89-80-5

Usage

Uses

Used in Flavor and Fragrance Industry:
MENTHONE is used as a flavoring agent for its cooling, minty, and refreshing taste characteristics. It is commonly found in food products, beverages, and confectionery items to impart a minty flavor.
Used in Aromatherapy and Perfumery:
MENTHONE is used as a fragrance ingredient in perfumes, colognes, and other scented products due to its characteristic mint-like odor and refreshing, cooling aroma.
Used in Cosmetics and Personal Care Products:
MENTHONE is used in cosmetics and personal care products, such as creams, lotions, and shampoos, for its cooling and refreshing properties, as well as its pleasant minty scent.
Used in Pharmaceutical Industry:
MENTHONE is used in the pharmaceutical industry for its potential medicinal properties, such as its cooling effect and its ability to provide a refreshing sensation when used in topical applications.
Used in Natural Products:
MENTHONE is found in various natural products, such as essential oils from plants like peppermint, geranium, and others, and can be used in their natural form for various applications, including aromatherapy and as a flavoring agent.

Preparation

By oxidation of menthol.

Flammability and Explosibility

Notclassified

Safety Profile

Moderately toxic by ingestion, intravenous, and subcutaneous routes. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.

Metabolism

H?m?l?inen (1912) claimed that menthone was probably oxidized in the rabbit to ketomenthone, since the glucuronide produced was converted by warm dilute H2SO4 to a substance which was probably △4(8 -p-menthen-3-one (pulegone). Williams (1940), however, showed that it underwent reduction in the rabbit with the production of d-neomenthol. The presence of l-menthol, the other possible reduction product, was not detected and it appeared that the biological reduction was asymmetric (Williams, 1959).

InChI:InChI=1/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 
• 59781-47-4 r-2-Acetyl-t-3-methyl-c-6-(1-methylethyl)-1-cyclohexanon 
• 74-88-4 methyl iodide 
• 6485-40-1 (R)-Carvone 
• 1214906-07-6 (-)-menthol 
• 36392-06-0 3,7-dimethyl-6-octenoyl chloride 
• 53282-30-7 trifluoro-methanesulfonic acid 2-methyl-propenyl ester 
• 95465-47-7 potassium menthyl oxide 
• 15356-70-4 menthol 
• 89-48-5 rac-2-isopropyl-5-methylcyclohexyl acetate 
• 40940-58-7 allyl menthyl ether 
• 89-78-1 2-isopropyl-5-methylcyclohexan-1-ol 

Downstream Products

• 1538-17-6 (+/-)-Menthon-2,4-DNP 
• 491-07-6 isomenthone 
• 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 
• 138490-36-5 (2R,3S,6S,7R,10S)-2-Cyclohexyl-7-isopropyl-3,10-dimethyl-1,5-dioxa-spiro[5.5]undecane 
• 138490-36-5 (2R,3S,6S,7S,10R)-2-Cyclohexyl-7-isopropyl-3,10-dimethyl-1,5-dioxa-spiro[5.5]undecane 
• 138604-11-2 (2R,3S,6S,7S,10R)-2-Cyclohexyl-7-isopropyl-3,10-dimethyl-1,5-dioxa-spiro[5.5]undecane 
• 138490-36-5 (2S,3R,6R,7S,10R)-2-Cyclohexyl-7-isopropyl-3,10-dimethyl-1,5-dioxa-spiro[5.5]undecane 
• 115346-74-2 (2R,6S,7R,10S)-7-Isopropyl-10-methyl-2-phenethyl-1,5-dioxa-spiro[5.5]undecane 
• 115346-74-2 (2R,6S,7S,10R)-7-Isopropyl-10-methyl-2-phenethyl-1,5-dioxa-spiro[5.5]undecane 
• 73808-92-1 C₁₈H₂₉NO₂S 
• 73808-92-1 C₁₈H₂₉NO₂S 
• 73808-92-1 C₁₈H₂₉NO₂S 

Relevant academic research and scientific papers

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.

