l-Menthol

Base Information

• Chemical Name: l-Menthol
• CAS No.: 20747-49-3
• Deprecated CAS: 15356-70-4,98167-53-4,95650-44-5
• Molecular Formula: C10H20O
• Molecular Weight: 156.268
• Hs Code.: 2906199090
• European Community (EC) Number: 201-939-0,218-690-9,624-350-4,810-475-3
• NSC Number: 758395,62788,2603
• UNII: YS08XHA860,BZ1R15MTK7
• DSSTox Substance ID: DTXSID1020805,DTXSID1022180
• Nikkaji Number: J9.251G
• Wikipedia: Menthol
• Wikidata: Q407418
• NCI Thesaurus Code: C61809,C75073
• RXCUI: 236388,1430390
• Pharos Ligand ID: D4NYDDUYGWT3
• Metabolomics Workbench ID: 28091
• ChEMBL ID: CHEMBL470670
• Mol file: 20747-49-3.mol

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

Chemical Property of l-Menthol

Chemical Property:

• Vapor Pressure: 0.0323mmHg at 25°C
• Melting Point: 66.81°C (estimate)
• Refractive Index: n20/D 1.461
• Boiling Point: 215.4°Cat760mmHg
• Flash Point: 93.3°C
• PSA: 20.23000
• Density: 0.89g/cm³
• LogP: 2.43950
• 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%, ^*data from raw suppliers

Neomenthol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CC1CCC(C(C1)O)C(C)C
• Isomeric SMILES: C[C@@H]1CC[C@H]([C@@H](C1)O)C(C)C
• Recent ClinicalTrials: Antiperistaltic Effect and Safety of L-menthol in the Elderly With Contraindication to Buscopan
• 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
• Recent NIPH Clinical Trials: Effects of olfactory stimulation by L-menthol on dyspnea on exertion in chronic lung disease: A pilot study
• Uses: Neomenthol is an essential oil which has potential to prevent or cure stress related diseases. Inhibitory activity in such compounds may improve dimentia, onset of cancer.

Technology Process of l-Menthol

There total 59 articles about l-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:

DL-neomenthol

l-menthone

2-(2,6-dimethyl-5-heptenyl)-1,3-oxathiolan-5-one

Dodecanoic acid (1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester

Downstream raw materials:

(1S)-2-oxo-bornane-10-sulfonic acid-((1S)-neomenthyl ester)

menthol

Neomenthol

(+/-)-O-(Naphthoyl-⁽²⁾)-neomenthol

Refernces

• 1、 Read,Grubb. "-". . p. 167,169. Retrieved 1933.
• 2、 Barnes,Jackman,Macbeth. "-". . p. 1848,1850. Retrieved 1951.
• 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.