491-04-3

Basic information

• Product Name: 6-(isopropyl)-3-methylcyclohex-2-en-1-ol
• Synonyms: 6-(isopropyl)-3-methylcyclohex-2-en-1-ol;(Z)-piperitol,1-p-menthen-3-ol;2-Cyclohexen-1-ol, 3-methyl-6-(1-methylethyl)-;PARA-MENTH-1-EN-3-OL;(3R,4S)-p-Menth-1-en-3-ol;[1R,2S,(+)]-5-Methyl-2-(1-methylethyl)-5-cyclohexen-1-ol;d-cis-Piperitol;1-p-Menthen-3-ol
• CAS NO: 491-04-3
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.24932
• EINECS: 207-725-3
• Mol File: 491-04-3.mol

Chemical Properties

• Boiling Point: 237.64°C (rough estimate)
• Flash Point: 89.8°C
• Appearance: /
• Density: 0.9119
• Vapor Pressure: 0.0205mmHg at 25°C
• Refractive Index: 1.4729
• PKA: 14.70±0.60(Predicted)
• CAS DataBase Reference: 6-(isopropyl)-3-methylcyclohex-2-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(isopropyl)-3-methylcyclohex-2-en-1-ol(491-04-3)
• EPA Substance Registry System: 6-(isopropyl)-3-methylcyclohex-2-en-1-ol(491-04-3)

Safety Data

• Hazardous Substances Data: 491-04-3(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
6-(isopropyl)-3-methylcyclohex-2-en-1-ol is used as a flavor and fragrance ingredient due to its fresh, pungent odor and taste. It provides a cooling impact, fresh and clean minty body, and candy cane confection-like aroma when used at 1.0% concentration.
Used in Essential Oils:
6-(isopropyl)-3-methylcyclohex-2-en-1-ol is found in pennyroyal and other mentha oils, as well as in essential oils from various plants such as dill herb, lemon balm, black currant, ginger, myrtle, berry, nutmeg, rosemary, and sweet marjoram. It contributes to the unique aroma and flavor profile of these essential oils, making it a valuable component in the production of natural fragrances and flavors.
Used in the Production of Synthetic Fragrances and Flavors:
6-(isopropyl)-3-methylcyclohex-2-en-1-ol can be synthesized through chemical reactions, such as the reduction of racemic piperitone with lithium aluminum hydride or aluminum isopropoxide. The synthetic version of this compound can be used in the production of fragrances and flavors, offering a more consistent and cost-effective alternative to natural sources.
Used in the Cosmetics Industry:
Due to its pleasant aroma and cooling sensation, 6-(isopropyl)-3-methylcyclohex-2-en-1-ol can be used as an additive in the cosmetics industry, particularly in products like perfumes, colognes, and personal care items that require a refreshing and invigorating scent.
Used in the Pharmaceutical Industry:
As a monoterpene alcohol, 6-(isopropyl)-3-methylcyclohex-2-en-1-ol may have potential applications in the pharmaceutical industry, particularly in the development of new drugs or as an intermediate in the synthesis of bioactive compounds. Its unique structure and properties could make it a valuable candidate for further research and development in this field.

Preparation

By reduction of racemic pipertone with lithium aluminum hydride or aluminum isopropoxide; the d-form is isolated from natural sources.

InChI:InChI=1/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9-11H,4-5H2,1-3H3

Upstream product

• 89-81-6 piperitone 
• 4573-50-6 (-)-piperitone 
• 4573-50-6 (S)-(+)-piperitone 
• 555-31-7 aluminum isopropoxide 
• 124-41-4 sodium methylate 
• 74-88-4 methyl iodide 
• 61585-35-1 p-menth-1-ene 
• 112068-28-7 (3R,4R)-1-methyl-4-(1-methylethyl)-cyclohex-1-en-3-yl acetate 
• 28582-40-3 trans-piperityl chloride 
• 138-86-3 limonene. 
• 4221-98-1 (R)-5-isopropyl-2-methylcyclohexa-1,3-diene 

