3-Methylcyclohexanol

• CAS: 591-23-1
• Catalog Number: ACM591231
• Category: Main Products
• Molecular Weight: 114.19
• Molecular Formula: C₇H₁₄O
• Synonyms: 3-methyl-cyclohexanol; M-METHYLCYCLOHEXANOL; 3-METHYLHEXALIN; m-methyl-cyclohexano; 3-methyl-2-cyclohexanol; Cyclohexanol,3-methyl; Cyclohexanol,m-methyl; trans 3-methylcyclohexanol; 3-methyl-cyclohexano; (1R,3R)-(-)-3-methyl cyclohexanol; 3-methylcyclohexan-1-ol
• IUPAC Name: 3-methylcyclohexan-1-ol
• SMILES: CC1CCCC(C1)O
• InChI Key: HTSABYAWKQAHBT-UHFFFAOYSA-N
• Boiling Point: 163ºC
• Melting Point: -74ºC
• Flash Point: 62ºC
• Density: 0.91
• EC Number: 209-709-1
• Exact Mass: 114.10400
• Hazard Statements: Xn
• Safety Description: S24/25
• WGK Germany: 1

Case Study

A study on 3-methylcyclohexanol produced by fungal biotransformation

Coccia, Francesca, et al. Nanomaterials 8.10 (2018): 853.

Cycloalkanes account for up to 45% of hydrocarbon components and are mainly found in crude oil or refined petroleum products, primarily in the form of alkylated cyclohexane derivatives, and are increasingly appearing in environmental samples from soil and water. This study highlights the biotransformation of methyl and ethyl cyclohexane by the alkane-assimilating yeast Candida maltosa and the yeast Trichosporon mucoides, which utilizes phenols and benzoates, under laboratory conditions. During this biotransformation, 25 different metabolites, including 3-methylcyclohexanol, were detected and analyzed by HPLC and GC-MS. This is the first report of several novel transformation reactions of alkylated cycloalkanes by eukaryotic microorganisms.
To analyze the transformation products such as 3-methylcyclohexanol by gas chromatography-mass spectrometry (GC-MS), the culture supernatant obtained after centrifugation after 24 hours of cultivation was extracted three times with half the sample volume of diethyl ether at pH 9. The aqueous residue was then acidified to pH 2 and extracted three more times. The organic phase was dried over anhydrous sodium sulfate, and the solvent was evaporated. The resulting residues were dissolved in n-hexane (alkaline extraction) or methanol (acidic extraction), respectively.

3-Methylcyclohexanol used to visualize the characteristic relationships arising from UV-Vis spectra

Ware, Madeleine. (2021).

A large number of acid-catalyzed reactions involving cyclopentanol, cyclohexanol, cyclopentene, and cyclohexene were conducted. In these reactions, methylated or unmethylated cyclic alcohols or alkenes are protonated to generate cycloalkanes and allyl carbocations. The kinetics of these allyl carbocation formations were investigated using UV-Vis spectrophotometry. Unique analytical methods were developed to explore unknown relationships between the initial structure of the analyte and the characteristic absorption wavelengths observed in a given spectrum. These methods were used to determine how variations in temperature, sulfuric acid concentration, and cycloalkylation position affect the λmax absorption wavelength. The λmax peaks for most catalytic formation of allyl carbocations via cyclohexanol, cyclopentanol, cyclohexene, and cyclopentenoic acid are located in the 280-320 nm wavelength range. In experiments with cyclohexanol, 3-methylcyclohexanol, and 4-methylcyclohexanol, λmax appears to undergo a blue shift with increasing acidity.
Attempts were made to determine the wavelength range in which λmax appears when reacting with various molecules. Based on the starting materials, the reaction spectra were divided into four groups: cyclohexanol, cyclopentanol, cyclohexene, and cyclopentene. For each spectrum analyzed, several significant components and their corresponding wavelengths, λmax, minor peaks, and shoulders were recorded. The temperature and acidity of each reaction were also recorded. The 3-methylcyclohexanol reactions were sorted by acidity, with columns for wavelength (nm) and rows for reaction acidity and starting materials for each time series spectrum. The shift of λmax towards shorter wavelengths for 3-methylcyclohexanol appears to begin when the sulfuric acid concentration is above 90%. Light green indicates higher acidity, and dark green indicates lower acidity.

3-Methylcyclohexanol used in studies on the biocatalytic reduction of cyclohexanone by filamentous fungi

Melgar, Gliseida Zelayarán, et al. Glob J Sci Front Res Chem 13.5 (2013): 13-19.

