1196-31-2

Basic information

• Product Name: (+)-isomenthone
• Synonyms: D-ISOMENTHONE;(1R,4R)-p-Menthane-3-one;(2R)-2β-Isopropyl-5β-methylcyclohexane-1-one;(2R)-2βα-Isopropyl-5β-methylcyclohexanone;[1R,4R,(+)]-p-Menthan-3-one;(2R,5R)-2-isopropyl-5-methyl-cyclohexanone;(2R,5R)-5-methyl-2-propan-2-yl-cyclohexan-1-one;(2R,5R)-5-methyl-2-propan-2-ylcyclohexan-1-one
• CAS NO: 1196-31-2
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.2493
• EINECS: 214-813-5
• Mol File: 1196-31-2.mol
• Article Data: 97

Chemical Properties

• Melting Point: 27.18°C (estimate)
• Boiling Point: 217.64°C (estimate)
• Appearance: /
• Density: 0.8947
• Refractive Index: 1.4503
• Storage Temp.: Hygroscopic, Refrigerator, Under inert atmosphere
• Solubility: Chloroform (Soluble), Ethanol (Slightly), Methanol (Sparingly)
• Stability: Hygroscopic
• CAS DataBase Reference: (+)-isomenthone(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-isomenthone(1196-31-2)
• EPA Substance Registry System: (+)-isomenthone(1196-31-2)

Safety Data

• Hazardous Substances Data: 1196-31-2(Hazardous Substances Data)

Usage

Uses

Used in Pesticide Industry:
(+)-Isomenthone is used as a natural pesticide for its insecticidal properties, providing an eco-friendly alternative to synthetic pesticides. It is effective in controlling pests and protecting crops without causing harm to the environment or human health.
Used in Flavor and Fragrance Industry:
(+)-Isomenthone is used as a flavoring agent and fragrance component in the food, beverage, and cosmetics industries. Its unique aroma and taste profile contribute to the overall sensory experience of products, enhancing their appeal to consumers.
Used in Pharmaceutical Industry:
(+)-Isomenthone is used as an active pharmaceutical ingredient or as an intermediate in the synthesis of various drugs. Its unique chemical properties make it a promising candidate for the development of new medications with potential therapeutic benefits.
Used in Essential Oils Industry:
(+)-Isomenthone is used in the production of essential oils, which are widely used in aromatherapy, massage therapy, and other alternative medicine practices. Its presence in essential oils contributes to their therapeutic properties and overall effectiveness in promoting relaxation, stress relief, and overall well-being.

InChI:InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9-/m0/s1

Upstream product

• 89-82-7 pulegone 
• 72311-09-2 3-Methyl-6-(1-methylethyl)-1-trimethylsilyloxy-1-cyclohexen 
• 75-36-5 acetyl chloride 
• 89-83-8 thymol 
• 109-99-9 tetrahydrofuran 
• 53282-30-7 trifluoro-methanesulfonic acid 2-methyl-propenyl ester 
• 95465-47-7 potassium menthyl oxide 
• 89-78-1 2-isopropyl-5-methylcyclohexan-1-ol 
• 490-99-3 DL-neomenthol 
• 106-23-0 3,7-dimethyl-oct-6-enal 
• 89-79-2 Isopulegol 
• 4573-50-6 (-)-piperitone 
• 20752-34-5 neoisomenthol 
• 23283-97-8 (+)-(1S,2R,5R)-isomenthol 

Downstream Products

• 74185-00-5 (3R,6S)-3-methyl-6-(prop-2-yl)-1-trimethylsilyloxy-cyclohexene 
• 105367-46-2 ((3S,6S)-6-Isopropyl-3-methyl-cyclohex-1-enyloxy)-trimethyl-silane 
• 13143-66-3 (+/-)-isonicotinic acid menthylidenehydrazide 
• 490-99-3 DL-neomenthol 
• 15356-70-4 menthol 
• 10458-14-7 (2R,5S)-menthone 
• 127129-06-0 (3S,6R)-3-methyl-6-(prop-2-yl)-1-trimethylsilyloxy-cyclohexene 
• 4884-25-7 2-cyclopentylcyclopentanol 
• 89-78-1 2-isopropyl-5-methylcyclohexan-1-ol 
• 121642-44-2 (E)-2'-cis-5'-trans-4-(1-hydroxy-2-isopropyl-5-methylcyclohexyl)but-2-enoic acid 
• 148460-10-0 1-(α-Hydroxy-isopropyl)-2-isopropyl-5-methyl-cyclohexanol 
• 165874-36-2 (-)-2-Isopropyl-5-methylcyclohexanone oxime 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 2216-51-5 (-)-menthol 