Downstream Products

• 116977-43-6 piperityl phloroglucinol 
• 906433-07-6 (+/-) linderatin 
• 99-83-2 p-mentha-1,5-diene 
• 555-10-2 beta-phellandrene 
• 94281-61-5 (4-isopropyl-1-methyl-2-cyclohexenyl) methyl ether 
• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 
• 54982-74-0 (4-isopropyl-1-methyl-2-cyclohexenyl) ethyl ether 
• 54982-75-1 cis-(6-isopropyl-3-methyl-2-cyclohexenyl) ethyl ether 
• 54982-75-1 trans-(6-isopropyl-3-methyl-2-cyclohexenyl) ethyl ether 
• 1204-30-4 2-cyclohexen-1-ol, 3-methyl-6-(1-methylethyl)-, acetate 

Relevant articles and documents

Linderapyrone: A Wnt signal inhibitor isolated from Lindera umbellata

Linderapyrone, a Wnt signal inhibitor was isolated from the methanolic extract of the stems and twigs of Lindera umbellata together with epi-(-)-linderol A. Linderapyrone inhibited TCF/β-catenin transcriptional activity that was evaluated using cell-based TOPFlash luciferase assay system. To evaluate the structure-activity relationship and mechanism, we synthesized linderapyrone and its derivatives from piperitone. As the results of further bioassay for synthesized compounds, we found both of pyrone and monoterpene moieties were necessary for inhibitory effect. cDNA microarray analysis in a linderapyrone derivative treated human colorectal cancer cells showed that this compound downregulates Wnt signaling pathway. Moreover, we successes to synthesize the derivative of linderapyrone that has stronger inhibitory effect than linderapyrone and ICG-001 (positive control).

Transition-Metal-Free Allylic Borylation of 1,3-Dienes

This work explains the reactivity of diboron reagents with 1,3-dienes in a transition-metal-free context. The sole addition of Na2CO3 (30 mol %) to bis(pinacolato)diboron in MeOH allows the 1,4-hydroboration of cyclic and noncyclic 1,3-dienes. The electronic influence on the substrate guarantees the conjugated 1,4-hydroboration versus 1,2-diboration. DFT calculations show that the distribution of charge in the allylic anion intermediate governs the selectivity toward 1,4-hydroboration, while the favored trans configuration in diene reagents determines the preference for the E allyl boronate products.

Enantioselective Total Syntheses of (+)-Hostmanin A, (-)-Linderol A, (+)-Methyllinderatin and Structural Reassignment of Adunctin E

A one-step protocol has been developed for the enantioselective synthesis of hexahydrodibenzofuran derivatives using a modified Friedel-Crafts reaction. The developed method was applied to the synthesis of a series of natural products including (+)-hostmanin A, (+)-methyllinderatin, and (-)-linderol A. The synthetic and spectroscopic data investigations led to the structural reassignment of natural product adunctin E, which was further confirmed by single-crystal X-ray analysis. (Chemical Presented).

Enzymatic resolution of racemic secondary cyclic allylic alcohols

The resolutions of five racemic cyclic alcohols: 6,6-dimethylcyclohex-2-en-1-ol (±)-5, 4,4-dimethylcyclohex-2-en-1-ol (±)-7, 5,5-dimethylcyclohex-2-en-1-ol (±)-11 and isomeric trans-(±)-13 and cis-piperitols (±)-14 are presented. They were resolved by enzymatic esterification with vinyl esters or by enzymatic hydrolysis of their racemic esters in phosphate buffer. The following lipases were used as biocatalysts: Novozyme 435 (Candida antarctica), Amano PS (Burkholderia cepacia) and lipase from Candida cylindracea. All isomers of alcohols were obtained with at least 96% ee.