The growth of filamentous fungal mycelia in malt extract medium was recorded at 32°C for 10 days to facilitate the biocatalytic reduction of cyclohexanone 1-3. Growth curves for marine and terrestrial fungi were plotted, with mycelial dry weight as the x-axis. When cyclohexanone 1-3 was added as a substrate during the exponential growth phase (72 hours), the mycelia of Aspergillus sp. and Rhizopus sp. efficiently catalyzed the biocatalytic reduction of cyclohexanone. The biocatalytic reduction produced products such as 3-methylcyclohexanol.
The ketone bodies exhibited excellent biotransformation capabilities through the mycelia of *Rhizopus* and *Aspergillus*. *Rhizopus* showed high yields in the catalytic reduction of cyclohexanones to 3-methylcyclohexanol. *Aspergillus* converted 83% of the cyclohexanone to 3-methylcyclohexanol after 96 hours of incubation. The transformation of 3-methylcyclohexanol by fungi was measured by GC-MS analysis and compared with the amount of 3-methylcyclohexanol. Stereoisomes were not separated by GC-FID and GC-MS analysis.

3-Methylcyclohexanol used in bimetallic nickel-iron catalyst studies

Nie, Lei, et al. Journal of Molecular Catalysis A: Chemical 388 (2014): 47-55.

The catalytic conversion of m-cresol in the presence of H₂ was investigated at 300°C and atmospheric pressure on silicon-supported nickel, iron, and bimetallic nickel-iron catalysts. On the monometallic nickel catalyst, the dominant product was 3-methylcyclohexanone, with a smaller amount of 3-methylcyclohexanol also present. On the iron and nickel-iron bimetallic catalysts, the major product was toluene, while the hydrogenation products (3-methylcyclohexanone and 3-methylcyclohexanol) were negligible throughout the conversion range.
The gas-phase conversion of m-cresol in nickel, nickel-iron, and iron catalysts was evaluated in a tubular quartz reactor at atmospheric pressure. The flow reaction system was equipped with a mass flow controller and an injection pump for continuous injection of m-cresol. The reactor was filled with 40-60 mesh granular catalyst sandwiched between two layers of quartz wool and preheated glass beads at the top to improve temperature uniformity. The catalyst was reduced in situ at 60 mL/min at 450°C for 1 h, followed by a temperature reduction to the reaction temperature of 300°C. The H/m-Creshol molar ratio was maintained at 60:1 for all runs. Products were quantified by gas chromatography using a capillary column and flame ionization detector. Hydrogenation of the carbonyl group yields a highly reactive unsaturated alcohol that readily dehydrates to toluene. This explains the high selectivity of Fe and Ni-Fe for toluene. Hydrogenation of the ring yields 3-methylcyclohexanone, which is further hydrogenated to 3-methylcyclohexanol.

Custom Q&A

What is the molecular formula of 3-Methylcyclohexanol?

The molecular formula of 3-Methylcyclohexanol is C7H14O.

What are the synonyms of 3-Methylcyclohexanol?

The synonyms of 3-Methylcyclohexanol are 3-METHYLCYCLOHEXANOL, 591-23-1, 3-methylcyclohexan-1-ol, m-Methylcyclohexanol, and Cyclohexanol, 3-methyl-.

What is the molecular weight of 3-Methylcyclohexanol?

The molecular weight of 3-Methylcyclohexanol is 114.19 g/mol.

What is the IUPAC name of 3-Methylcyclohexanol?

The IUPAC name of 3-Methylcyclohexanol is 3-methylcyclohexan-1-ol.

What is the InChI code of 3-Methylcyclohexanol?

The InChI code of 3-Methylcyclohexanol is InChI=1S/C7H14O/c1-6-3-2-4-7(8)5-6/h6-8H,2-5H2,1H3.

What is the CAS number of 3-Methylcyclohexanol?

The CAS number of 3-Methylcyclohexanol is 591-23-1.

What is the boiling point of 3-Methylcyclohexanol?

The boiling point of 3-Methylcyclohexanol is 162.00 to 164.00 °C.

What is the melting point of 3-Methylcyclohexanol?

The melting point of 3-Methylcyclohexanol is -5.5 °C (cis-isomer).

What is the color and physical description of 3-Methylcyclohexanol?

3-Methylcyclohexanol is a colorless viscous liquid.

How many hydrogen bond donor counts does 3-Methylcyclohexanol have?

3-Methylcyclohexanol has one hydrogen bond donor count.