Relevant articles and documents

Synthesis, structural characterization and alcohol oxidation activity of a new mononuclear manganese(II) complex

A manganese(II) complex of 2,4,6-tris(2-pyridyl)-1,3,5-triazine (tptz) has been synthesized and characterized by single-crystal X-ray diffraction, elemental analyses, IR, and UV-Vis spectroscopic techniques. Oxidation of alcohols to their corresponding aldehydes and ketones was conducted by this catalyst using oxone (2KHSO5KH-SO4K2SO4) as an oxidant under biphasic reaction conditions (CH2Cl2/H 2O) and tetra-n-butylammonium bromide as phase transfer agent under air at room temperature. Easy preparation, mild reaction conditions, high yields of the products, short reaction times, no further oxidation to the corresponding carboxylic acids, high selectivity and inexpensive reagents make this catalytic system a useful oxidation method for aliphatic and benzylic alcohols. Springer Science+Business Media B.V. 2010.

Characterization of two enone reductases from Nicotiana tabacum cell cultures

Two enone reductases, designated Reductase-I and -II, were isolated from Nicotiana tabacum cell cultures. These two reductases have different Mrs, pH optimum, coenzyme requirement and substrate specificity. Reductase-I catalyses the reduction of the endocyclic CC double bond of enones which bear a hydrogen-substituent at the position β to the carbonyl, while Reductase-II catalyses the reduction of the exocyclic CC double bond of enones.

A new vanadium Schiff base complex as catalyst for oxidation of alcohols

The monoanionic bidentate Schiff base, N-(phenolyl)-benzaldimine (HL), has been employed to synthesize a new vanadium(IV) complex of general composition [VO(L)2] (where L = O, N donor of Schiff base). The ligand and complex have been fully characterized by elemental analyses, molar conductance data, FT-IR, 1H- and 13C-NMR, and UV-Vis spectroscopies. Oxidation of alcohols to their corresponding aldehydes and ketones was conducted by this complex catalyst using Oxone as oxidant under biphasic reaction conditions (CH2Cl2/H2O) and tetra-n-butylammonium bromide as phase transfer agent under air at room temperature.

Stereoselectivity in Oxidative and Reductive Transformations of p-Menthane Derivatives with the Cultured Cells of Nicotiana tabacum

The biotransformation of the enantiomeric pairs of 2- and 3-oxygenated p-methane derivatives with the cultured cells of Nicotiana tabacum was investigated.It was found that (I) the cultured cells transform only 2-oxygenated p-menthane derivatives to a great extent, (ii) the cultured cells cause the highly stereospecific reduction for (1R,4R)-2-oxo-p-menthane, whereas this is not the case for its enantiomer, and (iii) the cultured cells enantioselectively oxidize the hydroxyl group of 2-hydroxyl-p-methanes.

Oxidation of secondary terpene alcohols by chlorine dioxide

Secondary terpene alcohols cis- and trans-verbenol, neo-iso-verbanol, borneol, iso-borneol, and menthol were oxidized by chlorine dioxide into the corresponding ketones. It was shown that the nature of the solvent and catalyst and the structure of the starting compound, including the stereochemistry of the hydroxyl, influenced the oxidation process.

Origin of High Diastereoselectivity in Reactions of Seven-Membered-Ring Enolates

Unlike many reactions of their six-membered-ring counterparts, the reactions of chiral seven-membered-ring enolates are highly diastereoselective. Diastereoselectivity was observed for a range of substrates, including lactam, lactone, and cyclic ketone derivatives. The stereoselectivity arises from torsional and steric interactions that develop when electrophiles approach the diastereotopic π-faces of the enolates, which are distinguished by subtle differences in the orientation of nearby atoms of the ring.