Enantiomeric differentiation of oxygenated p-menthane derivatives by 13C NMR using Yb(hfc)3

The 13C NMR behaviour of 21 p-menthanic terpene bearing an oxygenated function (alcohol, ketone, acetate) was examined in the presence of a chiral lanthanide shift reagent (Yb(hfc)3). For each monocyclic compound, we measured the lanthanide-induced shift (LIS) on the signals of the carbons and the splitting of signals allowing the enantiomeric differentiation. Some general features were found about their LIS behaviour: experimental data establishing distinct patterns for carvomenthone-like compounds and menthone-like compounds. The enantiomeric splitting was observed for the majority of signals in the spectrum of each compound. In the case of alcohols and acetates, the influence of the relative stereochemistry (cis vs trans) of isopropyl(ene) and the binding function was discussed. Copyright

Lipase-catalyzed resolution of p-menthan-3-ols monoterpenes: Preparation of the enantiomer-enriched forms of menthol, isopulegol, trans- and cis-piperitol, and cis-isopiperitenol

A study on the enzymic resolution of the most common p-menthan-3-ol monoterpene isomers is described. Enantioenriched alcohols 1, 5, 10, 11 and 12 are obtained by means of the lipase-mediated kinetic acetylation of the corresponding racemic materials. The stereochemical aspects of the enzymic process have been investigated. We found that the structural features of the starting p-menthan-3-ol as well as the kind of lipase used, impacted strongly on the enantioselectivity of the resolution. The potentialities of this approach for preparative purposes are discussed.

Microbial Allyl Rearrangement and Resolution of Acetates of Unsaturated Cyclic Terpene Alcohols by Pseudomonas sp. NOF-5 Strain

Microbial hydrolysis of the acetates of unsaturated cyclic terpene alcohols by Pseudomonas sp.NOF-5 isolated from soil was investigated. (+/-)-trans-Carveyl acetate ((+/-)-trans-3) was enantioselectively hydrolyzed with NOF-5 strain to give (-)-trans-carveol ((-)-trans-2 of 86.6percent optical purity).However, the hydrolysis of (+/-)-cis-3 was less enantioselective, while (+/-)-piperitylacetate ((+/-)-6, a cis and trans mixture) was hydrolyzed to give the (-)-trans- and (-)-cis-piperitols ((-)-trans-5 and (-)-cis-5) in a poor optical yield.In this case, other tert-alcohols, (+)-trans- and (-)-cis-2-p-menthen-1-ols ((+/-)-trans-7 and (-)-cis-7, were also produced.Furthermore, microbial and enzymic allyl rearrangements of (+)-trans-6 and (-)-trans-verbenylacetate ((-)-trans-11) were studied.Biological treatment of (+)-trans-6 and (-)-trans-11 with NOF-5 or its esterase gave (+)-trans- and (-)-cis-7 and (+)-cis-3-pinen-2-ol ((+)-cis-12), respectively.

Carvone- and Piperitone-Derived Allylic Stannanes and Aspects of Their Electrophilic Substitution

cis- and trans-Carvotanacetols and -piperitols have been converted into the corresponding allylic chlorides, which were made to react with both trimethyltinlithium and triphenyltinlithium.The resulting allylic stannanes were characterized by 1H, 13C and 119Sn n.m.r. spectroscopy, which permitted assignment of the relative configurations.Triphenyltinlithium appears to react in a (substantially) concerted fashion with the (optically active) chloride from the carvotanacetols yielding an optically active stannane.The corresponding trimethylstannane is optically inactive.Substitution reactions (SE') with acid and sulfur dioxide (in chloroform) are preferentially γ-anti and specifically γ-syn respectively, in line with conclusions based on other cyclohex-2-enyl systems.

COMPOSITION OF ESSENTIAL OIL FROM LEAVES OF EUCALYPTUS DELEGATENSIS

The major components of a dichloromethane extract of mature Eucalyptus delegatensis leaves were cis- and trans-p-2-menthen-1-ol, trans-piperitol, α- and β-eudesmol, 4-phenyl-2-butanone and methyl cinnamate.The major terpenoid was considered to be trans-piperitol, which was responsible for the peppermint aroma of freshly crushed leaves.The steam distillate of the same leaves contained the above compounds together with a number of monoterpene hydrocarbons which were considered to be artefacts.Use of these hydrocarbons as chemotaxonomic markers was considered to be erroneous.Key Word Index-Eucalyptus delegatensis; Myrtaceae; alpine ash; essential oil; cis- and trans-p-2-menthen-1-ol; trans-piperitol; monoterpenoids; sesquiterpenoids; phenylpropanoids; peppermint aroma; chemotaxonomy.