29606-79-9

Basic information

• Product Name: trans-5-methyl-2-(1-methylvinyl)cyclohexan-1-one
• Synonyms: trans-5-methyl-2-(1-methylvinyl)cyclohexan-1-one;Cyclohexanone, 5-methyl-2-(1-methylethenyl)-, (2R,5S)-rel-;trans-Isopulegone;p-menth-8-en-3-one
• CAS NO: 29606-79-9
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23344
• EINECS: 249-725-6
• Mol File: 29606-79-9.mol

Chemical Properties

• Boiling Point: 234.73°C (rough estimate)
• Flash Point: 79.5°C
• Appearance: /
• Density: 0.9198
• Vapor Pressure: 0.14mmHg at 25°C
• Refractive Index: 1.4675 (estimate)
• CAS DataBase Reference: trans-5-methyl-2-(1-methylvinyl)cyclohexan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: trans-5-methyl-2-(1-methylvinyl)cyclohexan-1-one(29606-79-9)
• EPA Substance Registry System: trans-5-methyl-2-(1-methylvinyl)cyclohexan-1-one(29606-79-9)

Safety Data

• Hazardous Substances Data: 29606-79-9(Hazardous Substances Data)

Usage

Preparation

The structure of isopulegone was defined by Tiemann and Schmidt as well as by Hugh, Kon and Linstead; usually prepared from isopulegol

InChI:InChI=1/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-9H,1,4-6H2,2-3H3/t8-,9+/m1/s1

Upstream product

• 2385-77-5 (R)-Citronellal 
• 89-82-7 pulegone 
• 89-79-2 Isopulegol 
• 7786-67-6 isopulegol 
• 20549-46-6 (+)-neoisopulegol 
• 78782-00-0 Lithium 5-Methyl-cyclohexanone Enolate 
• 591-24-2 3-Methylcyclohexanone 
• 106-22-9 Citronellol 
• 89-82-7 pulegone 
• 89-79-2 isopulegol 
• 76480-48-3 benzyl p-menth-8-en-3-yl ether 
• 106-23-0 3,7-dimethyl-oct-6-enal 
• 75197-50-1 C₅H₅Fe(CO)2(CHCH₃CHOC₂H₅)⁽¹⁺⁾*BF₄^(1-) 
• 7540-51-4 (S)-3,7-dimethyl-6-octen-1-ol 

Downstream Products

• 65448-03-5 7-isopropenyl-10-methyl-1,5-dithia-spiro[5.5]undecane 
• 65448-04-6 2-(1,1-dimethyl-5-mercapto-2-thiapentyl)-5-methyl-1-cyclohexanone 
• 42413-80-9 1,5-dimethyl-2-(prop-1-en-2-yl)cyclohexan-1-ol 
• 89-82-7 pulegone 
• 10458-14-7 (2R,5S)-menthone 
• 1196-31-2 (1R,4R)-(+)-isomenthone 
• 135594-71-7 3-phenylisopulegol 
• 3391-90-0 (S)-(-)-pulegone 
• 80183-38-6 (6S)-3,6-dimethyl-4,5,6,7-tetrahydrobenzo[b]furan 
• 57707-92-3 (2R/S,5S)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanone 
• 122517-58-2 (-)-(1R,2S,5S)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanol 
• 57707-91-2 (1S,2R,5S)-8-(+)-phenylmenthol 
• 89-49-6 epiisopulegol acetate 
• 38049-01-3 2-((1R,2R,4S)-2-Hydroxy-4-methyl-cyclohexyl)-propenal 

Relevant articles and documents

DOUBLE BOND MIGRATION OVER SOLID KOH SUSPENDED IN APROTIC SOLVENTS

KOH suspended in DME is a good reagent to effect olefin double bond migration, especially deconjugation of α-enones.

Method of preparing L-menthone from R-citronellal

The invention discloses a method of preparing L-menthone from R-citronellal. Under the action of a Pd-Co-MOF-MMT catalyst, R-citronellal carries out heterogeneous catalytic reactions to generate L-menthone, the conversion rate of R-citronellal can reach 90-99.9%, the yield of L-menthone can reach 85-98%, and the ee value of menthone can reach 95-99.99%.

Copper Nanoparticles Immobilized on Nanocellulose: A Novel and Efficient Heterogeneous Catalyst for Controlled and Selective Oxidation of Sulfides and Alcohols

In this work, we have described the versatility of low metal loading copper nanoparticles immobilized on nanocellulose for the controlled and selective oxidation of sulfides to sulfoxides and primary alcohols to aldehydes using green oxidant at room temperature. Aromatic, aliphatic and heterocyclic sulfides were oxidized to their corresponding sulfoxides with high yields without formation of over oxidized sulfones. Similarly, benzylic, allylic and aliphatic alcohols were selectively oxidized to aldehydes without traces of carboxylic acids in good to excellent yields.

