Menthol

Base Information

• Chemical Name: Menthol
• CAS No.: 1490-04-6
• Molecular Formula: C₁₀H₂₀O
• Molecular Weight: 156.268
• Hs Code.: 29061100
• European Community (EC) Number: 201-939-0,216-074-4,624-350-4
• DSSTox Substance ID: DTXSID8029650
• Nikkaji Number: J2.129F
• Wikipedia: Menthol
• Wikidata: Q27109870,Q104625119,Q99693372
• NCI Thesaurus Code: C80301
• RXCUI: 6750
• Pharos Ligand ID: D4NAHHQY55AV
• Metabolomics Workbench ID: 129775
• ChEMBL ID: CHEMBL256087
• Mol file: 1490-04-6.mol

Synonyms:Cyclohexanol, 5-methyl-2-(1-methylethyl)-;Menthol;Menthol, (1alpha,2beta,5alpha)-Isomer

Chemical Property of Menthol

Chemical Property:

• Appearance/Colour: colourless crystals
• Vapor Pressure: 0.8 mm Hg ( 20 °C)
• Melting Point: 34-36 °C(lit.)
• Boiling Point: 215.383 °C at 760 mmHg
• PKA: 15.30±0.60(Predicted)
• Flash Point: 93.333 °C
• PSA: 20.23000
• Density: 0.89 g/cm³
• LogP: 2.43950
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Very soluble in ethanol (95%), chloroform, ether, fatty oils and liquid paraffin; freely soluble in glacial acetic acid;soluble in acetone and benzene; very slightly soluble in glycerin; practically insoluble in water.
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 156.151415257
• Heavy Atom Count: 11
• Complexity: 120

Purity/Quality:

99%min ^*data from raw suppliers

Menthol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 37/38-41-48/20/22-40-22
• Safety Statements: 36/37/39-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CC1CCC(C(C1)O)C(C)C
• Recent ClinicalTrials: The Influence of Menthol Gel During Exercise With Heat
• Recent EU Clinical Trials: A multi-centre, randomised, placebo and active-controlled, double-blind, cross-over, phase IIa proof-of-concept trial to investigate the efficacy and safety of AX-8 Tablets 5 mg in patients with chronic refractory cough and associated upper airway symptoms
• Uses: menthol is a fragrance. It is also said to be anti-septic, cooling, refreshing, and a blood-circulation stimulant. Menthol gives the skin a “cool” feeling after use. It constitutes almost 50 percent of peppermint oil but can also be synthetically produced through the hydrogenation of thymol. It is non-toxic in low doses, but in high concentrations it can be irritating to the skin, especially the mucous membranes. Labelled Menthol. Used for oral gel patch or film containing herb extracts or Chinese medicine, fruit extract, spearmint, and menthol for smoking cessation. Menthol is used in confectionery, perfumery, cough drops, cigarettes, liqueurs, etc.; topical antipruritic; local anesthetic; gastric sedative.

Technology Process of Menthol

There total 47 articles about Menthol 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: 65.58%

thymol (89-83-8) → DL-neomenthol (490-99-3,491-01-0,491-02-1,1490-04-6,2216-51-5,2216-52-6,3623-51-6,3623-52-7,3623-53-8,15356-60-2,15356-70-4,20747-49-3,20752-33-4,20752-34-5,23283-97-8,64282-88-8,89-78-1) + isomenthol (3623-52-7) + menthol (15356-70-4)

Guidance literature:

With hydrogen; at 190 ℃; under 15001.5 Torr; Temperature; Pressure;

Reference yield: 49.0%

thymol (89-83-8) → DL-neomenthol (490-99-3,491-01-0,491-02-1,1490-04-6,2216-51-5,2216-52-6,3623-51-6,3623-52-7,3623-53-8,15356-60-2,15356-70-4,20747-49-3,20752-33-4,20752-34-5,23283-97-8,64282-88-8,89-78-1) + isomenthol (3623-52-7)

Guidance literature:

With hydrogen; In cyclohexane; at 120 ℃; for 1.5h; under 22502.3 Torr; Time; Reagent/catalyst;

Reference yield: 2.0%

rac-neomenthyl-4-tolylsulfonate (14539-76-5) → p-4(8)-menthene (1124-27-2) + (Z)-p-menthan-4-ol (3239-03-0) + cis-p-menthan-4-ol (3239-02-9) + DL-neomenthol (490-99-3,491-01-0,491-02-1,1490-04-6,2216-51-5,2216-52-6,3623-51-6,3623-52-7,3623-53-8,15356-60-2,15356-70-4,20747-49-3,20752-33-4,20752-34-5,23283-97-8,64282-88-8,89-78-1) + 3-p-menthene (500-00-5)

Guidance literature:

2,6-dimethylpyridine; In water; at 20 ℃; Product distribution; other solvent and temperature;

DOI:10.1021/jo01305a003

upstream raw materials:

(2R,5S)-menthone

thymol

(+/-)-menthone

aluminum isopropoxide

Downstream raw materials:

L-menthylsuccinic acid

(+/-)-phthalic acid mono-neomenthyl ester

menthol

(-)-neomenthol

Refernces

• 1、 Cirujano,Llabres I Xamena,Corma. "MOFs as multifunctional catalysts: One-pot synthesis of menthol from citronellal over a bifunctional MIL-101 catalyst". . p. 4249 - 4254. Retrieved 2012.
• 2、 Nasipuri, Dhanonjoy,Gupta, Mita Datta,Banerjee, Satinath. "STEREOCHEMICAL EVIDENCE FOR SINGLE ELECTRON TRANSFER MECHANISM IN THE REDUCTION OF CYCLIC KETONES WITH ALKOXYALUMINIUM DICHLORIDES". . p. 5551 - 5554. Retrieved 1984.
• 3、 Zuliani, Alessio,Cova, Camilla Maria,Manno, Roberta,Sebastian, Victor,Romero, Antonio A.,Luque, Rafael. "Continuous flow synthesis of menthol: Via tandem cyclisation-hydrogenation of citronellal catalysed by scrap catalytic converters". . p. 379 - 387. Retrieved 2020/02/13.
• 4、 Ilie, Adriana,Agudo, Rubén,Roiban, Gheorghe-Doru,Reetz, Manfred T.. "P450-catalyzed regio- and stereoselective oxidative hydroxylation of disubstituted cyclohexanes: Creation of three centers of chirality in a single CH-activation event This paper is dedicated to the memory of Harry H. Wasserman". . p. 470 - 475. Retrieved 2015/02/02.