Chemoselective Hydrogenation of α,β-Unsaturated Carbonyls Catalyzed by Biomass-Derived Cobalt Nanoparticles in Water

Herein, we report highly chemoselective hydrogenation of α,β-unsaturated carbonyls to saturated carbonyls catalyzed by cobalt nanoparticles supported on the biomass-derived carbon from bamboo shoots with molecular hydrogen in water, which is the first prototype using a heterogeneous non-noble metal catalyst for such organic transformation as far as we know. The optimal cobalt nanocatalyst, CoOx@NC-800, manifested remarkable activity and selectivity for hydrogenation of C=C in α,β-unsaturated carbonyls under mild conditions. A broad set of α,β-aromatic and aliphatic unsaturated carbonyls were selectively reduced to their corresponding saturated carbonyls in up to 99 % yields with good tolerance of various functional groups. Meanwhile, a new straightforward one-pot cascade synthesis of saturated carbonyls was realized with high activity and selectivity via the cross-aldol condensation of ketones with aldehydes followed by selective hydrogenation. More importantly, this one-pot strategy is applicable for the expedient synthesis of Loureirin A, a versatile bioactive and medicinal molecule, from readily available starting materials, further highlighting the practical utility of the catalyst. In addition, the catalyst can be easily separated for successive reuses without significant loss in both activity and selectivity.

Heterogeneous Ru(iii) oxidation catalysts: Via 'click' bidentate ligands on a periodic mesoporous organosilica support

A 100% monoallyl ring-type Periodic Mesoporous Organosilica (PMO) is prepared as a novel, versatile and exceptionally stable catalytic support with a high internal surface area and 5.0 nm pores. Thiol-ene 'click' chemistry allows straightforward attachment of bifunctional thiols (-NH2, -OH, -SH) which, exploiting the thioether functionality formed, give rise to 'solid' bidentate ligands. [Ru(acac)2(CH3CN)2]PF6 is attached and complex formation on the solid is studied via density functional theory. All resulting solid catalysts show high activity and selectivity in alcohol oxidation reactions performed in green conditions (25 °C/water). The PMO catalysts do not leach Ru during reaction and are thus easily recuperated and re-used for several runs. Furthermore, oxidation of poorly water-soluble (±)-menthol illustrates the benefits of using hydrophobic PMOs as catalytic supports.

3,4-Dihydroisoquinolinium trichloroacetatochromate: A mild and effective new reagent for oxidation of alcohols to carbonyl compounds and arenes to their quinones

A new chromium(VI) reagent, 3,4-dihydroisoqinolinium trichloroacetatochromate was prepared by reacting trichloroacetic acid with CrO3in water. This reagent is suitable to oxidize various primary and secondary alcohols to the corresponding carbonyl compounds and anthracene to antraquinone in a good yields.

ALPHA-HYDROGEN SUBSTITUTED NITROXYLS AND DERIVATIVES THEREOF AS CATALYSTS

The present invention relates to novel alpha-hydrogen substituted nitroxyl compounds and their corresponding oxidized (oxoammonium cations) and reduced (hydroxylamine) forms, and to the use of such compounds, inter alia, for (1) oxidation of primary and secondary alcohols to aldehydes and ketones, respectively; (2) resolution of racemic alcohols; (3) desymmetrization of meso-alcohol; (4) as radicals and spin trapping reagents; and (5) as polymerization agents. The present invention further relates to processes for preparing the novel nitroxyl/oxoammonium/ hydroxylamine compounds from the corresponding amines, and to certain novel amine derivatives and their uses. The compounds of the invention as well as the amine precursors are also useful as ligands for transition metals and as organocatalysts in e.g., aldol reactions.

