(+)-Menthol

Base Information

• Chemical Name: (+)-Menthol
• CAS No.: 15356-60-2
• Molecular Formula: C10H20O
• Molecular Weight: 156.268
• Hs Code.: 29061100
• European Community (EC) Number: 201-939-0,239-387-8,239-388-3
• UNII: C6B1OE8P3W
• DSSTox Substance ID: DTXSID8029733
• Nikkaji Number: J9.252E
• Wikidata: Q27084428
• RXCUI: 1648123
• Pharos Ligand ID: D4N6NA3R9J2J
• Metabolomics Workbench ID: 126880
• ChEMBL ID: CHEMBL2106989
• Mol file: 15356-60-2.mol

Synonyms:(+)-Menthol;15356-60-2;d-Menthol;(1S,2R,5S)-(+)-Menthol;(1S,2R,5S)-Menthol;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1S,2R,5S)-;(1S,2R,5S)-2-Isopropyl-5-methylcyclohexanol;Hexahydrothymol;Menthol, (+)-;(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexan-1-ol;(1S,2R,5S)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol;Menthol, (1S,3S,4R)-(+)-;UNII-C6B1OE8P3W;C6B1OE8P3W;rac-Menthol;DTXSID8029733;CHEBI:76306;(+)-(1S,2R,5S)-menthol;(+)-(1S,3S,4R)-menthol;p-Menthan-3-ol;EINECS 239-387-8;(1S,2R,5S)-5-methyl-2-(1-methylethyl)cyclohexanol;89-78-1;EC 239-387-8;Menthol, racemic;3-p-Menthanol;D - menthol;MFCD00062983;Racementhol [BAN:INN];(+)-p-Menthan-3-ol;Fisherman's friend lozenges;(1R,2S,5R)-Menthol;Menthol, cis-1,3,trans-1,4-;Fancol menthol;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1.alpha.,2.beta.,5.alpha.)-;(DL)-Menthol;(+) - menthol;(.+/-.)-Menthol;(1S)-(+)-menthol;(+/-)-Menthol racemic;MENTHOL, D-;Ciclohexanol, 5-metil-2-(1-metiletil)-, (1r, 2s, 5r)-rel-;SCHEMBL521946;DTXCID409733;GTPL2471;CHEMBL2106989;(1s, 2r, 5s)-(+)-menthol;Menthol, (1S,3S,4R)-()-;Tox21_201043;AKOS006281173;CS-W017993;DB11344;HY-W017277;NCGC00248905-01;NCGC00258596-01;AS-69562;(1S,2R,5S)-(+)-Menthol, 99%;CAS-15356-60-2;M0826;M3170;EN300-92162;A815982;(1S,2R,5S)-2-Isopropyl-5-methylcyclohexan-1-ol;(1S,2R,5S)-5-methyl-2-propan-2-yl-1-cyclohexanol;Q27084428;(1S,2R,5S)-5-methyl-2-propan-2-yl-cyclohexan-1-ol;F8889-8741;Z1198149783;5.alpha.-Methyl-2.beta.-(1.alpha.-methylethyl)cyclohexanol;Cyclohexanol,5-methyl-2-(1-methylethyl)-,(1S,2R,5S)-;2-Isopropyl-5-methylcyclohexanol, (1.alpha.,2.beta.,5.alpha.)-;5-Methyl-2-(1-methylethyl)cyclohexanol, (1.alpha.,2.beta.,5.alpha.)-;Cyclohexanol, 2-isopropyl-5-methyl-, (1.alpha.,2.beta.,5.alpha.)-;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1S-(1alpha,2beta,5alpha))-;(+)-Menthol, puriss. p.a., terpene standard for GC, >=99.0% (sum of enantiomers, GC);Cyclohexanol, 5-methyl-2-(1-methylethyl)-, [1S-(1.alpha.,2.beta.,5.alpha.)]-

Chemical Property of (+)-Menthol

Chemical Property:

• Vapor Pressure: 0.8 mm Hg ( 20 °C)
• Melting Point: 43-44 °C(lit.)
• Refractive Index: 50 ° (C=10, EtOH)
• 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.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in methanol (almost transparency), chloroform, alcohols, water (456 mg/L at 25°C), and ether.
• 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:

99.9% ^*data from raw suppliers

(1S,2R,5S)-(+)-Menthol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39

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
• Description: (+)-Menthol is a monoterpene alcohol that has been found in Cannabis and has antifungal activity. It inhibits the growth of F. verticillioides (MIC = 1.5 mM). Unlike (–)-menthol, (+)-menthol does not exhibit analgesia, antibacterial, anticancer, or cholinesterase inhibitory activities.
• Uses: (1S,2R,5S)-(+)-menthol can undergo acylation with acid anhydrides in the presence of trimethylsilyl trifluoromethanesulfonate to form the corresponding acylated products. (+)-MENTHOL is used for oral gel patch or film containing herb extracts or Chinese medicine, fruit extract, spearmint, and menthol for smoking cessation.

Technology Process of (+)-Menthol

There total 120 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

(1R,4R)-(+)-isomenthone

menthol

Menthone

Downstream raw materials:

di-((1S)-menthyl)-oxalate

Malonsaeure-bis<(1R)-menthyl>ester

phenylcarbamic acid-((1S)-menthyl ester)

d-menthol tetra-O-acetyl-β-D-glucoside

Refernces

Synthesis of enantiopure C₁ symmetric diphosphines and phosphino-phosphonites with ortho-phenylene backbones

10.1016/S0957-4166(01)00175-6

The research focuses on the synthesis of enantiopure C1 symmetric diphosphines and phosphino-phosphonites with ortho-phenylene backbones, which are valuable in asymmetric catalysis using coordination complexes of transition metals. The study utilizes various reactants, including 2-(diphenylphosphino)phenylphosphonous acid tetramethyldiamide, (+)-menthol, (1S,2S,3S,5R)-isopinocampheol, and (1R,2R)-trans-cyclohexanediol, to produce enantiopure phosphino-phosphonite ligands. The experiments involve Pd-catalyzed P–C coupling, halogen–metal exchange, and metallation–alkylation procedures. X-ray structural analysis was employed to determine the structures of the synthesized compounds, and various analytical techniques such as 31P{1H} NMR, 13C{1H} NMR, and optical rotation measurements were used to characterize the products and confirm the success of the reactions.

Toward stereoselective lactide polymerization catalysts: Cationic zinc complexes supported by a chiral phosphinimine scaffold

10.1021/ic201139b

The research focuses on the development of stereoselective lactide polymerization catalysts using cationic zinc complexes supported by a chiral phosphinimine scaffold. The main objective is to create catalysts that can operate at ambient temperature, enhancing efficiency and improving the kinetics of polymerization by reducing undesirable side reactions. The study involves the synthesis of chiral phosphinimine ligands based on the dibenzofuran (dbf) framework, specifically ligands (dbf)MePhPdNDipp (7) and (dbf)MePhPdNMes (8). These ligands are protonated with Br?nsted acids to form aminophosphonium salts, which then react with organozinc reagents to create cationic zinc complexes. The experiments utilized various reactants, including dichlorophenylphosphine, (+)-menthol, BH3, and organoazides, among others, to synthesize the ligands and their subsequent complexes. The synthesized compounds were analyzed using techniques such as NMR spectroscopy, X-ray crystallography, and elemental analysis to confirm their structures and compositions. The study also investigated the behavior of one of the complexes towards the ring-opening polymerization (ROP) of rac-lactide, aiming to produce polylactide (PLA) with improved physical properties.