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

(+)-Isomenthone is an isomer of L-Menthone. L-Menthone, is s a constituent of the essential oils of pennyroyal, peppermint, Pelargonium geraniums, and others. It is also a naturally occurring pesticide.

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

• 6485-40-1 (R)-Carvone 
• 89-83-8 thymol 
• 53282-30-7 trifluoro-methanesulfonic acid 2-methyl-propenyl ester 
• 95465-47-7 potassium menthyl oxide 
• 4573-50-6 (-)-piperitone 
• 20752-34-5 neoisomenthol 
• 23283-97-8 (+)-(1S,2R,5R)-isomenthol 
• 89-82-7 pulegone 
• 3391-87-5 l-menthone 
• 10458-14-7 (2R,5S)-menthone 
• 74173-21-0 l-menthone enol trimethylsilyl ether 
• 89-82-7 pulegone 
• 64-17-5 ethanol 
• 60-29-7 diethyl ether 

Downstream Products

• 18368-87-1 1-ethyl-2-isopropyl-5-methyl-cyclohexanol 
• 23283-97-8 (+)-(1S,2R,5R)-isomenthol 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 18427-47-9 2,6-Dibromo-2-isopropyl-5-methylcyclohexanone 
• 10458-14-7 (2R,5S)-menthone 
• 7231-40-5 (+)-(1R,3S,4S)-neomenthylamine 
• 20752-34-5 neoisomenthol 
• 18368-90-6 2-Isopropyl-5-methyl-1-phenyl-cyclohexanol 
• 162551-92-0 3-isopropyl-6-methyl-2-oxo-cyclohexanecarboxylic acid 
• 7616-79-7 (1R,4S)-(+)-4-hydroxy-p-menth-3-one 
• 7599-80-6 (1R,4R)-(-)-4-hydroxy-p-menth-3-one 
• 148460-10-0 1-(α-Hydroxy-isopropyl)-2-isopropyl-5-methyl-cyclohexanol 
• 611-69-8 rac-2-methyl-1-phenylpropan-1-ol 
• 89-78-1 2-isopropyl-5-methylcyclohexan-1-ol 

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.

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.

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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.

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.

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.