3937-48-2

Basic information

• Product Name: (1α,4α)-1-Hydroxymethyl-4-methylcyclohexane
• Synonyms: (cis-4-Methyl-cyclohexyl)-methanol;Cyclohexanemethanol, 4-methyl-, cis-;(1α,4α)-1-Hydroxymethyl-4-methylcyclohexane
• CAS NO: 3937-48-2
• Molecular Formula: C₈H₁₆O
• Molecular Weight: 128.21
• Mol File: 3937-48-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 90-91 °C(Press: 12 Torr)
• Appearance: /
• Density: 0.884±0.06 g/cm3(Predicted)
• PKA: 15.05±0.10(Predicted)
• CAS DataBase Reference: (1α,4α)-1-Hydroxymethyl-4-methylcyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: (1α,4α)-1-Hydroxymethyl-4-methylcyclohexane(3937-48-2)
• EPA Substance Registry System: (1α,4α)-1-Hydroxymethyl-4-methylcyclohexane(3937-48-2)

Safety Data

• Hazardous Substances Data: 3937-48-2(Hazardous Substances Data)

Usage

General Description

(1α,4α)-1-Hydroxymethyl-4-methylcyclohexane, also known as menthol, is a naturally occurring organic compound commonly found in mint plants. It is widely used in various consumer products, including food, pharmaceuticals, and cosmetics, due to its strong peppermint odor and cooling sensation. Menthol has been shown to have analgesic and anti-inflammatory properties, making it a popular ingredient in topical pain relief products such as ointments and creams. Additionally, it is used as a flavoring agent in foods, beverages, and oral hygiene products. In pharmaceuticals, menthol is used as a cough suppressant and in the treatment of sore throat and respiratory conditions. Overall, menthol is a versatile and widely used chemical with a range of applications in different industries.

Upstream product

• 934-67-8 (cis)-4-methylcyclohexanecarboxylic acid 
• 39155-38-9 (4-methylcyclohex-3-en-1-yl)methanol 
• 6493-79-4 methyl 4-methyl-3-cyclohexene-1-carboxylate 
• 20292-15-3 4-methyl-cyclohex-3-enecarboxylic acid ethyl ester 
• 78-79-5 isoprene 
• 99-94-5 p-Toluic acid 
• 2808-80-2 4-methyl-1-methylidenecyclohexane 
• 25244-23-9 cis-4-methyl-1-(ethoxycarbonyl)cyclohexane 

Downstream Products

• 7133-04-2 cis-4-methylcyclohexane carbaldehyde 

Relevant articles and documents

Hydrogenation of alkenes via cooperative hydrogen atom transfer

Radical hydrogenation via hydrogen atom transfer (HAT) to alkenes is an increasingly important transformation for the formation of thermodynamic alkane isomers. Current single-catalyst methods require stoichiometric oxidant in addition to hydride (H-) source to function. Here we report a new approach to radical hydrogenation: cooperative hydrogen atom transfer (cHAT), where each hydrogen atom donated to the alkene arrives from a different catalyst. Further, these hydrogen atom (H?) equivalents are generated from complementary hydrogen atom precursors, with each alkane requiring one hydride (H-) and one proton (H+) equivalent and no added oxidants. Preliminary mechanistic study supports this reaction manifold and shows the intersection of metal-catalyzed HAT and thiol radical trapping HAT catalytic cycles to be essential for effective catalysis. Together, this unique catalyst system allows us to reduce a variety of unactivated alkene substrates to their respective alkanes in high yields and diastereoselectivities and introduces a new approach to radical hydrogenation.

Simple, chemoselective hydrogenation with thermodynamic stereocontrol

Few methods permit the hydrogenation of alkenes to a thermodynamically favored configuration when steric effects dictate the alternative trajectory of hydrogen delivery. Dissolving metal reduction achieves this control, but with extremely low functional group tolerance. Here we demonstrate a catalytic hydrogenation of alkenes that affords the thermodynamic alkane products with remarkably broad functional group compatibility and rapid reaction rates at standard temperature and pressure.

Axial and equatorial cyclohexylacyl and tetrahydropyranyl-2-acyl radicals. An experimental and theoretical study

(Chemical Equation Presented) Axial and equatorial cyclohexylacyl and tetrahydropyranyl-2-acyl radicals gave distinct EPR spectra thanks to surprisingly large β-hydrogen atom hyperfine splittings that enabled them to be characterized and monitored. DFT computations indicated that the axial species (X = CH2) had a higher barrier to rotation about the (O)Cα-Cα bond. The computed difference ΔH° for the axial and equatorial radicals (R = H, X = CH2) was 0.8 kcal mol -1.