l-Menthol

Base Information

• Chemical Name: l-Menthol
• CAS No.: 2216-51-5
• Deprecated CAS: 15356-70-4,98167-53-4,95650-44-5
• Molecular Formula: C10H20O
• Molecular Weight: 156.268
• Hs Code.: 29061100
• 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: 2216-51-5.mol

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

Chemical Property of l-Menthol

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 41-44 °C(lit.)
• Refractive Index: 1.46
• 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
• Water Solubility.: insoluble
• 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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:; R41:
• Safety Statements: S26:; S37/39:

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
• Sources: l-Menthol is a naturally occurring substance found in peppermint oil.^[1]
• Chemical Composition and Structure: l-Menthol has the molecular formula C₁₀H₂₀O and belongs to the class of organic compounds known as menthane monoterpenoids. Its chemical structure consists of a cyclic terpene backbone with an alcohol functional group.
• Medical Uses: l-Menthol is used in analgesic balms, oral hygiene products, and lozenges for its cooling sensation and analgesic properties. It has been shown to reduce thermal sensation, increase work-rate, and extend time to exhaustion in hot environments.^[2]
• Cosmetic Uses: l-Menthol is used in skincare products for its cooling and soothing effects.
• Mechanism of Action: l-Menthol enhances cooling by sensitizing the cold-sensitive TRPM8 receptor, primarily located on cutaneous Aδ fibers. It also exhibits analgesic properties, although the exact mechanisms are still being investigated.^[3]
• History and Development: The use of l-Menthol for its cooling sensation and analgesic properties dates back to ancient times. It was first suggested for pain relief in 1870 by Dr. A. Wright and has since been widely used in various medicinal and cosmetic products.^[1]
• References: [1] High-Concentration L-Menthol Exhibits Counter-Irritancy to Neurogenic Inflammation, Thermal and Mechanical Hyperalgesia Caused by Trans-cinnamaldehyde; DOI 10.1016/j.jpain.2016.05.004; [2] Oral L-menthol reduces thermal sensation, increases work-rate and extends time to exhaustion, in the heat at a fixed rating of perceived exertion; DOI 10.1007/s00421-017-3645-6; [3] Topical application of l-menthol induces heat analgesia, mechanical allodynia, and a biphasic effect on cold sensitivity in rats; DOI 10.1016/j.bbr.2010.04.015

Technology Process of l-Menthol

There total 357 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:

carbonic acid-(2-diethylamino-ethyl ester)-menthyl ester → (-)-menthol (2216-51-5) + 2-(Diethylamino)ethanol (100-37-8)

Guidance literature:

zerfaellt beim Erhitzen;

upstream raw materials:

pulegone

cyclohexane

(1R,2S,5R)-1-ethoxy-2-isopropyl-5-methylcyclohexane

ethyl sodium

Downstream raw materials:

Maleinsaeure-mono-(1'R,3'R,4'S)-3-menthylester

di-<(1R,2S,5R)-(-)-menthyl>maleate

2-bromo-propionic acid menthyl ester

pyruvic acid menthyl ester

Refernces

• 1、 Dauben et al.. "-". . p. 2579. Retrieved 1956.
• 2、 Delogu, Giovanna,Fabbri, Davide,Dettori, Maria Antonietta,Forni, Alessandra,Casalone, Gianluigi. "C2-Symmetric sulfur derivatives of 2,2′,3,3′'-tetramethoxybiphenyl". . p. 1451 - 1458. Retrieved 2001.
• 3、 Braga, Patricia R.S.,Costa, Andréia A.,De Freitas, Elon F.,Rocha, Rafael O.,De MacEdo, Julio L.,Araujo, Antonio S.,Dias, José A.,Dias, Sílvia C.L.. "Intramolecular cyclization of (+)-citronellal using supported 12-tungstophosphoric acid on MCM-41". . p. 99 - 105. Retrieved 2012.
• 4、 Murai, Toshiaki,Izumi, Chiyoko,Itoh, Toshihide,Kato, Shinzi. "Reactions of selenothioic acid S-esters with trivalent phosphorus compounds: New synthetic methods for α-phosphoryl alkyl sulfides and alkyl selenides". . p. 917 - 924. Retrieved 2000.
• 5、 Mironowicz, Agnieszka,Kukulczanka, Krystyna,Krasinski, Krzysztof,Siewinski, Antoni. "TRANSFORMATION OF ISOPRENOIDS BY ORCHIDS IN TISSUE CULTURE". . p. 1959 - 1960. Retrieved 1987.
• 6、 Kim, Yong Hae,Kim, Yong Il,Kim, Joong Young. "Facile oxidation of benzyl ethers by the 2-nitrobenzene-sulfonylperoxyl intermediate generated from 2-nitrobenzenesulfonyl chloride and superoxide". . p. 633 - 634. Retrieved 1998.
• 7、 Aoki, Toshiki,Kaneko, Takashi,Liu, Lijia,Suzuki, Junpei,Tang, Yanan,Teraguchi, Masahiro. "Novel highly efficient absolute optical resolution method by serial combination of two asymmetric reactions from acetylene monomers having racemic substituents". supporting information. p. 450 - 461. Retrieved 2022/01/15.
• 8、 Cook, Adam,MacLean, Haydn,St. Onge, Piers,Newman, Stephen G.. "Nickel-catalyzed reductive deoxygenation of diverse C-O bond-bearing functional groups". . p. 13337 - 13347. Retrieved 2021/11/20.