Chemoenzymatic Synthesis of the Intermediates in the Peppermint Monoterpenoid Biosynthetic Pathway

A chemoenzymatic approach providing access to all four intermediates in the peppermint biosynthetic pathway between limonene and menthone/isomenthone, including noncommercially available intermediates (-)-trans-isopiperitenol (2), (-)-isopiperitenone (3), and (+)-cis-isopulegone (4), is described. Oxidation of (+)-isopulegol (13) followed by enolate selenation and oxidative elimination steps provides (-)-isopiperitenone (3). A chemical reduction and separation route from (3) provides both native (-)-trans-isopiperitenol (2) and isomer (-)-cis-isopiperitenol (18), while enzymatic conjugate reduction of (-)-isopiperitenone (3) with IPR [(-)-isopiperitenone reductase)] provides (+)-cis-isopulegone (4). This undergoes facile base-mediated chemical epimerization to (+)-pulegone (5), which is subsequently shown to be a substrate for NtDBR (Nicotiana tabacum double-bond reductase) to afford (-)-menthone (7) and (+)-isomenthone (8).

METHOD FOR PREPARING MENTHONE FROM ISOPULEGOL

The present invention relates to a method for preparing menthone, starting from isopulegol, using specific homogeneous catalysts.

Gold nanoparticles supported on magnesium oxide as catalysts for the aerobic oxidation of alcohols under alkali-free conditions

Gold nanoparticles supported on magnesium oxide were shown to be efficient heterogeneous catalysts for the liquid-phase oxidation of a wide range of alcohols using molecular oxygen as a sole oxidant in the absence of co-catalysts or additives. The Au/MgO material was prepared through the deposition- precipitation method and characterized by XRD, XPS, XAS, HRTEM, UV-Vis spectroscopy, and N2 adsorption techniques. The formation of gold nanoparticles on the MgO surface under temperature programmed reduction was monitored by in situ UV-Vis-Mass spectroscopy. Various carbonylic monoterpenoids important for fragrance and pharmaceutical industries were obtained in good to excellent yields starting from biomass-based monoterpenic alcohols, such as isoborneol, perillyl alcohol, and carveol. The Au/MgO catalyst also performs a selective one-pot oxidative esterification of benzyl alcohol in alkali-free methanol solutions in the absence of any additive to give methyl benzoate in a virtually quantitative yield.

Applications of a high performance platinum nanocatalyst for the oxidation of alcohols in water

Nanoparticles of platinum (NP-Pt), have been synthesized by supporting high nuclearity anionic carbonyl cluster (Chini cluster) on a water soluble anion exchanger, and the performance of this material, 1, as an oxidation catalyst for alcohols in water has been studied. The E-factor for the synthesis of NP-Pt by this method has been calculated and compared with that of other NP-Pt recently reported in the literature. With 1 as a catalyst, oxidations of a variety of primary and secondary alcohols by dioxygen are achieved and high turnover numbers and selectivities are obtained. The performances of 1 in the oxidation of benzyl alcohol and 1-phenylethanol are compared with those of three other platinum catalysts. These are platinum nanoparticles 2 prepared by the hydrogen reduction of [PtCl6]2- supported on the same water soluble polymer, 5% Pt on carbon, and 5% Pt on alumina, designated as 3 and 4, respectively. 1 has been found to be considerably more active than 2-4 and also other reported water soluble platinum nanocatalysts. After many turnovers (～1000 and ～165 for benzyl alcohol and 1-phenyl ethanol, respectively) partial deactivation (～ 40%) is observed, but the deactivated catalyst can be fully regenerated by treatment with dihydrogen. The TEM data of fresh, deactivated and regenerated 1 show a correlation between the particle size and activity. A mechanism consistent with this and other experimental observations including XPS data is proposed.

3-Alkyl-p-menthan-3-ol derivatives: synthesis and evaluation of their physiological cooling activity

Different 3-alkyl-p-methan-3-ol derivatives provide a strong physiological cooling effect with potential application as food and cosmetic additives. In order to investigate the influence of the chemical structure on the cooling sensation, the stereoselective syntheses of 29 different 3-alkyl-p-methan-3-ol derivatives were accomplished. All the compounds obtained are odorless and were evaluated by taste, considering two sensations: a cooling effect and bitterness. The results of this structure-activity relationship study highlight that compounds with a (1R,4S)-configuration are the isomers with the more intense cooling effect and lower bitterness. In addition, the structure of the 3-alkyl chain affected the latter properties. Increasing the chain length over two carbon atoms does not change the cooling power, but enhances the bitterness with the additional feature that the branched isomers are considerably more bitter than the linear ones. Overall, the 3-alkyl-p-menthan-3-ol isomers with the best quality in terms of high cooling power and low bitterness are (1R,4S)-3-(hydroxymethyl)-p-menthan-3-ol diastereoisomers (-)-38 and (-)-42.

Oxidation of alcohols to carbonyl compounds with CrO3· SiO2 in supercritical carbon dioxide

Supercritical carbon dioxide (scCO2) is an effective reaction medium to perform the oxidation of primary and secondary aliphatic alcohols to the corresponding carbonyl compounds with chromium trioxide supported on silica. These reactions were performed by flowing a solution of the alcohol in scCO2 through a column containing the supported reagent and recovering the product by depressurization. This method avoids the use of organic solvents and the contamination of the products with chromium species.

Cyclization of citronellal to menthone and isomenthone catalyzed by Al/Fe-Pillared Clays

The cyclization of citronellal to a mixture of menthone and isomenthone (2:1) is catalyzed by Al/Fe-Pillared Clay (Al/Fe-PILC) at 80 °C in 1,2-dichloroethane in good yield. At room temperature the products are isopulegol and neo-isopulegol, the isomer ratio depending on the reaction conditions.