Rapid, chemoselective and mild oxidation protocol for alcohols and ethers with recyclable N-chloro-N-(phenylsulfonyl)benzenesulfonamide

Chlorine is the 20th most abundant element on the earth compared to bromine, iodine, and fluorine, a sulfonimide reagent, N-chloro-N-(phenylsulfonyl)benzenesulfonamide (NCBSI) was identified as a mild and selective oxidant. Without activation, the reagent was proved to oxidize primary and secondary alcohols as well as their symmetrical and mixed ethers to corresponding aldehydes and ketones. With recoverable PS-TEMPO catalyst, selective oxidation over chlorination of primary and secondary alcohols and their ethers with electron-donating substituents was achieved. The reagent precursor of NCBSI was recovered quantitatively and can be reused for synthesizing NCBSI.

Menthylamine synthesis via gold-catalyzed hydrogenation of menthone oxime

In the current work gold nanoparticles supported on oxides (MgO, Al2O3, ZrO2, TiO2) were used for menthylamine synthesis via menthone oxime hydrogenation. An increase of the gold nanoparticles size and application of metal oxides with a strong basic character such as magnesia favored deoximation to menthone. Au/Al2O3 catalyst with the gold nanoparticles size of 2.0 nm afforded high catalytic activity and selectivity to menthylamine. The reaction kinetics including stereoselectivity to the reaction products and recyclability of the catalyst was studied using Au/Al2O3 in the temperature range 90?110 °C under hydrogen pressure of 5.5–7.5 bar. The catalytic behavior was influenced by the solvent nature, with higher selectivity to desired amine achieved using methanol. The reaction rate was pressure independent, while has first order with respect to menthone oxime concentration. Stereoselectivity to menthylamines and menthones was independent on the reaction temperature and the hydrogen pressure.

Heterogeneously Catalysed Oxidative Dehydrogenation of Menthol in a Fixed-Bed Reactor in the Gas Phase

For the first time, the oxidative dehydrogenation of (?)-menthol to (?)-menthone and (+)-isomenthone in a marketable quality was carried out in a continuous gas phase reactor as a sustainable process using molecular oxygen as green oxidant and solid catalysts which do not contaminate the product mixture and which are easily to remove. The diastereomeric purity remained largely unchanged. Three types of catalysts were found to be very active and selective in the formation of menthone and isomenthone: AgSr/SiO2, CuO distributed on a basic support and RuMnCe/CeO2, where Ru, Mn and Ce exist in an oxidized state. The best overall yield of menthon/isomenthone obtained with an Ag-based catalyst was 58 % at 64 % selectivity, with a Cu-based catalyst 41 % at 51 % selectivity and with a Ru-based catalyst 68 % at 73 % selectivity. Reaction conditions were widely optimized.

Cucurbit[5]uril-mediated electrochemical hydrogenation of α,β-unsaturated ketones

The potential of cucurbit[5]uril to be used as inverse phase transfer catalyst in electrocatalytic hydrogenation of α,β-unsaturated ketones is illustrated. The interaction behavior among isophorone and cucurbit[5]uril was also investigated using cyclic voltammetry and UV/vis absorption spectroscopy. The results concerning to both techniques revealed an enhancement in the intensity of the absorption peak and also in the current cathodic peak of isophorone in presence of cucurbit[5]uril. This achievement is related to the increase of the isophorone solubility in the medium being an indicative of a host-guest complex formation. The electrochemical hydrogenation of isophorone using cucurbit[5]uril was more efficient than others well-stablish methodologies. Regarding to (R)-(+)-pulegone and (S)-(+)-carvone, the use of cucurbit[5]uril leads to an increase of 17% and 9%, on average, respectively, in the yields when compared to the control reaction. The efficiency of selective C=O bond hydrogenation of 1-acetyl-1-cyclohexene was evaluated. The presence of cucurbit[5]uril increased by 12% the hydrogenations yields of 1-acetyl-1-cyclohexene when compared to the control reaction. In this sense, these results open up an opportunity to carry out electrocatalytic reactions within the cucurbit[5]uril environment.