Grafting of oxo-vanadium Schiff base on graphene nanosheets and its catalytic activity for the oxidation of alcohols

Graphene oxide was found to be a convenient and efficient supporting material for grafting of oxo-vanadium Schiff base via covalent attachment. The low dimensionality and rich surface chemistry of graphene oxide play critical roles in order to achieve a good degree of such grafting. Catalytic potential of the so prepared graphene-bound oxo-vanadium Schiff base and comparison with its homogeneous analogue was studied for the oxidation of various alcohols to carbonyl compounds using tert-butylhydroperoxide as oxidant. The structural and chemical nature of the catalyst was characterized by a variety of techniques including XRD, FTIR, TGA, TEM, and ICP-AES. The immobilized complex was found to be highly efficient and showed comparable catalytic reactivity as its homogenous analogue with the added benefits of facile recovery and recycling of the heterogeneous catalyst. The graphene-bound oxo-vanadium Schiff base was successfully reused for several runs without significant loss in its catalytic activity. The Royal Society of Chemistry 2012.

Cyclization of citronellal in a supercritical solvent in a flow reactor in the presence of Al2O3

The reactivity of citronellal under supercritical solvent conditions in a flow reactor in the presence of Al2O3 is examined. It is shown that at 160°C, the main transformation product of citronellal is isopulegol, and when the temperature is increased to 190°C, they are monoterpenes with a para-menthane framework and myrcene. Pleiades Publishing, Ltd., 2012.

The oxidation of pyridine and alcohol using the Keggin-type lacunary polytungstophosphate as a temperature-controlled phase transfer catalyst

A novel temperature-controlled phase transfer catalyst of [(C 18H37)2(CH3)2N] 7[PW11O39] has been developed for the oxidation of pyridines and alcohols with hydrogen peroxide. The reactions were conducted in 1,4-dioxane, and high yields of the corresponding heterocyclic N-oxides and ketones were obtained under relative mild conditions. The catalyst could be easily recovered and reused after reaction with cooling. There was no discernable loss in activity and selectivity after several reaction cycles.

Menthone aryl acid hydrazones: A new class of anticonvulsants

A series of ten compounds (Compounds J1-J10) of (±) 3-menthone aryl acid hydrazone was synthesized and characterized by thin layer chromatography and spectral analysis. Synthesized compounds were evaluated for anticonvulsant activity after intraperitoneal (i.p) administration to mice by maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) induced seizure method and minimal clonic seizure test. Minimal motor impairment was also determined for these compounds. Results obtained showed that four compounds out of ten afforded significant protection in the minimal clonic seizure screen at 6 Hz. Compound J6, 4-Chloro-N-(2-isopropyl-5- methylcyclohexylidene) benzohydrazide was found to be the most active compound with MES ED50 of 16.1 mg/kg and protective index (pI) of greater than 20, indicating that (±) 3-menthone aryl acid hydrazone possesses better and safer anticonvulsant properties than other reported menthone derivatives viz. menthone Schiff bases, menthone semicarbazides and thiosemicarbazides.

Menthone semicarbazides and thiosemicarbazides as anticonvulsant agents

A series of novel (±) 3-menthone semicarbazides (1-7) and thiosemicarbazides (8-14) were synthesized using an appropriate synthetic route and characterized by thin layer chromatography and spectral analysis. The anticonvulsant activity of synthesized compounds was established after intraperitoneal administration in three seizure models in mice which include maximal electroshock seizure (MES), subcutaneous pentylene tetrazole (scPTZ) induced seizure and minimal neurotoxicity test. Seven compounds exhibited protection in both models and N1 - (4-fluorophenyl) - N4- (menth-3-one) semicarbazide (4) emerged as the most active compound with MES ED50 of 44.15mg/kg and scPTZ ED50 of 38.68mg/kg at 0.25h duration. These compounds were found to elevate γ-amino butyric acid (GABA) levels in the midbrain region, thus indicating that (±) 3-menthone semicarbazides could be considered as a lead molecule in designing of a potent anticonvulsant drug.