(C)C
• Uses: L-Menthyl Acetate is a component of essential oils extracted from natural sources. Perfumery, flavoring.

Technology Process of Menthyl acetate

There total 49 articles about Menthyl 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:

Menthane

menthol

(-)-menthol

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

Refernces

• 1、 -. "A Method For Preparing (Meth)Acrylic Acid Ester Based Compound". Paragraph 0071-0072. . Retrieved 2021/05/07.
• 2、 Adarme, Carlos A.A.,Le?o, Raquel A.C.,de Souza, Stefania P.,Itabaiana, Ivaldo,de Souza, Rodrigo O.M.A.,Rezende, Claudia M.. "Continuous-Flow Chemo and Enzymatic Synthesis of Monoterpenic Esters with Integrated Purification". . p. 39 - 46. Retrieved 2018/05/22.